13647-35-3,MFCD00199295
Catalog No.:AA0011TS

13647-35-3 | Androst-2-ene-2-carbonitrile, 4,5-epoxy-3,17-dihydroxy-, (4α,5α,17β)-

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Purity
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5mg
≥98%
in stock  
$72.00   $50.00
- +
10mg
≥98%
in stock  
$135.00   $94.00
- +
100mg
98%
in stock  
$185.00   $129.00
- +
250mg
95%
in stock  
$416.00   $291.00
- +
1g
98%
in stock  
$548.00   $384.00
- +
5g
98%
in stock  
$2,277.00   $1,594.00
- +
  • Technical Information
  • Properties
  • Literature
  • Request for Quotation
  • Download SDS
Technical Information
Catalog Number:
AA0011TS
Chemical Name:
Androst-2-ene-2-carbonitrile, 4,5-epoxy-3,17-dihydroxy-, (4α,5α,17β)-
CAS Number:
13647-35-3
Molecular Formula:
C20H27NO3
Molecular Weight:
329.4333
MDL Number:
MFCD00199295
SMILES:
N#CC1=C(O)[C@@H]2[C@]3([C@@](C1)(C)[C@H]1CC[C@]4([C@H]([C@@H]1CC3)CC[C@@H]4O)C)O2
Properties
Computed Properties
 
Complexity:
692  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
8  
Defined Bond Stereocenter Count:
0  
Formal Charge:
0  
Heavy Atom Count:
24  
Hydrogen Bond Acceptor Count:
4  
Hydrogen Bond Donor Count:
2  
Isotope Atom Count:
0  
Rotatable Bond Count:
0  
Undefined Atom Stereocenter Count:
0  
Undefined Bond Stereocenter Count:
0  
XLogP3:
2.9  

Literature

Title: Temporal changes in biological responses and uncertainty in assessing risks of endocrine-disrupting chemicals: insights from intensive time-course studies with fish.

Journal: Toxicological sciences : an official journal of the Society of Toxicology 20150401

Title: 17β-trenbolone, an anabolic-androgenic steroid as well as an environmental hormone, contributes to neurodegeneration.

Journal: Toxicology and applied pharmacology 20150101

Title: Expression of LH receptor in nonpregnant mouse endometrium: LH induction of 3β-HSD and de novo synthesis of progesterone.

Journal: The Journal of endocrinology 20121001

Title: Effects of fibroblast growth factor 9 (FGF9) on steroidogenesis and gene expression and control of FGF9 mRNA in bovine granulosa cells.

Journal: Endocrinology 20120901

Title: The influence of trilostane on steroid hormone metabolism in canine adrenal glands and corpora lutea-an in vitro study.

Journal: Veterinary research communications 20120301

Title: Feline pituitary-dependent hyperadrenocorticism and insulin resistance due to a plurihormonal adenoma.

Journal: Topics in companion animal medicine 20120201

Title: Effects of nonylphenol on aldosterone release from rat zona glomerulosa cells.

Journal: Chemico-biological interactions 20120105

Title: The antidepressant-like effects of the 3β-hydroxysteroid dehydrogenase inhibitor trilostane in mice is related to changes in neuroactive steroid and monoamine levels.

Journal: Neuropharmacology 20120101

Title: Long-term follow-up of renal function in dogs after treatment for ACTH-dependent hyperadrenocorticism.

Journal: Journal of veterinary internal medicine 20120101

Title: Pharmaceutical evaluation of compounded trilostane products.

Journal: Journal of the American Animal Hospital Association 20120101

Title: Trilostane dose versus body weight in the treatment of naturally occurring pituitary-dependent hyperadrenocorticism in dogs.

Journal: Journal of veterinary internal medicine 20120101

Title: Gh is produced by the testis of Japanese eel and stimulates proliferation of spermatogonia.

Journal: Reproduction (Cambridge, England) 20111201

Title: Transcriptional regulatory dynamics of the hypothalamic-pituitary-gonadal axis and its peripheral pathways as impacted by the 3-beta HSD inhibitor trilostane in zebrafish (Danio rerio).

Journal: Ecotoxicology and environmental safety 20110901

Title: Temporal evaluation of effects of a model 3β-hydroxysteroid dehydrogenase inhibitor on endocrine function in the fathead minnow.

Journal: Environmental toxicology and chemistry 20110901

Title: Decreased cytochrome c oxidase IV expression reduces steroidogenesis.

Journal: The Journal of pharmacology and experimental therapeutics 20110801

Title: Evaluation of twice-daily lower-dose trilostane treatment administered orally in dogs with naturally occurring hyperadrenocorticism.

Journal: Journal of the American Veterinary Medical Association 20110601

Title: Determination of the concentrations of trilostane and ketotrilostane that inhibit ex vivo canine adrenal gland synthesis of cortisol, corticosterone, and aldosterone.

Journal: American journal of veterinary research 20110501

Title: Effects of the 3β-hydroxysteroid dehydrogenase inhibitor trilostane on luteal progesterone production in the dog.

Journal: Theriogenology 20110415

Title: Adrenocorticotropic hormone, but not trilostane, causes severe adrenal hemorrhage, vacuolization, and apoptosis in rats.

Journal: Domestic animal endocrinology 20110401

Title: Anti-ovulatory effects of RU486 and trilostane involve impaired cyclooxygenase-2 expression and mitotic activity of follicular granulosa cells in rats.

Journal: Prostaglandins & other lipid mediators 20110401

Title: The antidepressant-like effect of the 3β-hydroxysteroid dehydrogenase inhibitor trilostane involves a regulation of β-type estrogen receptors.

Journal: Psychopharmacology 20110301

Title: A comparison of factors that influence survival in dogs with adrenal-dependent hyperadrenocorticism treated with mitotane or trilostane.

Journal: Journal of veterinary internal medicine 20110101

Title: Long-term efficacy of trilostane for Cushing's syndrome due to adrenocorticotropin-independent bilateral macronodular adrenocortical hyperplasia.

Journal: Internal medicine (Tokyo, Japan) 20110101

Title: Retrospective evaluation of the effect of trilostane on insulin requirement and fructosamine concentration in eight diabetic dogs with hyperadrenocorticism.

Journal: The Journal of small animal practice 20101201

Title: Trilostane, an inhibitor of 3β-hydroxysteroid dehydrogenase, has an agonistic activity on androgen receptor in human prostate cancer cells.

Journal: Cancer letters 20101128

Title: Prochloraz-induced oocyte maturation in rainbow trout (Oncorhynchus mykiss), a molecular and functional analysis.

Journal: Toxicological sciences : an official journal of the Society of Toxicology 20101101

Title: Evaluation of the use of baseline cortisol concentration as a monitoring tool for dogs receiving trilostane as a treatment for hyperadrenocorticism.

Journal: Journal of the American Veterinary Medical Association 20101001

Title: Aldosterone, hypertension and heart failure: insights from clinical trials.

Journal: Hypertension research : official journal of the Japanese Society of Hypertension 20100901

Title: 3beta-hydroxysteroid dehydrogenase is a possible pharmacological target in the treatment of castration-resistant prostate cancer.

Journal: Endocrinology 20100801

Title: The functions of key residues in the inhibitor, substrate and cofactor sites of human 3beta-hydroxysteroid dehydrogenase type 1 are validated by mutagenesis.

Journal: The Journal of steroid biochemistry and molecular biology 20100601

Title: Induction of progesterone receptor A form attenuates the induction of cytosolic phospholipase A2alpha expression by cortisol in human amnion fibroblasts.

Journal: Reproduction (Cambridge, England) 20100501

Title: Monitoring the response of canine hyperadrenocorticism to trilostane treatment by assessment of acute phase protein concentrations.

Journal: The Journal of small animal practice 20100401

Title: Hypophysectomy for a dog with coexisting Cushing's disease and diabetes mellitus.

Journal: The Journal of veterinary medical science 20100301

Title: Trilostane in dogs.

Journal: The Veterinary clinics of North America. Small animal practice 20100301

Title: Effects of trilostane on the pituitary-adrenocortical and renin-aldosterone axis in dogs with pituitary-dependent hypercortisolism.

Journal: Veterinary journal (London, England : 1997) 20100101

Title: Management of Cushing's syndrome in dogs.

Journal: The Veterinary record 20091024

Title: Trilostane exerts antidepressive effects among wild-type, but not estrogen receptor [beta] knockout mice.

Journal: Neuroreport 20090805

Title: The 3beta-hydroxysteroid dehydrogenase inhibitor trilostane shows antidepressant properties in mice.

Journal: Psychoneuroendocrinology 20090601

Title: Expression and regulation of tumor necrosis factor (TNF) and TNF-receptor family members in the macaque corpus luteum during the menstrual cycle.

Journal: Molecular reproduction and development 20090401

Title: Trilostane, FAD286, and the role of aldosterone in the central regulation of blood pressure: focus on 'Role of central nervous system aldosterone synthase and mineralocorticoid receptors in salt-induced hypertension in Dahl salt-sensitive rats'.

Journal: American journal of physiology. Regulatory, integrative and comparative physiology 20090401

Title: Structural basis for the selective inhibition of human 3beta-hydroxysteroid dehydrogenase 1 in human breast tumor MCF-7 cells.

Journal: Molecular and cellular endocrinology 20090325

Title: The effects of luteinizing hormone ablation/replacement versus steroid ablation/replacement on gene expression in the primate corpus luteum.

Journal: Molecular human reproduction 20090301

Title: Trilostane-induced inhibition of cortisol secretion results in reduced negative feedback at the hypothalamic-pituitary axis.

Journal: Domestic animal endocrinology 20090101

Title: Cushing's disease in dogs and humans.

Journal: Hormone research 20090101

Title: Urinary corticoid: creatinine ratios in dogs with pituitary-dependent hypercortisolism during trilostane treatment.

Journal: Journal of veterinary internal medicine 20090101

Title: Persistent isolated hypocortisolism following brief treatment with trilostane.

Journal: Australian veterinary journal 20081201

Title: Serum concentrations of cortisol and cortisone in healthy dogs and dogs with pituitary-dependent hyperadrenocorticism treated with trilostane.

Journal: The Veterinary record 20081018

Title: Trilostane therapy for hyperadrenocorticism in three dogs with adrenocortical metastasis.

Journal: The Veterinary record 20080809

Title: Effects of a 3beta-hydroxysteroid dehydrogenase inhibitor, trilostane, on the fathead minnow reproductive axis.

Journal: Toxicological sciences : an official journal of the Society of Toxicology 20080701

Title: Structure/function of the inhibition of human 3beta-hydroxysteroid dehydrogenase type 1 and type 2 by trilostane.

Journal: The Journal of steroid biochemistry and molecular biology 20080701

Title: Evaluation of twice-daily, low-dose trilostane treatment administered orally in dogs with naturally occurring hyperadrenocorticism.

Journal: Journal of the American Veterinary Medical Association 20080501

Title: Involvement of neurosteroids in the anxiolytic-like effects of AC-5216 in mice.

Journal: Pharmacology, biochemistry, and behavior 20080401

Title: The effect of trilostane treatment on circulating thyroid hormone concentrations in dogs with pituitary-dependent hyperadrenocorticism.

Journal: The Journal of small animal practice 20080301

Title: Aldosterone-, corticosterone- and cortisol-secreting adrenocortical carcinoma in a dog: case report.

Journal: The Journal of veterinary medical science 20080301

Title: Rapid estrogen regulation of DHEA metabolism in the male and female songbird brain.

Journal: Journal of neurochemistry 20080101

Title: Comparison of non-selective adrenocorticolysis with mitotane or trilostane for the treatment of dogs with pituitary-dependent hyperadrenocorticism.

Journal: The Veterinary record 20071215

Title: Follicle-stimulating hormone induces spermatogenesis mediated by androgen production in Japanese eel, Anguilla japonica.

Journal: Biology of reproduction 20071201

Title: The influence of di-(2-ethylhexyl) phthalate on steroidogenesis by the ovarian granulosa cells of immature female rats.

Journal: The Journal of endocrinology 20070901

Title: Rv1106c from Mycobacterium tuberculosis is a 3beta-hydroxysteroid dehydrogenase.

Journal: Biochemistry 20070807

Title: Cushing's syndrome in a guinea pig.

Journal: The Veterinary record 20070623

Title: Changes of cytosol glucocorticoid receptor and renal Na(+)-K(+)-ATPase activity after swimming training in rat.

Journal: The Journal of sports medicine and physical fitness 20070601

Title: Evidence that the preovulatory rise in intrafollicular progesterone may not be required for ovulation in cattle.

Journal: The Journal of endocrinology 20070301

Title: Hyperadrenocorticism: treating dogs.

Journal: Compendium (Yardley, PA) 20070301

Title: Histological evaluation of the adrenal glands of seven dogs with hyperadrenocorticism treated with trilostane.

Journal: The Veterinary record 20070217

Title: Medical management of pituitary-dependent hyperadrenocorticism: mitotane versus trilostane.

Journal: Clinical techniques in small animal practice 20070201

Title: Trilostane in advanced breast cancer.

Journal: Expert opinion on pharmacotherapy 20061201

Title: Effects of crude adlay hull acetone extract on corticosterone release from rat zona fasciculata-reticularis cells.

Journal: Naunyn-Schmiedeberg's archives of pharmacology 20061101

Title: Regulation of hepatic steroid receptors and enzymes by the 3beta-hydroxysteroid dehydrogenase inhibitor trilostane.

Journal: The Journal of steroid biochemistry and molecular biology 20061001

Title: Relationship between the expression of hepatic but not testicular 3beta-hydroxysteroid dehydrogenase with androstenone deposition in pig adipose tissue.

Journal: Journal of animal science 20061001

Title: Update on drugs used to treat endocrine diseases in small animals.

Journal: The Veterinary clinics of North America. Small animal practice 20060901

Title: Study of the effects of once daily doses of trilostane on cortisol concentrations and responsiveness to adrenocorticotrophic hormone in hyperadrenocorticoid dogs.

Journal: The Veterinary record 20060826

Title: Comparison of effects of 4-hydroxy tamoxifen and trilostane on oestrogen-regulated gene expression in MCF-7 cells: up-regulation of oestrogen receptor beta.

Journal: The Journal of steroid biochemistry and molecular biology 20060801

Title: Cortisol, aldosterone, cortisol precursor, androgen and endogenous ACTH concentrations in dogs with pituitary-dependant hyperadrenocorticism treated with trilostane.

Journal: Domestic animal endocrinology 20060701

Title: [Adrenocortical adenoma].

Journal: Nihon rinsho. Japanese journal of clinical medicine 20060528

Title: In vitro effects of insulin-like growth factors and insulin on oocyte maturation and maturation-inducing steroid production in ovarian follicles of common carp, Cyprinus carpio.

Journal: Comparative biochemistry and physiology. Part A, Molecular & integrative physiology 20060501

Title: Long-term efficacy of trilostane administered twice daily in dogs with pituitary-dependent hyperadrenocorticism.

Journal: Journal of the American Animal Hospital Association 20060101

Title: Dehydroepiandrosterone restoration of growth hormone gene expression in aging female rats, in vivo and in vitro: evidence for actions via estrogen receptors.

Journal: Endocrinology 20051201

Title: Canine hyperadrenocorticism: effects of trilostane on parathyroid hormone, calcium and phosphate concentrations.

Journal: The Journal of small animal practice 20051101

Title: Haptoglobin concentrations in dogs undergoing trilostane treatment for hyperadrenocorticism.

Journal: Veterinary clinical pathology 20050901

Title: Identification of key amino acids responsible for the substantially higher affinities of human type 1 3beta-hydroxysteroid dehydrogenase/isomerase (3beta-HSD1) for substrates, coenzymes, and inhibitors relative to human 3beta-HSD2.

Journal: The Journal of biological chemistry 20050603

Title: Labor induction abortion utilizing trilostane, a 3beta-hydroxysteroid dehydrogenase inhibitor.

Journal: Contraception 20050501

Title: Dynamic expression of caspase-2, -3, -8, and -9 proteins and enzyme activity, but not messenger ribonucleic acid, in the monkey corpus luteum during the menstrual cycle.

Journal: The Journal of clinical endocrinology and metabolism 20050401

Title: Reversal of caffeine-induced anxiety by neurosteroid 3-alpha-hydroxy-5-alpha-pregnane-20-one in rats.

Journal: Neuropharmacology 20050401

Title: Effect of 3beta-hydroxysteroid dehydrogenase inhibition by trilostane on blood pressure in the Dahl salt-sensitive rat.

Journal: American journal of physiology. Regulatory, integrative and comparative physiology 20050201

Title: The use of trilostane for the treatment of alopecia X in Alaskan malamutes.

Journal: Journal of the American Animal Hospital Association 20050101

Title: A comparison of the survival times of dogs treated with mitotane or trilostane for pituitary-dependent hyperadrenocorticism.

Journal: Journal of veterinary internal medicine 20050101

Title: Treatment of canine Alopecia X with trilostane.

Journal: Veterinary dermatology 20041001

Title: Effect of trilostane on serum concentrations of aldosterone, cortisol, and potassium in dogs with pituitary-dependent hyperadrenocorticism.

Journal: American journal of veterinary research 20040901

Title: ADAMTS-1/METH-1 and TIMP-3 expression in the primate corpus luteum: divergent patterns and stage-dependent regulation during the natural menstrual cycle.

Journal: Molecular human reproduction 20040801

Title: Modulation of the firing activity of female dorsal raphe nucleus serotonergic neurons by neuroactive steroids.

Journal: The Journal of endocrinology 20040701

Title: Adrenal necrosis in a dog receiving trilostane for the treatment of hyperadrenocorticism.

Journal: The Journal of small animal practice 20040601

Title: Trilostane treatment of bilateral adrenal enlargement and excessive sex steroid hormone production in a cat.

Journal: The Journal of small animal practice 20040501

Title: Serum insulin concentrations in horses with equine Cushing's syndrome: response to a cortisol inhibitor and prognostic value.

Journal: Equine veterinary journal 20040401

Title: Adrenocorticotropic hormone levels in dogs with pituitary-dependent hyperadrenocorticism following trilostane therapy.

Journal: The Veterinary record 20040327

Title: Gonadotropin and steroid regulation of matrix metalloproteinases and their endogenous tissue inhibitors in the developed corpus luteum of the rhesus monkey during the menstrual cycle.

Journal: Biology of reproduction 20040101

Title: Trilostane therapy for treatment of pituitary-dependent hyperadrenocorticism in 5 cats.

Journal: Journal of veterinary internal medicine 20040101

Title: Antisteroidogenic actions of hydrogen peroxide on rat Leydig cells.

Journal: Journal of cellular biochemistry 20031215

Title: Effects of dehydroepiandrosterone on corticosterone release in rat zona fasciculata-reticularis cells.

Journal: Naunyn-Schmiedeberg's archives of pharmacology 20031201

Title: Trilostane treatment in dogs with pituitary-dependent hyperadrenocorticism.

Journal: Australian veterinary journal 20031001

Title: The luteinizing hormone surge is preceded by an estrogen-induced increase of hypothalamic progesterone in ovariectomized and adrenalectomized rats.

Journal: Neuroendocrinology 20030701

Title: Use of trilostane for the treatment of pituitary-dependent hyperadrenocorticism in a cat.

Journal: The Journal of small animal practice 20030601

Title: Efficacy of trilostane for the treatment of equine Cushing's syndrome.

Journal: Equine veterinary journal 20030601

Title: 3 beta-hydroxysteroid dehydrogenase isomerase (3beta-HSD) activity in the rat sciatic nerve: kinetic analysis and regulation by steroids.

Journal: The Journal of steroid biochemistry and molecular biology 20030501

Title: Trilostane treatment of a dog with functional adrenocortical neoplasia.

Journal: The Journal of small animal practice 20030301

Title: Characterization and regulation of the 3beta-hydroxysteroid dehydrogenase isomerase enzyme in the rat sciatic nerve.

Journal: Journal of neurochemistry 20030101

Title: Exogenous steroid substrate modifies the effect of 2,3,7,8-tetrachlorodibenzo-p-dioxin on estradiol production of human luteinized granulosa cells in vitro.

Journal: Biology of reproduction 20030101

Title: Changes in ultrasonographic appearance of adrenal glands in dogs with pituitary-dependent hyperadrenocorticism treated with trilostane.

Journal: Veterinary radiology & ultrasound : the official journal of the American College of Veterinary Radiology and the International Veterinary Radiology Association 20030101

Title: Medical treatment of hyperadrenocorticism in the dog.

Journal: Australian veterinary journal 20030101

Title: Effects of prostaglandins E2 and F2alpha (PGE2; PGF2alpha), trilostane, mifepristone, palmitic acid (PA), indomethacin (INDO), ethamoxytriphetol (MER-25), PGE2 + PA, or PGF2alpha + PA on PGE2, PGF2alpha, and progesterone secretion by bovine corpora lutea of mid-pregnancy in vitro.

Journal: The Chinese journal of physiology 20021231

Title: Non-competitive steroid inhibition of oestrogen receptor functions.

Journal: International journal of cancer 20020901

Title: Seasonal changes in plasma steroid levels in Indian major carp Labeo rohita: influence of homologous pituitary extract on steroid production and development of oocyte maturational competence.

Journal: General and comparative endocrinology 20020901

Title: Inhibition of testosterone production by propylthiouracil in rat Leydig cells.

Journal: Biology of reproduction 20020801

Title: Trilostane treatment of 78 dogs with pituitary-dependent hyperadrenocorticism.

Journal: The Veterinary record 20020629

Title: Inhibition of progesterone secretion with trilostane for mid-trimester termination of pregnancy: randomized controlled trials.

Journal: Human reproduction (Oxford, England) 20020601

Title: Results of clinical examinations, laboratory tests, and ultrasonography in dogs with pituitary-dependent hyperadrenocorticism treated with trilostane.

Journal: American journal of veterinary research 20020401

Title: Effects of fasting on corticosterone production by zona fasciculata-reticularis cells in ovariectomized rats.

Journal: Journal of investigative medicine : the official publication of the American Federation for Clinical Research 20020301

Title: [Secondary forms of hypertension. 5. Hypertension caused by Cushing syndrome and Conn's disease].

Journal: MMW Fortschritte der Medizin 20020227

Title: Cortisol/progesterone antagonism in regulation of 15-hydroxysteroid dehydrogenase activity and mRNA levels in human chorion and placental trophoblast cells at term.

Journal: The Journal of clinical endocrinology and metabolism 20020201

Title: Effects of indomethacin, luteinizing hormone (LH), prostaglandin E2 (PGE2), trilostane, mifepristone, ethamoxytriphetol (MER-25) on secretion of prostaglandin E (PGE), prostaglandin F2alpha (PGF2alpha) and progesterone by ovine corpora lutea of pregnancy or the estrous cycle.

Journal: Prostaglandins & other lipid mediators 20010301

Title: Inhibition of human placental progesterone synthesis and aromatase activity by synthetic steroidogenic inhibitors in vitro.

Journal: Fertility and sterility 19830601

Title: Treatment of Cushing's syndrome with trilostane (WIN 24,540), an inhibitor of adrenal steroid biosynthesis.

Journal: The Journal of clinical endocrinology and metabolism 19781101

Title: Helm JR, et al. A comparison of factors that influence survival in dogs with adrenal-dependent hyperadrenocorticism treated with mitotane or trilostane. J Vet Intern Med. 2011 Mar-Apr;25(2):251-60.

Title: Feldman EC, et al. Trilostane dose versus body weight in the treatment of naturally occurring pituitary-dependent hyperadrenocorticism in dogs. J Vet Intern Med. 2012 Jul-Aug;26(4):1078-80.

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Tags:13647-35-3 Molecular Formula|13647-35-3 MDL|13647-35-3 SMILES|13647-35-3 Androst-2-ene-2-carbonitrile, 4,5-epoxy-3,17-dihydroxy-, (4α,5α,17β)-
Catalog No.: AA0011TS
13647-35-3,MFCD00199295
13647-35-3 | Androst-2-ene-2-carbonitrile, 4,5-epoxy-3,17-dihydroxy-, (4α,5α,17β)-
Pack Size: 5mg
Purity: ≥98%
in stock
$72.00 $50.00
Pack Size: 10mg
Purity: ≥98%
in stock
$135.00 $94.00
Pack Size: 100mg
Purity: 98%
in stock
$185.00 $129.00
Pack Size: 250mg
Purity: 95%
in stock
$416.00 $291.00
Pack Size: 1g
Purity: 98%
in stock
$548.00 $384.00
Pack Size: 5g
Purity: 98%
in stock
$2,277.00 $1,594.00
Quantity
- +
Add to Card
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Technical Information
Catalog Number: AA0011TS
Chemical Name: Androst-2-ene-2-carbonitrile, 4,5-epoxy-3,17-dihydroxy-, (4α,5α,17β)-
CAS Number: 13647-35-3
Molecular Formula: C20H27NO3
Molecular Weight: 329.4333
MDL Number: MFCD00199295
SMILES: N#CC1=C(O)[C@@H]2[C@]3([C@@](C1)(C)[C@H]1CC[C@]4([C@H]([C@@H]1CC3)CC[C@@H]4O)C)O2
Properties
Complexity: 692  
Covalently-Bonded Unit Count: 1  
Defined Atom Stereocenter Count: 8  
Defined Bond Stereocenter Count: 0  
Formal Charge: 0  
Heavy Atom Count: 24  
Hydrogen Bond Acceptor Count: 4  
Hydrogen Bond Donor Count: 2  
Isotope Atom Count: 0  
Rotatable Bond Count: 0  
Undefined Atom Stereocenter Count: 0  
Undefined Bond Stereocenter Count: 0  
XLogP3: 2.9  
Literature fold

Title: Temporal changes in biological responses and uncertainty in assessing risks of endocrine-disrupting chemicals: insights from intensive time-course studies with fish.

Journal: Toxicological sciences : an official journal of the Society of Toxicology20150401

Title: 17β-trenbolone, an anabolic-androgenic steroid as well as an environmental hormone, contributes to neurodegeneration.

Journal: Toxicology and applied pharmacology20150101

Title: Expression of LH receptor in nonpregnant mouse endometrium: LH induction of 3β-HSD and de novo synthesis of progesterone.

Journal: The Journal of endocrinology20121001

Title: Effects of fibroblast growth factor 9 (FGF9) on steroidogenesis and gene expression and control of FGF9 mRNA in bovine granulosa cells.

Journal: Endocrinology20120901

Title: The influence of trilostane on steroid hormone metabolism in canine adrenal glands and corpora lutea-an in vitro study.

Journal: Veterinary research communications20120301

Title: Feline pituitary-dependent hyperadrenocorticism and insulin resistance due to a plurihormonal adenoma.

Journal: Topics in companion animal medicine20120201

Title: Effects of nonylphenol on aldosterone release from rat zona glomerulosa cells.

Journal: Chemico-biological interactions20120105

Title: The antidepressant-like effects of the 3β-hydroxysteroid dehydrogenase inhibitor trilostane in mice is related to changes in neuroactive steroid and monoamine levels.

Journal: Neuropharmacology20120101

Title: Long-term follow-up of renal function in dogs after treatment for ACTH-dependent hyperadrenocorticism.

Journal: Journal of veterinary internal medicine20120101

Title: Pharmaceutical evaluation of compounded trilostane products.

Journal: Journal of the American Animal Hospital Association20120101

Title: Trilostane dose versus body weight in the treatment of naturally occurring pituitary-dependent hyperadrenocorticism in dogs.

Journal: Journal of veterinary internal medicine20120101

Title: Gh is produced by the testis of Japanese eel and stimulates proliferation of spermatogonia.

Journal: Reproduction (Cambridge, England)20111201

Title: Transcriptional regulatory dynamics of the hypothalamic-pituitary-gonadal axis and its peripheral pathways as impacted by the 3-beta HSD inhibitor trilostane in zebrafish (Danio rerio).

Journal: Ecotoxicology and environmental safety20110901

Title: Temporal evaluation of effects of a model 3β-hydroxysteroid dehydrogenase inhibitor on endocrine function in the fathead minnow.

Journal: Environmental toxicology and chemistry20110901

Title: Decreased cytochrome c oxidase IV expression reduces steroidogenesis.

Journal: The Journal of pharmacology and experimental therapeutics20110801

Title: Evaluation of twice-daily lower-dose trilostane treatment administered orally in dogs with naturally occurring hyperadrenocorticism.

Journal: Journal of the American Veterinary Medical Association20110601

Title: Determination of the concentrations of trilostane and ketotrilostane that inhibit ex vivo canine adrenal gland synthesis of cortisol, corticosterone, and aldosterone.

Journal: American journal of veterinary research20110501

Title: Effects of the 3β-hydroxysteroid dehydrogenase inhibitor trilostane on luteal progesterone production in the dog.

Journal: Theriogenology20110415

Title: Adrenocorticotropic hormone, but not trilostane, causes severe adrenal hemorrhage, vacuolization, and apoptosis in rats.

Journal: Domestic animal endocrinology20110401

Title: Anti-ovulatory effects of RU486 and trilostane involve impaired cyclooxygenase-2 expression and mitotic activity of follicular granulosa cells in rats.

Journal: Prostaglandins & other lipid mediators20110401

Title: The antidepressant-like effect of the 3β-hydroxysteroid dehydrogenase inhibitor trilostane involves a regulation of β-type estrogen receptors.

Journal: Psychopharmacology20110301

Title: A comparison of factors that influence survival in dogs with adrenal-dependent hyperadrenocorticism treated with mitotane or trilostane.

Journal: Journal of veterinary internal medicine20110101

Title: Long-term efficacy of trilostane for Cushing's syndrome due to adrenocorticotropin-independent bilateral macronodular adrenocortical hyperplasia.

Journal: Internal medicine (Tokyo, Japan)20110101

Title: Retrospective evaluation of the effect of trilostane on insulin requirement and fructosamine concentration in eight diabetic dogs with hyperadrenocorticism.

Journal: The Journal of small animal practice20101201

Title: Trilostane, an inhibitor of 3β-hydroxysteroid dehydrogenase, has an agonistic activity on androgen receptor in human prostate cancer cells.

Journal: Cancer letters20101128

Title: Prochloraz-induced oocyte maturation in rainbow trout (Oncorhynchus mykiss), a molecular and functional analysis.

Journal: Toxicological sciences : an official journal of the Society of Toxicology20101101

Title: Evaluation of the use of baseline cortisol concentration as a monitoring tool for dogs receiving trilostane as a treatment for hyperadrenocorticism.

Journal: Journal of the American Veterinary Medical Association20101001

Title: Aldosterone, hypertension and heart failure: insights from clinical trials.

Journal: Hypertension research : official journal of the Japanese Society of Hypertension20100901

Title: 3beta-hydroxysteroid dehydrogenase is a possible pharmacological target in the treatment of castration-resistant prostate cancer.

Journal: Endocrinology20100801

Title: The functions of key residues in the inhibitor, substrate and cofactor sites of human 3beta-hydroxysteroid dehydrogenase type 1 are validated by mutagenesis.

Journal: The Journal of steroid biochemistry and molecular biology20100601

Title: Induction of progesterone receptor A form attenuates the induction of cytosolic phospholipase A2alpha expression by cortisol in human amnion fibroblasts.

Journal: Reproduction (Cambridge, England)20100501

Title: Monitoring the response of canine hyperadrenocorticism to trilostane treatment by assessment of acute phase protein concentrations.

Journal: The Journal of small animal practice20100401

Title: Hypophysectomy for a dog with coexisting Cushing's disease and diabetes mellitus.

Journal: The Journal of veterinary medical science20100301

Title: Trilostane in dogs.

Journal: The Veterinary clinics of North America. Small animal practice20100301

Title: Effects of trilostane on the pituitary-adrenocortical and renin-aldosterone axis in dogs with pituitary-dependent hypercortisolism.

Journal: Veterinary journal (London, England : 1997)20100101

Title: Management of Cushing's syndrome in dogs.

Journal: The Veterinary record20091024

Title: Trilostane exerts antidepressive effects among wild-type, but not estrogen receptor [beta] knockout mice.

Journal: Neuroreport20090805

Title: The 3beta-hydroxysteroid dehydrogenase inhibitor trilostane shows antidepressant properties in mice.

Journal: Psychoneuroendocrinology20090601

Title: Expression and regulation of tumor necrosis factor (TNF) and TNF-receptor family members in the macaque corpus luteum during the menstrual cycle.

Journal: Molecular reproduction and development20090401

Title: Trilostane, FAD286, and the role of aldosterone in the central regulation of blood pressure: focus on 'Role of central nervous system aldosterone synthase and mineralocorticoid receptors in salt-induced hypertension in Dahl salt-sensitive rats'.

Journal: American journal of physiology. Regulatory, integrative and comparative physiology20090401

Title: Structural basis for the selective inhibition of human 3beta-hydroxysteroid dehydrogenase 1 in human breast tumor MCF-7 cells.

Journal: Molecular and cellular endocrinology20090325

Title: The effects of luteinizing hormone ablation/replacement versus steroid ablation/replacement on gene expression in the primate corpus luteum.

Journal: Molecular human reproduction20090301

Title: Trilostane-induced inhibition of cortisol secretion results in reduced negative feedback at the hypothalamic-pituitary axis.

Journal: Domestic animal endocrinology20090101

Title: Cushing's disease in dogs and humans.

Journal: Hormone research20090101

Title: Urinary corticoid: creatinine ratios in dogs with pituitary-dependent hypercortisolism during trilostane treatment.

Journal: Journal of veterinary internal medicine20090101

Title: Persistent isolated hypocortisolism following brief treatment with trilostane.

Journal: Australian veterinary journal20081201

Title: Serum concentrations of cortisol and cortisone in healthy dogs and dogs with pituitary-dependent hyperadrenocorticism treated with trilostane.

Journal: The Veterinary record20081018

Title: Trilostane therapy for hyperadrenocorticism in three dogs with adrenocortical metastasis.

Journal: The Veterinary record20080809

Title: Effects of a 3beta-hydroxysteroid dehydrogenase inhibitor, trilostane, on the fathead minnow reproductive axis.

Journal: Toxicological sciences : an official journal of the Society of Toxicology20080701

Title: Structure/function of the inhibition of human 3beta-hydroxysteroid dehydrogenase type 1 and type 2 by trilostane.

Journal: The Journal of steroid biochemistry and molecular biology20080701

Title: Evaluation of twice-daily, low-dose trilostane treatment administered orally in dogs with naturally occurring hyperadrenocorticism.

Journal: Journal of the American Veterinary Medical Association20080501

Title: Involvement of neurosteroids in the anxiolytic-like effects of AC-5216 in mice.

Journal: Pharmacology, biochemistry, and behavior20080401

Title: The effect of trilostane treatment on circulating thyroid hormone concentrations in dogs with pituitary-dependent hyperadrenocorticism.

Journal: The Journal of small animal practice20080301

Title: Aldosterone-, corticosterone- and cortisol-secreting adrenocortical carcinoma in a dog: case report.

Journal: The Journal of veterinary medical science20080301

Title: Rapid estrogen regulation of DHEA metabolism in the male and female songbird brain.

Journal: Journal of neurochemistry20080101

Title: Comparison of non-selective adrenocorticolysis with mitotane or trilostane for the treatment of dogs with pituitary-dependent hyperadrenocorticism.

Journal: The Veterinary record20071215

Title: Follicle-stimulating hormone induces spermatogenesis mediated by androgen production in Japanese eel, Anguilla japonica.

Journal: Biology of reproduction20071201

Title: The influence of di-(2-ethylhexyl) phthalate on steroidogenesis by the ovarian granulosa cells of immature female rats.

Journal: The Journal of endocrinology20070901

Title: Rv1106c from Mycobacterium tuberculosis is a 3beta-hydroxysteroid dehydrogenase.

Journal: Biochemistry20070807

Title: Cushing's syndrome in a guinea pig.

Journal: The Veterinary record20070623

Title: Changes of cytosol glucocorticoid receptor and renal Na(+)-K(+)-ATPase activity after swimming training in rat.

Journal: The Journal of sports medicine and physical fitness20070601

Title: Evidence that the preovulatory rise in intrafollicular progesterone may not be required for ovulation in cattle.

Journal: The Journal of endocrinology20070301

Title: Hyperadrenocorticism: treating dogs.

Journal: Compendium (Yardley, PA)20070301

Title: Histological evaluation of the adrenal glands of seven dogs with hyperadrenocorticism treated with trilostane.

Journal: The Veterinary record20070217

Title: Medical management of pituitary-dependent hyperadrenocorticism: mitotane versus trilostane.

Journal: Clinical techniques in small animal practice20070201

Title: Trilostane in advanced breast cancer.

Journal: Expert opinion on pharmacotherapy20061201

Title: Effects of crude adlay hull acetone extract on corticosterone release from rat zona fasciculata-reticularis cells.

Journal: Naunyn-Schmiedeberg's archives of pharmacology20061101

Title: Regulation of hepatic steroid receptors and enzymes by the 3beta-hydroxysteroid dehydrogenase inhibitor trilostane.

Journal: The Journal of steroid biochemistry and molecular biology20061001

Title: Relationship between the expression of hepatic but not testicular 3beta-hydroxysteroid dehydrogenase with androstenone deposition in pig adipose tissue.

Journal: Journal of animal science20061001

Title: Update on drugs used to treat endocrine diseases in small animals.

Journal: The Veterinary clinics of North America. Small animal practice20060901

Title: Study of the effects of once daily doses of trilostane on cortisol concentrations and responsiveness to adrenocorticotrophic hormone in hyperadrenocorticoid dogs.

Journal: The Veterinary record20060826

Title: Comparison of effects of 4-hydroxy tamoxifen and trilostane on oestrogen-regulated gene expression in MCF-7 cells: up-regulation of oestrogen receptor beta.

Journal: The Journal of steroid biochemistry and molecular biology20060801

Title: Cortisol, aldosterone, cortisol precursor, androgen and endogenous ACTH concentrations in dogs with pituitary-dependant hyperadrenocorticism treated with trilostane.

Journal: Domestic animal endocrinology20060701

Title: [Adrenocortical adenoma].

Journal: Nihon rinsho. Japanese journal of clinical medicine20060528

Title: In vitro effects of insulin-like growth factors and insulin on oocyte maturation and maturation-inducing steroid production in ovarian follicles of common carp, Cyprinus carpio.

Journal: Comparative biochemistry and physiology. Part A, Molecular & integrative physiology20060501

Title: Long-term efficacy of trilostane administered twice daily in dogs with pituitary-dependent hyperadrenocorticism.

Journal: Journal of the American Animal Hospital Association20060101

Title: Dehydroepiandrosterone restoration of growth hormone gene expression in aging female rats, in vivo and in vitro: evidence for actions via estrogen receptors.

Journal: Endocrinology20051201

Title: Canine hyperadrenocorticism: effects of trilostane on parathyroid hormone, calcium and phosphate concentrations.

Journal: The Journal of small animal practice20051101

Title: Haptoglobin concentrations in dogs undergoing trilostane treatment for hyperadrenocorticism.

Journal: Veterinary clinical pathology20050901

Title: Identification of key amino acids responsible for the substantially higher affinities of human type 1 3beta-hydroxysteroid dehydrogenase/isomerase (3beta-HSD1) for substrates, coenzymes, and inhibitors relative to human 3beta-HSD2.

Journal: The Journal of biological chemistry20050603

Title: Labor induction abortion utilizing trilostane, a 3beta-hydroxysteroid dehydrogenase inhibitor.

Journal: Contraception20050501

Title: Dynamic expression of caspase-2, -3, -8, and -9 proteins and enzyme activity, but not messenger ribonucleic acid, in the monkey corpus luteum during the menstrual cycle.

Journal: The Journal of clinical endocrinology and metabolism20050401

Title: Reversal of caffeine-induced anxiety by neurosteroid 3-alpha-hydroxy-5-alpha-pregnane-20-one in rats.

Journal: Neuropharmacology20050401

Title: Effect of 3beta-hydroxysteroid dehydrogenase inhibition by trilostane on blood pressure in the Dahl salt-sensitive rat.

Journal: American journal of physiology. Regulatory, integrative and comparative physiology20050201

Title: The use of trilostane for the treatment of alopecia X in Alaskan malamutes.

Journal: Journal of the American Animal Hospital Association20050101

Title: A comparison of the survival times of dogs treated with mitotane or trilostane for pituitary-dependent hyperadrenocorticism.

Journal: Journal of veterinary internal medicine20050101

Title: Treatment of canine Alopecia X with trilostane.

Journal: Veterinary dermatology20041001

Title: Effect of trilostane on serum concentrations of aldosterone, cortisol, and potassium in dogs with pituitary-dependent hyperadrenocorticism.

Journal: American journal of veterinary research20040901

Title: ADAMTS-1/METH-1 and TIMP-3 expression in the primate corpus luteum: divergent patterns and stage-dependent regulation during the natural menstrual cycle.

Journal: Molecular human reproduction20040801

Title: Modulation of the firing activity of female dorsal raphe nucleus serotonergic neurons by neuroactive steroids.

Journal: The Journal of endocrinology20040701

Title: Adrenal necrosis in a dog receiving trilostane for the treatment of hyperadrenocorticism.

Journal: The Journal of small animal practice20040601

Title: Trilostane treatment of bilateral adrenal enlargement and excessive sex steroid hormone production in a cat.

Journal: The Journal of small animal practice20040501

Title: Serum insulin concentrations in horses with equine Cushing's syndrome: response to a cortisol inhibitor and prognostic value.

Journal: Equine veterinary journal20040401

Title: Adrenocorticotropic hormone levels in dogs with pituitary-dependent hyperadrenocorticism following trilostane therapy.

Journal: The Veterinary record20040327

Title: Gonadotropin and steroid regulation of matrix metalloproteinases and their endogenous tissue inhibitors in the developed corpus luteum of the rhesus monkey during the menstrual cycle.

Journal: Biology of reproduction20040101

Title: Trilostane therapy for treatment of pituitary-dependent hyperadrenocorticism in 5 cats.

Journal: Journal of veterinary internal medicine20040101

Title: Antisteroidogenic actions of hydrogen peroxide on rat Leydig cells.

Journal: Journal of cellular biochemistry20031215

Title: Effects of dehydroepiandrosterone on corticosterone release in rat zona fasciculata-reticularis cells.

Journal: Naunyn-Schmiedeberg's archives of pharmacology20031201

Title: Trilostane treatment in dogs with pituitary-dependent hyperadrenocorticism.

Journal: Australian veterinary journal20031001

Title: The luteinizing hormone surge is preceded by an estrogen-induced increase of hypothalamic progesterone in ovariectomized and adrenalectomized rats.

Journal: Neuroendocrinology20030701

Title: Use of trilostane for the treatment of pituitary-dependent hyperadrenocorticism in a cat.

Journal: The Journal of small animal practice20030601

Title: Efficacy of trilostane for the treatment of equine Cushing's syndrome.

Journal: Equine veterinary journal20030601

Title: 3 beta-hydroxysteroid dehydrogenase isomerase (3beta-HSD) activity in the rat sciatic nerve: kinetic analysis and regulation by steroids.

Journal: The Journal of steroid biochemistry and molecular biology20030501

Title: Trilostane treatment of a dog with functional adrenocortical neoplasia.

Journal: The Journal of small animal practice20030301

Title: Characterization and regulation of the 3beta-hydroxysteroid dehydrogenase isomerase enzyme in the rat sciatic nerve.

Journal: Journal of neurochemistry20030101

Title: Exogenous steroid substrate modifies the effect of 2,3,7,8-tetrachlorodibenzo-p-dioxin on estradiol production of human luteinized granulosa cells in vitro.

Journal: Biology of reproduction20030101

Title: Changes in ultrasonographic appearance of adrenal glands in dogs with pituitary-dependent hyperadrenocorticism treated with trilostane.

Journal: Veterinary radiology & ultrasound : the official journal of the American College of Veterinary Radiology and the International Veterinary Radiology Association20030101

Title: Medical treatment of hyperadrenocorticism in the dog.

Journal: Australian veterinary journal20030101

Title: Effects of prostaglandins E2 and F2alpha (PGE2; PGF2alpha), trilostane, mifepristone, palmitic acid (PA), indomethacin (INDO), ethamoxytriphetol (MER-25), PGE2 + PA, or PGF2alpha + PA on PGE2, PGF2alpha, and progesterone secretion by bovine corpora lutea of mid-pregnancy in vitro.

Journal: The Chinese journal of physiology20021231

Title: Non-competitive steroid inhibition of oestrogen receptor functions.

Journal: International journal of cancer20020901

Title: Seasonal changes in plasma steroid levels in Indian major carp Labeo rohita: influence of homologous pituitary extract on steroid production and development of oocyte maturational competence.

Journal: General and comparative endocrinology20020901

Title: Inhibition of testosterone production by propylthiouracil in rat Leydig cells.

Journal: Biology of reproduction20020801

Title: Trilostane treatment of 78 dogs with pituitary-dependent hyperadrenocorticism.

Journal: The Veterinary record20020629

Title: Inhibition of progesterone secretion with trilostane for mid-trimester termination of pregnancy: randomized controlled trials.

Journal: Human reproduction (Oxford, England)20020601

Title: Results of clinical examinations, laboratory tests, and ultrasonography in dogs with pituitary-dependent hyperadrenocorticism treated with trilostane.

Journal: American journal of veterinary research20020401

Title: Effects of fasting on corticosterone production by zona fasciculata-reticularis cells in ovariectomized rats.

Journal: Journal of investigative medicine : the official publication of the American Federation for Clinical Research20020301

Title: [Secondary forms of hypertension. 5. Hypertension caused by Cushing syndrome and Conn's disease].

Journal: MMW Fortschritte der Medizin20020227

Title: Cortisol/progesterone antagonism in regulation of 15-hydroxysteroid dehydrogenase activity and mRNA levels in human chorion and placental trophoblast cells at term.

Journal: The Journal of clinical endocrinology and metabolism20020201

Title: Effects of indomethacin, luteinizing hormone (LH), prostaglandin E2 (PGE2), trilostane, mifepristone, ethamoxytriphetol (MER-25) on secretion of prostaglandin E (PGE), prostaglandin F2alpha (PGF2alpha) and progesterone by ovine corpora lutea of pregnancy or the estrous cycle.

Journal: Prostaglandins & other lipid mediators20010301

Title: Inhibition of human placental progesterone synthesis and aromatase activity by synthetic steroidogenic inhibitors in vitro.

Journal: Fertility and sterility19830601

Title: Treatment of Cushing's syndrome with trilostane (WIN 24,540), an inhibitor of adrenal steroid biosynthesis.

Journal: The Journal of clinical endocrinology and metabolism19781101

Title: Helm JR, et al. A comparison of factors that influence survival in dogs with adrenal-dependent hyperadrenocorticism treated with mitotane or trilostane. J Vet Intern Med. 2011 Mar-Apr;25(2):251-60.

Title: Feldman EC, et al. Trilostane dose versus body weight in the treatment of naturally occurring pituitary-dependent hyperadrenocorticism in dogs. J Vet Intern Med. 2012 Jul-Aug;26(4):1078-80.

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