Ganaxolone

Ganaxolone
Clinical data
ATC code	none;
Legal status
Legal status	investigational;
Identifiers
	IUPAC name (3α,5α)-3-hydroxy-3-methylpregnan-20-one;; 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;
CAS Number	38398-32-2 ;
PubChem CID	6918305;
UNII	98WI44OHIQ;
KEGG	D04300 ;
ChEMBL	ChEMBL161915 ;
E number	{{#property:P628}}
ECHA InfoCard	{{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
Formula	C22H36O2
Molar mass	332.520 g/mol
3D model (JSmol)	Interactive image;
	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;
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Ganaxolone (INN, also known as CCD-1042) is a steroid drug related to allopregnanolone that has sedative, anxiolytic, and anticonvulsant effects. It is a potent and selective positive allosteric modulator of GABA_A receptors.^[1] Ganaxolone protects against seizures in diverse animal models, including the 6 Hz and amygdala kindling models.^[2]^[3]^[4] Unlike for benzodiazepines, there is no tolerance to the anticonvulsant effects of ganaxolone ^[5]

Ganaxolone is being investigated for potential medical use in the treatment of epilepsy. It is well tolerated in human trials (with exposure of >900 patients), with the main side-effects being sedation, dizziness, and headache.^[6] Trials in adults with partial seizures and in infantile spasms have recently been completed.^[7]^[8]^[9]

References

↑ Carter RB, Wood PL, Wieland S, Hawkinson JE, Belelli D, Lambert JJ, White HS, Wolf HH, Mirsadeghi S, Tahir SH, Bolger MB, Lan NC, Gee KW. Characterization of the anticonvulsant properties of ganaxolone (CCD 1042; 3α-hydroxy-3β-methyl-5α-pregnan-20-one), a selective, high-affinity, steroid modulator of the γ-aminobutyric acid_A receptor. Journal of Pharmacology and Experimental Therapeutics. 1997 Mar;280(3):1284-95. PMID 9067315
↑ Kaminski RM, Livingood MR, Rogawski MA. Allopregnanolone analogs that positively modulate GABA receptors protect against partial seizures induced by 6-Hz electrical stimulation in mice. Epilepsia. 2004 Jul;45(7):864-7. PMID 15230714.
↑ Reddy DS, Rogawski MA. Ganaxolone suppression of behavioral and electrographic seizures in the mouse amygdala kindling model. Epilepsy Res. 2010 May;89(2-3):254-60. PMID 20172694.
↑ Reddy DS, Rogawski MA. Neurosteroid replacement therapy for catamenial epilepsy. Neurotherapeutics. 2009 Apr;6(2):392-401. PMID 20172694
↑ Reddy DS, Rogawski MA. Chronic treatment with the neuroactive steroid ganaxolone in the rat induces anticonvulsant tolerance to diazepam but not to itself. J Pharmacol Exp Ther. 2000 Dec;295(3):1241-8. PMID 11082461
↑ Monaghan EP, Navalta LA, Shum L, Ashbrook DW, Lee DA. Initial human experience with ganaxolone, a neuroactive steroid with antiepileptic activity. Epilepsia. 1997 Sep;38(9):1026-31. PMID 9579942
↑ Nohria V, Giller E. Ganaxolone. Neurotherapeutics. 2007 Jan;4(1):102-5. PMID 17199022
↑ Pieribone VA, Tsai J, Soufflet C, Rey E, Shaw K, Giller E, Dulac O. Clinical evaluation of ganaxolone in pediatric and adolescent patients with refractory epilepsy. Epilepsia. 2007 Oct;48(10):1870-4. PMID 17634060
↑ Bialer M, Johannessen SI, Levy RH, Perucca E, Tomson T, White HS. Progress report on new antiepileptic drugs: a summary of the Tenth Eilat Conference (EILAT X). Epilepsy Res. 2010 Dec;92(2-3):89-124. PMID 20970964.

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it:Ganaxolone

[1] Carter RB, Wood PL, Wieland S, Hawkinson JE, Belelli D, Lambert JJ, White HS, Wolf HH, Mirsadeghi S, Tahir SH, Bolger MB, Lan NC, Gee KW. Characterization of the anticonvulsant properties of ganaxolone (CCD 1042; 3α-hydroxy-3β-methyl-5α-pregnan-20-one), a selective, high-affinity, steroid modulator of the γ-aminobutyric acid_A receptor. Journal of Pharmacology and Experimental Therapeutics. 1997 Mar;280(3):1284-95. PMID 9067315

[2] Kaminski RM, Livingood MR, Rogawski MA. Allopregnanolone analogs that positively modulate GABA receptors protect against partial seizures induced by 6-Hz electrical stimulation in mice. Epilepsia. 2004 Jul;45(7):864-7. PMID 15230714.

[3] Reddy DS, Rogawski MA. Ganaxolone suppression of behavioral and electrographic seizures in the mouse amygdala kindling model. Epilepsy Res. 2010 May;89(2-3):254-60. PMID 20172694.

[4] Reddy DS, Rogawski MA. Neurosteroid replacement therapy for catamenial epilepsy. Neurotherapeutics. 2009 Apr;6(2):392-401. PMID 20172694

[5] Reddy DS, Rogawski MA. Chronic treatment with the neuroactive steroid ganaxolone in the rat induces anticonvulsant tolerance to diazepam but not to itself. J Pharmacol Exp Ther. 2000 Dec;295(3):1241-8. PMID 11082461

[6] Monaghan EP, Navalta LA, Shum L, Ashbrook DW, Lee DA. Initial human experience with ganaxolone, a neuroactive steroid with antiepileptic activity. Epilepsia. 1997 Sep;38(9):1026-31. PMID 9579942

[7] Nohria V, Giller E. Ganaxolone. Neurotherapeutics. 2007 Jan;4(1):102-5. PMID 17199022

[8] Pieribone VA, Tsai J, Soufflet C, Rey E, Shaw K, Giller E, Dulac O. Clinical evaluation of ganaxolone in pediatric and adolescent patients with refractory epilepsy. Epilepsia. 2007 Oct;48(10):1870-4. PMID 17634060

[9] Bialer M, Johannessen SI, Levy RH, Perucca E, Tomson T, White HS. Progress report on new antiepileptic drugs: a summary of the Tenth Eilat Conference (EILAT X). Epilepsy Res. 2010 Dec;92(2-3):89-124. PMID 20970964.

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Ganaxolone

See also

References

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Clinical data

ATC code	none
Legal status
Legal status	investigational
Identifiers
IUPAC name (3α,5α)-3-hydroxy-3-methylpregnan-20-one; 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
CAS Number	38398-32-2^Y
PubChem CID	6918305
UNII	98WI44OHIQ
KEGG	D04300^Y
ChEMBL	ChEMBL161915^N
E number	{{#property:P628}}
ECHA InfoCard	{{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
Formula	C₂₂H₃₆O₂
Molar mass	332.520 g/mol
3D model (JSmol)	Interactive image
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
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