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ACTIVE PHARMA INGREDIENTS

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Synopsis

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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

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 Formula	C₂₃H₃₂O₂
Molecular Weight	340.5 g/mol
XLogP3	4.4
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	1
Exact Mass	340.240230259 g/mol
Monoisotopic Mass	340.240230259 g/mol
Topological Polar Surface Area	37.3 Å²
Heavy Atom Count	25
Formal Charge	0
Complexity	706
Isotope Atom Count	0
Defined Atom Stereocenter Count	7
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

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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