<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <id type="integer">2528</id>
  <title>T3D2487</title>
  <common-name>Apamin (Apis mellifera)</common-name>
  <description>Apamin is a component of bee venom and was originally isolated in the Western honey bee (Apis mellifera). It is a polypeptide neurotoxin that acts by blocking SK channels in the central nervous system. Apamin can have therapeutic applications, as the SK channels have been proposed as targets for the treatment of ataxia, epilepsy, memory disorders, and possibly schizophrenia and Parkinson's disease. (L1012)</description>
  <cas>24345-16-2</cas>
  <pubchem-id>16129677</pubchem-id>
  <chemical-formula nil="true"/>
  <weight>5223.3049999999985</weight>
  <appearance>Clear solution.</appearance>
  <melting-point></melting-point>
  <boiling-point></boiling-point>
  <density nil="true"/>
  <solubility>&gt;10 mg/mL</solubility>
  <specific-gravity nil="true"/>
  <flash-point nil="true"/>
  <vapour-pressure nil="true"/>
  <route-of-exposure>Injection (sting/bite) (L1811)</route-of-exposure>
  <target nil="true"/>
  <mechanism-of-toxicity>Apamin binds to the SK channels (small conductance Ca2+-activated K+ channels) in the brain and spinal cord and inhibits them, likely by acting as a pore blocker. Inhibition of SK channels by apamin increases the neuronal excitability and lowers the threshold for generating an action potential. (L1012)</mechanism-of-toxicity>
  <metabolism>Free toxin may be removed by opsonization via the reticuloendothelial system (primarily the liver and kidneys) or it may be degraded through cellular internalization via the lysosomes. Lysosomes are membrane-enclosed organelles that contain an array of digestive enzymes, including several proteases.</metabolism>
  <toxicity>LD50: 6.00 mg/kg (Intravenous, Mouse) (A686)</toxicity>
  <lethaldose></lethaldose>
  <carcinogenicity>No indication of carcinogenicity to humans (not listed by IARC).</carcinogenicity>
  <use-source>Apamin is a the main component of the venom of the Western honey bee (Apis mellifera). Apamin can have therapeutic applications, as the SK channels have been proposed as targets for the treatment of ataxia, epilepsy, memory disorders, and possibly schizophrenia and Parkinson's disease. (L1012)</use-source>
  <min-risk-level></min-risk-level>
  <health-effects>Apamin poisoning  may cause development of optic neuritis and atrophy. Serious cases may lead to atrial fibrillation, cerebral infarction, acute myocardial infarction, Fisher's syndrome, Guillain-Barre syndrome, claw hand caused by Ulnar nerve entrapment, and haemorrhaging in the lungs. (L1012)</health-effects>
  <symptoms>Apamin poisoning is characterized by burning or stinging pain, swelling, and redness at the site of the bee sting, and may be followed by swelling of the tongue and throat, difficulty breathing, and shock. (L1012)</symptoms>
  <treatment>Patients poisoned with bee venom can be treated with anti-inflammatory medication, antihistamines and oral prednisolone. (L1012)</treatment>
  <created-at type="dateTime">2009-07-03T22:18:55Z</created-at>
  <updated-at type="dateTime">2014-12-24T20:25:35Z</updated-at>
  <interacting-proteins nil="true"/>
  <wikipedia></wikipedia>
  <uniprot-id>P01500</uniprot-id>
  <kegg-compound-id></kegg-compound-id>
  <omim-id></omim-id>
  <chebi-id></chebi-id>
  <biocyc-id></biocyc-id>
  <ctd-id></ctd-id>
  <stitch-id>Apamin</stitch-id>
  <drugbank-id></drugbank-id>
  <pdb-id></pdb-id>
  <actor-id></actor-id>
  <organism nil="true"/>
  <export type="boolean">true</export>
  <metabolizing-proteins nil="true"/>
  <transporting-proteins nil="true"/>
  <moldb-smiles nil="true"/>
  <moldb-formula>C79H131N31O24S4</moldb-formula>
  <moldb-inchi>InChI=1/C79H131N31O24S4/c1-35(2)26-49-70(127)107-51-31-136-135-30-41(81)63(120)105-50(28-57(84)114)71(128)108-53(73(130)99-42(12-7-8-22-80)64(121)96-38(5)77(134)110-25-11-15-54(110)75(132)102-47(18-21-58(115)116)69(126)109-59(39(6)111)76(133)95-37(4)62(119)104-49)33-138-137-32-52(106-66(123)44(14-10-24-92-79(88)89)98-65(122)43(13-9-23-91-78(86)87)97-61(118)36(3)94-72(51)129)74(131)101-45(16-19-55(82)112)67(124)100-46(17-20-56(83)113)68(125)103-48(60(85)117)27-40-29-90-34-93-40/h29,34-39,41-54,59,111H,7-28,30-33,80-81H2,1-6H3,(H2,82,112)(H2,83,113)(H2,84,114)(H2,85,117)(H,90,93)(H,94,129)(H,95,133)(H,96,121)(H,97,118)(H,98,122)(H,99,130)(H,100,124)(H,101,131)(H,102,132)(H,103,125)(H,104,119)(H,105,120)(H,106,123)(H,107,127)(H,108,128)(H,109,126)(H,115,116)(H4,86,87,91)(H4,88,89,92)</moldb-inchi>
  <moldb-inchikey>InChIKey=YVIIHEKJCKCXOB-UHFFFAOYNA-N</moldb-inchikey>
  <moldb-average-mass type="decimal">2027.339</moldb-average-mass>
  <moldb-mono-mass type="decimal">2025.886607035</moldb-mono-mass>
  <origin>Exogenous</origin>
  <state>Liquid</state>
  <logp></logp>
  <hmdb-id></hmdb-id>
  <chembl-id></chembl-id>
  <chemspider-id>17286484</chemspider-id>
  <structure-image-file-name>800px-Apamin.svg.png</structure-image-file-name>
  <structure-image-content-type>image/png</structure-image-content-type>
  <structure-image-file-size type="integer">47155</structure-image-file-size>
  <structure-image-updated-at type="dateTime">2014-10-14T18:12:35Z</structure-image-updated-at>
  <biodb-id>BSEQ0008419</biodb-id>
  <synthesis-reference></synthesis-reference>
  <structure-image-caption nil="true"/>
</compound>
