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Ganaxolone

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Chemistry

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Also known as: 38398-32-2, Ccd 1042, Ztalmy, Ccd-1042, 3alpha-hydroxy-3beta-methyl-5alpha-pregnan-20-one, 98wi44ohiq

Molecular Formula

C₂₂H₃₆O₂

Molecular Weight

332.5 g/mol

InChI Key

PGTVWKLGGCQMBR-FLBATMFCSA-N

FDA UNII

98WI44OHIQ

Ganaxolone is an orally bioavailable synthetic analog of the neuroactive steroid allopregnanolone and positive allosteric modulator of the gamma-aminobutyric acid (GABA)-A receptor, with anxiolytic, sedative, antidepressant and anticonvulsant activities. Upon oral administration, ganaxolone specifically targets and binds to the allosteric sites of the synaptic and extrasynaptic GABA-A receptor-chloride ionophore complex in the central nervous system (CNS). This leads to an increase in the opening of chloride channels, membrane hyperpolarization, increases the inhibitory effect of GABA on the CNS, and inhibits neurotransmission. This blocks seizure propagation and elevates seizure thresholds.

1 2D Structure

Ganaxolone

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

1-[(3R,5S,8R,9S,10S,13S,14S,17S)-3-hydroxy-3,10,13-trimethyl-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]ethanone

2.1.2 InChI

InChI=1S/C22H36O2/c1-14(23)17-7-8-18-16-6-5-15-13-20(2,24)11-12-21(15,3)19(16)9-10-22(17,18)4/h15-19,24H,5-13H2,1-4H3/t15-,16-,17+,18-,19-,20+,21-,22+/m0/s1

2.1.3 InChI Key

PGTVWKLGGCQMBR-FLBATMFCSA-N

2.1.4 Canonical SMILES

CC(=O)C1CCC2C1(CCC3C2CCC4C3(CCC(C4)(C)O)C)C

2.1.5 Isomeric SMILES

CC(=O)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC[C@@H]4[C@@]3(CC[C@@](C4)(C)O)C)C

2.2 Other Identifiers

2.2.1 UNII

98WI44OHIQ

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 3alpha-hydroxy-3beta-methyl-5alpha-pregnan-20-one

2. Ccd 1042

3. Ccd-1042

4. Ztalmy

2.3.2 Depositor-Supplied Synonyms

1. 38398-32-2

2. Ccd 1042

3. Ztalmy

4. Ccd-1042

5. 3alpha-hydroxy-3beta-methyl-5alpha-pregnan-20-one

6. 98wi44ohiq

7. 1-((3r,5s,8r,9s,10s,13s,14s,17s)-3-hydroxy-3,10,13-trimethylhexadecahydro-1h-cyclopenta[a]phenanthren-17-yl)ethanone

8. 1-[(3r,5s,8r,9s,10s,13s,14s,17s)-3-hydroxy-3,10,13-trimethyl-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]ethanone

9. Pregnan-20-one, 3-hydroxy-3-methyl-, (3a,5a)-

10. Ncgc00165802-02

11. Dsstox_cid_26503

12. Dsstox_rid_81672

13. Dsstox_gsid_46503

14. 1-((3r,5s,8r,9s,10s,13s,14s,17s)-3-hydroxy-3,10,13-trimethylhexadecahydro-1h-cyclopenta[a]phenanthren-17-yl)ethan-1-one

15. Cas-38398-32-2

16. Ganaxolone [usan]

17. Ganaxolone [usan:inn]

18. Unii-98wi44ohiq

19. Ganaxolone, Solid

20. Ganaxolone [mi]

21. Ganaxolone [inn]

22. Ganaxolone (usan/inn)

23. Ganaxolone [who-dd]

24. Schembl144522

25. (3alpha,5alpha)-3-hydroxy-3-methylpregnan-20-one

26. Chembl1568698

27. Dtxsid6046503

28. Gtpl11942

29. Ccd1042

30. Chebi:177658

31. Dea No. 2401

32. Hms3261k19

33. Amy38916

34. Zinc3824281

35. Tox21_112264

36. Tox21_500379

37. Bdbm50369240

38. Mfcd09971088

39. Akos027327586

40. Tox21_112264_1

41. Ccg-221683

42. Db05087

43. Lp00379

44. Sdccgsbi-0633706.p001

45. Ncgc00165802-03

46. Ncgc00261064-01

47. Ncgc00263545-01

48. As-35253

49. B7092

50. (3?,5?)-3-hydroxy-3-methyl-pregnan-20-one

51. 3alpha-hydroxy-3-methyl-5alpha-pregnan-20-one

52. D04300

53. A901692

54. (3alpha,5alpha)-3-hydroxy-3-methyl-pregnan-20-one

55. Q3758034

56. 3.alpha.-hydroxy-3-methyl-5.alpha.-pregnan-20-one

57. Pregnan-20-one, 3-hydroxy-3-methyl-, (3alpha,5alpha)-

58. Pregnan-20-one, 3-hydroxy-3-methyl-, (3.alpha.,5.alpha.)-

59. 1-[(3r,5s,8r,9s,10s,13s,14s,17s)-3-hydroxy-3,10,13-trimethyl-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]ethanone.

2.4 Create Date

2006-07-28

3 Chemical and Physical Properties

Molecular Formula	C₂₂H₃₆O₂
Molecular Weight	332.5 g/mol
XLogP3	5
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	1
Exact Mass	332.271530387 g/mol
Monoisotopic Mass	332.271530387 g/mol
Topological Polar Surface Area	37.3 Å²
Heavy Atom Count	24
Formal Charge	0
Complexity	542
Isotope Atom Count	0
Defined Atom Stereocenter Count	8
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

Investigated for use/treatment in pediatric indications and seizure disorders.

Treatment of cyclin-dependent kinase-like 5 deficiency disorder

5 Pharmacology and Biochemistry

5.1 Pharmacology

Ganaxolone is a powerful positive allosteric modulator of GABAA receptors with potency and efficacy comparable to its endogenous analog 3a,5a-P (Carter et al., 1997). As with 3a,5a-P, Ganaxolone potentiation of the GABAA receptor occurs at a site distinct from the benzodiazepine site. Ganaxolone has protective activity in diverse rodent seizure models, including clonic seizures induced by pentylenetetrazol (PTZ) and bicuculline (BIC), limbic seizures in the 6 Hz model, and amygdala kindled seizures (Carter et al., 1997; Rogawski and Reddy, 2004; Kaminski et al., 2004).

5.2 MeSH Pharmacological Classification

GABA Modulators

Substances that do not act as agonists or antagonists but do affect the GAMMA-AMINOBUTYRIC ACID receptor-ionophore complex. GABA-A receptors (RECEPTORS, GABA-A) appear to have at least three allosteric sites at which modulators act: a site at which BENZODIAZEPINES act by increasing the opening frequency of GAMMA-AMINOBUTYRIC ACID-activated chloride channels; a site at which BARBITURATES act to prolong the duration of channel opening; and a site at which some steroids may act. GENERAL ANESTHETICS probably act at least partly by potentiating GABAergic responses, but they are not included here. (See all compounds classified as GABA Modulators.)

Neurosteroids

Endogenous compounds or drugs that affect neuronal excitability through modulation of specific ionotropic receptors (e.g., GABA-A RECEPTORS). Endogenous neurosteroids are steroid hormones de novo synthesized by neurons and glial cells from steroid metabolite precursors (e.g., PREGNENOLONE). (See all compounds classified as Neurosteroids.)

5.3 ATC Code

N - Nervous system

N03 - Antiepileptics

N03A - Antiepileptics

N03AX - Other antiepileptics

N03AX27 - Ganaxolone

5.4 Biological Half-Life

1.3-1.9 hours

5.5 Mechanism of Action

Ganaxolone belongs to a novel class of neuroactive steroids called epalons, which specifically modulate the -aminobutyric acid type A (GABAA) receptor in the central nervous system (CNS). Chemically related to progesterone but devoid of any hormonal activity, the epalons have potent antiepileptic, anxiolytic, sedative, and hypnotic activities in animals.

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