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Also known as: Carfentanyl, 59708-52-0, Carfentanila, Carfentanilum, Wildnil, Carfentanil [inn]

Molecular Formula

C₂₄H₃₀N₂O₃

Molecular Weight

394.5 g/mol

InChI Key

YDSDEBIZUNNPOB-UHFFFAOYSA-N

FDA UNII

LA9DTA2L8F

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 1020 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.

1 2D Structure

Carfentanil

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

methyl 1-(2-phenylethyl)-4-(N-propanoylanilino)piperidine-4-carboxylate

2.1.2 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

2.1.3 InChI Key

YDSDEBIZUNNPOB-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CCC(=O)N(C1=CC=CC=C1)C2(CCN(CC2)CCC3=CC=CC=C3)C(=O)OC

2.2 Other Identifiers

2.2.1 UNII

LA9DTA2L8F

2.3 Synonyms

2.3.1 MeSH Synonyms

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

2.3.2 Depositor-Supplied Synonyms

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

2.4 Create Date

2005-03-28

3 Chemical and Physical Properties

Molecular Formula	C₂₄H₃₀N₂O₃
Molecular Weight	394.5 g/mol
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 Å²
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

4 Drug and Medication Information

4.1 Therapeutic Uses

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.

4.2 Drug Indication

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

5 Pharmacology and Biochemistry

5.1 Pharmacology

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.

5.2 MeSH Pharmacological Classification

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.)

5.3 Metabolism/Metabolites

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)

5.4 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.

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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Malladi Drugs & Pharmaceuticals Lim...

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Malladi is a leader in Ephedrine, Pseudoephedrine Salts & Phenylephrine HCl // USFDA, EDQM, ANSM, KFDA, and TGA inspected.

I-Benzyl-4-phenylamino-piperidine-4-carbonitrile

CAS Number : 968-86-5

End Use API : Carfentanil

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Malladi Drugs & Pharmaceuticals Lim...

India

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Not Confirmed

Malladi is a leader in Ephedrine, Pseudoephedrine Salts & Phenylephrine HCl // USFDA, EDQM, ANSM, KFDA, and TGA inspected.

1-Benzyl-4-phenylamino-piperidine-4-carboxamide

CAS Number : 1096-03-3

End Use API : Carfentanil

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Malladi Drugs & Pharmaceuticals Lim...

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Not Confirmed

Malladi is a leader in Ephedrine, Pseudoephedrine Salts & Phenylephrine HCl // USFDA, EDQM, ANSM, KFDA, and TGA inspected.

1-Benzyl-4-phenylamino-piperidine-4-carboxylic aci...

CAS Number : 85098-64-2

End Use API : Carfentanil

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Carfentanil Manufacturers

A Carfentanil manufacturer is defined as any person or entity involved in the manufacture, preparation, processing, compounding or propagation of Carfentanil, including repackagers and relabelers. The FDA regulates Carfentanil manufacturers to ensure that their products comply with relevant laws and regulations and are safe and effective to use. Carfentanil API Manufacturers are required to adhere to Good Manufacturing Practices (GMP) to ensure that their products are consistently manufactured to meet established quality criteria.

Carfentanil Suppliers

A Carfentanil supplier is an individual or a company that provides Carfentanil active pharmaceutical ingredient (API) or Carfentanil finished formulations upon request. The Carfentanil suppliers may include Carfentanil API manufacturers, exporters, distributors and traders.

click here to find a list of Carfentanil suppliers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PharmaCompass.

Carfentanil USDMF

A Carfentanil DMF (Drug Master File) is a document detailing the whole manufacturing process of Carfentanil active pharmaceutical ingredient (API) in detail. Different forms of Carfentanil DMFs exist exist since differing nations have different regulations, such as Carfentanil USDMF, ASMF (EDMF), JDMF, CDMF, etc.

A Carfentanil DMF submitted to regulatory agencies in the US is known as a USDMF. Carfentanil USDMF includes data on Carfentanil's chemical properties, information on the facilities and procedures used, and details about packaging and storage. The Carfentanil USDMF is kept confidential to protect the manufacturer’s intellectual property.

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Carfentanil GMP

Carfentanil Active pharmaceutical ingredient (API) is produced in GMP-certified manufacturing facility.

GMP stands for Good Manufacturing Practices, which is a system used in the pharmaceutical industry to make sure that goods are regularly produced and monitored in accordance with quality standards. The FDA’s current Good Manufacturing Practices requirements are referred to as cGMP or current GMP which indicates that the company follows the most recent GMP specifications. The World Health Organization (WHO) has its own set of GMP guidelines, called the WHO GMP. Different countries can also set their own guidelines for GMP like China (Chinese GMP) or the EU (EU GMP).

PharmaCompass offers a list of Carfentanil GMP manufacturers, exporters & distributors, which can be sorted by USDMF, JDMF, KDMF, CEP (COS), WC, API price, and more, enabling you to easily find the right Carfentanil GMP manufacturer or Carfentanil GMP API supplier for your needs.

Carfentanil CoA

A Carfentanil CoA (Certificate of Analysis) is a formal document that attests to Carfentanil's compliance with Carfentanil specifications and serves as a tool for batch-level quality control.

Carfentanil CoA mostly includes findings from lab analyses of a specific batch. For each Carfentanil CoA document that a company creates, the USFDA specifies specific requirements, such as supplier information, material identification, transportation data, evidence of conformity and signature data.

Carfentanil may be tested according to a variety of international standards, such as European Pharmacopoeia (Carfentanil EP), Carfentanil JP (Japanese Pharmacopeia) and the US Pharmacopoeia (Carfentanil USP).

Inform the supplier about your product requirements, specifying if you need a product with particular monograph like EP (Ph. Eur.), USP, JP, BP, or any other quality. In addition, clarify whether you need hydrochloride (HCl), anhydricum, base, micronisatum or a specific level of purity. To find reputable suppliers, utilize the filters and select those certified by GMP, FDA, or any other certification as per your requirement.
For your convenience, we have listed synonyms and CAS numbers to help you find the best supplier. The use of synonyms and CAS numbers can be helpful in identifying potential suppliers, but it is crucial to note that they might not always indicate the exact same product. It is important to confirm the product details with the supplier before making a purchase to ensure that it meets your requirements.

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