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Identification
NameCarfentanil
Accession NumberDB01535
TypeSmall Molecule
GroupsExperimental, Illicit
DescriptionNot Available
Structure
Thumb
SynonymsNot Available
SaltsNot Available
Brand namesNot Available
Brand mixturesNot Available
CategoriesNot Available
CAS number59708-52-0
WeightAverage: 394.5066
Monoisotopic: 394.225642836
Chemical FormulaC24H30N2O3
InChI KeyYDSDEBIZUNNPOB-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
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassHeterocyclic Compounds
ClassPiperidines
SubclassFentanyls
Direct parentFentanyls
Alternative parentsAlpha Amino Acids and Derivatives; Anilides; Phenethylamines; Piperidinecarboxylic Acids; Aminopiperidines; Tertiary Carboxylic Acid Amides; Carboxylic Acid Esters; Tertiary Amines; Enolates; Polyamines; Carboxylic Acids; Ethers
Substituentsalpha-amino acid or derivative; acetanilide; phenethylamine; piperidinecarboxylic acid; 4-aminopiperidine; benzene; tertiary carboxylic acid amide; carboxamide group; tertiary amine; carboxylic acid ester; polyamine; ether; carboxylic acid; enolate; carboxylic acid derivative; amine; organonitrogen compound
Classification descriptionThis compound belongs to the 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.
Pharmacology
IndicationCarfentanil is similar (but more potent) to the opioid analgesic fentanyl. It is used as a tranquilizer for large animals.
PharmacodynamicsCarfentanil 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 actionCarfentanil 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.
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 0.8605
Blood Brain Barrier + 0.9762
Caco-2 permeable - 0.5069
P-glycoprotein substrate Substrate 0.7011
P-glycoprotein inhibitor I Inhibitor 0.8424
P-glycoprotein inhibitor II Non-inhibitor 0.6298
Renal organic cation transporter Non-inhibitor 0.6504
CYP450 2C9 substrate Non-substrate 0.8368
CYP450 2D6 substrate Non-substrate 0.8791
CYP450 3A4 substrate Substrate 0.6667
CYP450 1A2 substrate Non-inhibitor 0.9279
CYP450 2C9 substrate Non-inhibitor 0.7664
CYP450 2D6 substrate Non-inhibitor 0.8561
CYP450 2C19 substrate Non-inhibitor 0.7325
CYP450 3A4 substrate Non-inhibitor 0.6284
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.6023
Ames test Non AMES toxic 0.7779
Carcinogenicity Non-carcinogens 0.869
Biodegradation Not ready biodegradable 0.9474
Rat acute toxicity 2.9219 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.9613
hERG inhibition (predictor II) Inhibitor 0.6716
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
Statesolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0259ALOGPS
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
Polarizability44.6 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
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 Reference
  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. Pubmed
External Links
ResourceLink
PubChem Compound62156
PubChem Substance46505501
ChemSpider55986
BindingDB50012477
ChEBI61084
ChEMBL
WikipediaCarfentanil
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

1. Mu-type opioid receptor

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: agonist

Components

Name UniProt ID Details
Mu-type opioid receptor P35372 Details

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. Pubmed
  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. Pubmed
  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. Pubmed
  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. Pubmed
  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. Pubmed

2. Delta-type opioid receptor

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: agonist

Components

Name UniProt ID Details
Delta-type opioid receptor P41143 Details

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. Pubmed
  2. Barry U, Zuo Z: Opioids: old drugs for potential new applications. Curr Pharm Des. 2005;11(10):1343-50. Pubmed

3. Kappa-type opioid receptor

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: agonist

Components

Name UniProt ID Details
Kappa-type opioid receptor P41145 Details

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. Pubmed
  2. Barry U, Zuo Z: Opioids: old drugs for potential new applications. Curr Pharm Des. 2005;11(10):1343-50. Pubmed

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Drug created on July 31, 2007 07:10 / Updated on September 16, 2013 17:15