Sufentanil

Sufentanil
Clinical data
Trade names	Dsuvia, Sufenta, Zalviso, others
Other names	R30730
AHFS/Drugs.com	Monograph
License data	US DailyMed: Sufentanil;
Routes of; administration	Intravenous therapy (IV), intramuscular injection (IM), subcutaneous injection (SQ), epidural, intrathecal, sublingual
ATC code	N01AH03 (WHO) ;
Legal status
Legal status	AU: S8 (Controlled drug); BR: Class A1 (Narcotic drugs); CA: Schedule I; DE: Anlage III (Special prescription form required); UK: Class A; US: Schedule II; EU: Rx-only; In general: ℞ (Prescription only);
Pharmacokinetic data
Bioavailability	Sublingual: 53% IV/IM/SC: 100%
Elimination half-life	162 minutes
Duration of action	30 to 60 min
Identifiers
	IUPAC name N-[4-(Methoxymethyl)-1-(2-thiofuran-2-ylethyl)-4-piperidyl]-N-phenylpropanamide;
CAS Number	56030-54-7 ;
PubChem CID	41693;
IUPHAR/BPS	3534;
DrugBank	DB00708 ;
ChemSpider	38043 ;
UNII	AFE2YW0IIZ;
KEGG	D05938 ; as salt: D00845 ;
ChEBI	CHEBI:9316 ;
ChEMBL	ChEMBL658 ;
CompTox Dashboard (EPA)	DTXSID6023604 ;
ECHA InfoCard	100.168.858
Chemical and physical data
Formula	C22H30N2O2S
Molar mass	386.55 g·mol−1
3D model (JSmol)	Interactive image;
Melting point	97 °C (207 °F)
	SMILES O=C(N(c1ccccc1)C2(COC)CCN(CC2)CCc3sccc3)CC;
	InChI InChI=1S/C22H30N2O2S/c1-3-21(25)24(19-8-5-4-6-9-19)22(18-26-2)12-15-23(16-13-22)14-11-20-10-7-17-27-20/h4-10,17H,3,11-16,18H2,1-2H3 ; Key:GGCSSNBKKAUURC-UHFFFAOYSA-N ;
	(verify)

Sufentanil, sold under the brand names Sufenta among others, is a synthetic opioid analgesic drug approximately 5 to 10 times as potent as its parent drug, fentanyl, and 500 to 1,000 times as potent as morphine. Structurally, sufentanil differs from fentanyl through the addition of a methoxymethyl group on the piperidine ring (which increases potency but is believed to reduce duration of action^[6]), and the replacement of the phenyl ring by thiophene. Sufentanil first was synthesized at Janssen Pharmaceutica in 1974.^[7]

^ Anvisa (31 March 2023). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 4 April 2023). Archived from the original on 3 August 2023. Retrieved 16 August 2023.
^ "Sufenta- sufentanil citrate solution". DailyMed. 2 July 2008. Retrieved 13 September 2024.
^ "Dsuvia- sufentanil tablet". DailyMed. 18 December 2023. Retrieved 13 September 2024.
^ "Dzuveo EPAR". European Medicines Agency (EMA). 25 June 2018. Retrieved 13 September 2024.
^ Shaw LM (2001). The clinical toxicology laboratory : contemporary practice of poisoning evaluation. Washington, DC: AACC Press. p. 89. ISBN 978-1-890883-53-9.
^ Vucković S, Prostran M, Ivanović M, Dosen-Mićović Lj, Todorović Z, Nesić Z, et al. (2009). "Fentanyl analogs: structure-activity-relationship study". Current Medicinal Chemistry. 16 (19): 2468–2474. doi:10.2174/092986709788682074. PMID 19601792.
^ Niemegeers CJ, Schellekens KH, Van Bever WF, Janssen PA (1976). "Sufentanil, a very potent and extremely safe intravenous morphine-like compound in mice, rats and dogs". Arzneimittel-Forschung. 26 (8): 1551–1556. PMID 12772.

[1] Anvisa (31 March 2023). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 4 April 2023). Archived from the original on 3 August 2023. Retrieved 16 August 2023.

[Sufenta_FDA_label-2] "Sufenta- sufentanil citrate solution". DailyMed. 2 July 2008. Retrieved 13 September 2024.

[3] "Dsuvia- sufentanil tablet". DailyMed. 18 December 2023. Retrieved 13 September 2024.

[4] "Dzuveo EPAR". European Medicines Agency (EMA). 25 June 2018. Retrieved 13 September 2024.

[5] Shaw LM (2001). The clinical toxicology laboratory : contemporary practice of poisoning evaluation. Washington, DC: AACC Press. p. 89. ISBN 978-1-890883-53-9.

[Vuckovic_2009-6] Vucković S, Prostran M, Ivanović M, Dosen-Mićović Lj, Todorović Z, Nesić Z, et al. (2009). "Fentanyl analogs: structure-activity-relationship study". Current Medicinal Chemistry. 16 (19): 2468–2474. doi:10.2174/092986709788682074. PMID 19601792.

[Niemegeers_1976-7] Niemegeers CJ, Schellekens KH, Van Bever WF, Janssen PA (1976). "Sufentanil, a very potent and extremely safe intravenous morphine-like compound in mice, rats and dogs". Arzneimittel-Forschung. 26 (8): 1551–1556. PMID 12772.

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