NAV

Carfentanil

Identification

Generic Name
Carfentanil
DrugBank Accession Number
DB01535
Background

Carfentanil or carfentanyl (Wildnil) is an analogue of the popular synthetic opioid analgesic fentanyl, and is one of the most potent opioids known (also the most potent opioid used commercially). Carfentanil was first synthesized in 1974 by a team of chemists at Janssen Pharmaceutica which included Paul Janssen. It has a quantitative potency approximately 10,000 times that of morphine and 100 times that of fentanyl, with activity in humans starting at about 1 microgram. It is marketed under the trade name Wildnil as a general anaesthetic agent for large animals. Carfentanil is intended for large-animal use only as its extreme potency makes it inappropriate for use in humans. Currently sufentanil, approximately 10–20 times less potent (500 to 1000 times the efficacy of morphine per weight) than carfentanil, is the maximum strength fentanyl analog for use in humans.

Type
Small Molecule
Groups
Illicit, Investigational, Vet approved
Structure
3D
Similar Structures
Weight
Average: 394.5066
Monoisotopic: 394.225642836
Chemical Formula
C24H30N2O3
Synonyms
  • Carfentanil
  • carfentanila
  • Carfentanyl

Pharmacology

Indication

Carfentanil is similar (but more potent) to the opioid analgesic fentanyl. It is used as a tranquilizer for large animals.

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Carfentanil acts primarily on the mu (some kappa and delta) opioid receptors as an agonist. It will induce similar effects of analgesia as other opioids, however, due to its potency, it will also induce strong side effects such as sedation. Consequently, that is why it is used as a tranquilizer for large animals.

Carfentanil interacts predominately with the opioid mu-receptor. These mu-binding sites are discretely distributed in the brain, spinal cord, and other tissues. It exerts its principal pharmacologic effects on the central nervous system. Its primary actions of therapeutic value are analgesia and sedation. Carfentanil also depresses the respiratory centers, depresses the cough reflex, and constricts the pupils.

Mechanism of action

Carfentanil binds very strongly to mu opioid receptors and acts as a competitive agonist. Opiate receptors are coupled with G-protein receptors and function as both positive and negative regulators of synaptic transmission via G-proteins that activate effector proteins. Binding of the opiate stimulates the exchange of GTP for GDP on the G-protein complex. As the effector system is adenylate cyclase and cAMP located at the inner surface of the plasma membrane, opioids decrease intracellular cAMP by inhibiting adenylate cyclase. Subsequently, the release of nociceptive neurotransmitters such as substance P, GABA, dopamine, acetylcholine and noradrenaline is inhibited. Opioids also inhibit the release of vasopressin, somatostatin, insulin and glucagon. Opioids close N-type voltage-operated calcium channels (OP2-receptor agonist) and open calcium-dependent inwardly rectifying potassium channels (OP3 and OP1 receptor agonist). This results in hyperpolarization and reduced neuronal excitability.

TargetActionsOrganism
AMu-type opioid receptor
agonist
Humans
ADelta-type opioid receptor
agonist
Humans
UKappa-type opioid receptor
agonist
Humans
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
PathwayCategory
Carfentanil Action PathwayDrug action
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
Integrate drug-drug
interactions in your software
1,2-BenzodiazepineThe risk or severity of adverse effects can be increased when Carfentanil is combined with 1,2-Benzodiazepine.
AcetazolamideThe risk or severity of CNS depression can be increased when Acetazolamide is combined with Carfentanil.
AcetophenazineThe risk or severity of hypotension and CNS depression can be increased when Acetophenazine is combined with Carfentanil.
AclidiniumThe risk or severity of adverse effects can be increased when Aclidinium is combined with Carfentanil.
AgomelatineThe risk or severity of CNS depression can be increased when Carfentanil is combined with Agomelatine.
AlfentanilThe risk or severity of adverse effects can be increased when Alfentanil is combined with Carfentanil.
AlimemazineThe risk or severity of hypotension and CNS depression can be increased when Alimemazine is combined with Carfentanil.
AlloinThe therapeutic efficacy of Alloin can be decreased when used in combination with Carfentanil.
AlmotriptanThe risk or severity of CNS depression can be increased when Almotriptan is combined with Carfentanil.
AlosetronThe risk or severity of CNS depression can be increased when Alosetron is combined with Carfentanil.
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Food Interactions
Not Available

Products

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Product Ingredients
IngredientUNIICASInChI Key
Carfentanil citrate7LG286J8GV61380-27-6ZSLYVCXNFQPCGT-UHFFFAOYSA-N

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as fentanyls. These are compounds containing the fentanyl moiety or a derivative, which is based on a N-(1-(2-phenylethyl)-4-piperidinyl)-N-phenylpropanamide skeleton.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Piperidines
Sub Class
Fentanyls
Direct Parent
Fentanyls
Alternative Parents
Alpha amino acids and derivatives / Piperidinecarboxylic acids / Phenethylamines / Anilides / Aralkylamines / Tertiary carboxylic acid amides / Methyl esters / Trialkylamines / Monocarboxylic acids and derivatives / Azacyclic compounds
show 4 more
Substituents
Alpha-amino acid or derivatives / Amine / Amino acid or derivatives / Anilide / Aralkylamine / Aromatic heteromonocyclic compound / Azacycle / Benzenoid / Carbonyl group / Carboxamide group
show 18 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
piperidines, tertiary amino compound, methyl ester, carboxamide (CHEBI:61084)
Affected organisms
Not Available

Chemical Identifiers

UNII
LA9DTA2L8F
CAS number
59708-52-0
InChI Key
YDSDEBIZUNNPOB-UHFFFAOYSA-N
InChI
InChI=1S/C24H30N2O3/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/h4-13H,3,14-19H2,1-2H3
IUPAC Name
methyl 1-(2-phenylethyl)-4-(N-phenylpropanamido)piperidine-4-carboxylate
SMILES
CCC(=O)N(C1=CC=CC=C1)C1(CCN(CCC2=CC=CC=C2)CC1)C(=O)OC

References

Synthesis Reference

Louis P. Reiff, Paul B. Sollman, "Process of making carfentanil and related analgesics." U.S. Patent US5106983, issued January, 1981.

US5106983
General References
  1. Wax PM, Becker CE, Curry SC: Unexpected "gas" casualties in Moscow: a medical toxicology perspective. Ann Emerg Med. 2003 May;41(5):700-5. [Article]
PubChem Compound
62156
PubChem Substance
46505501
ChemSpider
55986
BindingDB
50012477
ChEBI
61084
ChEMBL
CHEMBL290429
ZINC
ZINC000004215196
Wikipedia
Carfentanil

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2TerminatedTreatmentNeuropathic Pain1
1CompletedScreeningSubstance-related Discorder1
1RecruitingOtherHealthy Subjects (HS)1
1RecruitingTreatmentOpioid Use Disorder (OUD)1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0259 mg/mLALOGPS
logP3.7ALOGPS
logP3.67Chemaxon
logS-4.2ALOGPS
pKa (Strongest Basic)8.05Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count3Chemaxon
Hydrogen Donor Count0Chemaxon
Polar Surface Area49.85 Å2Chemaxon
Rotatable Bond Count8Chemaxon
Refractivity114.38 m3·mol-1Chemaxon
Polarizability44.4 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.8605
Blood Brain Barrier+0.9762
Caco-2 permeable-0.5069
P-glycoprotein substrateSubstrate0.7011
P-glycoprotein inhibitor IInhibitor0.8424
P-glycoprotein inhibitor IINon-inhibitor0.6298
Renal organic cation transporterNon-inhibitor0.6504
CYP450 2C9 substrateNon-substrate0.8368
CYP450 2D6 substrateNon-substrate0.8791
CYP450 3A4 substrateSubstrate0.6667
CYP450 1A2 substrateNon-inhibitor0.9279
CYP450 2C9 inhibitorNon-inhibitor0.7664
CYP450 2D6 inhibitorNon-inhibitor0.8561
CYP450 2C19 inhibitorNon-inhibitor0.7325
CYP450 3A4 inhibitorNon-inhibitor0.6284
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6023
Ames testNon AMES toxic0.7779
CarcinogenicityNon-carcinogens0.869
BiodegradationNot ready biodegradable0.9474
Rat acute toxicity2.9219 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9613
hERG inhibition (predictor II)Inhibitor0.6716
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Targets

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insights and accelerate drug research.
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Details1. Mu-type opioid receptor
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Agonist
General Function
Voltage-gated calcium channel activity
Specific Function
Receptor for endogenous opioids such as beta-endorphin and endomorphin. Receptor for natural and synthetic opioids including morphine, heroin, DAMGO, fentanyl, etorphine, buprenorphin and methadone...
Gene Name
OPRM1
Uniprot ID
P35372
Uniprot Name
Mu-type opioid receptor
Molecular Weight
44778.855 Da
References
  1. Bencherif B, Wand GS, McCaul ME, Kim YK, Ilgin N, Dannals RF, Frost JJ: Mu-opioid receptor binding measured by [11C]carfentanil positron emission tomography is related to craving and mood in alcohol dependence. Biol Psychiatry. 2004 Feb 1;55(3):255-62. [Article]
  2. Bencherif B, Stumpf MJ, Links JM, Frost JJ: Application of MRI-based partial-volume correction to the analysis of PET images of mu-opioid receptors using statistical parametric mapping. J Nucl Med. 2004 Mar;45(3):402-8. [Article]
  3. Jewett DM, Kilbourn MR: In vivo evaluation of new carfentanil-based radioligands for the mu opiate receptor. Nucl Med Biol. 2004 Apr;31(3):321-5. [Article]
  4. Mayberg HS, Sadzot B, Meltzer CC, Fisher RS, Lesser RP, Dannals RF, Lever JR, Wilson AA, Ravert HT, Wagner HN Jr, et al.: Quantification of mu and non-mu opiate receptors in temporal lobe epilepsy using positron emission tomography. Ann Neurol. 1991 Jul;30(1):3-11. [Article]
  5. Bartenstein PA, Prevett MC, Duncan JS, Hajek M, Wieser HG: Quantification of opiate receptors in two patients with mesiobasal temporal lobe epilepsy, before and after selective amygdalohippocampectomy, using positron emission tomography. Epilepsy Res. 1994 Jun;18(2):119-25. [Article]
Details2. Delta-type opioid receptor
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Agonist
General Function
Opioid receptor activity
Specific Function
G-protein coupled receptor that functions as receptor for endogenous enkephalins and for a subset of other opioids. Ligand binding causes a conformation change that triggers signaling via guanine n...
Gene Name
OPRD1
Uniprot ID
P41143
Uniprot Name
Delta-type opioid receptor
Molecular Weight
40368.235 Da
References
  1. Mayberg HS, Sadzot B, Meltzer CC, Fisher RS, Lesser RP, Dannals RF, Lever JR, Wilson AA, Ravert HT, Wagner HN Jr, et al.: Quantification of mu and non-mu opiate receptors in temporal lobe epilepsy using positron emission tomography. Ann Neurol. 1991 Jul;30(1):3-11. [Article]
  2. Barry U, Zuo Z: Opioids: old drugs for potential new applications. Curr Pharm Des. 2005;11(10):1343-50. [Article]
Details3. Kappa-type opioid receptor
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Agonist
General Function
Opioid receptor activity
Specific Function
G-protein coupled opioid receptor that functions as receptor for endogenous alpha-neoendorphins and dynorphins, but has low affinity for beta-endorphins. Also functions as receptor for various synt...
Gene Name
OPRK1
Uniprot ID
P41145
Uniprot Name
Kappa-type opioid receptor
Molecular Weight
42644.665 Da
References
  1. Mayberg HS, Sadzot B, Meltzer CC, Fisher RS, Lesser RP, Dannals RF, Lever JR, Wilson AA, Ravert HT, Wagner HN Jr, et al.: Quantification of mu and non-mu opiate receptors in temporal lobe epilepsy using positron emission tomography. Ann Neurol. 1991 Jul;30(1):3-11. [Article]
  2. Barry U, Zuo Z: Opioids: old drugs for potential new applications. Curr Pharm Des. 2005;11(10):1343-50. [Article]

Drug created at July 31, 2007 13:10 / Updated at February 21, 2021 18:51