Home Other Building Blocks 18,19-Dinorpregna-4,9,11-trien-20-yn-3-one, 13-ethyl-17-hydroxy-, (17α)-

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

CAS No.:
16320-04-0
Catalog Number:
AG001TUP
Molecular Formula:
C21H24O2
Molecular Weight:
308.4141
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
5mg
99%
1 week
United States
$157
- +
10mg
99%
1 week
United States
$207
- +
Product Description
Catalog Number:
AG001TUP
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
IUPAC Name:
(8S,13S,14S,17R)-13-ethyl-17-ethynyl-17-hydroxy-1,2,6,7,8,14,15,16-octahydrocyclopenta[a]phenanthren-3-one
InChI:
InChI=1S/C21H24O2/c1-3-20-11-9-17-16-8-6-15(22)13-14(16)5-7-18(17)19(20)10-12-21(20,23)4-2/h2,9,11,13,18-19,23H,3,5-8,10,12H2,1H3/t18-,19+,20+,21+/m1/s1
InChI Key:
BJJXHLWLUDYTGC-ANULTFPQSA-N
SMILES:
CC[C@]12C=CC3=C4CCC(=O)C=C4CC[C@H]3[C@@H]1CC[C@@]2(O)C#C
UNII:
1421533RCM
Properties
Complexity:
713  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
4  
Defined Bond Stereocenter Count:
0
Exact Mass:
308.178g/mol
Formal Charge:
0
Heavy Atom Count:
23  
Hydrogen Bond Acceptor Count:
2  
Hydrogen Bond Donor Count:
1  
Isotope Atom Count:
0
Molecular Weight:
308.421g/mol
Monoisotopic Mass:
308.178g/mol
Rotatable Bond Count:
2  
Topological Polar Surface Area:
37.3A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
2.2  
Literature
Title Journal
Identifying environmental chemicals as agonists of the androgen receptor by using a quantitative high-throughput screening platform. Toxicology 20170615
The androgenic anabolic steroid tetrahydrogestrinone produces dioxin-like effects via the aryl hydrocarbon receptor. Toxicology in vitro : an international journal published in association with BIBRA 20121001
Interventions for emergency contraception. The Cochrane database of systematic reviews 20120815
New ELISA bulks up detection ability of steroid screening methods. Bioanalysis 20120601
Chinese herbal medicine for endometriosis. The Cochrane database of systematic reviews 20120516
Progestagens and anti-progestagens for pain associated with endometriosis. The Cochrane database of systematic reviews 20120314
Innovative oral treatments of uterine leiomyoma. Obstetrics and gynecology international 20120101
Bio-Photonic Sensing Cells over transparent substrates for anti-gestrinone antibodies biosensing. Biosensors & bioelectronics 20110815
Endometriosis, a modern syndrome. The Indian journal of medical research 20110601
Breast pain. BMJ clinical evidence 20110101
Laparoscopic approach of a unicornuate uterus with noncommunicating rudimentary horns. ISRN obstetrics and gynecology 20110101
The state-of-the-art of emergency contraception with the cutting edge drug. German medical science : GMS e-journal 20110101
Vaginal adenosarcoma arising from refractory endometriosis: a case report. The Australian & New Zealand journal of obstetrics & gynaecology 20101201
The progins progesterone receptor gene polymorphism is not related to endometriosis-associated infertility or to idiopathic infertility. Clinics (Sao Paulo, Brazil) 20101101
Enzyme-linked immunosorbent assays for the synthetic steroid gestrinone. Talanta 20100915
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. Drug testing and analysis 20100701
Generic sample preparation combined with high-resolution liquid chromatography-time-of-flight mass spectrometry for unification of urine screening in doping-control laboratories. Analytical and bioanalytical chemistry 20100401
Gestrinone compared with mifepristone for emergency contraception: a randomized controlled trial. Obstetrics and gynecology 20100401
Endometriosis. BMJ clinical evidence 20100101
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 of traditional Chinese medicine = Chung i tsa chih ying wen pan 20091201
Endometriosis in Italy: from cost estimates to new medical treatment. Gynecological endocrinology : the official journal of the International Society of Gynecological Endocrinology 20091101
Tetrahydrogestrinone analysis and designer steroids revisited. Bioanalysis 20091101
Searching for in silico predicted metabolites and designer modifications of (cortico)steroids in urine by high-resolution liquid chromatography/time-of-flight mass spectrometry. Rapid communications in mass spectrometry : RCM 20090801
Chinese herbal medicine for endometriosis. The Cochrane database of systematic reviews 20090708
Ovulation-stimulation drugs and cancer risks: a long-term follow-up of a British cohort. British journal of cancer 20090602
Detection and pharmacokinetics of tetrahydrogestrinone in horses. Journal of veterinary pharmacology and therapeutics 20090401
A simple and rapid ESI-LC-MS/MS method for simultaneous screening of doping agents in urine samples. Indian journal of pharmacology 20090401
Endometriosis: current therapies and new pharmacological developments. Drugs 20090101
Endometriosis presenting as an acute groin swelling: a case report. Cases journal 20090101
[Treatment for endometriosis]. Revista de medicina de la Universidad de Navarra 20090101
Treatment of pelvic pain associated with endometriosis. Fertility and sterility 20081101
Detection of anabolic steroid abuse using a yeast transactivation system. Steroids 20081001
Medical management of fibroids. Best practice & research. Clinical obstetrics & gynaecology 20080801
Does gestrinone antagonize the effects of estrogen on endometrial implants upon the peritoneum of rats? Clinics (Sao Paulo, Brazil) 20080801
[Determination of three anabolic steroids by liquid chromatography-mass spectrometry]. Se pu = Chinese journal of chromatography 20080701
Comprehensive screening of acidic and neutral drugs in equine plasma by liquid chromatography-tandem mass spectrometry. Journal of chromatography. A 20080502
Structure-activity relationships of synthetic progestins in a yeast-based in vitro androgen bioassay. The Journal of steroid biochemistry and molecular biology 20080501
Induction of micronuclei in V79 cells by the anabolic doping steroids tetrahydrogestrinone and trenbolone. Archives of toxicology 20080401
Endometriosis: current and future medical therapies. Best practice & research. Clinical obstetrics & gynaecology 20080401
Screening of in vitro synthesised metabolites of 4,9,11-trien-3-one steroids by liquid chromatography mass spectrometry. European journal of mass spectrometry (Chichester, England) 20080101
Recognising, understanding and managing endometriosis. Journal of human reproductive sciences 20080101
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. The Journal of biological chemistry 20071019
Mechanism of emergency contraception with gestrinone: a preliminary investigation. Contraception 20070901
Nanomolar concentrations of anabolic-androgenic steroids amplify excitotoxic neuronal death in mixed mouse cortical cultures. Brain research 20070824
Expressions of VEGF and Ki-67 in eutopic endometrium of patients with endometriosis and effect of Quyu Jiedu Recipe on VEGF expression. Chinese journal of integrative medicine 20070601
Neuroendocrine-immune disequilibrium and endometriosis: an interdisciplinary approach. Seminars in immunopathology 20070601
Analysis of synthetic 19-norsteroids trenbolone, tetrahydrogestrinone and gestrinone by gas chromatography-mass spectrometry. Journal of chromatography. A 20070525
Preparation of antibodies for the designer steroid tetrahydrogestrinone and development of an enzyme-linked immunosorbent assay for human urine analysis. Analytical chemistry 20070515
Effects of gestrinone on uterine leiomyoma and expression of c-Src in a guinea pig model. Acta pharmacologica Sinica 20070501
Multi-detection of corticosteroids in sports doping and veterinary control using high-resolution liquid chromatography/time-of-flight mass spectrometry. Analytica chimica acta 20070314
[Outcome analysis of stage III - IV endometriosis after conservative surgery]. Zhonghua fu chan ke za zhi 20070201
Endometriosis. BMJ clinical evidence 20070101
Breast pain. BMJ clinical evidence 20070101
Preoperative treatment for hysteroscopic surgery. Fertility and sterility 20061001
Comparative study on the efficacy of Yiweining and Gestrinone for post-operational treatment of stage III endometriosis. Chinese journal of integrative medicine 20060901
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. Analytica chimica acta 20060728
Dehydroepiandrosterone (DHEA) is an anabolic steroid like dihydrotestosterone (DHT), the most potent natural androgen, and tetrahydrogestrinone (THG). The Journal of steroid biochemistry and molecular biology 20060701
Tetrahydrogestrinone is a potent but unselective binding steroid and affects glucocorticoid signalling in the liver. Toxicology letters 20060620
Comparison of crystal structures of human androgen receptor ligand-binding domain complexed with various agonists reveals molecular determinants responsible for binding affinity. Protein science : a publication of the Protein Society 20060501
Gestrinone versus danazol as preoperative treatment for hysteroscopic surgery: a prospective, randomized evaluation. Fertility and sterility 20060401
[Anti progestins]. Nihon rinsho. Japanese journal of clinical medicine 20060401
Urine testing for designer steroids by liquid chromatography with androgen bioassay detection and electrospray quadrupole time-of-flight mass spectrometry identification. Analytical chemistry 20060115
Games of hormones: the para-endocrinology of sport. Endocrine practice : official journal of the American College of Endocrinology and the American Association of Clinical Endocrinologists 20060101
A fast liquid chromatographic/mass spectrometric screening method for the simultaneous detection of synthetic glucocorticoids, some stimulants, anti-oestrogen drugs and synthetic anabolic steroids. Rapid communications in mass spectrometry : RCM 20060101
The role of progestins in treating the pain of endometriosis. Journal of minimally invasive gynecology 20060101
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. Endocrinology 20051001
Cardiovascular toxicities of performance-enhancing substances in sports. Mayo Clinic proceedings 20051001
Tetrahydrogestrinone: the discovery of a designer steroid. Current sports medicine reports 20050801
Screening for unknown synthetic steroids in human urine by liquid chromatography-tandem mass spectrometry. Journal of mass spectrometry : JMS 20050701
Detecting doping. Analytical chemistry 20050601
Medical treatment of endometriosis. Minerva ginecologica 20050601
Discovery, biosynthesis, and structure elucidation of metabolites of a doping agent and a direct analogue, tetrahydrogestrinone and gestrinone, using human hepatocytes. Analytical chemistry 20050515
[Effect of gestrinone on growth and apoptosis in isolated ectopic endometrium cells in vitro]. Zhonghua fu chan ke za zhi 20050501
Screening of anabolic steroids in horse urine by liquid chromatography-tandem mass spectrometry. Journal of pharmaceutical and biomedical analysis 20050429
[Effect of gestrinone on the lipid metabolic parameters and bone mineral density in patients with endometriosis]. Zhonghua fu chan ke za zhi 20050301
Tetrahydrogestrinone induces a genomic signature typical of a potent anabolic steroid. The Journal of endocrinology 20050201
Gestrinone in the treatment of uterine leiomyomata: effects on uterine blood supply. Fertility and sterility 20041201
Anabolic-androgenic steroids and testosterone precursors: ergogenic aids and sport. Current sports medicine reports 20040801
Tetrahydrogestrinone is a potent androgen and progestin. The Journal of clinical endocrinology and metabolism 20040501
Medical management of endometriosis: a systematic review. IDrugs : the investigational drugs journal 20040501
Emerging drugs for endometriosis. Expert opinion on emerging drugs 20040501
Doping by design. Scientific American 20040201
Benefits and risks of pharmacological agents used for the treatment of menorrhagia. Drug safety 20040101
FDA warning on unapproved performance enhancer. FDA consumer 20040101
Tetrahydrogestrinone: discovery, synthesis, and detection in urine. Rapid communications in mass spectrometry : RCM 20040101
Potential action of androstenedione on the proliferation and apoptosis of stromal endometrial cells. Reproductive biology and endocrinology : RB&E 20040101
Drugs in sport: no dope. Nature 20031113
Athletes' 'designer steroid' leads to widening scandal. Lancet (London, England) 20031101
'Fish on Steroids'? Alternative medicine review : a journal of clinical therapeutic 20031101
Drugs bust reveals athletes' secret steroid. Nature 20031023
Evaluation of progesterone and estrogen receptor expression in 15 meningiomas of dogs and cats. American journal of veterinary research 20031001
Medical therapy of endometriosis. Seminars in reproductive medicine 20030501
Medical management of endometriosis-associated pain. Obstetrics and gynecology clinics of North America 20030301
Ovulation suppression for endometriosis. The Cochrane database of systematic reviews 20030101
Gonadotrophin-releasing hormone analogues for endometriosis: bone mineral density. The Cochrane database of systematic reviews 20030101
Breast pain. Clinical evidence 20021201
Breast pain. Clinical evidence 20020601
A benefit-risk assessment of medical treatment for uterine leiomyomas. Drug safety 20020101
Long-term follow-up of a controlled trial of laser laparoscopy for pelvic pain. JSLS : Journal of the Society of Laparoendoscopic Surgeons 20010101
Properties