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Chemistry

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Also known as: 21362-69-6, Thioderon, O00404969k, (1s,3as,3br,5as,6as,7ar,8as,8bs,10as)-1-((1-methoxycyclopentyl)oxy)-8a,10a-dimethylhexadecahydro-1h-cyclopenta[7,8]phenanthro[2,3-b]thiirene, Mepitiostano, Mepitiostanum
Molecular Formula
C25H40O2S
Molecular Weight
404.7  g/mol
InChI Key
IVDYZAAPOLNZKG-KWHRADDSSA-N
FDA UNII
O00404969K

Mepitiostane
Mepitiostane is an anabolic ether-modified form of the steroid epitiostanol. It has anti-estrogenic effect, which inhibits the progression of estrogen-stimulated cancers by competitive inhibition of estrogen binding to estrogen receptors. (NCI)
1 2D Structure

Mepitiostane

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(1S,2S,4R,6S,8S,11R,12S,15S,16S)-15-(1-methoxycyclopentyl)oxy-2,16-dimethyl-5-thiapentacyclo[9.7.0.02,8.04,6.012,16]octadecane
2.1.2 InChI
InChI=1S/C25H40O2S/c1-23-13-10-19-17(7-6-16-14-20-21(28-20)15-24(16,19)2)18(23)8-9-22(23)27-25(26-3)11-4-5-12-25/h16-22H,4-15H2,1-3H3/t16-,17-,18-,19-,20-,21+,22-,23-,24-/m0/s1
2.1.3 InChI Key
IVDYZAAPOLNZKG-KWHRADDSSA-N
2.1.4 Canonical SMILES
CC12CCC3C(C1CCC2OC4(CCCC4)OC)CCC5C3(CC6C(C5)S6)C
2.1.5 Isomeric SMILES
C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2OC4(CCCC4)OC)CC[C@@H]5[C@@]3(C[C@@H]6[C@H](C5)S6)C
2.2 Other Identifiers
2.2.1 UNII
O00404969K
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 10364-s

2. 2-alpha,3 Alpha-epithio-5 Alpha-androstan-17 Beta-yl-1-methoxycyclopentyl Ether

2.3.2 Depositor-Supplied Synonyms

1. 21362-69-6

2. Thioderon

3. O00404969k

4. (1s,3as,3br,5as,6as,7ar,8as,8bs,10as)-1-((1-methoxycyclopentyl)oxy)-8a,10a-dimethylhexadecahydro-1h-cyclopenta[7,8]phenanthro[2,3-b]thiirene

5. Mepitiostano

6. Mepitiostanum

7. Thioderon (tn)

8. Mepitiostane [inn:jan]

9. Mepitiostane [mi]

10. Mepitiostane [inn]

11. Mepitiostane [jan]

12. Mepitiostanum [inn-latin]

13. Mepitiostane (jp17/inn)

14. Mepitiostano [inn-spanish]

15. Schembl13123

16. Mepitiostane [mart.]

17. Mepitiostane [who-dd]

18. Ccris 2779

19. Chembl2104860

20. Chebi:31818

21. Dtxsid001016882

22. Unii-o00404969k

23. Zinc4216860

24. Akos015904663

25. Ncgc00522025-01

26. 10364s

27. D01602

28. S 10364

29. Q6817819

30. 2-alpha,3-alpha-epithio-17-beta-yl 1-methoxycyclopentyl Ether

31. 5-alpha-androstane, 2-alpha,3-alpha-epithio-17-beta-(1-methoxycyclopentyloxy)-

32. Androstane, 2,3-epithio-17-((1-methoxycyclopentyl)oxy)-, (2alpha,3alpha,5alpha,17beta)-

33. Cyclopentanone 2alpha,3alpha-epithio-5alpha-androstan-17beta-yl Methyl Acetal

34. Cyclopentanone, 2-alpha, 3-alpha-epithio-5-alpha-androstan-17-beta-yl Methyl Acetal

35. (1s,2s,4r,6s,8s,11r,12s,15s,16s)-15-(1-methoxycyclopentyl)oxy-2,16-dimethyl-5-thiapentacyclo[9.7.0.02,8.04,6.012,16]octadecane

36. Androstane, 2,3-epithio-17-((1-methoxycyclopentyl)oxy)-, (2-alpha,3-alpha,5-alpha,17-beta)

37. Cyclopentanone 2.alpha.,3.alpha.-epithio-5.alpha.-androstan-17.beta.-yl Methyl Acetal

2.4 Create Date
2006-10-25
3 Chemical and Physical Properties
Molecular Weight 404.7 g/mol
Molecular Formula C25H40O2S
XLogP36.6
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count3
Rotatable Bond Count3
Exact Mass404.27490169 g/mol
Monoisotopic Mass404.27490169 g/mol
Topological Polar Surface Area43.8 Ų
Heavy Atom Count28
Formal Charge0
Complexity630
Isotope Atom Count0
Defined Atom Stereocenter Count9
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Pharmacology and Biochemistry
4.1 MeSH Pharmacological Classification

Anabolic Agents

These compounds stimulate anabolism and inhibit catabolism. They stimulate the development of muscle mass, strength, and power. (See all compounds classified as Anabolic Agents.)


Antineoplastic Agents

Substances that inhibit or prevent the proliferation of NEOPLASMS. (See all compounds classified as Antineoplastic Agents.)


Estrogen Antagonists

Compounds which inhibit or antagonize the action or biosynthesis of estrogenic compounds. (See all compounds classified as Estrogen Antagonists.)


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