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fasedienol   Click here for help

GtoPdb Ligand ID: 14431

Synonyms: 4-androstadienol | [3β]-androsta-4,16-dien-3-ol | aloradine | PH-94B | PH94B
Compound class: Synthetic organic
Comment: Fasedienol (PH94B; VistaGen Therapeutics, formerly Pherin Pharmaceuticals) is a pherine, or vomeropherin [4]. Pherines are synthetic neuroactive steroids that are intended to acts as human pheromones via interactions with receptors on nasal chemosensory neurons within the vomeronasal organ (VNO). They are proposed to alter central nervous system activity (e.g., within the limbic amygdala and hypothalamus) through the olfactory system, and without crossing the blood-brain barrier, in turn inducing physiological, pharmacological and behavioural changes. Note that whilst intranasal administration of fasedienol in human subjects is reported to elicit biological and physiological responses [2-3], the functional capacity of vomeronasal receptors and the VNO in humans is open to debate [1,5-7].

fasedienol is commercially available from our sponsors

2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 1
Hydrogen bond donors 1
Rotatable bonds 0
Topological polar surface area 20.23
Molecular weight 272.43
XLogP 5.7
No. Lipinski's rules broken 1

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES C[C@]12C=CC[C@H]2[C@@H]3CCC4=C[C@H](CC[C@]4(C)[C@H]3CC1)O
Isomeric 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
InChI Key NYVFCEPOUVGTNP-DYKIIFRCSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
References
1. Giorgi D, Friedman C, Trask BJ, Rouquier S. (2000)
Characterization of nonfunctional V1R-like pheromone receptor sequences in human.
Genome Res, 10 (12): 1979-85. [PMID:11116092]
2. Liebowitz MR, Hanover R, Draine A, Lemming R, Careri J, Monti L. (2016)
Effect of as-needed use of intranasal PH94B on social and performance anxiety in individuals with social anxiety disorder.
Depress Anxiety, 33 (12): 1081-1089. [PMID:27561175]
3. Monti L, Hanover R, Salmán E, Baker RA, Lappalainen J, Smith M. (2024)
Effect of fasedienol (PH94B) pherine nasal spray and steroidal hormones on electrogram responses and autonomic nervous system activity in healthy adult volunteers.
Hum Psychopharmacol, 39 (2): e2892. [PMID:38193849]
4. Monti-Bloch L. (2013)
Acute Treatment of Social Phobia.
Patent number: US20130172305A1. Assignee: Pherin Pharmaceuticals Inc. Priority date: 13/08/2012. Publication date: 04/07/2013.
5. Monti-Bloch L, Jennings-White C, Dolberg DS, Berliner DL. (1994)
The human vomeronasal system.
Psychoneuroendocrinology, 19 (5-7): 673-86. [PMID:7938363]
6. Rodriguez I, Greer CA, Mok MY, Mombaerts P. (2000)
A putative pheromone receptor gene expressed in human olfactory mucosa.
Nat Genet, 26 (1): 18-9. [PMID:10973240]
7. Savic I, Hedén-Blomqvist E, Berglund H. (2009)
Pheromone signal transduction in humans: what can be learned from olfactory loss.
Hum Brain Mapp, 30 (9): 3057-65. [PMID:19235878]