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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
Structure of CARFENTANIL CITRATE

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)

HIDE SMILES / InChI
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

PubMed

TitleDatePubMed
Carfentanil citrate used as an oral anesthetic agent for brown bears (Ursus arctos).
2001 Jun
Sedation and chemical restraint of deer.
2002 Dec
Serial immobilization of a Brazilian tapir (Tapirus terrestrus) with oral detomidine and oral carfentanil.
2003 Dec
Analysis of 13 fentanils, including sufentanil and carfentanil, in human urine by liquid chromatography-atmospheric-pressure ionization-tandem mass spectrometry.
2006 Jun
Dysregulation of endogenous opioid emotion regulation circuitry in major depression in women.
2006 Nov
Pharmacokinetics and pharmacodynamics of carfentanil and naltrexone in female common eland (Taurotragus oryx).
2006 Sep
Imaging genomics applied to anxiety, stress response, and resiliency.
2006 Winter
Smoking modulation of mu-opioid and dopamine D2 receptor-mediated neurotransmission in humans.
2007 Feb
Buprenorphine duration of action: mu-opioid receptor availability and pharmacokinetic and behavioral indices.
2007 Jan 1
Placebo and nocebo effects are defined by opposite opioid and dopaminergic responses.
2008 Feb
Differences in delta- and mu-opioid receptor blockade measured by positron emission tomography in naltrexone-treated recently abstinent alcohol-dependent subjects.
2008 Feb
Intranasal naltrexone and atipamezole for reversal of white-tailed deer immobilized with carfentanil and medetomidine.
2010 May
Carfentanil--an ultra potent opioid.
2010 May
Brain mu-opioid receptor binding predicts treatment outcome in cocaine-abusing outpatients.
2010 Oct 15
Comparison of thiafenantil-xylazine and carfentanil-xylazine for immobilization of gemsbok (Oryx gazella).
2010 Sep
Patents
Name Type Language
CARFENTANIL CITRATE
GREEN BOOK   MART.   USAN  
USAN  
Official Name English
4-PIPERIDINECARBOXYLIC ACID, 4-(1-OXOPROPYL)PHENYLAMINO)1-(2-PHENYLETHYL)-, METHYL ESTER, 2-HYDROXY-1,2,3-PROPANETRICARBOXYLATE (1:1)
Common Name English
CARFENTANIL CITRATE [MART.]
Common Name English
CARFENTANIL CITRATE [USAN]
Common Name English
Methyl 1-phenethyl-4-(N-phenylpropionamido)isonipecotate citrate (1:1)
Systematic Name English
R-33799
Code English
R 33,799
Code English
CARFENTANIL CITRATE [GREEN BOOK]
Common Name English
Classification Tree Code System Code
CFR 21 CFR 522.300
Created by admin on Fri Dec 15 16:34:47 GMT 2023 , Edited by admin on Fri Dec 15 16:34:47 GMT 2023
NCI_THESAURUS C67413
Created by admin on Fri Dec 15 16:34:47 GMT 2023 , Edited by admin on Fri Dec 15 16:34:47 GMT 2023
Code System Code Type Description
ChEMBL
CHEMBL290429
Created by admin on Fri Dec 15 16:34:47 GMT 2023 , Edited by admin on Fri Dec 15 16:34:47 GMT 2023
PRIMARY
CAS
61380-27-6
Created by admin on Fri Dec 15 16:34:47 GMT 2023 , Edited by admin on Fri Dec 15 16:34:47 GMT 2023
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FDA UNII
7LG286J8GV
Created by admin on Fri Dec 15 16:34:47 GMT 2023 , Edited by admin on Fri Dec 15 16:34:47 GMT 2023
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SMS_ID
100000174886
Created by admin on Fri Dec 15 16:34:47 GMT 2023 , Edited by admin on Fri Dec 15 16:34:47 GMT 2023
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MESH
C017114
Created by admin on Fri Dec 15 16:34:47 GMT 2023 , Edited by admin on Fri Dec 15 16:34:47 GMT 2023
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NCI_THESAURUS
C77280
Created by admin on Fri Dec 15 16:34:47 GMT 2023 , Edited by admin on Fri Dec 15 16:34:47 GMT 2023
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ECHA (EC/EINECS)
262-748-6
Created by admin on Fri Dec 15 16:34:47 GMT 2023 , Edited by admin on Fri Dec 15 16:34:47 GMT 2023
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DRUG BANK
DBSALT001611
Created by admin on Fri Dec 15 16:34:47 GMT 2023 , Edited by admin on Fri Dec 15 16:34:47 GMT 2023
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EPA CompTox
DTXSID50976923
Created by admin on Fri Dec 15 16:34:47 GMT 2023 , Edited by admin on Fri Dec 15 16:34:47 GMT 2023
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PUBCHEM
9851365
Created by admin on Fri Dec 15 16:34:47 GMT 2023 , Edited by admin on Fri Dec 15 16:34:47 GMT 2023
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