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Showing toxin card for Sufentanil (T3D2865)

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Version 1.0
Creation Date 2009-07-21 20:27:27
Update Date 2010-05-18 21:00:29
Accession Number T3D2865
Name Sufentanil
Compound Type
  • Adjuvant, Anesthesia
  • Analgesic, Opioid
  • Anesthetic, Intravenous
  • Drug
  • Narcotic
  • Opiate Agonist
Description An opioid analgesic that is used as an adjunct in anesthesia, in balanced anesthesia, and as a primary anesthetic agent. [PubChem]
Synonyms
  1. sufentanil
  2. Sufentanil Citrate
  3. Sufentanilum [INN-Latin]
  4. Sufentanyl
  5. Sulfentanil Citrate
Chemical IUPAC Name N-[4-(methoxymethyl)-1-[2-(thiophen-2-yl)ethyl]piperidin-4-yl]-N-phenylpropanamide
Chemical Formula C22H30N2O2S
Chemical Structure Structure
CAS Registry Number 56030-54-7
InChI Identifier 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
InChI Key InChIKey=GGCSSNBKKAUURC-UHFFFAOYSA-N
PubChem Compound ID 41693 Link Image
KEGG ID C08022 Link Image
UniProt ID Not Available
OMIM ID Not Available
ChEBI ID Not Available
BioCyc ID Not Available
SuperToxic ID Not Available
CTD ID Not Available
Stitch ID Sufentanil Link Image
DrugBank ID DB00708 Link Image
PDB ID Not Available
ACToR ID Not Available
Wikipedia Link http://en.wikipedia.org/wiki/Sufentanil Link Image
Monoisotopic Mass 386.202799
MOL File Show
PDB File Show
SDF File Show
SMILES CCC(=O)N(C1=CC=CC=C1)C1(COC)CCN(CCC2=CC=CS2)CC1
Appearance Not Available
Melting Point 97 oC
Solubility 76 mg/L
Predicted LogP 3.6052
Route of Exposure Epidural; parenteral(intravenous)
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.
Metabolism Not Available
Toxicity Values LD50: 18.7 mg/kg (parenteral-intravenous, mouse)
Lethal Dose Not Available
Carcinogenicity (IARC Classification) Not Available
Uses/Sources 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 anaesthetic regimen during an operation. [Wikipedia]
Minimum Risk Level Not Available
Health Effects may cause respiratory arrest. [Wikipedia] Medical problems can include congested lungs, liver disease, tetanus, infection of the heart valves, skin abscesses, anemia and pneumonia. Death can occur from overdose.
Symptoms Respiratory depression. [Wikipedia]
Treatment Not Available
General References
  • U216 - Drugs.com
Targets
  1. Mu-type opioid receptor
Target 1 [top]
Target 1 ID 1155
Target 1 Name Mu-type opioid receptor
Target 1 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.
Target 1 Description Inhibits neurotransmitter release by reducing calcium ion currents and increasing potassium ion conductance. Receptor for beta-endorphin
Target 1 Synonyms
  1. MOR-1
Target 1 Gene Name OPRM1
Target 1 Protein Sequence >Mu-type opioid receptor 
MDSSAAPTNASNCTDALAYSSCSPAPSPGSWVNLSHLDGNLSDPCGPNRTDLGGRDSLCP
PTGSPSMITAITIMALYSIVCVVGLFGNFLVMYVIVRYTKMKTATNIYIFNLALADALAT
STLPFQSVNYLMGTWPFGTILCKIVISIDYYNMFTSIFTLCTMSVDRYIAVCHPVKALDF
RTPRNAKIINVCNWILSSAIGLPVMFMATTKYRQGSIDCTLTFSHPTWYWENLLKICVFI
FAFIMPVLIITVCYGLMILRLKSVRMLSGSKEKDRNLRRITRMVLVVVAVFIVCWTPIHI
YVIIKALVTIPETTFQTVSWHFCIALGYTNSCLNPVLYAFLDENFKRCFREFCIPTSSNI
EQQNSTRIRQNTRDHPSTANTVDRTNHQLENLEAETAPLP
Target 1 Number of Residues 400
Target 1 Molecular Weight 44778.9
Target 1 Theoretical pI 8.29
Target 1 GO Classification
Function
peptide receptor activity, G-protein coupled
opioid receptor activity
mu-opioid receptor activity
signal transducer activity
receptor activity
transmembrane receptor activity
G-protein coupled receptor activity
rhodopsin-like receptor activity
Process
cellular process
cell communication
signal transduction
cell surface receptor linked signal transduction
G-protein coupled receptor protein signaling pathway
Component
cell
membrane
intrinsic to membrane
integral to membrane
Target 1 General Function Involved in mu-opioid receptor activity
Target 1 Pathways Not Available
Target 1 Reactions Not Available
Target 1 Signals
  • None
Target 1 Transmembrane Regions
  • 67-96
  • 106-123
  • 146-165
  • 196-211
  • 237-259
  • 283-305
  • 314-330
Target 1 Essentiality Non Essential
Target 1 Domain Function PF00001:7tm_1
Target 1 GenBank ID Protein Not Available
Target 1 UniProtKB ID P35372 Link Image
Target 1 Cellular Location Cell membrane
Target 1 Gene Sequence >1203 bp 
ATGGACAGCAGCGCTGCCCCCACGAACGCCAGCAATTGCACTGATGCCTTGGCGTACTCA
AGTTGCTCCCCAGCACCCAGCCCCGGTTCCTGGGTCAACTTGTCCCACTTAGATGGCAAC
CTGTCCGACCCATGCGGTCCGAACCGCACCAACCTGGGCGGGAGAGACAGCCTGTGCCCT
CCGACCGGCAGTCCCTCCATGATCACGGCCATCACGATCATGGCCCTCTACTCCATCGTG
TGCGTGGTGGGGCTCTTCGGAAACTTCCTGGTCATGTATGTGATTGTCAGATACACCAAG
ATGAAGACTGCCACCAACATCTACATTTTCAACCTTGCTCTGGCAGATGCCTTAGCCACC
AGTACCCTGCCCTTCCAGAGTGTGAATTACCTAATGGGAACATGGCCATTTGGAACCATC
CTTTGCAAGATAGTGATCTCCATAGATTACTATAACATGTTCACCAGCATATTCACCCTC
TGCACCATGAGTGTTGATCGATACATTGCAGTCTGCCACCCTGTCAAGGCCTTAGATTTC
CGTACTCCCCGAAATGCCAAAATTATCAATGTCTGCAACTGGATCCTCTCTTCAGCCATT
GGTCTTCCTGTAATGTTCATGGCTACAACAAAATACAGGCAAGGTTCCATAGATTGTACA
CTAACATTCTCTCATCCAACCTGGTACTGGGAAAACCTCGTGAAGATCTGTGTTTTCATC
TTCGCCTTCATTATGCCAGTGCTCATCATTACCGTGTGCTATGGACTGATGATCTTGCGC
CTCAAGAGTGTCCGCATGCTCTCTGGCTCCAAAGAAAAGGACAGGAATCTTCGAAGGATC
ACCAGGATGGTGCTGGTGGTGGTGGCTGTGTTCATCGTCTGCTGGACTCCCATTCACATT
TACGTCATCATTAAAGCCTTGGTTACAATCCCAGAAACTACGTTCCAGACTGTTTCTTGG
CACTTCTGCATTGCTCTAGGTTACACAAACAGCTGCCTCAACCCAGTCCTTTATGCATTT
CTGGATGAAAACTTCAAACGATGCTTCAGAGAGTTCTGTATCCCAACCTCTTCCAACATT
GAGCAACAAAACTCCACTCGAATTCGTCAGAACACTAGAGACCACCCCTCCACGGCCAAT
ACAGTGGATAGAACTAATCATCAGCTAGAAAATCTGGAAGCAGAAACTGCTCCGTTGCCC
TAA
Target 1 GenBank Gene ID Not Available
Target 1 GeneCard ID OPRM1 Link Image
Target 1 GenAtlas ID OPRM1 Link Image
Target 1 HGNC ID HGNC:8156 Link Image
Target 1 Chromosome Location Not Available
Target 1 Locus 6q24-q25
Target 1 SNPs SNPJam Report Link Image
Target 1 Toxin References
  • S918 - Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed Link Image]
  • U221 - Leysen JE, Gommeren W: In vitro binding properties of 3H-sufenta, a superior ligand for the mu-opiate receptor. Arch Int Pharmacodyn Ther. 1982 Dec;260(2):287-9. [PubMed Link Image]
  • U218 - Levron JC: [Pharmacokinetics and pharmacodynamics of morphinomimetics in the central nervous system] Agressologie. 1991;32(6-7):318-20. [PubMed Link Image]
  • U217 - 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 Link Image]
  • U219 - 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 Link Image]
  • U220 - Colpaert FC, Leysen JE, Michiels M, van den Hoogen RH: Epidural and intravenous sufenta in the rat: analgesia, opiate receptor binding, and drug concentrations in plasma and brain. Anesthesiology. 1986 Jul;65(1):41-9. [PubMed Link Image]
Target 1 General References 7905839; 7957926; 7891175; 12589820; 15893644; 19077058; 14702039

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