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1. (4-methoxycarbonyl)fentanyl
2. 11c-carfentanil
3. 4-methoxycarbonyl Fentanyl
4. 4-methoxycarbonylfentanyl
5. Carfentanil Citrate
6. Carfentanil Oxalate
7. Carfentanil, (+-)-isomer
8. Carfentanyl
9. R 31833
10. R 33799
11. R-31833
12. R31833
1. Carfentanyl
2. 59708-52-0
3. Carfentanila
4. Carfentanilum
5. Wildnil
6. Carfentanil [inn]
7. Methyl 1-phenylethyl-4-(n-phenylpropionamido)isonipecotate
8. 4-carbomethoxyfentanyl
9. Chebi:61084
10. Methyl 4-(n-(1-oxopropyl)-n-phenylamino)-1-(2-phenylethyl)-4-piperidinecarboxylate
11. Methyl 4-(n-propionyl-n-phenylamino)-1-(2-phenylethyl)-4-piperidine-carboxylate
12. 4-((1-oxopropyl)phenylamino)-1-(2-phenylethyl)-4-piperidinecarboxylic Acid Methyl Ester
13. La9dta2l8f
14. (4-carbomethoxy Fentanyl)
15. R 31833
16. Chembl290429
17. R-31833
18. Carfentanil (inn)
19. Methyl 1-phenethyl-4-(n-phenylpropionamido)isonipecotate
20. Methyl 1-(2-phenylethyl)-4-(n-propanoylanilino)piperidine-4-carboxylate
21. Carfentanila [spanish]
22. Methyl 1-(2-phenylethyl)-4-[phenyl(propionyl)amino]piperidine-4-carboxylate
23. Carfentanilum [inn-latin]
24. Carfentanila [inn-spanish]
25. Unii-la9dta2l8f
26. (4-methoxycarbonyl)fentanyl
27. Brn 0456976
28. Dea No. 9743
29. Epitope Id:153509
30. R31833
31. 4-piperidinecarboxylic Acid, 4((1-oxopropyl)phenylamino)-1-(2-phenylethyl)-, Methyl Ester
32. Schembl116222
33. Gtpl10040
34. Hsdb 8376
35. Dtxsid40208427
36. Zinc4215196
37. Bdbm50012477
38. Akos005067304
39. Db01535
40. D07620
41. Q423386
42. Methyl 1-(2-phenylethyl)-4-(phenyl-propanoylamino)piperidine-4-carboxylate
43. Methyl 1-(2-phenylethyl)-4-(propionylanilino)-4-piperidinecarboxylate #
44. 1-phenethyl-4-(phenyl-propionyl-amino)-piperidine-4-carboxylic Acid Methyl Ester
45. Carfentanil1-phenethyl-4-(phenyl-propionyl-amino)-piperidine-4-carboxylic Acid Methyl Ester
46. 1-phenethyl-4-(phenyl-propionyl-amino)-piperidine-4-carboxylic Acid Methyl Ester(carefentanil)
47. 4-piperidinecarboxylic Acid, 4-((1-oxopropyl)phenylamino)-1-(2-phenylethyl)-, Methyl Ester
| Molecular Weight | 394.5 g/mol |
|---|---|
| Molecular Formula | C24H30N2O3 |
| XLogP3 | 3.8 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 4 |
| Rotatable Bond Count | 8 |
| Exact Mass | 394.22564282 g/mol |
| Monoisotopic Mass | 394.22564282 g/mol |
| Topological Polar Surface Area | 49.8 Ų |
| Heavy Atom Count | 29 |
| Formal Charge | 0 |
| Complexity | 530 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Covalently Bonded Unit Count | 1 |
Analgesics, Opioid
National Library of Medicine's Medical Subject Headings. Carfentanil. Online file (MeSH, 2017). Available from, as of April 26, 2017: https://www.nlm.nih.gov/mesh/2017/mesh_browser/MBrowser.html
VET: Large animal immobilizing agent use in Cervidae (Deer, elk, moose) /Carfentanil citrate/
US FDA; Freedom of Information Act (FOIA) Drug Summaries. Wildnil. NADA 139-633. Available from, as of May 11, 2017: https://www.fda.gov/downloads/AnimalVeterinary/Products/ApprovedAnimalDrugProducts/FOIADrugSummaries/UCM473748.pdf
VET: Safe anesthesia of zoo animals is of special concern. Many procedures routinely accomplished on domestic animals with minimal restraint require anesthesia of zoologic species for the welfare and safety of both zoo animals and personnel. ... The potent opioids etorphine, carfentanil, and thiofentanil, alone or in combination with other agents (eg, azaparone, acepromazine, xylazine, detomidine), have been used extensively for anesthesia of ungulates, elephants, and rhinoceros.
Kahn, C.M (ed.).; The Merck Veterinary Manual 10th Edition. Merck & Co. Whitehouse Station NJ. 2010, p. 1814-5
VET: October 2001 to January 2002, captive free-ranging white-tailed deer (Odocoileus virginianus) were immobilized with a combination of carfentanil citrate and xylazine hydrochloride. From this study, we selected a dose of carfentanil/xylazine for the purpose of comparing immobilization parameters and physiologic effects with those of a combination of tiletamine and zolazepam (Telazol) and xylazine. Animals were initially given intramuscular injections of 10 mg xylazine and one of four doses of carfentanil (i.e., 0.5, 1.0, 1.5, and 2.0 mg). A carfentanil dose of 1.2 mg (x +/- SD = 23.5 +/- 3.2 microg/kg) and 10 mg xylazine (0.2 +/- 0.03 mg/kg) were selected, based on induction times and previously published reports, to compare with a combination of 230 mg of Telazol (4.5 +/- 0.6 mg/kg) and 120 mg xylazine (2.3 +/- 0.3 mg/kg). Time to first observable drug effects and to induction were significantly longer for deer treated with carfentanil/xylazine than with Telazol/xylazine (P < 0.01). Hyperthermia was common in deer immobilized with carfentanil/xylazine, but heart rate, respiration rate, and hemoglobin saturation were within acceptable levels. Degree of anesthesia of deer immobilized with Telazol/xylazine was superior to deer immobilized with carfentanil/xylazine. The combination of 120 mg of naltrexone hydrochloride and 6.5 mg of yohimbine hydrochloride provided rapid and complete reversal (1.9 +/- 1.1 min) of carfentanil/xylazine immobilization. Animals immobilized with Telazol/xylazine had long recovery times with occasional resedation after antagonism with 6.5 mg of yohimbine. The combination of carfentanil and xylazine at the doses tested did not provide reliable induction or immobilization of white-tailed deer even though drug reversal was rapid and safe using naltrexone and yohimbine.
PMID:14733280 Miller BF et al; J Wildl Dis 39 (4): 851-8 (2003)
For more Therapeutic Uses (Complete) data for Carfentanil (8 total), please visit the HSDB record page.
Carfentanil is similar (but more potent) to the opioid analgesic fentanyl. It is used as a tranquilizer for large animals.
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.
Analgesics, Opioid
Compounds with activity like OPIATE ALKALOIDS, acting at OPIOID RECEPTORS. Properties include induction of ANALGESIA or NARCOSIS. (See all compounds classified as Analgesics, Opioid.)
Carfentanil is an ultra-potent synthetic opioid. No human carfentanil metabolism data are available. Reportedly, Russian police forces used carfentanil and remifentanil to resolve a hostage situation in Moscow in 2002. This alleged use prompted interest in the pharmacology and toxicology of carfentanil in humans. Our study was conducted to identify human carfentanil metabolites and to assess carfentanil's metabolic clearance, which could contribute to its acute toxicity in humans. We used Simulations Plus's ADMET Predictor and Molecular Discovery's MetaSite to predict possible metabolite formation. Both programs gave similar results that were generally good but did not capture all metabolites seen in vitro. We incubated carfentanil with human hepatocytes for up to 1 hr and analyzed samples on a Sciex 3200 QTRAP mass spectrometer to measure parent compound depletion and extrapolated that to represent intrinsic clearance. Pooled primary human hepatocytes were then incubated with carfentanil up to 6 h and analyzed for metabolite identification on a Sciex 5600+ TripleTOF (QTOF) high-resolution mass spectrometer. MS and MS/MS analyses elucidated the structures of the most abundant metabolites. Twelve metabolites were identified in total. N-Dealkylation and monohydroxylation of the piperidine ring were the dominant metabolic pathways. Two N-oxide metabolites and one glucuronide metabolite were observed. Surprisingly, ester hydrolysis was not a major metabolic pathway for carfentanil. While the human liver microsomal system demonstrated rapid clearance by CYP enzymes, the hepatocyte incubations showed much slower clearance, possibly providing some insight into the long duration of carfentanil's effects.
PMID:27495118 Feasel MG et al; AAPS J 18 (6): 1489-1499 (2016)
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.
The positron emission tomography (PET) ligand [(11)C]carfentanil is a selective agonist for mu-opioid receptors and has been used for studying mu-opioid receptors in the human brain. However, it is unknown if [(11)C]carfentanil binding differentiates between subtype receptors mu1 and mu2. In this study, we investigated whether mu1 and mu2 can be studied separately through receptor subtype-selective inhibition of [(11)C]carfentanil by pharmacologic intervention. [(11)C]Carfentanil binding characteristics on rat brain sections were assessed either alone or in the presence of the mu-receptor inhibitor cyprodime or the mu1-specific inhibitor naloxonazine. [(11)C]Carfentanil binding in the living rat brain was similarly studied by small animal PET/computed tomography during baseline conditions or following displacement by cyprodime or naloxonazine. Autoradiography binding studies on rat brain sections demonstrated that [(11)C]carfentanil has higher affinity and binding potential for mu1 than for mu2. [(11)C]Carfentanil binding to mu2 in vivo could not be detected following specific blocking of mu1, as predicted from the low binding potential for mu2 as measured in vitro. [(11)C]Carfentanil binding is preferential for mu1 compared to mu2 in vitro and in vivo. Clinical studies employing [(11)C]carfentanil are therefore likely biased to measure mu1 rather than mu2.
PMID:26461068 Eriksson O, Antoni G; Mol Imaging 14:476-83 (2015)
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