Ethynylandrostanediol

Ethynylandrostanediol
Clinical data
Other names	HE3235; Apoptone; 17α-Ethynyl-5α-androstane-3α,17β-diol; 5α-Pregn-20-yne-3α,17α-diol
Identifiers
	IUPAC name (3R,5S,8R,9S,10S,13S,14S,17R)-17-ethynyl-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthrene-3,17-diol;
CAS Number	183387-50-0;
PubChem CID	42611099;
ChemSpider	32698509;
UNII	891O182ZP5;
Chemical and physical data
Formula	C21H32O2
Molar mass	316.485 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C[C@]12CC[C@H](C[C@@H]1CC[C@@H]3[C@@H]2CC[C@]4([C@H]3CC[C@]4(C#C)O)C)O;
	InChI InChI=1S/C21H32O2/c1-4-21(23)12-9-18-16-6-5-14-13-15(22)7-10-19(14,2)17(16)8-11-20(18,21)3/h1,14-18,22-23H,5-13H2,2-3H3/t14-,15+,16+,17-,18-,19-,20-,21-/m0/s1; Key:CKAXZOYFIHQCBN-JRRMKBMNSA-N;

Ethynylandrostanediol (developmental code name HE-3235), or 17α-ethynyl-5α-androstane-3α,17β-diol, also known as Apoptone, is a synthetic, orally active, 17α-substituted analogue of the androstanediols which was under development for the treatment of prostate cancer and breast cancer but was discontinued.^[1]^[2]^[3] It has very low affinity for steroid receptors, including the AR, ERα, ERβ, PR, and GR, and its mechanism of action is not well-characterized.^[1]^[4] It produces 5α-dihydroethisterone as an active metabolite, which may contribute importantly to its biological activity.^[1]

Ethandrostate, also known as 17α-ethynylandrost-5-ene-3β,17β-diol 3β-cyclohexanepropionate, is a related steroid.^[5]^[6]

References

↑ ^1.0 ^1.1 ^1.2 "17α-alkynyl 3α, 17β-androstanediol non-clinical and clinical pharmacology, pharmacokinetics and metabolism". Invest New Drugs 30 (1): 59–78. 2012. doi:10.1007/s10637-010-9517-0. PMID 20814732.
↑ "Inhibition of androstenediol-dependent LNCaP tumour growth by 17alpha-ethynyl-5alpha-androstane-3alpha, 17beta-diol (HE3235)". Br. J. Cancer 100 (7): 1068–72. 2009. doi:10.1038/sj.bjc.6604987. PMID 19337256.
↑ http://webcache.googleusercontent.com/search?q=cache:Jy1DYIHEUtQJ:adisinsight.springer.com/drugs/800025305
↑ "HE3235 inhibits growth of castration-resistant prostate cancer". Neoplasia 11 (11): 1216–25. 2009. doi:10.1593/neo.09960. PMID 19881957.
↑ Ralph I. Dorfman (1962). Bioassay. Elsevier. pp. 224–228. ISBN 978-1-4832-7276-4. https://books.google.com/books?id=WS_LBAAAQBAJ&pg=PA224.
↑ "Ethandrostate: endocrine effects and studies in treatment of cancer". Cancer 11 (3): 537–45. 1958. doi:10.1002/1097-0142(195805/06)11:3<537::aid-cncr2820110313>3.0.co;2-w. PMID 13523561.

External links

HE-3235 - AdisInsight

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[pmid20814732-1] 1.0 ^1.1 ^1.2 "17α-alkynyl 3α, 17β-androstanediol non-clinical and clinical pharmacology, pharmacokinetics and metabolism". Invest New Drugs 30 (1): 59–78. 2012. doi:10.1007/s10637-010-9517-0. PMID 20814732.

[pmid19337256-2] "Inhibition of androstenediol-dependent LNCaP tumour growth by 17alpha-ethynyl-5alpha-androstane-3alpha, 17beta-diol (HE3235)". Br. J. Cancer 100 (7): 1068–72. 2009. doi:10.1038/sj.bjc.6604987. PMID 19337256.

[AdisInsight-3] ttp://webcache.googleusercontent.com/search?q=cache:Jy1DYIHEUtQJ:adisinsight.springer.com/drugs/800025305

[pmid19881957-4] "HE3235 inhibits growth of castration-resistant prostate cancer". Neoplasia 11 (11): 1216–25. 2009. doi:10.1593/neo.09960. PMID 19881957.

[Dorfman1962-5] Ralph I. Dorfman (1962). Bioassay. Elsevier. pp. 224–228. ISBN 978-1-4832-7276-4. https://books.google.com/books?id=WS_LBAAAQBAJ&pg=PA224.

[pmid13523561-6] "Ethandrostate: endocrine effects and studies in treatment of cancer". Cancer 11 (3): 537–45. 1958. doi:10.1002/1097-0142(195805/06)11:3<537::aid-cncr2820110313>3.0.co;2-w. PMID 13523561.

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Ethynylandrostanediol

Topic: Chemistry

References

External links