Bicifadine

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Chemical compound

title: "Bicifadine" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["abandoned-drugs", "analgesics", "cyclopropanes", "pyrrolidines", "serotonin–norepinephrine–dopamine-reuptake-inhibitors", "4-tolyl-compounds"] description: "Chemical compound" topic_path: "arts/music" source: "https://en.wikipedia.org/wiki/Bicifadine" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

::summary Chemical compound ::

| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 462798006 | IUPAC_name = 1-(4-Methylphenyl)-3-azabicyclo[3.1.0]hexane | image = Bicifadine.svg | image_class = skin-invert-image | width = 170

| tradename = | pregnancy_AU = | pregnancy_US = | pregnancy_category = | legal_AU = | legal_CA = | legal_UK = | legal_US = Unscheduled | legal_status = | routes_of_administration = Oral

| bioavailability = | protein_bound = | metabolism = | elimination_half-life = 1.6 hours | excretion = renal

| CAS_number_Ref = | CAS_number = 71195-57-8 | ATC_prefix = none | ATC_suffix = | ChEMBL_Ref = | ChEMBL = 511099 | PubChem = 47953 | UNII_Ref = | UNII = B0SV3N7J3H | ChemSpiderID_Ref = | ChemSpiderID = 9889978 | smiles = c1cc(ccc1C)[C@]32CNC[C@@H]2C3 | StdInChI_Ref = | StdInChI = 1S/C12H15N/c1-9-2-4-10(5-3-9)12-6-11(12)7-13-8-12/h2-5,11,13H,6-8H2,1H3/t11-,12+/m0/s1 | StdInChIKey_Ref = | StdInChIKey = OFYVIGTWSQPCLF-NWDGAFQWSA-N

| C=12 | H=15 | N=1 | melting_point = | melting_high =

Bicifadine (DOV-220,075) is a serotonin-norepinephrine-dopamine reuptake inhibitor (SNDRI) discovered at American Cyanamid as an analgesic drug candidate, and licensed to DOV Pharmaceutical in 1998 after American Cyanamid was acquired by Wyeth.

In January 2007, Dov licensed the rights to bicifadine to XTL Biopharmaceuticals after bicifadine failed in a Phase III clinical trial for chronic lower back pain. XTL ran a PhaseIIb clinical trial for pain caused by diabetic neuropathy, which failed in 2008; XTL terminated the agreement in 2010. In 2010 Dov was acquired by Euthymics Bioscience which intended to continue development of other candidates from Dov's portfolio.

Bicifadine has a non-opioid, non-NSAID mechanism for the treatment of pain, which should have less abuse potential than opioid drugs and less propensity to cause gastric ulcers than NSAID drugs. While the drug is purported to be a serotonin (SERT) and noradrenaline transporter (NET) inhibitor, it also has effects at the dopamine transporter (DAT), effectively making it a broad-spectrum monoamine transporter inhibitor or "triple reuptake inhibitor."

References

References

  1. (September 2008). "Triple reuptake inhibitors: a premise and promise". Psychiatry Investigation.
  2. [https://www.sec.gov/Archives/edgar/data/1066833/000114420404018172/v08017_ex10-51.txt SEC Filing: Wyeth-DOV Restated License Agreement] Page accessed July 15, 2015]
  3. (2010). "GABA and Sleep: Molecular, Functional and Clinical Aspects". Springer Science & Business Media.
  4. (26 July 2010). "Bear Out of Hibernation". BioCentury.
  5. (December 5, 2011). "Euthymics: Balancing act". BioCentury, The Bernstein Report on Biobusiness.
  6. (7 January 2007). "XTL licenses development rights to pain therapy". Fierce Biotech.
  7. Fierce Biotech. December 9, 2008 [http://www.fiercebiotech.com/story/tiny-xtl-cuts-costs-jobs/2008-12-09 Tiny XTL cuts costs, jobs]
  8. "XTL Form 6-K March, 2013".
  9. Fierce Biotech July 22, 2010 [http://www.fiercebiotech.com/story/euthymics-lands-24m-fund-antidepressant-work/2010-07-22 Euthymics lands $24M to fund antidepressant work]
  10. (April 1982). "The oral analgesic efficacy of bicifadine hydrochloride in postoperative pain". Journal of Clinical Pharmacology.
  11. (June 2007). "Characterization of the antinociceptive actions of bicifadine in models of acute, persistent, and chronic pain". The Journal of Pharmacology and Experimental Therapeutics.

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abandoned-drugsanalgesicscyclopropanespyrrolidinesserotonin–norepinephrine–dopamine-reuptake-inhibitors4-tolyl-compounds