Fasedienol

Fasedienol (INNTooltip International Nonproprietary Name; developmental code names PH94B and Aloradine), also known as 4-androstadienol or as 4,16-androstadien-3β-ol, is a pherine which is under development by VistaGen Therapeutics^[1][2] in a nasal spray formulation used as needed(PRN) for the acute treatment of social anxiety disorder.^{[3][4][5][6][7][8][9]} It is also being investigated by VistaGen Therapeutics for the treatment of generalized anxiety disorder (GAD) and post-traumatic stress disorder (PTSD).^[10][11] The pherine is a positional isomer of the endogenous pheromone androstadienol (5-androstadienol or 5,16-androstadien-3β-ol). Fasedienol failed to show effectiveness in phase 3 clinical trials.^[12][13]

Other namesPH94B; Aloradine; 4-Androstadienol; 3β-Androsta-4,16-dien-3-ol, Androsta-4,16-dien-3β-ol; Androstadienol

Routes of
administrationIntranasal

Drug classVomeropherine

ATC code

• None

Quick facts Clinical data, Other names ...

Fasedienol

Clinical data
Other names	PH94B; Aloradine; 4-Androstadienol; 3β-Androsta-4,16-dien-3-ol, Androsta-4,16-dien-3β-ol; Androstadienol
Routes of administration	Intranasal
Drug class	Vomeropherine
ATC code	None
Identifiers
IUPAC name (3S,8S,9S,10R,13R,14S)-10,13-Dimethyl-2,3,6,7,8,9,11,12,14,15-decahydro-1H-cyclopenta[a]phenanthren-3-ol
CAS Number	23062-06-8
PubChem CID	9925482
DrugBank	DB04968
ChemSpider	8101117
UNII	DTW1NJ7IJH
KEGG	D12524 Y
CompTox Dashboard (EPA)	DTXSID901032322
Chemical and physical data
Formula	C19H28O
Molar mass	272.432 g·mol−1
3D model (JSmol)	Interactive image
SMILES C[C@]12CC[C@H]3[C@H]([C@@H]1CC=C2)CCC4=C[C@H](CC[C@]34C)O
InChI InChI=1S/C19H28O/c1-18-9-3-4-16(18)15-6-5-13-12-14(20)7-11-19(13,2)17(15)8-10-18/h3,9,12,14-17,20H,4-8,10-11H2,1-2H3/t14-,15-,16-,17-,18-,19-/m0/s1 Key:NYVFCEPOUVGTNP-DYKIIFRCSA-N

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Fasedienol lacks affinity for steroid hormone receptors and has instead been found to directly activate isolated human vomeronasal receptor cells at nanomolar concentrations (EC₅₀ = 200 nM).^[8]

The closely related pheromone androstenol (5α-androst-16-en-3α-ol) has been found to act as a potent positive allosteric modulator of the GABA_A receptor, and it has been proposed that this action may mediate its pheromone effects.^[14] It produces anxiolytic-like effects in animals.^[14] Androstadienol, androstadienone, and androstenone, all of which are also pheromones, have been found to be converted into androstenol, and as such, it may be responsible for their pheromone effects.^[14] As fasedienol is very closely related structurally to androstadienol, it might be converted into androstenol similarly and hence potentiation of the GABA_A receptor could contribute to its mechanism of action.^[14]