8887. Sufentanil

Nomenclature

CAS number: 56030-54-7
N-[4-(Methoxymethyl)-1-[2-(2-thienyl)ethyl]-4-piperidinyl]-N-phenylpropanamide; N-[4-(methoxymethyl)-1-[2-(2-thienyl)ethyl]-4-piperidyl]propionanilide; sufentanyl; R-30730.
C22H30N2O2S; mol wt 386.55.
C 68.36%, H 7.82%, N 7.25%, O 8.28%, S 8.30%.

Description and references

Synthetic opioid analgesic; derivative of fentanyl, q.v. Prepn: P. A. J. Janssen, G. H. P. Van Daele, DE 2610228; eidem, US 3998834 (both 1976 to Janssen); G. H. P. Van Daele et al., Arzneim.-Forsch. 26, 1521 (1976). Analgesic activity and safety assessment: W. F. M. Van Bever et al., ibid. 1548; C. J. E. Niemegeers et al., ibid. 1551. In vitro binding properties to mu-opiate receptor: J. E. Leyson et al., Eur. J. Pharmacol. 87, 209 (1983). LC-MS/MS determn in plasma: R. Schmidt et al., J. Chromatogr. B 836, 98 (2006). Comparative review of clinical pharmacokinetics: J. Scholz et al., Clin. Pharmacokinet. 31, 275-292 (1996). Review of clinical efficacy in postoperative analgesia: J. A. Grass, J. Pain Symptom Manage. 7, 271-286 (1992).

Chemical structure

Properties

Crystals from petr ether, mp 96.6°. pKa 8.01. Partition coefficient (octanol/water): 1727. LD50 i.v. in mice: 18.7 mg/kg (Van Bever).

Derivative

Citrate.

Nomenclature

CAS number: 60561-17-3
R-33800; Fentatienil (Angelini); Sufenta (Janssen-Cilag).
C22H30N2O2S.C6H8O7; mol wt 578.67.
C 58.12%, H 6.62%, N 4.84%, O 24.88%, S 5.54%.

Properties

White powder. Sol in water; freely sol in methanol; sparingly sol in acetone, ethanol, chloroform.

Note

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

Therapeutic Category

Analgesic; anesthesia adjunct.

Keywords

Analgesic; Opioids; Phenylpiperidines