Structure via PubChem · Public domain (PubChem)
sufentanil
Sign in to saveAlso known as Sufenta®, sufentanil citrate, N-(4-(Methoxymethyl)-1-(2-(2-thienyl)ethyl)-4-piperidyl)propionanilide, N-(4-(Methoxymethyl)-1-(2-(2-thienyl)ethyl)-4-piperidinyl)-N-phenylpropanamide, Sufentanyl, Sufentanilo, Sufentanilum
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), and the replacement of the phenyl ring by thiophene. Sufentanil first was synthesized at Janssen Pharmaceutica in 1974.
Chemical data
- Formula
- C22H30N2O2S
- Molecular weight
- 386.6 g/mol
- IUPAC name
- N-[4-(methoxymethyl)-1-(2-thiophen-2-ylethyl)piperidin-4-yl]-N-phenylpropanamide
- SMILES
- CCC(=O)N(C1=CC=CC=C1)C2(CCN(CC2)CCC3=CC=CS3)COC
- InChIKey
- GGCSSNBKKAUURC-UHFFFAOYSA-N
- XLogP
- 4
- Polar surface area
- 61 Ų
- H-bond donors
- 0
- H-bond acceptors
- 4
- Formal charge
- 0
via PubChem
Research
4,382 papers- Sufentanil Sublingual Tablet: A New Option for Acute Pain Management.The Annals of pharmacotherapy · 2019
- Hydromorphone vs sufentanil in patient-controlled analgesia for postoperative pain management: A meta-analysis.Medicine · 2022
- Sufentanil 30 µg Sublingual Tablet: A Review in Acute Pain.Clinical drug investigation · 2019
- Spinal sufentanil.Anaesthesia · 1998
- Sufentanil in anaesthesiology and intensive therapy.Anaesthesiology intensive therapy · 2012
via PubMed
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 386.202799
- Has use
- medication
Show 8 more facts
- chemical formula
- C₂₂H₃₀N₂O₂S
- medical condition treated
- pain
- Commons category
- Sufentanil
- canonical SMILES
- CCC(=O)N(C1=CC=CC=C1)C2(CCN(CC2)CCC3=CC=CS3)COC
- legal status (medicine)
- boxed warning
- World Health Organisation international non-proprietary name
- sufentanil
- significant drug interaction
- primidone
- stylized name
- SUFentanil
Sources (6)
via Wikidata · CC0
~3 min read
Encyclopedic overview
7 sectionsContents
- Medical uses
- Overdose
- Management
- Society and culture
- Brand names
- Veterinary use
- References
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), and the replacement of the phenyl ring by thiophene. Sufentanil first was synthesized at Janssen Pharmaceutica in 1974.
==Medical uses== Sufentanil offers properties of sedation and can be used as analgesic component of anesthetic regimen during an operation.
Excerpted from Wikipedia’s “sufentanil” article, available under the CC BY-SA 4.0 licence.