Fasedienol

Fasedienol
Clinical data
Other namesPH94B; Aloradine; 4-Androstadienol; 3β-Androsta-4,16-dien-3-ol, Androsta-4,16-dien-3β-ol; Androstadienol
Routes of
administration		Intranasal
ATC code
  • None
Identifiers
  • (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
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC19H28O
Molar mass272.432 g·mol−1
3D model (JSmol)
  • C[C@]12CC[C@H]3[C@H]([C@@H]1CC=C2)CCC4=C[C@H](CC[C@]34C)O
  • 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

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 (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). As of 2020, it is in phase III clinical trials for social anxiety disorder.[12]

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 GABAA receptor, and it has been proposed that this action may mediate its pheromone effects.[13] It produces anxiolytic-like effects in animals.[13] 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.[13] As fasedienol is very closely related structurally to androstadienol, it might be converted into androstenol similarly and hence potentiation of the GABAA receptor could contribute to its mechanism of action.[13]

See also

References

  1. ^ "VistaGen Therapeutics Acquires Worldwide License of Phase 3-Ready CNS Drug Candidate from Pherin Pharmaceuticals for As-Needed Treatment of Social Anxiety Disorder :: VistaGen Therapeutics, Inc. (VTGN)". VistaGen Therapeutics, Inc. Archived from the original on 2019-12-19. Retrieved 2019-12-19.
  2. ^ Al Idrus A (13 September 2018). "VistaGen nabs phase 3-ready social anxiety drug from Pherin". FierceBiotech. Retrieved 2019-12-19.
  3. ^ Murphy J (10 December 2019). "FDA Grants Fast Track Designation to PH94B for Treatment of Social Anxiety Disorder". Pharmacy Times. Retrieved 2019-12-19.
  4. ^ Griebel G, Holmes A (September 2013). "50 years of hurdles and hope in anxiolytic drug discovery" (PDF). Nature Reviews. Drug Discovery. 12 (9): 667–87. doi:10.1038/nrd4075. PMC 4176700. PMID 23989795.
  5. ^ Monti-Bloch L, Jennings-White C, Dolberg DS, Berliner DL (1994). "The human vomeronasal system". Psychoneuroendocrinology. 19 (5–7): 673–86. doi:10.1016/0306-4530(94)90049-3. PMID 7938363. S2CID 36129626.
  6. ^ Rolls ET (November 2013). Emotion and Decision Making Explained. Oxford University Press. pp. 356–. ISBN 978-0-19-965989-0.
  7. ^ BioScan. Oryx Press. 2009.
  8. ^ a b Liebowitz MR, Salman E, Nicolini H, Rosenthal N, Hanover R, Monti L (June 2014). "Effect of an acute intranasal aerosol dose of PH94B on social and performance anxiety in women with social anxiety disorder". The American Journal of Psychiatry. 171 (6): 675–82. doi:10.1176/appi.ajp.2014.12101342. PMID 24700254. S2CID 38510058.
  9. ^ US patent 8722652, Louis Monti-Bloch, "Acute Treatment of Social Phobia", published 13 November 2012, assigned to Pherin Pharmaceuticals, Inc. 
  10. ^ "Generalized Anxiety Disorder :: VistaGen Therapeutics, Inc. (VTGN)". VistaGen Therapeutics, Inc. Archived from the original on 2019-12-19. Retrieved 2019-12-19.
  11. ^ "Post-traumatic Stress Disorder :: VistaGen Therapeutics, Inc. (VTGN)". VistaGen Therapeutics, Inc. Retrieved 2019-12-19.
  12. ^ "Positive Pilot Phase 3 Data Position VistaGen's PH94B Neuroactive Nasal Spray for Pivotal Phase 3 Development as a Novel, As-Needed Treatment for Social Anxiety Disorder :: VistaGen Therapeutics, Inc. (VTGN)". VistaGen Therapeutics, Inc. Archived from the original on 2019-12-19. Retrieved 2019-12-19.
  13. ^ a b c d Kaminski RM, Marini H, Ortinski PI, Vicini S, Rogawski MA (May 2006). "The pheromone androstenol (5 alpha-androst-16-en-3 alpha-ol) is a neurosteroid positive modulator of GABAA receptors". The Journal of Pharmacology and Experimental Therapeutics. 317 (2): 694–703. doi:10.1124/jpet.105.098319. PMID 16415088. S2CID 95393004.

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