Bicifadine free base

For research use only. Not for therapeutic Use.

  • CAT Number: I023372
  • CAS Number: 71195-57-8
  • Molecular Formula: C12H15N
  • Molecular Weight: 173.25
  • Purity: 98%
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Bicifadine (Cat.No:I023372), also known as DOV-220075, CL 220,075, is a SNDR inhibitor potentially for the treatment of lower back pain. 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."


Catalog Number I023372
CAS Number 71195-57-8
Synonyms

Bicifadine (free base); CL220075; CL-220075; CL 220075

Molecular Formula C12H15N
Purity 98%
Solubility Soluble in DMSO
Appearance Solid powder
Storage Dry, dark and at 0 - 4℃ for short term (days to weeks) or -20℃ for long term (months to years).
IUPAC Name 3-Azabicyclo(3.1.0)hexane, 1-(4-methylphenyl)-, (+-)-
InChI InChI=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
InChIKey OFYVIGTWSQPCLF-UHFFFAOYSA-N
SMILES CC1=CC=C(C23CNCC2C3)C=C1
Reference

1: Di Cesare Mannelli L, Micheli L, Crocetti L, Giovannoni MP, Vergelli C, Ghelardini C. α2 Adrenoceptor: a Target for Neuropathic Pain Treatment. Mini Rev Med Chem. 2017;17(2):95-107. doi: 10.2174/1389557516666160609065535. PMID: 27292786.
2: Srinivas NR, Ahlawat P. Prediction of human pharmacokinetic parameters using animal data and principles of allometry. A case using bicifadine, a non-narcotic analgesic, as an example. Arzneimittelforschung. 2009;59(12):625-30. doi: 10.1055/s-0031-1296450. PMID: 20108647.
3: Nicholson KL, Balster RL, Golembiowska K, Kowalska M, Tizzano JP, Skolnick P, Basile AS. Preclinical evaluation of the abuse potential of the analgesic bicifadine. J Pharmacol Exp Ther. 2009 Jul;330(1):236-48. doi: 10.1124/jpet.109.150540. Epub 2009 Apr 8. PMID: 19357320; PMCID: PMC3202431.
4: Musick TJ, Gohdes M, Duffy A, Erickson DA, Krieter PA. Pharmacokinetics, disposition, and metabolism of bicifadine in the mouse, rat, and monkey. Drug Metab Dispos. 2008 Feb;36(2):241-51. doi: 10.1124/dmd.107.017863. Epub 2007 Nov 8. PMID: 17991767.
5: Krieter PA, Gohdes M, Musick TJ, Duncanson FP, Bridson WE. Pharmacokinetics, disposition, and metabolism of bicifadine in humans. Drug Metab Dispos. 2008 Feb;36(2):252-9. doi: 10.1124/dmd.107.017871. Epub 2007 Nov 8. PMID: 17991768.
6: 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. J Pharmacol Exp Ther. 2007 Jun;321(3):1208-25. doi: 10.1124/jpet.106.116483. Epub 2007 Feb 26. PMID: 17325229.
7: Zhang M, Jovic F, Vickers T, Dyck B, Tamiya J, Grey J, Tran JA, Fleck BA, Pick R, Foster AC, Chen C. Studies on the structure-activity relationship of bicifadine analogs as monoamine transporter inhibitors. Bioorg Med Chem Lett. 2008 Jul 1;18(13):3682-6. doi: 10.1016/j.bmcl.2008.05.077. Epub 2008 May 23. PMID: 18539031.
8: 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. Org Lett. 2006 Aug 17;8(17):3885-8. doi: 10.1021/ol061650w. PMID: 16898842.

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