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Fasedienol

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Also known as: 23062-06-8, Fasedienol, Aloradine, 4,16-androstadien-3-beta-ol, 4,16-androstadien-3beta-ol, Dtw1nj7ijh

Molecular Formula

C₁₉H₂₈O

Molecular Weight

272.4 g/mol

InChI Key

NYVFCEPOUVGTNP-DYKIIFRCSA-N

FDA UNII

DTW1NJ7IJH

PH94B is being developed by Pherin Pharmaceuticals, Inc. for the treatment of social phobias (generalized anxiety disorder). It is a member of a new family of pharmaceutical compounds called vomeropherins.

1 2D Structure

Fasedienol

2 Identification

2.1 Computed Descriptors

2.1.1 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

2.1.2 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

2.1.3 InChI Key

NYVFCEPOUVGTNP-DYKIIFRCSA-N

2.1.4 Canonical SMILES

CC12CCC3C(C1CC=C2)CCC4=CC(CCC34C)O

2.1.5 Isomeric SMILES

C[C@]12CC[C@H]3[C@H]([C@@H]1CC=C2)CCC4=C[C@H](CC[C@]34C)O

2.2 Other Identifiers

2.2.1 UNII

DTW1NJ7IJH

2.3 Synonyms

2.3.1 Depositor-Supplied Synonyms

1. 23062-06-8

2. Fasedienol

3. Aloradine

4. 4,16-androstadien-3-beta-ol

5. 4,16-androstadien-3beta-ol

6. Dtw1nj7ijh

7. (3s,8s,9s,10r,13r,14s)-10,13-dimethyl-2,3,6,7,8,9,10,11,12,13,14,15-dodecahydro-1h-cyclopenta[a]phenanthren-3-ol

8. Androsta-4,16-dien-3-ol, (3b)-

9. (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

10. (3as,3bs,7s,9ar,9bs,11ar)-9a,11a-dimethyl-3h,3ah,3bh,4h,5h,7h,8h,9h,9ah,9bh,10h,11h,11ah-cyclopenta[a]phenanthren-7-ol

11. 4-androstadienol

12. Unii-dtw1nj7ijh

13. Fasedienol [inn]

14. Aloradine [who-dd]

15. Ph94b

16. Androsta-4,16-dien-3beta-ol

17. Schembl4075431

18. Androsta-4,16-diene-3beta-ol

19. Dtxsid901032322

20. (3b)-androsta-4,16-dien-3-ol

21. Yaa06206

22. Mfcd00271236

23. Zinc34031047

24. Akos028109412

25. As-60043

26. Androsta-4,16-dien-3-ol, (3.beta.)-

27. Hy-145567

28. Cs-0376082

29. Q20707597

2.4 Create Date

2006-10-25

3 Chemical and Physical Properties

Molecular Formula	C₁₉H₂₈O
Molecular Weight	272.4 g/mol
XLogP3	4.6
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	1
Rotatable Bond Count	0
Exact Mass	272.214015512 g/mol
Monoisotopic Mass	272.214015512 g/mol
Topological Polar Surface Area	20.2 Å²
Heavy Atom Count	20
Formal Charge	0
Complexity	476
Isotope Atom Count	0
Defined Atom Stereocenter Count	6
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

Intended for the acute treatment of social phobia.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Vomeropherin compounds are directly delivered to the nasal passages using either a metered nasal spray or a metered nasal aerosol. By virtue of the chemoreceptors location in the nasal passages, direct connections to the hypothalamus and limbic system and the ability of our compounds to act locally, vomeropherins do not need to achieve systemic absorption and distribution. This provides a significant therapeutic advantage over traditional therapeutics targeted at the hypothalamus and limbic system that require access to systemic circulation and must cross the blood-brain barrier followed by uptake into the brain to exert effects.

5.2 Absorption, Distribution and Excretion

Absorption

Absorbed following nasal administration.

5.3 Mechanism of Action

There is little information available on the mechanism of action of vomeropherins. These compounds are delivered to the nasal passages and bind to chemoreceptors that in turn affect the hypothalamus and the limbic system.

Drugs in Development