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Bicifadine


Bicifadine
Systematic (IUPAC) name
1-(4-methylphenyl)-3-azabicyclo[3.1.0]hexane
Identifiers
CAS number	71195-57-8
ATC code	?
PubChem	47953
Chemical data
Formula	C₁₂H₁₅N
Mol. mass	173.25 g/mol
Pharmacokinetic data
Bioavailability	?
Metabolism	?
Half life	1.6 hours
Excretion	renal
Therapeutic considerations
Pregnancy cat.	?
Legal status
Routes	oral

Bicifadine is a serotonin-norepinephrine reuptake inhibitor (SNRI) developed by DOV Pharmaceutical.^[1] It has been developed as an analgesic and is currently under development for the treatment of various pain conditions.^[2] Phase III trials were completed in 2006 for treating chronic low back pain, and the drug is currently being tested to assess its efficacy in treating pain associated with osteoarthritis, acute post-surgical pain, neuropathic pain and pain associated with dental surgery.[1]

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Bicifadine represents a novel class of drug using a non-opioid, non-NSAID mechanism for the treatment of pain,^[3]^[4] which should have less abuse potential than opioid drugs. It is not the first SNRI used for pain treatment, as the older drug duloxetine has previously been approved for the treatment of neuropathic pain, and also some atypical opioid drugs such as tramadol and the newer agent tapentadol exhibit some reuptake inhibition properties that contribute to their therapeutic effects.

Preliminary results suggest that bicifadine has an analgesic efficacy slightly stronger than codeine and approximately equivalent to tramadol, although side effects such as nausea and headache were more common with bicifadine than with tramadol.[2]

References

^ Xu F, Murry JA, Simmons B, Corley E, Fitch K, Karady S, Tschaen D. Stereocontrolled synthesis of trisubstituted cyclopropanes: expedient, atom-economical, asymmetric syntheses of (+)-Bicifadine and DOV21947. Organic Letters. 2006 Aug 17;8(17):3885-8.
^ Krieter PA, Gohdes M, Musick TJ, Duncanson FP, Bridson WE. Pharmacokinetics, Disposition, and Metabolism of Bicifadine in Humans. Drug Metabolism and Disposition. 2007 Nov 8.
^ Wang RI, Johnson RP, Lee JC, Waite EM. The oral analgesic efficacy of bicifadine hydrochloride in postoperative pain. Journal of Clinical Pharmacology. 1982 Apr;22(4):160-4.
^ Basile AS, Janowsky A, Golembiowska K, Kowalska M, Tam E, Benveniste M, Popik P, Nikiforuk A, Krawczyk M, Nowak G, Krieter PA, Lippa AS, Skolnick P, Koustova E. Characterization of the antinociceptive actions of bicifadine in models of acute, persistent, and chronic pain. Journal of Pharmacology and Experimental Therapeutics. 2007 Jun;321(3):1208-25.

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