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Identification
Name Sufentanil
Accession Number DB00708 (APRD00671)
Type small molecule
Groups approved
Description

An opioid analgesic that is used as an adjunct in anesthesia, in balanced anesthesia, and as a primary anesthetic agent. [PubChem]
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  • sufentanil
  • Sufentanil Citrate
  • Sufentanilum [INN-Latin]
  • Sufentanyl
  • Sulfentanil Citrate
Brand names
  • Chronogesic
  • Sufenta
Brand name mixtures Not Available
Categories
  • Narcotics
  • Adjuvants, Anesthesia
  • Anesthetics, Intravenous
  • Opiate Agonists
  • Analgesics, Opioid
CAS number 56030-54-7
Weight Average: 386.551
Monoisotopic: 386.202798904
Chemical Formula C22H30N2O2S
InChI Key InChIKey=GGCSSNBKKAUURC-UHFFFAOYSA-N
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
Plain Text
IUPAC Name
N-[4-(methoxymethyl)-1-[2-(thiophen-2-yl)ethyl]piperidin-4-yl]-N-phenylpropanamide
SMILES
CCC(=O)N(C1=CC=CC=C1)C1(COC)CCN(CCC2=CC=CS2)CC1
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Fentanyls
Substructures
  • Amino Ketones
  • Ethers
  • Benzene and Derivatives
  • Aliphatic and Aryl Amines
  • Acetanilides
  • Fentanyls
  • Heterocyclic compounds
  • Aromatic compounds
  • Carboxamides and Derivatives
  • Thiophenes
  • Anilines
  • Piperidines
Pharmacology
Indication Used as an analgesic adjunct in anesthesia and as a primary anesthetic drug in procedures requiring assisted ventilation and in the relief of pain.
Pharmacodynamics Sufentanil is a synthetic opioid analgesic. Sufentanil interacts predominately with the opioid mu-receptor. These mu-binding sites are discretely distributed in the human brain, spinal cord, and other tissues. In clinical settings, sufentanil exerts its principal pharmacologic effects on the central nervous system. Its primary actions of therapeutic value are analgesia and sedation. Sufentanil may increase the patient's tolerance for pain and decrease the perception of suffering, although the presence of the pain itself may still be recognized. In addition to analgesia, alterations in mood, euphoria and dysphoria, and drowsiness commonly occur. Sufentanil depresses the respiratory centers, depresses the cough reflex, and constricts the pupils.
Mechanism of action Opiate receptors are coupled with G-protein receptors and function as both positive and negative regulators of synaptic transmission via G-proteins that activate effector proteins. Binding of the opiate stimulates the exchange of GTP for GDP on the G-protein complex. As the effector system is adenylate cyclase and cAMP located at the inner surface of the plasma membrane, opioids decrease intracellular cAMP by inhibiting adenylate cyclase. Subsequently, the release of nociceptive neurotransmitters such as substance P, GABA, dopamine, acetylcholine and noradrenaline is inhibited. Opioids also inhibit the release of vasopressin, somatostatin, insulin and glucagon. Sufentanil's analgesic activity is, most likely, due to its conversion to morphine. Opioids open calcium-dependent inwardly rectifying potassium channels (OP1 receptor agonist). This results in hyperpolarization and reduced neuronal excitability.
Absorption Not Available
Volume of distribution Not Available
Protein binding Not Available
Metabolism
Route of elimination Not Available
Half life 265 minutes
Clearance Not Available
Toxicity LD50: 18.7 mg/kg (IV in mice)
Affected organisms
  • Humans and other mammals
Pathways
Pathway Name SMPDB ID
Smp00417 Sufentanil Pathway SMP00417
Pharmacoeconomics
Manufacturers
  • Akorn inc
  • Baxter healthcare corp anesthesia and critical care
  • Hospira inc
  • Watson laboratories inc
Packagers
Dosage forms
Form Route Strength
Liquid Intravenous
Solution Epidural
Prices
Unit description Cost Unit
Sufentanil citrate powder 18927.0 USD g
Sufenta 50 mcg/ml ampul 5.38 USD ml
Sufentanil 50 mcg/ml ampul 3.92 USD ml
Patents Not Available
Properties
State solid
Melting point 97 oC
Experimental Properties
Property Value Source
water solubility 76 mg/L PhysProp
logP 2.8 PhysProp
logS -3.71 [ADME Research, USCD] PhysProp
Predicted Properties
Property Value Source
water solubility 1.20e-02 g/l ALOGPS
logP 3.40 ALOGPS
logP 3.61 ChemAxon Molconvert
logS -4.51 ALOGPS
pKa ChemAxon Molconvert
hydrogen acceptor count 3 ChemAxon Molconvert
hydrogen donor count 0 ChemAxon Molconvert
polar surface area 32.78 ChemAxon Molconvert
rotatable bond count 8 ChemAxon Molconvert
refractivity 111.42 ChemAxon Molconvert
polarizability 43.85 ChemAxon Molconvert
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
KEGG Drug D05938 Link_out
KEGG Compound C08022 Link_out
PubChem Compound 41693 Link_out
PubChem Substance 46504737 Link_out
ChemSpider 38043 Link_out
BindingDB 50012490 Link_out
ChEBI 9316 Link_out
ChEMBL 9316 Link_out
Therapeutic Targets Database DAP000357 Link_out
PharmGKB PA451527 Link_out
Drug Product Database 2244147 Link_out
Drugs.com http://www.drugs.com/cdi/sufentanil.html Link_out
Wikipedia http://en.wikipedia.org/wiki/Sufentanil Link_out
ATC Codes
  • N01AH03
AHFS Codes
  • 28:08.08
PDB Entries Not Available
FDA label Not Available
MSDS show (47.6 KB)
Interactions
Drug Interactions Not Available
Food Interactions Not Available
Targets

1. Mu-type opioid receptor

Pharmacological action: yes
Actions: agonist

Inhibits neurotransmitter release by reducing calcium ion currents and increasing potassium ion conductance. Receptor for beta-endorphin

Organism class: human
UniProt ID: P35372 Link_out
Gene: OPRM1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Hurle MA: Changes in the expression of G protein-coupled receptor kinases and beta-arrestin 2 in rat brain during opioid tolerance and supersensitivity. J Neurochem. 2001 Apr;77(2):486-92. Pubmed
  2. Levron JC: [Pharmacokinetics and pharmacodynamics of morphinomimetics in the central nervous system] Agressologie. 1991;32(6-7):318-20. Pubmed
  3. Ilien B, Galzi JL, Mejean A, Goeldner M, Hirth C: A mu-opioid receptor-filter assay. Rapid estimation of binding affinity of ligands and reversibility of long-lasting ligand-receptor complexes. Biochem Pharmacol. 1988 Oct 15;37(20):3843-51. Pubmed
  4. Colpaert FC, Leysen JE, Michiels M, van den Hoogen RH: Epidural and intravenous sufentanil in the rat: analgesia, opiate receptor binding, and drug concentrations in plasma and brain. Anesthesiology. 1986 Jul;65(1):41-9. Pubmed
  5. Leysen JE, Gommeren W: In vitro binding properties of 3H-sufentanil, a superior ligand for the mu-opiate receptor. Arch Int Pharmacodyn Ther. 1982 Dec;260(2):287-9. Pubmed
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed

2. Delta-type opioid receptor

Pharmacological action: unknown
Actions: agonist

Inhibits neurotransmitter release by reducing calcium ion currents and increasing potassium ion conductance. Highly stereoselective. receptor for enkephalins

Organism class: human
UniProt ID: P41143 Link_out
Gene: OPRD1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Freye E, Latasch L, Portoghese PS: The delta receptor is involved in sufentanil-induced respiratory depression—opioid subreceptors mediate different effects. Eur J Anaesthesiol. 1992 Nov;9(6):457-62. Pubmed
  2. Zhu J, Xue JC, Law PY, Claude PA, Luo LY, Yin J, Chen C, Liu-Chen LY: The region in the mu opioid receptor conferring selectivity for sufentanil over the delta receptor is different from that over the kappa receptor. FEBS Lett. 1996 Apr 15;384(2):198-202. Pubmed

3. Kappa-type opioid receptor

Pharmacological action: unknown
Actions: other

Inhibits neurotransmitter release by reducing calcium ion currents and increasing potassium ion conductance. Receptor for dynorphins. May play a role in arousal and regulation of autonomic and neuroendocrine functions

Organism class: human
UniProt ID: P41145 Link_out
Gene: OPRK1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Zhu J, Xue JC, Law PY, Claude PA, Luo LY, Yin J, Chen C, Liu-Chen LY: The region in the mu opioid receptor conferring selectivity for sufentanil over the delta receptor is different from that over the kappa receptor. FEBS Lett. 1996 Apr 15;384(2):198-202. Pubmed
  2. Chang HM, Berde CB, Holz GG 4th, Steward GF, Kream RM: Sufentanil, morphine, met-enkephalin, and kappa-agonist (U-50,488H) inhibit substance P release from primary sensory neurons: a model for presynaptic spinal opioid actions. Anesthesiology. 1989 Apr;70(4):672-7. Pubmed
Enzymes

1. Cytochrome P450 3A4

Actions: substrate

Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4- hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. The enzyme also hydroxylates etoposide

UniProt ID: P08684 Link_out
Gene: CYP3A4
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed
Comments
Drug created on June 13, 2005 07:24 / Updated on April 19, 2011 15:05

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.