Sufentanil

Sufentanil

Clinical data
Trade names	Sufenta
AHFS/Drugs.com	Monograph
Pregnancy category	US: C (Risk not ruled out)
Routes of administration	IV, IM, SubQ, epidural, intrathecal, transdermal patch (in clinical trials)
ATC code	N01AH03 (WHO)
Legal status
Legal status	AU: S8 (Controlled) CA: Schedule I DE: Anlage III (Prescription only) UK: Class A US: Schedule II ℞ (Prescription only)
Pharmacokinetic data
Biological 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 Y
PubChem (CID)	41693
IUPHAR/BPS	3534
DrugBank	DB00708 Y
ChemSpider	38043 Y
UNII	AFE2YW0IIZ Y
KEGG	D05938 Y
ChEBI	CHEBI:9316 Y
ChEMBL	CHEMBL658 Y
ECHA InfoCard	100.168.858
Chemical and physical data
Formula	C22H30N2O2S
Molar mass	386.552 g/mol
3D model (Jmol)	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 Y Key:GGCSSNBKKAUURC-UHFFFAOYSA-N Y

Sufentanil (R30730, brand name Sufenta) is a synthetic opioid analgesic drug approximately five to 10 times more potent than its parent drug, fentanyl, and 500 times as potent as morphine. Structurally, sufentanil differs from fentanyl through the addition of a methoxymethyl group on the piperidine ring (which 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.

Sufentanil is marketed for use by specialist centers 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.

The main use of this medication is in operating suites and critical care where pain relief is required for a short period of time. It also offers properties of sedation and this makes it a good analgesic component of anesthetic regimen during an operation. It is usually administered under the doctor's order through an intravenous route. In some countries, sufentanil is only indicated for epidural use. Despite this, it is often used off-label both intravenously and intranasally. A transdermal sufentanil patch called Transdur-sufentanil is about to enter Stage III clinical trials by Durect Corp for the relief of chronic pain, and has the advantage over fentanyl patches such as Duragesic of only needing to be applied once per week. Sufentanil is also used off-label in intrathecal pumps.

Because of its extremely high potency, it is often used in surgery and post-operative pain management for patients that are heavily opioid dependent/opioid tolerant because of long term opiate use for chronic pain or illicit opiate use. Currently sufentanil is the strongest opioid painkiller available for use in humans. Although stronger narcotic pain medications do exist, all medications stronger than sufentanil are approved for veterinary use only. It is also used in surgery and post operative pain control in patients that are taking high dose buprenorphine for chronic pain because it is the only opioid that has a potency and binding affinity strong enough to displace buprenorphine from the opioid receptors in the central nervous system and provide analgesia.