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16320-04-0,MFCD00865561
Catalog No.:AA001TRX

16320-04-0 | 18,19-Dinorpregna-4,9,11-trien-20-yn-3-one, 13-ethyl-17-hydroxy-, (17α)-

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  • Technical Information
  • Properties
  • Literature
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  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA001TRX
Chemical Name:
18,19-Dinorpregna-4,9,11-trien-20-yn-3-one, 13-ethyl-17-hydroxy-, (17α)-
CAS Number:
16320-04-0
Molecular Formula:
C21H24O2
Molecular Weight:
308.4141
MDL Number:
MFCD00865561
SMILES:
CC[C@]12C=CC3=C4CCC(=O)C=C4CC[C@H]3[C@@H]1CC[C@@]2(O)C#C
Properties
Properties
 
MP:
148 - 150°C  
Storage:
-20 ℃;  

Computed Properties
 
Complexity:
713  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
4  
Heavy Atom Count:
23  
Hydrogen Bond Acceptor Count:
2  
Hydrogen Bond Donor Count:
1  
Rotatable Bond Count:
2  
XLogP3:
2.2  

Literature

Title: Identifying environmental chemicals as agonists of the androgen receptor by using a quantitative high-throughput screening platform.

Journal: Toxicology 20170615

Title: The androgenic anabolic steroid tetrahydrogestrinone produces dioxin-like effects via the aryl hydrocarbon receptor.

Journal: Toxicology in vitro : an international journal published in association with BIBRA 20121001

Title: Interventions for emergency contraception.

Journal: The Cochrane database of systematic reviews 20120815

Title: New ELISA bulks up detection ability of steroid screening methods.

Journal: Bioanalysis 20120601

Title: Chinese herbal medicine for endometriosis.

Journal: The Cochrane database of systematic reviews 20120516

Title: Progestagens and anti-progestagens for pain associated with endometriosis.

Journal: The Cochrane database of systematic reviews 20120314

Title: Innovative oral treatments of uterine leiomyoma.

Journal: Obstetrics and gynecology international 20120101

Title: Bio-Photonic Sensing Cells over transparent substrates for anti-gestrinone antibodies biosensing.

Journal: Biosensors & bioelectronics 20110815

Title: Endometriosis, a modern syndrome.

Journal: The Indian journal of medical research 20110601

Title: Breast pain.

Journal: BMJ clinical evidence 20110101

Title: Laparoscopic approach of a unicornuate uterus with noncommunicating rudimentary horns.

Journal: ISRN obstetrics and gynecology 20110101

Title: The state-of-the-art of emergency contraception with the cutting edge drug.

Journal: German medical science : GMS e-journal 20110101

Title: Vaginal adenosarcoma arising from refractory endometriosis: a case report.

Journal: The Australian & New Zealand journal of obstetrics & gynaecology 20101201

Title: The progins progesterone receptor gene polymorphism is not related to endometriosis-associated infertility or to idiopathic infertility.

Journal: Clinics (Sao Paulo, Brazil) 20101101

Title: Enzyme-linked immunosorbent assays for the synthetic steroid gestrinone.

Journal: Talanta 20100915

Title: A rapid screening LC-MS/MS method based on conventional HPLC pumps for the analysis of low molecular weight xenobiotics: application to doping control analysis.

Journal: Drug testing and analysis 20100701

Title: Generic sample preparation combined with high-resolution liquid chromatography-time-of-flight mass spectrometry for unification of urine screening in doping-control laboratories.

Journal: Analytical and bioanalytical chemistry 20100401

Title: Gestrinone compared with mifepristone for emergency contraception: a randomized controlled trial.

Journal: Obstetrics and gynecology 20100401

Title: Endometriosis.

Journal: BMJ clinical evidence 20100101

Title: Effect of Yikun Neiyi Wan on the expression of aromatase P450, COX-2, and ER related receptor in endometrial cells in vitro from patients with endometriosis.

Journal: Journal of traditional Chinese medicine = Chung i tsa chih ying wen pan 20091201

Title: Endometriosis in Italy: from cost estimates to new medical treatment.

Journal: Gynecological endocrinology : the official journal of the International Society of Gynecological Endocrinology 20091101

Title: Tetrahydrogestrinone analysis and designer steroids revisited.

Journal: Bioanalysis 20091101

Title: Searching for in silico predicted metabolites and designer modifications of (cortico)steroids in urine by high-resolution liquid chromatography/time-of-flight mass spectrometry.

Journal: Rapid communications in mass spectrometry : RCM 20090801

Title: Chinese herbal medicine for endometriosis.

Journal: The Cochrane database of systematic reviews 20090708

Title: Ovulation-stimulation drugs and cancer risks: a long-term follow-up of a British cohort.

Journal: British journal of cancer 20090602

Title: Detection and pharmacokinetics of tetrahydrogestrinone in horses.

Journal: Journal of veterinary pharmacology and therapeutics 20090401

Title: A simple and rapid ESI-LC-MS/MS method for simultaneous screening of doping agents in urine samples.

Journal: Indian journal of pharmacology 20090401

Title: Endometriosis: current therapies and new pharmacological developments.

Journal: Drugs 20090101

Title: Endometriosis presenting as an acute groin swelling: a case report.

Journal: Cases journal 20090101

Title: [Treatment for endometriosis].

Journal: Revista de medicina de la Universidad de Navarra 20090101

Title: Treatment of pelvic pain associated with endometriosis.

Journal: Fertility and sterility 20081101

Title: Detection of anabolic steroid abuse using a yeast transactivation system.

Journal: Steroids 20081001

Title: Medical management of fibroids.

Journal: Best practice & research. Clinical obstetrics & gynaecology 20080801

Title: Does gestrinone antagonize the effects of estrogen on endometrial implants upon the peritoneum of rats?

Journal: Clinics (Sao Paulo, Brazil) 20080801

Title: [Determination of three anabolic steroids by liquid chromatography-mass spectrometry].

Journal: Se pu = Chinese journal of chromatography 20080701

Title: Comprehensive screening of acidic and neutral drugs in equine plasma by liquid chromatography-tandem mass spectrometry.

Journal: Journal of chromatography. A 20080502

Title: Structure-activity relationships of synthetic progestins in a yeast-based in vitro androgen bioassay.

Journal: The Journal of steroid biochemistry and molecular biology 20080501

Title: Induction of micronuclei in V79 cells by the anabolic doping steroids tetrahydrogestrinone and trenbolone.

Journal: Archives of toxicology 20080401

Title: Endometriosis: current and future medical therapies.

Journal: Best practice & research. Clinical obstetrics & gynaecology 20080401

Title: Screening of in vitro synthesised metabolites of 4,9,11-trien-3-one steroids by liquid chromatography mass spectrometry.

Journal: European journal of mass spectrometry (Chichester, England) 20080101

Title: Recognising, understanding and managing endometriosis.

Journal: Journal of human reproductive sciences 20080101

Title: Structural characterization of the human androgen receptor ligand-binding domain complexed with EM5744, a rationally designed steroidal ligand bearing a bulky chain directed toward helix 12.

Journal: The Journal of biological chemistry 20071019

Title: Mechanism of emergency contraception with gestrinone: a preliminary investigation.

Journal: Contraception 20070901

Title: Nanomolar concentrations of anabolic-androgenic steroids amplify excitotoxic neuronal death in mixed mouse cortical cultures.

Journal: Brain research 20070824

Title: Expressions of VEGF and Ki-67 in eutopic endometrium of patients with endometriosis and effect of Quyu Jiedu Recipe on VEGF expression.

Journal: Chinese journal of integrative medicine 20070601

Title: Neuroendocrine-immune disequilibrium and endometriosis: an interdisciplinary approach.

Journal: Seminars in immunopathology 20070601

Title: Analysis of synthetic 19-norsteroids trenbolone, tetrahydrogestrinone and gestrinone by gas chromatography-mass spectrometry.

Journal: Journal of chromatography. A 20070525

Title: Preparation of antibodies for the designer steroid tetrahydrogestrinone and development of an enzyme-linked immunosorbent assay for human urine analysis.

Journal: Analytical chemistry 20070515

Title: Effects of gestrinone on uterine leiomyoma and expression of c-Src in a guinea pig model.

Journal: Acta pharmacologica Sinica 20070501

Title: Multi-detection of corticosteroids in sports doping and veterinary control using high-resolution liquid chromatography/time-of-flight mass spectrometry.

Journal: Analytica chimica acta 20070314

Title: [Outcome analysis of stage III - IV endometriosis after conservative surgery].

Journal: Zhonghua fu chan ke za zhi 20070201

Title: Endometriosis.

Journal: BMJ clinical evidence 20070101

Title: Breast pain.

Journal: BMJ clinical evidence 20070101

Title: Preoperative treatment for hysteroscopic surgery.

Journal: Fertility and sterility 20061001

Title: Comparative study on the efficacy of Yiweining and Gestrinone for post-operational treatment of stage III endometriosis.

Journal: Chinese journal of integrative medicine 20060901

Title: Doping control analysis in human urine by liquid chromatography-electrospray ionization ion trap mass spectrometry for the Olympic Games Athens 2004: determination of corticosteroids and quantification of ephedrines, salbutamol and morphine.

Journal: Analytica chimica acta 20060728

Title: Dehydroepiandrosterone (DHEA) is an anabolic steroid like dihydrotestosterone (DHT), the most potent natural androgen, and tetrahydrogestrinone (THG).

Journal: The Journal of steroid biochemistry and molecular biology 20060701

Title: Tetrahydrogestrinone is a potent but unselective binding steroid and affects glucocorticoid signalling in the liver.

Journal: Toxicology letters 20060620

Title: Comparison of crystal structures of human androgen receptor ligand-binding domain complexed with various agonists reveals molecular determinants responsible for binding affinity.

Journal: Protein science : a publication of the Protein Society 20060501

Title: Gestrinone versus danazol as preoperative treatment for hysteroscopic surgery: a prospective, randomized evaluation.

Journal: Fertility and sterility 20060401

Title: [Anti progestins].

Journal: Nihon rinsho. Japanese journal of clinical medicine 20060401

Title: Urine testing for designer steroids by liquid chromatography with androgen bioassay detection and electrospray quadrupole time-of-flight mass spectrometry identification.

Journal: Analytical chemistry 20060115

Title: Games of hormones: the para-endocrinology of sport.

Journal: Endocrine practice : official journal of the American College of Endocrinology and the American Association of Clinical Endocrinologists 20060101

Title: A fast liquid chromatographic/mass spectrometric screening method for the simultaneous detection of synthetic glucocorticoids, some stimulants, anti-oestrogen drugs and synthetic anabolic steroids.

Journal: Rapid communications in mass spectrometry : RCM 20060101

Title: The role of progestins in treating the pain of endometriosis.

Journal: Journal of minimally invasive gynecology 20060101

Title: Tetrahydrogestrinone is an androgenic steroid that stimulates androgen receptor-mediated, myogenic differentiation in C3H10T1/2 multipotent mesenchymal cells and promotes muscle accretion in orchidectomized male rats.

Journal: Endocrinology 20051001

Title: Cardiovascular toxicities of performance-enhancing substances in sports.

Journal: Mayo Clinic proceedings 20051001

Title: Tetrahydrogestrinone: the discovery of a designer steroid.

Journal: Current sports medicine reports 20050801

Title: Screening for unknown synthetic steroids in human urine by liquid chromatography-tandem mass spectrometry.

Journal: Journal of mass spectrometry : JMS 20050701

Title: Detecting doping.

Journal: Analytical chemistry 20050601

Title: Medical treatment of endometriosis.

Journal: Minerva ginecologica 20050601

Title: Discovery, biosynthesis, and structure elucidation of metabolites of a doping agent and a direct analogue, tetrahydrogestrinone and gestrinone, using human hepatocytes.

Journal: Analytical chemistry 20050515

Title: [Effect of gestrinone on growth and apoptosis in isolated ectopic endometrium cells in vitro].

Journal: Zhonghua fu chan ke za zhi 20050501

Title: Screening of anabolic steroids in horse urine by liquid chromatography-tandem mass spectrometry.

Journal: Journal of pharmaceutical and biomedical analysis 20050429

Title: [Effect of gestrinone on the lipid metabolic parameters and bone mineral density in patients with endometriosis].

Journal: Zhonghua fu chan ke za zhi 20050301

Title: Tetrahydrogestrinone induces a genomic signature typical of a potent anabolic steroid.

Journal: The Journal of endocrinology 20050201

Title: Gestrinone in the treatment of uterine leiomyomata: effects on uterine blood supply.

Journal: Fertility and sterility 20041201

Title: Anabolic-androgenic steroids and testosterone precursors: ergogenic aids and sport.

Journal: Current sports medicine reports 20040801

Title: Tetrahydrogestrinone is a potent androgen and progestin.

Journal: The Journal of clinical endocrinology and metabolism 20040501

Title: Medical management of endometriosis: a systematic review.

Journal: IDrugs : the investigational drugs journal 20040501

Title: Emerging drugs for endometriosis.

Journal: Expert opinion on emerging drugs 20040501

Title: Doping by design.

Journal: Scientific American 20040201

Title: Benefits and risks of pharmacological agents used for the treatment of menorrhagia.

Journal: Drug safety 20040101

Title: FDA warning on unapproved performance enhancer.

Journal: FDA consumer 20040101

Title: Tetrahydrogestrinone: discovery, synthesis, and detection in urine.

Journal: Rapid communications in mass spectrometry : RCM 20040101

Title: Potential action of androstenedione on the proliferation and apoptosis of stromal endometrial cells.

Journal: Reproductive biology and endocrinology : RB&E 20040101

Title: Drugs in sport: no dope.

Journal: Nature 20031113

Title: Athletes' 'designer steroid' leads to widening scandal.

Journal: Lancet (London, England) 20031101

Title: 'Fish on Steroids'?

Journal: Alternative medicine review : a journal of clinical therapeutic 20031101

Title: Drugs bust reveals athletes' secret steroid.

Journal: Nature 20031023

Title: Evaluation of progesterone and estrogen receptor expression in 15 meningiomas of dogs and cats.

Journal: American journal of veterinary research 20031001

Title: Medical therapy of endometriosis.

Journal: Seminars in reproductive medicine 20030501

Title: Medical management of endometriosis-associated pain.

Journal: Obstetrics and gynecology clinics of North America 20030301

Title: Ovulation suppression for endometriosis.

Journal: The Cochrane database of systematic reviews 20030101

Title: Gonadotrophin-releasing hormone analogues for endometriosis: bone mineral density.

Journal: The Cochrane database of systematic reviews 20030101

Title: Breast pain.

Journal: Clinical evidence 20021201

Title: Breast pain.

Journal: Clinical evidence 20020601

Title: A benefit-risk assessment of medical treatment for uterine leiomyomas.

Journal: Drug safety 20020101

Title: Long-term follow-up of a controlled trial of laser laparoscopy for pelvic pain.

Journal: JSLS : Journal of the Society of Laparoendoscopic Surgeons 20010101

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SDS
Tags:16320-04-0 Molecular Formula|16320-04-0 MDL|16320-04-0 SMILES|16320-04-0 18,19-Dinorpregna-4,9,11-trien-20-yn-3-one, 13-ethyl-17-hydroxy-, (17α)-