Sufentanil

Sufentanil
Clinical data
Trade names	Dsuvia, Sufenta, Zalviso
Other names	R30730
AHFS/Drugs.com	Monograph
License data	EU EMA: by INN; 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: WARNINGSchedule II; EU: Rx-only; In general: ℞ (Prescription only);
Pharmacokinetic data
Bioavailability	53% (sublingual)
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 Dsuvia and Sufenta, 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^[4]), and the replacement of the phenyl ring by thiophene. Sufentanil first was synthesized at Janssen Pharmaceutica in 1974.^[5]

Sufentanil is marketed for use by specialist centers^{[clarification needed]} under different trade names, such as Sufenta and Sufentil. Sufentanil with and without lidocaine or mepivacaine is available as a transdermal patch similar to Duragesic in Europe under trade names such as Chronogesic. It is available as a sublingual tablet under the trade name Dsuvia.^[6]

^ "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 Oct 2023.
^ Anvisa (2023-03-31). "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 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.
^ Shaw, Leslie M. (2001). The clinical toxicology laboratory : contemporary practice of poisoning evaluation. Washington, DC: AACC Press. p. 89. ISBN 9781890883539.
^ Vucković S, Prostran M, Ivanović M, Dosen-Mićović Lj, Todorović Z, Nesić Z, Stojanović R, Divac N, Miković Z (2009). "Fentanyl analogs: structure-activity-relationship study". Curr Med Chem. 16 (9): 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): 1551–6. PMID 12772.
^ Silverman, Ed (November 2, 2018). "Despite criticism and concerns, FDA approves a new opioid 10 times more powerful than fentanyl". Pharmalot. Retrieved November 2, 2018.

[FDA-AllBoxedWarnings-1] "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 Oct 2023.

[2] Anvisa (2023-03-31). "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 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.

[3] Shaw, Leslie M. (2001). The clinical toxicology laboratory : contemporary practice of poisoning evaluation. Washington, DC: AACC Press. p. 89. ISBN 9781890883539.

[pmid19601792-4] Vucković S, Prostran M, Ivanović M, Dosen-Mićović Lj, Todorović Z, Nesić Z, Stojanović R, Divac N, Miković Z (2009). "Fentanyl analogs: structure-activity-relationship study". Curr Med Chem. 16 (9): 2468–2474. doi:10.2174/092986709788682074. PMID 19601792.

[pmid12772-5] 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): 1551–6. PMID 12772.

[6] Silverman, Ed (November 2, 2018). "Despite criticism and concerns, FDA approves a new opioid 10 times more powerful than fentanyl". Pharmalot. Retrieved November 2, 2018.

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