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ACTIVE PHARMA INGREDIENTS

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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 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 Formula	C₂₅H₄₀O₂S
Molecular Weight	404.7 g/mol
XLogP3	6.6
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	3
Exact Mass	404.27490169 g/mol
Monoisotopic Mass	404.27490169 g/mol
Topological Polar Surface Area	43.8 Å²
Heavy Atom Count	28
Formal Charge	0
Complexity	630
Isotope Atom Count	0
Defined Atom Stereocenter Count	9
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

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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