Details
Stereochemistry | ACHIRAL |
Molecular Formula | C24H30N2O3.C6H8O7 |
Molecular Weight | 586.6301 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
OC(=O)CC(O)(CC(O)=O)C(O)=O.CCC(=O)N(C1=CC=CC=C1)C2(CCN(CCC3=CC=CC=C3)CC2)C(=O)OC
InChI
InChIKey=ZSLYVCXNFQPCGT-UHFFFAOYSA-N
InChI=1S/C24H30N2O3.C6H8O7/c1-3-22(27)26(21-12-8-5-9-13-21)24(23(28)29-2)15-18-25(19-16-24)17-14-20-10-6-4-7-11-20;7-3(8)1-6(13,5(11)12)2-4(9)10/h4-13H,3,14-19H2,1-2H3;13H,1-2H2,(H,7,8)(H,9,10)(H,11,12)
Carfentanil is a synthetic fentanyl analog. It is a mu-opioid receptor agonist with an estimated analgesic potency approximately 10,000 times that of morphine and 20-30 times that of fentanyl, based on animal studies. Receptor binding studies have shown that carfentanil binds selectively and competitively to the μ subtype of opioid receptors relative to δ and κ opioid receptors. Preclinical studies have
demonstrated that the pharmacodynamic effects, such as analgesia and constipation, produced by
carfentanil are similar to other μ opioid agonists. Its extreme potency and propensity to produce
rapid and profound respiratory depression has prompted recommendations that an opioid antagonist, such as naloxone or naltrexone, be available whenever carfentanil is used or suspected to be present. Carfentanil (Wildnil) has been used in veterinary as a prescription-only general anesthetic for intramuscular injection in large animals. Carfentanil is no longer FDA-approved for use in animals after Wildlife Laboratories withdrew the application for Wildnil. Carfentanyl is increasingly involved in opioid overdose deaths among illicit opioid users.
Approval Year
PubMed
Title | Date | PubMed |
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Carfentanil citrate used as an oral anesthetic agent for brown bears (Ursus arctos). | 2001 Jun |
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Sedation and chemical restraint of deer. | 2002 Dec |
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Serial immobilization of a Brazilian tapir (Tapirus terrestrus) with oral detomidine and oral carfentanil. | 2003 Dec |
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Analysis of 13 fentanils, including sufentanil and carfentanil, in human urine by liquid chromatography-atmospheric-pressure ionization-tandem mass spectrometry. | 2006 Jun |
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Dysregulation of endogenous opioid emotion regulation circuitry in major depression in women. | 2006 Nov |
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Pharmacokinetics and pharmacodynamics of carfentanil and naltrexone in female common eland (Taurotragus oryx). | 2006 Sep |
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Imaging genomics applied to anxiety, stress response, and resiliency. | 2006 Winter |
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Smoking modulation of mu-opioid and dopamine D2 receptor-mediated neurotransmission in humans. | 2007 Feb |
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Buprenorphine duration of action: mu-opioid receptor availability and pharmacokinetic and behavioral indices. | 2007 Jan 1 |
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Placebo and nocebo effects are defined by opposite opioid and dopaminergic responses. | 2008 Feb |
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Differences in delta- and mu-opioid receptor blockade measured by positron emission tomography in naltrexone-treated recently abstinent alcohol-dependent subjects. | 2008 Feb |
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Intranasal naltrexone and atipamezole for reversal of white-tailed deer immobilized with carfentanil and medetomidine. | 2010 May |
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Carfentanil--an ultra potent opioid. | 2010 May |
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Brain mu-opioid receptor binding predicts treatment outcome in cocaine-abusing outpatients. | 2010 Oct 15 |
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Comparison of thiafenantil-xylazine and carfentanil-xylazine for immobilization of gemsbok (Oryx gazella). | 2010 Sep |
Patents
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CFR |
21 CFR 522.300
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NCI_THESAURUS |
C67413
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CHEMBL290429
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61380-27-6
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7LG286J8GV
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100000174886
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C017114
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C77280
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262-748-6
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DBSALT001611
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DTXSID50976923
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9851365
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ACTIVE MOIETY
PARENT (SALT/SOLVATE)
SUBSTANCE RECORD