4,16-Androstadien-3β-ol

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4,16-Androstadien-3β-ol
200px
Systematic (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
Clinical data
Routes of
administration		 Intranasal
Identifiers
CAS Number 23062-06-8
ATC code None
PubChem CID: 9925482
DrugBank DB04968
ChemSpider 8101117
Synonyms 3β-Androsta-4,16-dien-3-ol, androsta-4,16-dien-3β-ol, androstadienol
Chemical data
Formula C19H28O
Molecular mass 272.43 g·mol−1
  • 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

4,16-Androstadien-3β-ol (developmental code name PH94B; tentative commercial name Aloradine or Aloradine IN) is a pherine which is under development by Pherin Pharmaceuticals, Inc. in a nasal spray formulation for the acute (p.r.n.) treatment of social anxiety disorder in women.[1][2][3][4][5][6][7][8] It is also being investigated by Pherin Pharmaceuticals for the treatment of generalized anxiety disorder in women.[2] As of 2015, it is in phase III clinical trials.[9]

The compound 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).[6]

The pheromone androstenol 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.[10] It produces anxiolytic-like effects in animals.[10] 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.[10] As 4,16-androstadien-3β-ol is very closely related structurally to androstadienol (which is 5,16-androstadien-3β-ol), being a positional isomer of the steroid, the mechanism of action of 4,16-androstadien-3β-ol could similarly be potentiation of the GABAA receptor.[10]

See also

References

  1. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  2. ↑ 2.0 2.1 Lua error in package.lua at line 80: module 'strict' not found.
  3. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  4. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  5. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  6. ↑ 6.0 6.1 Lua error in package.lua at line 80: module 'strict' not found.
  7. ↑ http://ascpmeeting.org/wp-content/uploads/2014/05/ASCP-Poster-Abstract-Book-Online.pdf
  8. ↑ US patent 8722652, Louis Monti-Bloch, "Acute Treatment of Social Phobia", published 13 November 2012, assigned to Pherin Pharmaceuticals, Inc. 
  9. ↑ http://www.pherin.com/products.html
  10. ↑ 10.0 10.1 10.2 10.3 Lua error in package.lua at line 80: module 'strict' not found.

External links


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