<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <id type="integer">2907</id>
  <title>T3D2865</title>
  <common-name>Sufentanil</common-name>
  <description>Sufentanil is only found in individuals that have used or taken this drug. It is an opioid analgesic that is used as an adjunct in anesthesia, in balanced anesthesia, and as a primary anesthetic agent. [PubChem]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.</description>
  <cas>56030-54-7</cas>
  <pubchem-id>41693</pubchem-id>
  <chemical-formula>C22H30N2O2S</chemical-formula>
  <weight>386.202800</weight>
  <appearance>White powder.</appearance>
  <melting-point>97°C</melting-point>
  <boiling-point nil="true"/>
  <density nil="true"/>
  <solubility>76 mg/L (at 25°C)</solubility>
  <specific-gravity nil="true"/>
  <flash-point nil="true"/>
  <vapour-pressure nil="true"/>
  <route-of-exposure>Epidural; parenteral(intravenous)</route-of-exposure>
  <target nil="true"/>
  <mechanism-of-toxicity>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.</mechanism-of-toxicity>
  <metabolism>Half Life: 265 minutes</metabolism>
  <toxicity>LD50: 18.7 mg/kg (parenteral-intravenous, mouse)</toxicity>
  <lethaldose nil="true"/>
  <carcinogenicity>No indication of carcinogenicity to humans (not listed by IARC).</carcinogenicity>
  <use-source>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]. Also used as an analgesic adjunct in anesthesia and as a primary anesthetic drug in procedures requiring assisted ventilation and in the relief of pain.</use-source>
  <min-risk-level nil="true"/>
  <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.</health-effects>
  <symptoms>Respiratory depression. [Wikipedia]</symptoms>
  <treatment nil="true"/>
  <created-at type="dateTime">2009-07-21T20:27:27Z</created-at>
  <updated-at type="dateTime">2014-12-24T20:25:52Z</updated-at>
  <interacting-proteins nil="true"/>
  <wikipedia>Sufentanil</wikipedia>
  <uniprot-id></uniprot-id>
  <kegg-compound-id>C08022</kegg-compound-id>
  <omim-id></omim-id>
  <chebi-id>9316</chebi-id>
  <biocyc-id></biocyc-id>
  <ctd-id nil="true"/>
  <stitch-id>Sufentanil</stitch-id>
  <drugbank-id>DB00708</drugbank-id>
  <pdb-id></pdb-id>
  <actor-id nil="true"/>
  <organism nil="true"/>
  <export type="boolean">true</export>
  <metabolizing-proteins nil="true"/>
  <transporting-proteins nil="true"/>
  <moldb-smiles>CCC(=O)N(C1=CC=CC=C1)C1(COC)CCN(CCC2=CC=CS2)CC1</moldb-smiles>
  <moldb-formula>C22H30N2O2S</moldb-formula>
  <moldb-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</moldb-inchi>
  <moldb-inchikey>InChIKey=GGCSSNBKKAUURC-UHFFFAOYSA-N</moldb-inchikey>
  <moldb-average-mass type="decimal">386.551</moldb-average-mass>
  <moldb-mono-mass type="decimal">386.202798904</moldb-mono-mass>
  <origin>Exogenous</origin>
  <state>Solid</state>
  <logp>3.95</logp>
  <hmdb-id>HMDB14846</hmdb-id>
  <chembl-id>CHEMBL658</chembl-id>
  <chemspider-id>38043</chemspider-id>
  <structure-image-file-name nil="true"/>
  <structure-image-content-type nil="true"/>
  <structure-image-file-size type="integer" nil="true"/>
  <structure-image-updated-at type="dateTime" nil="true"/>
  <biodb-id nil="true"/>
  <synthesis-reference>&lt;p&gt;Jacob Mathew, J. Killgore, &amp;#8220;New methods for the synthesis of alfentanil, sufentanil, and remifentanil.&amp;#8221; U.S. Patent US20060149071, issued July 06, 2006.&lt;/p&gt;</synthesis-reference>
  <structure-image-caption nil="true"/>
</compound>
