Surinabant

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Chemical compound

title: "Surinabant" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["1-piperidinyl-compounds", "4-bromophenyl-compounds", "cannabinoids", "cb1-receptor-antagonists", "chloroarenes", "hallucinogen-antidotes", "hydrazides", "pyrazolecarboxamides", "pyrazoles"] description: "Chemical compound" topic_path: "general/1-piperidinyl-compounds" source: "https://en.wikipedia.org/wiki/Surinabant" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

::summary Chemical compound ::

| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 470475222 | IUPAC_name = 5-(4-bromophenyl)-1-(2,4-dichlorophenyl)-4-ethyl-N-(1-piperidinyl)-1H-pyrazole-3-carboxamide | image = Surinabant Structure.svg | image_class = skin-invert-image | alt = Skeletal formula of surinabant | width = 180 | image2 = Surinabant 3D spacefill.png | image_class2 = bg-transparent | alt2 = Space-filling model of the surinabant molecule | width2 = 220

| tradename = | pregnancy_AU = | pregnancy_US = | pregnancy_category = | legal_AU = | legal_CA = | legal_UK = | legal_US = | legal_status =

| bioavailability = | protein_bound = | metabolism = | elimination_half-life = | excretion =

| CAS_number_Ref = | CAS_number = 288104-79-0 | ATC_prefix = none | ATC_suffix = | PubChem = 9849616 | DrugBank_Ref = | DrugBank = | ChemSpiderID_Ref = | ChemSpiderID = 8025329 | UNII_Ref = | UNII = SF8R9VCB0X | ChEMBL_Ref = | ChEMBL = 189676

| chemical_formula = | C=23 | H=23 | Br=1 | Cl=2 | N=4 | O=1 | smiles = O=C(NN1CCCCC1)c4nn(c2ccc(Cl)cc2Cl)c(c3ccc(Br)cc3)c4CC | StdInChI_Ref = | StdInChI = 1S/C23H23BrCl2N4O/c1-2-18-21(23(31)28-29-12-4-3-5-13-29)27-30(20-11-10-17(25)14-19(20)26)22(18)15-6-8-16(24)9-7-15/h6-11,14H,2-5,12-13H2,1H3,(H,28,31) | StdInChIKey_Ref = | StdInChIKey = HMXDWDSNPRNUKI-UHFFFAOYSA-N

Surinabant (SR147778) is a cannabinoid receptor type 1 antagonist developed by Sanofi-Aventis. It is being investigated as a potential treatment for nicotine addiction, to assist smoking cessation. It may also be developed as an anorectic drug to assist with weight loss, however there are already several CB1 antagonists or inverse agonists on the market or under development for this application, so surinabant is at present mainly being developed as an anti-smoking drug, with possible application in the treatment of other addictive disorders such as alcoholism. Other potential applications such as treatment of ADHD have also been proposed.

A dose ranging study was done for smoking cessation in 2012; it did not improve success rate, but reduced weight gain. Inhibition of THC effects on heart rate was seen at 20 mg and 60 mg but not 5 mg.

References

References

  1. (September 2004). "SR147778 [5-(4-bromophenyl)-1-(2,4-dichlorophenyl)-4-ethyl-N-(1-piperidinyl)-1H-pyrazole-3-carboxamide], a new potent and selective antagonist of the CB1 cannabinoid receptor: biochemical and pharmacological characterization". The Journal of Pharmacology and Experimental Therapeutics.
  2. (March 2005). "Will the new CB1 cannabinoid receptor antagonist SR-147778 have advantages over rimonabant?". Expert Opinion on Investigational Drugs.
  3. (January 2008). "Effects of adolescent nicotine and SR 147778 (Surinabant) administration on food intake, somatic growth and metabolic parameters in rats". Neuropharmacology.
  4. (2005). "Suppressing effect of the cannabinoid CB1 receptor antagonist, SR147778, on alcohol intake and motivational properties of alcohol in alcohol-preferring sP rats". Alcohol and Alcoholism.
  5. (July 2006). "SR147778, a CB1 cannabinoid receptor antagonist, suppresses ethanol preference in chronically alcoholized Wistar rats". Alcohol.
  6. (2005). "Surinabant, a new CB1 receptor antagonist, displays efficacy in animal models of attention deficit/hyperactivity disorder". Behavioural Pharmacology.
  7. (July 2012). "Efficacy of a dose range of surinabant, a cannabinoid receptor blocker, for smoking cessation: a randomized controlled clinical trial". Journal of Psychopharmacology.
  8. (July 2013). "Surinabant, a selective cannabinoid receptor type 1 antagonist, inhibits Δ9-tetrahydrocannabinol-induced central nervous system and heart rate effects in humans". British Journal of Clinical Pharmacology.

::callout[type=info title="Wikipedia Source"] This article was imported from Wikipedia and is available under the Creative Commons Attribution-ShareAlike 4.0 License. Content has been adapted to SurfDoc format. Original contributors can be found on the article history page. ::

1-piperidinyl-compounds4-bromophenyl-compoundscannabinoidscb1-receptor-antagonistschloroareneshallucinogen-antidoteshydrazidespyrazolecarboxamidespyrazoles