Home Amines 50264-69-2
50264-69-2,MFCD00866285
Catalog No.:AA0037AT

50264-69-2 | Lonidamine

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5mg
99%(HPLC)
in stock  
$66.00   $46.00
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250mg
95%
in stock  
$103.00   $73.00
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1g
95%
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$303.00   $212.00
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5g
95%
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  • Technical Information
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  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA0037AT
Chemical Name:
Lonidamine
CAS Number:
50264-69-2
Molecular Formula:
C15H10Cl2N2O2
Molecular Weight:
321.1581
MDL Number:
MFCD00866285
SMILES:
Clc1ccc(c(c1)Cl)Cn1nc(c2c1cccc2)C(=O)O
Properties
Properties
 
BP:
537.9°C at 760 mmHg  
Form:
Solid  
MP:
207-209°C  
Refractive Index:
1.6070 (estimate)  
Storage:
Keep in dry area;2-8℃;  

Computed Properties
 
Complexity:
396  
Covalently-Bonded Unit Count:
1  
Heavy Atom Count:
21  
Hydrogen Bond Acceptor Count:
3  
Hydrogen Bond Donor Count:
1  
Rotatable Bond Count:
3  
XLogP3:
4.3  

Literature

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Journal: European journal of medicinal chemistry 20131001

Title: Identification of potent Yes1 kinase inhibitors using a library screening approach.

Journal: Bioorganic & medicinal chemistry letters 20130801

Title: 2-Deoxy-D-glucose cooperates with arsenic trioxide to induce apoptosis in leukemia cells: involvement of IGF-1R-regulated Akt/mTOR, MEK/ERK and LKB-1/AMPK signaling pathways.

Journal: Biochemical pharmacology 20121215

Title: Non-cytotoxic radiosensitizers in brain radiotherapy: journey till the first decade of this millennium.

Journal: Current cancer drug targets 20120301

Title: Polycystic kidney disease: a 2011 update.

Journal: Current opinion in nephrology and hypertension 20120301

Title: Rab25 increases cellular ATP and glycogen stores protecting cancer cells from bioenergetic stress.

Journal: EMBO molecular medicine 20120201

Title: Synergistic Apoptosis-Inducing Antileukemic Effects of Arsenic Trioxide and Mucuna macrocarpa Stem Extract in Human Leukemic Cells via a Reactive Oxygen Species-Dependent Mechanism.

Journal: Evidence-based complementary and alternative medicine : eCAM 20120101

Title: Cancer metabolism: current perspectives and future directions.

Journal: Cell death & disease 20120101

Title: Coxiella burnetii induces apoptosis during early stage infection via a caspase-independent pathway in human monocytic THP-1 cells.

Journal: PloS one 20120101

Title: Antiproliferative property of n-hexane and chloroform extracts of Anisomeles malabarica (L). R. Br. in HPV16-positive human cervical cancer cells.

Journal: Journal of pharmacology & pharmacotherapeutics 20120101

Title: Mechanism-based screen establishes signalling framework for DNA damage-associated G1 checkpoint response.

Journal: PloS one 20120101

Title: Implications of therapy-induced selective autophagy on tumor metabolism and survival.

Journal: International journal of cell biology 20120101

Title: Increased apoptotic efficacy of lonidamine plus arsenic trioxide combination in human leukemia cells. Reactive oxygen species generation and defensive protein kinase (MEK/ERK, Akt/mTOR) modulation.

Journal: Biochemical pharmacology 20111201

Title: Lonidamine extends lifespan of adult Caenorhabditis elegans by increasing the formation of mitochondrial reactive oxygen species.

Journal: Hormone and metabolic research = Hormon- und Stoffwechselforschung = Hormones et metabolisme 20110901

Title: Pharmacokinetics and biodistribution of lonidamine/paclitaxel loaded, EGFR-targeted nanoparticles in an orthotopic animal model of multi-drug resistant breast cancer.

Journal: Nanomedicine : nanotechnology, biology, and medicine 20110801

Title: Monoamine carboxylate transporters are involved in BI-1-associated cancer metastasis in HT1080 colon fibrosarcoma cells.

Journal: International journal of oncology 20110701

Title: Metabolism and brain cancer.

Journal: Clinics (Sao Paulo, Brazil) 20110601

Title: Discovery of N-hydroxyindole-based inhibitors of human lactate dehydrogenase isoform A (LDH-A) as starvation agents against cancer cells.

Journal: Journal of medicinal chemistry 20110324

Title: Development of EGFR-targeted polymer blend nanocarriers for combination paclitaxel/lonidamine delivery to treat multi-drug resistance in human breast and ovarian tumor cells.

Journal: Molecular pharmaceutics 20110207

Title: Uptake of 2-NBDG as a method to monitor therapy response in breast cancer cell lines.

Journal: Breast cancer research and treatment 20110201

Title: Stereocomplexes Formed From Select Oligomers of Polymer d-lactic Acid (PDLA) and l-lactate May Inhibit Growth of Cancer Cells and Help Diagnose Aggressive Cancers-Applications of the Warburg Effect.

Journal: Perspectives in medicinal chemistry 20110101

Title: Metabolic markers in relation to hypoxia; staining patterns and colocalization of pimonidazole, HIF-1α, CAIX, LDH-5, GLUT-1, MCT1 and MCT4.

Journal: BMC cancer 20110101

Title: Enabling anticancer therapeutics by nanoparticle carriers: the delivery of Paclitaxel.

Journal: International journal of molecular sciences 20110101

Title: Anticancer targets in the glycolytic metabolism of tumors: a comprehensive review.

Journal: Frontiers in pharmacology 20110101

Title: Therapeutic efficacy and safety of paclitaxel/lonidamine loaded EGFR-targeted nanoparticles for the treatment of multi-drug resistant cancer.

Journal: PloS one 20110101

Title: Mitochondrial peroxiredoxin III is a potential target for cancer therapy.

Journal: International journal of molecular sciences 20110101

Title: Glycolysis in the african trypanosome: targeting enzymes and their subcellular compartments for therapeutic development.

Journal: Molecular biology international 20110101

Title: Adjudin-mediated Sertoli-germ cell junction disassembly affects Sertoli cell barrier function in vitro and in vivo.

Journal: The international journal of biochemistry & cell biology 20101101

Title: Curcumin stimulates reactive oxygen species production and potentiates apoptosis induction by the antitumor drugs arsenic trioxide and lonidamine in human myeloid leukemia cell lines.

Journal: The Journal of pharmacology and experimental therapeutics 20101001

Title: The fourth isoform of the adenine nucleotide translocator inhibits mitochondrial apoptosis in cancer cells.

Journal: The international journal of biochemistry & cell biology 20100501

Title: AF-2364 is a prospective spermicide candidate.

Journal: Asian journal of andrology 20100501

Title: A target-based high throughput screen yields Trypanosoma brucei hexokinase small molecule inhibitors with antiparasitic activity.

Journal: PLoS neglected tropical diseases 20100401

Title: Cancer as a metabolic disease.

Journal: Nutrition & metabolism 20100101

Title: Improving outcome of chemotherapy of metastatic breast cancer by docosahexaenoic acid: a phase II trial.

Journal: British journal of cancer 20091215

Title: International guidelines for management of metastatic breast cancer: combination vs sequential single-agent chemotherapy.

Journal: Journal of the National Cancer Institute 20090902

Title: Development of a yeast bio-assay to screen anti-mitochondrial drugs.

Journal: Current drug discovery technologies 20090901

Title: Modulation of cellular radiation responses by 2-deoxy-D-glucose and other glycolytic inhibitors: implications for cancer therapy.

Journal: Journal of cancer research and therapeutics 20090901

Title: Human cytomegalovirus US9 protein contains an N-terminal signal sequence and a C-terminal mitochondrial localization domain, and does not alter cellular sensitivity to apoptosis.

Journal: The Journal of general virology 20090501

Title: Inhibition of glycolysis modulates prednisolone resistance in acute lymphoblastic leukemia cells.

Journal: Blood 20090226

Title: Whole brain radiotherapy with radiosensitizer for brain metastases.

Journal: Journal of experimental & clinical cancer research : CR 20090101

Title: Drugs targeting the mitochondrial pore act as cytotoxic and cytostatic agents in temozolomide-resistant glioma cells.

Journal: Journal of translational medicine 20090101

Title: Effects of fotemustine or dacarbasine on a melanoma cell line pretreated with therapeutic proton irradiation.

Journal: Journal of experimental & clinical cancer research : CR 20090101

Title: Quality of life in brain metastases radiation trials: a literature review.

Journal: Current oncology (Toronto, Ont.) 20081001

Title: Optimizing radiotherapy of brain tumours by a combination of temozolomide & lonidamine.

Journal: The Indian journal of medical research 20080801

Title: The anti-trypanosomal agent lonidamine inhibits Trypanosoma brucei hexokinase 1.

Journal: Molecular and biochemical parasitology 20080401

Title: Glycosyl and polyalcoholic prodrugs of lonidamine.

Journal: Bioorganic & medicinal chemistry letters 20080401

Title: Canadian supportive care recommendations for the management of neutropenia in patients with cancer.

Journal: Current oncology (Toronto, Ont.) 20080101

Title: [Treatment and post-treatment with lonidamine in human colon carcinoma HT-29 cell line].

Journal: Medicina 20080101

Title: Arsenic-based antineoplastic drugs and their mechanisms of action.

Journal: Metal-based drugs 20080101

Title: Neuropsychological testing and biomarkers in the management of brain metastases.

Journal: Radiation oncology (London, England) 20080101

Title: CFTR-dependent Cl- secretion in Xenopus laevis lung epithelium.

Journal: Respiratory physiology & neurobiology 20070815

Title: Evaluation of contraceptive activity of methanol extract of Dendrophthoe falcata stem in male albino rats.

Journal: Journal of ethnopharmacology 20070530

Title: Lonidamine affects testicular steroid hormones in immature mice.

Journal: Toxicology and applied pharmacology 20070515

Title: Mitomycin C and Vinorelbine for second-line chemotherapy in NSCLC--a phase II trial.

Journal: British journal of cancer 20070410

Title: Immunohistochemical profile of some neurotransmitters and neurotrophins in the seminiferous tubules of rats treated by lonidamine.

Journal: European journal of histochemistry : EJH 20070101

Title: The oncoprotein H-RasV12 increases mitochondrial metabolism.

Journal: Molecular cancer 20070101

Title: Pharmacologic inhibitors of extracellular signal-regulated kinase (ERKs) and c-Jun NH(2)-terminal kinase (JNK) decrease glutathione content and sensitize human promonocytic leukemia cells to arsenic trioxide-induced apoptosis.

Journal: Journal of cellular physiology 20061201

Title: The H+-linked monocarboxylate transporter (MCT1/SLC16A1): a potential therapeutic target for high-risk neuroblastoma.

Journal: Molecular pharmacology 20061201

Title: Ten years of experience with weekly chemotherapy in metastatic breast cancer patients: multivariate analysis of prognostic factors.

Journal: Anti-cancer drugs 20061101

Title: Chemosensitization by knockdown of adenine nucleotide translocase-2.

Journal: Cancer research 20060915

Title: Does granulocyte colony-stimulating factor worsen anemia in early breast cancer patients treated with epirubicin and cyclophosphamide?

Journal: Journal of clinical oncology : official journal of the American Society of Clinical Oncology 20060701

Title: Microsphere-based protease assays and screening application for lethal factor and factor Xa.

Journal: Cytometry. Part A : the journal of the International Society for Analytical Cytology 20060501

Title: Emerging drug therapies for benign prostatic hyperplasia.

Journal: Expert opinion on emerging drugs 20060301

Title: [Antimitochondrial agents: a new class of anticancer agents].

Journal: Archives de pediatrie : organe officiel de la Societe francaise de pediatrie 20060101

Title: Administration of zoledronic acid enhances the effects of docetaxel on growth of prostate cancer in the bone environment.

Journal: BMC cancer 20060101

Title: Surrogate markers and survival in women receiving first-line combination anthracycline chemotherapy for advanced breast cancer.

Journal: British journal of cancer 20051128

Title: Impact of five prophylactic filgrastim schedules on hematologic toxicity in early breast cancer patients treated with epirubicin and cyclophosphamide.

Journal: Journal of clinical oncology : official journal of the American Society of Clinical Oncology 20051001

Title: Lonidamine transiently affects spermatogenesis in pubertal CD1 mice.

Journal: Contraception 20051001

Title: Long-term effects of lonidamine on mouse testes.

Journal: Contraception 20051001

Title: Pharmacologic inhibitors of PI3K/Akt potentiate the apoptotic action of the antileukemic drug arsenic trioxide via glutathione depletion and increased peroxide accumulation in myeloid leukemia cells.

Journal: Blood 20050515

Title: Location of a common inhibitor binding site in the cytoplasmic vestibule of the cystic fibrosis transmembrane conductance regulator chloride channel pore.

Journal: The Journal of biological chemistry 20050311

Title: Mitomycin C, vinblastine and cisplatin (MVP): an active and well-tolerated salvage regimen for advanced breast cancer.

Journal: British journal of cancer 20050214

Title: Contribution of gap junctional communication between tumor cells and astroglia to the invasion of the brain parenchyma by human glioblastomas.

Journal: BMC cell biology 20050101

Title: The development of lonidamine for benign prostatic hyperplasia and other indications.

Journal: Reviews in urology 20050101

Title: Lonidamine: basic science and rationale for treatment of prostatic proliferative disorders.

Journal: Reviews in urology 20050101

Title: Clinical Evidence Supporting the Role of Lonidamine for the Treatment of BPH.

Journal: Reviews in urology 20050101

Title: Lonidamine causes inhibition of angiogenesis-related endothelial cell functions.

Journal: Neoplasia (New York, N.Y.) 20040901

Title: Contribution of caveolin-1 alpha and Akt to TNF-alpha-induced cell death.

Journal: American journal of physiology. Lung cellular and molecular physiology 20040701

Title: Apoptosis of human melanoma cells by a combination of lonidamine and radiation.

Journal: Journal of radiation research 20040601

Title: Mitochondrial modulation of Ca2+ sparks and transient KCa currents in smooth muscle cells of rat cerebral arteries.

Journal: The Journal of physiology 20040501

Title: Mitochondrial permeability transition-pore inhibition enhances functional recovery after long-time hypothermic heart preservation.

Journal: Transplantation 20031115

Title: Antioxidant MCI-186 inhibits mitochondrial permeability transition pore and upregulates Bcl-2 expression.

Journal: American journal of physiology. Heart and circulatory physiology 20031101

Title: Potentiation of antiproliferative drug activity by lonidamine in hepatocellular carcinoma cells.

Journal: Journal of chemotherapy (Florence, Italy) 20031001

Title: Addition of either lonidamine or granulocyte colony-stimulating factor does not improve survival in early breast cancer patients treated with high-dose epirubicin and cyclophosphamide.

Journal: Journal of clinical oncology : official journal of the American Society of Clinical Oncology 20030915

Title: Second window of ischemic preconditioning regulates mitochondrial permeability transition pore by enhancing Bcl-2 expression.

Journal: Cardiovascular research 20030801

Title: Synergistic effects of cystic fibrosis transmembrane conductance regulator and aquaporin-9 in the rat epididymis.

Journal: Biology of reproduction 20030501

Title: Phase II study of lonidamine and diazepam in the treatment of recurrent glioblastoma multiforme.

Journal: Journal of neuro-oncology 20030501

Title: Telomere dysfunction increases cisplatin and ecteinascidin-743 sensitivity of melanoma cells.

Journal: Molecular pharmacology 20030301

Title: Lonidamine: efficacy and safety in clinical trials for the treatment of solid tumors.

Journal: Drugs of today (Barcelona, Spain : 1998) 20030301

Title: Ultralow doses of various drugs in chemotherapy of experimental tumors.

Journal: Bulletin of experimental biology and medicine 20030101

Title: Indazole inhibition of cystic fibrosis transmembrane conductance regulator Cl(-) channels in rat epididymal epithelial cells.

Journal: Biology of reproduction 20021201

Title: Mechanism of lonidamine inhibition of the CFTR chloride channel.

Journal: British journal of pharmacology 20021101

Title: Lonidamine solid dispersions: in vitro and in vivo evaluation.

Journal: Drug development and industrial pharmacy 20021101

Title: Hepatocytes transgenic for the full hepatitis C virus open reading frame are resistant to fas-induced cell death.

Journal: Annals of the New York Academy of Sciences 20021101

Title: Mitochondrial targeting drug lonidamine triggered apoptosis in doxorubicin-resistant HepG2 cells.

Journal: Life sciences 20021025

Title: Time to progression in metastatic breast cancer patients treated with epirubicin is not improved by the addition of either cisplatin or lonidamine: final results of a phase III study with a factorial design.

Journal: Journal of clinical oncology : official journal of the American Society of Clinical Oncology 20021015

Title: Drug specific resistance to oxaliplatin is associated with apoptosis defect in a cellular model of colon carcinoma.

Journal: FEBS letters 20021009

Title: Sustained ER Ca2+ depletion suppresses protein synthesis and induces activation-enhanced cell death in mast cells.

Journal: The Journal of biological chemistry 20020419

Title: Recent studies on lonidamine, the lead compound of the antispermatogenic indazol-carboxylic acids.

Journal: Contraception 20020401

Title: [Are mitochondria targets of anticancer drugs responsible for apoptosis?].

Journal: Annales de biologie clinique 20020101

Title: Adenine nucleotide translocator mediates the mitochondrial membrane permeabilization induced by lonidamine, arsenite and CD437.

Journal: Oncogene 20011115

Title: Two new male contraceptives exert their effects by depleting germ cells prematurely from the testis.

Journal: Biology of reproduction 20010801

Title: Expression of the cystic fibrosis transmembrane conductance regulator in rat spermatids: implication for the site of action of antispermatogenic agents.

Journal: Molecular human reproduction 20010801

Title: Enhancement of hyperglycemia-induced acidification of human melanoma xenografts with inhibitors of respiration and ion transport.

Journal: Academic radiology 20010701

Title: Mitochondria-targeting drugs arsenic trioxide and lonidamine bypass the resistance of TPA-differentiated leukemic cells to apoptosis.

Journal: Blood 20010615

Title: Analysis of lonidamine in rat serum and testis by high performance liquid chromatography.

Journal: Biomedical chromatography : BMC 20010201

Title: Paclitaxel, cisplatin and lonidamine in advanced ovarian cancer. A phase II study.

Journal: European journal of cancer (Oxford, England : 1990) 20010201

Title: Changes in cell volume and internal sodium concentration in HeLa cells during exponential growth and following lonidamine treatment.

Journal: European journal of cell biology 20010201

Title: Effect of lonidamine on alpha2-macroglobulin, hemopexin and alpha1-antitrypsin in the rat testis and epididymis.

Journal: Research communications in molecular pathology and pharmacology 20010101

Title: Testin induction: the role of cyclic 3',5'-adenosine monophosphate/protein kinase A signaling in the regulation of basal and lonidamine-induced testin expression by rat sertoli cells.

Journal: Biology of reproduction 20001201

Title: Nancolas B, et al. The anti-tumour agent lonidamine is a potent inhibitor of the mitochondrial pyruvate carrier and plasma membrane monocarboxylate transporters. Biochem J. 2016 Apr 1;473(7):929-36.

Title: Ilya A Shutkov, et al. Ru(III) Complexes with Lonidamine-Modified Ligands. Int J Mol Sci. 2021 Dec 15;22(24):13468.

Title: Xueqian Yin, et al. Hexokinase 2 couples glycolysis with the profibrotic actions of TGF-β. Sci Signal. 2019 Dec 17;12(612):eaax4067.

Title: Gang Cheng, et al. Targeting lonidamine to mitochondria mitigates lung tumorigenesis and brain metastasis. Nat Commun. 2019 May 17;10(1):2205.

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Tags:50264-69-2 Molecular Formula|50264-69-2 MDL|50264-69-2 SMILES|50264-69-2 Lonidamine