Sufentanil

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Sufentanil
Sufentanil.svg
Sufentanil3Dan3.gif
Systematic (IUPAC) name
N-[4-(Methoxymethyl)-1-(2-thiofuran-2-ylethyl)-4-piperidyl]-N-phenylpropanamide
Clinical data
Trade names Sufenta
AHFS/Drugs.com monograph
Pregnancy cat.
Legal status
Routes IV, IM, SubQ, epidural, intrathecal, transdermal patch (in clinical trials)
Pharmacokinetic data
Half-life 162 minutes
Identifiers
CAS number 56030-54-7 YesY
ATC code N01AH03
PubChem CID 41693
IUPHAR ligand 3534
DrugBank DB00708
ChemSpider 38043 YesY
UNII AFE2YW0IIZ YesY
KEGG D05938 YesY
ChEBI CHEBI:9316 YesY
ChEMBL CHEMBL658 YesY
Chemical data
Formula C22H30N2O2S 
Mol. mass 386.552 g/mol
Physical data
Melt. point 97 °C (207 °F)
 YesY (what is this?)  (verify)

Sufentanil (R30730, brand name Sufenta) is a synthetic opioid analgesic drug approximately 5 to 10 times more potent than its parent drug, fentanyl, and 500 times as potent as morphine. Sufentanil is marketed for use by specialist centers under different trade names, such as Sufenta and Sufentil (India, by Claris Lifesciences Ltd.). Sufentanil was synthesized at Janssen Pharmaceutica in 1974.[1]

Sufentanil with and without lidocaine or mepivacaine is available as a transdermal patch similar to Duragesic in Europe under trade names such as Chronogesic.

Uses[edit]

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.[2] 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[when?] 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.

Side effects[edit]

It is essential for the administering medical professional to be trained in airway management with readily available airway equipment because the drug causes significant respiratory depression and may cause respiratory arrest if given too rapidly or in too high a dose. Other opioid side effects such as heart rhythm irregularity, blood pressure changes and nausea/vomiting can also be present in patients given this drug and should be dealt with accordingly.

Sufentanil has been associated with extremely rare instances of life-threatening anaphylaxis.[medical citation needed]

Synthesis[edit]

Sufentanil can by synthesized from N-benzyl-4-piperidone.[3][4]

Sufentanil synthesis

See also[edit]

References[edit]

  1. ^ 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. 
  2. ^ Savoia G, Loreto M, Gravino E (September 2001). "Sufentanil: an overview of its use for acute pain management". Minerva Anestesiologica 67 (9 Suppl 1): 206–216. PMID 11778119. 
  3. ^ Van Bever, W. F.; Niemegeers, C. J.; Schellekens, K. H.; Janssen, P. A. (1976). "N-4-Substituted 1-(2-arylethyl)-4-piperidinyl-N-phenylpropanamides, a novel series of extremely potent analgesics with unusually high safety margin". Arzneimittel-Forschung 26 (8): 1548–51. PMID 12771.  edit
  4. ^ Kiricojevic, V.; Ivanovic, M.; Micovic, I. V.; Djordjevic, J. B.; Roglic, G.; Dosen-Micovic, L. (2002). "An optimized synthesis of a key pharmaceutical intermediate methyl 4-[(1-oxopropyl)phenylamino]piperidine-4-carboxylate". Journal of the Serbian Chemical Society 67 (12): 793. doi:10.2298/JSC0212793K.  edit