Bicifadine
Basic information
- CAS
71195-57-8- Standard SMILES
Cc1ccc(C23CNCC2C3)cc1- InChIKey
OFYVIGTWSQPCLF-UHFFFAOYSA-N- Molecular formula
- C12H15N
- Average molar mass
- 173.25 g/mol
- Monoisotopic mass
- 173.12044948
Overview
Bicifadine (DOV-220075) is a nonopioid analgesic. It is an inhibitor of both the norepinephrine and serotonin transporters and an NMDA antagonist with a non-narcotic profile. Bicifadine was shown to have potent analgesic activity in vivo and was chosen for further development for the treatment of pain.
Names & identifiers
- Preferred name
- Bicifadine
- IUPAC
- 1-(4-methylphenyl)-3-azabicyclo[3.1.0]hexane
- English name
- Bicifadine
- Molecular formula
- C12H15N
- Molecular weight
- 173.25
Names & synonyms
BICIFADINE71195-57-8BicifadinaBicifadinumCL 220075(RS)-1-(4-Methylphenyl)-3-azabicyclo(3.1.0)hexanRefChem:917162B0SV3N7J3H1-(4-methylphenyl)-3-azabicyclo[3.1.0]hexane1-(p-Tolyl)-3-azabicyclo[3.1.0]hexane1-p-tolyl-3-azabicyclo[3.1.0]hexaneSCHEMBL38793
Show more names
BicifadinoBicifadine [inn]Bicifadine free baseBicifadinum [inn-latin]Bicifadino [inn-spanish]5-(4-methylphenyl)-3-azabicyclo[3.1.0]hexane
CHEMBL511099orb1737722DTXSID20867995OFYVIGTWSQPCLF-UHFFFAOYSA-NHMS3743C09MCV-4147NIH-9542BDBM50417944
Database identifiers
- CAS
71195-57-8- PubChem CID
- 47953
- DTXSID
DTXSID20867995- ChEMBL
CHEMBL511099- EC Number
- 615-260-6
Properties
Computed structural properties
- XLogP
- 2.1
- Topological polar surface area
- 12 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 1
- Rotatable bonds
- 1
- Heavy atoms
- 13
- Formal charge
- 0
- Complexity
- 205
Physicochemical properties
- FDA UNII
- 0 SV3N7J3H · B0SV3N7J3H
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 315 · H315-H319
- Precautionary statements
- 264 · P264-P280-P302+P352-P305+P351+P338-P332+P313-P337+P313-P362
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Hazard statements
- H315-H319
- Precautionary statements
- P264-P280-P302+P352-P305+P351+P338-P332+P313-P337+P313-P362
Chemistry & industry
Pharmacology
Pharmacodynamics
Bicifadine is a chemically distinct molecule with a unique profile of pharmacological activity. Its primary pharmacological action is to enhance and prolong the actions of norepinephrine and serotonin by inhibiting the transport proteins that terminate the physiological actions of the two biogenic amines. Bicifadine is not a narcotic and is well-tolerated and, in preclinical studies, has been shown not to act at any opiate receptor. Bicifadine does not exhibit any anti-inflammatory activity and does not inhibit prostaglandin synthetase in vitro.
Mechanism of ActionPreclinical studies and clinical trials indicate that bicifadine's analgesic properties result through the enhancement and prolongation of norepinephrine and serotonin actions, however other actions may be involved.
Metabolism/MetabolitesThe primary enzymes responsible for the primary metabolism of bicifadine in humans are MAO-B and CYP2D6.
Applications
UsesAnalgesic.
Related reactions
9 records
Compound notes
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