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Chemistry

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Also known as: Dimethisteron, Dimethisterone anhydrous, 79-64-1, Secrosteron, Lutogan, Dimetisterone [dcit]
Molecular Formula
C23H32O2
Molecular Weight
340.5  g/mol
InChI Key
LVHOURKCKUYIGK-RGUJTQARSA-N
FDA UNII
OIC9M646C5

Dimethisterone
A synthetic progestational hormone without significant estrogenic or androgenic properties. It was formerly used as the progestational component in SEQUENTIAL ORAL CONTRACEPTIVE AGENTS .
1 2D Structure

Dimethisterone

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(6S,8R,9S,10R,13S,14S,17S)-17-hydroxy-6,10,13-trimethyl-17-prop-1-ynyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-3-one
2.1.2 InChI
InChI=1S/C23H32O2/c1-5-9-23(25)12-8-19-17-13-15(2)20-14-16(24)6-10-21(20,3)18(17)7-11-22(19,23)4/h14-15,17-19,25H,6-8,10-13H2,1-4H3/t15-,17+,18-,19-,21+,22-,23-/m0/s1
2.1.3 InChI Key
LVHOURKCKUYIGK-RGUJTQARSA-N
2.1.4 Canonical SMILES
CC#CC1(CCC2C1(CCC3C2CC(C4=CC(=O)CCC34C)C)C)O
2.1.5 Isomeric SMILES
CC#C[C@@]1(CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2C[C@@H](C4=CC(=O)CC[C@]34C)C)C)O
2.2 Other Identifiers
2.2.1 UNII
OIC9M646C5
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Androst-4-en-3-one, 17-hydroxy-6-methyl-17-(1-propynyl)-, (6alpha,17beta)-

2. Dimethisterone Monohydrate

2.3.2 Depositor-Supplied Synonyms

1. Dimethisteron

2. Dimethisterone Anhydrous

3. 79-64-1

4. Secrosteron

5. Lutogan

6. Dimetisterone [dcit]

7. Dimethisterone [inn]

8. (6s,8r,9s,10r,13s,14s,17s)-17-hydroxy-6,10,13-trimethyl-17-prop-1-ynyl-2,6,7,8,9,11,12,14,15,16-decahydro-1h-cyclopenta[a]phenanthren-3-one

9. Chebi:4606

10. Oic9m646c5

11. Dimethisteronum

12. Dimetisterona

13. Dimetisterone

14. Dimethisteronum [inn-latin]

15. Dimetisterona [inn-spanish]

16. 6-alpha,21-dimethylethisterone

17. Einecs 201-215-4

18. Dimethisterone [progestins]

19. Unii-oic9m646c5

20. 6-alpha-methyl-17-(1-propynyl)testosterone

21. 6-alpha-methyl-17-alpha-propynyltestosterone

22. 6alpha,21-dimethyl-17alpha-ethinyltestosterone

23. P-5048

24. 6alpha,21-dimethyl-17alpha-ethinyl Testosterone

25. 17-alpha-ethynyl-6-alpha,21-dimethyltestosterone

26. 6-alpha,21-dimethyl-17-alpha-ethinyltestosterone

27. 17-beta-hydroxy-6-alpha-methyl-17-(1-propynyl)androst-4-en-3-one

28. 17-alpha-ethynyl-17-hydroxy-6-alpha,21-dimethylandrost-4-en-3-one

29. 17-alpha-pregn-4-en-20-yn-3-one, 6-alpha,21-dimethyl-17-hydroxy-

30. 6-alpha,21-dimethyl-17-beta-hydroxy-17-alpha-pregn-4-en-20-yn-3-one

31. (6-alpha,17-beta)-17-hydroxy-6-methyl-17-(1-propynyl)-androst-4-en-3-one

32. Androst-4-en-3-one, 17-hydroxy-6-methyl-17-(1-propynyl)-, (6alpha,17beta)-

33. Dimethisterone [mi]

34. Androst-4-en-3-one, 17-hydroxy-6-methyl-17-(1-propynyl)-, (6-alpha,17-beta)-

35. Dsstox_cid_31623

36. Dsstox_rid_97507

37. Dsstox_gsid_57834

38. Schembl146840

39. Dimethisterone [who-dd]

40. Chembl2106347

41. Dtxsid5057834

42. Zinc3875518

43. Tox21_113973

44. Androst-4-en-3-one, 17-beta-hydroxy-6-alpha-methyl-17-(1-propynyl)-

45. Cas-79-64-1

46. Ncgc00274271-01

47. C07628

48. Q5277305

49. Androst-4-en-3-one,17-hydroxy-6-methyl-17-(1-propynyl)-,(6a,17b)-

50. (6s,8r,9s,10r,13s,14s,17s)-17-hydroxy-6,10,13-trimethyl-17-(prop-1-ynyl)-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthren-3(2h)-one

2.4 Create Date
2005-06-24
3 Chemical and Physical Properties
Molecular Weight 340.5 g/mol
Molecular Formula C23H32O2
XLogP34.4
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count2
Rotatable Bond Count1
Exact Mass340.240230259 g/mol
Monoisotopic Mass340.240230259 g/mol
Topological Polar Surface Area37.3 Ų
Heavy Atom Count25
Formal Charge0
Complexity706
Isotope Atom Count0
Defined Atom Stereocenter Count7
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

Contraceptives, Oral, Synthetic

Oral contraceptives which owe their effectiveness to synthetic preparations. (See all compounds classified as Contraceptives, Oral, Synthetic.)


Contraceptives, Oral, Hormonal

Oral contraceptives which owe their effectiveness to hormonal preparations. (See all compounds classified as Contraceptives, Oral, Hormonal.)


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