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Sufentanil information


Sufentanil
Clinical data
Trade namesDsuvia, Sufenta, Zalviso
Other namesR30730
AHFS/Drugs.comMonograph
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)[2]
  • CA: Schedule I
  • DE: Anlage III (Special prescription form required)
  • UK: Class A
  • US: WARNING[1]Schedule II
  • EU: Rx-only
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability53% (sublingual)
Elimination half-life162 minutes
Duration of action30 to 60 min[3]
Identifiers
IUPAC name
  • N-[4-(Methoxymethyl)-1-(2-thiofuran-2-ylethyl)-4-piperidyl]-N-phenylpropanamide
CAS Number
  • 56030-54-7 checkY
PubChem CID
  • 41693
IUPHAR/BPS
  • 3534
DrugBank
  • DB00708 checkY
ChemSpider
  • 38043 checkY
UNII
  • AFE2YW0IIZ
KEGG
  • D05938 checkY
  • as salt: D00845 checkY
ChEBI
  • CHEBI:9316 checkY
ChEMBL
  • ChEMBL658 checkY
CompTox Dashboard (EPA)
  • DTXSID6023604 Edit this at Wikidata
ECHA InfoCard100.168.858 Edit this at Wikidata
Chemical and physical data
FormulaC22H30N2O2S
Molar mass386.55 g·mol−1
3D model (JSmol)
  • Interactive image
Melting point97 °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 checkY
  • Key:GGCSSNBKKAUURC-UHFFFAOYSA-N checkY
  (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]

  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.
  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.
  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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(3‑methylcarfentanyl), N-Methylnorcarfentanil, R-30490 (4‑methoxymethylfentanyl), sufentanil, and thiafentanil. Over three hundred cases of overdose related to fentanyl...

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Thiophene

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such as the NSAID lornoxicam, the thiophene analog of piroxicam, and sufentanil, the thiophene analog of fentanyl. International Union of Pure and Applied...

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Ketamine

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Racemethorphan Racemorphan Remifentanil Salsolinol SC-17599 Sinomenine Sufentanil Tapentadol Tetrahydropapaveroline TH-030418 Thebaine Thienorphine Tianeptine...

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Alfentanil

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Mathew, J. Kendall Killgore. Methods for the synthesis of alfentanil, sufentanil, and remifentanil. US Patent 7,208,604 "From DEA website, accessed 23...

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Premedication

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associated with separation from parents and induction of anesthesia. Sufentanil is also sometimes used as a premedication. Clonidine is becoming increasingly...

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Capsaicin

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Menthol

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Paracetamol

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Morphine

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Lethal injection

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fail-safe measure using intramuscular injection of midazolam, followed by sufentanil or hydromorphone in the event intravenous administration of the sodium...

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Remifentanil

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pulmonary function after laparoscopic gastric banding: remifentanil TCI vs sufentanil TCI in morbid obesity". British Journal of Anaesthesia. 99 (3): 404–11...

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Oxycodone

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Ticarcillin

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divalent sulfur is roughly equivalent to a vinyl group (cf methiopropamine, sufentanil, pizotyline etc.). One synthesis began by making the monobenzyl ester...

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Heroin

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General anaesthesia

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premedication agent, and often reduce need for opioids such as fentanyl or sufentanil. Also gastrokinetic agents such as metoclopramide, and histamine antagonists...

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Cannabis

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