4001. Fentanyl

Nomenclature

CAS number: 437-38-7
N-Phenyl-N-[1-(2-phenylethyl)-4-piperidinyl]propanamide; N-(1-phenethyl-4-piperidyl)propionanilide; N-(1-phenethyl-4-piperidinyl)-N-phenylpropionamide; phentanyl; R-4263; Matrifen (Nycomed); Duragesic (Ortho-McNeil); Durogesic (Janssen-Cilag).
C22H28N2O; mol wt 336.47.
C 78.53%, H 8.39%, N 8.33%, O 4.76%.

Description and references

Prototype anilidopiperidine opioid analgesic. Prepn: P. A. J. Janssen, FR 1344366; idem, US 3164600 (1963, 1965 both to Janssen). Pharmacology: J. F. Gardocki, J. Yelnosky, Toxicol. Appl. Pharmacol. 6, 48 (1964); R. Hess et al., J. Pharmacol. Exp. Ther. 179, 474 (1971). LC-MS/MS determn in human plasma and urine: N.-H. Huynh et al., J. Pharm. Biomed. Anal. 37, 1095 (2005). Effects on cerebral circulation and metabolism in rats: C. Carlsson et al., Anesthesiology 57, 375 (1982). Clinical studies: E. A. Welchew, J. A. Thornton, Anaesthesia 37, 309 (1982); M. J. Stephens et al., Med. J. Aust. 1, 419 (1982). Clinical comparison with morphine for post-operative pain: H. S. Minkowitz et al., Pain Med. 8, 657 (2007). Review of clinical experience with transdermal formulation: R. B. R. Muijsers, A. J. Wagstaff, Drugs 61, 2289-2307 (2001).

Chemical structure

Properties

Crystals, mp 83-84°. Partition coefficient (n-octanol/water): 860. pKa 8.4.

Derivative

Citrate.

Nomenclature

CAS number: 990-73-8
Actiq (Cephalon); Fentanest (Pharmacia); Leptanal (Janssen-Cilag); Sublimaze (Janssen-Cilag).
C22H28N2O.C6H8O7; mol wt 528.59.
C 63.62%, H 6.86%, N 5.30%, O 24.21%.

Properties

Crystalline powder, mp 149-151°. Bitter taste. One gram dissolves in about 40 ml water. Sol in methanol; sparingly sol in chloroform. LD50 in mice (mg/kg): 11.2 i.v.; 62 s.c. (Gardocki, Yelnosky).

Note

This is a controlled substance (opiate): 21 CFR, 1308.12.

Therapeutic Category

Analgesic.

Therapeutic Category (Veterinary)

Analgesic; tranquilizer.

Keywords

Analgesic; Opioids; Phenylpiperidines