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Substance Name: Apamin
RN: 24345-16-2
UNII: X644P85KUR
InChIKey: YVIIHEKJCKCXOB-STYWVVQQSA-N

Note

  • A highly neurotoxic polypeptide from the venom of the honey bee (Apis mellifera). It consists of 18 amino acids with two disulfide bridges and causes hyperexcitability resulting in convulsions and respiratory paralysis.

Molecular Formula

  • C79-H131-N31-O24-S4

Molecular Weight

  • 2027.3609
 

Classification Code

  • Drug / Therapeutic Agent
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Names and Synonyms

Name of Substance

  • Apamin

MeSH Heading

  • Apamin

Synonyms

  • Apamin (reduced) cyclic (1-11),(3-15)-bis(disulfide)
  • Apamine
  • EINECS 246-182-7
  • L-Histidinamide, L-cysteinyl-L-asparaginyl-L-cysteinyl-L-lysyl-L-alanyl-L-prolyl-L-alpha-glutamyl-L-threonyl-L-alanyl-L-leucyl-L-cysteinyl-L-alanyl-L-arginyl-L-arginyl-L-cysteinyl-L-glutaminyl-L-glutaminyl-, cyclic (1-11)(3-15)-bis(disulfide)
  • Ro 23-6721
  • UNII-X644P85KUR

Systematic Name

  • Apamin

Registry Numbers

CAS Registry Number

  • 24345-16-2

FDA UNII

  • X644P85KUR

Other Registry Numbers

  • 11049-84-6
  • 16812-94-5
  • 28883-82-1
  • 30797-89-8

System Generated Number

  • 0024345162

Structure Descriptors

InChI

1S/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)/t36-,37-,38-,39+,41-,42-,43-,44-,45-,46-,47-,48-,49-,50-,51-,52-,53-,54-,59-/m0/s1

InChIKey

YVIIHEKJCKCXOB-STYWVVQQSA-N

Smiles

CC(C)C[C@@H]1NC(=O)[C@H](C)NC(=O)[C@@H](NC(=O)[C@H](CCC(=O)O)NC(=O)[C@@H]2CCCN2C(=O)[C@H](C)NC(=O)[C@H](CCCCN)NC(=O)[C@@H]3CSSC[C@H](NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](C)NC(=O)[C@H](CSSC[C@H](N)C(=O)N[C@@H](CC(=O)N)C(=O)N3)NC1=O)C(=O)N[C@@H](CCC(=O)N)C(=O)N[C@@H](CCC(=O)N)C(=O)N[C@@H](Cc4c[nH]cn4)C(=O)N)[C@@H](C)O

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intracrebral 1800ng/kg (0.0018mg/kg)   Toxicon. Vol. 22, Pg. 308, 1984.
mouse LD50 intraperitoneal 3800ug/kg (3.8mg/kg)   Toxicon. Vol. 22, Pg. 308, 1984.
mouse LD50 intravenous 4mg/kg (4mg/kg) BEHAVIORAL: EXCITEMENT

BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)
Naunyn-Schmiedeberg's Archives of Pharmacology. Vol. 300, Pg. 189, 1977.
mouse LD50 parenteral 600mg/kg (600mg/kg)   Toxicon. Vol. 20, Pg. 157, 1982.
mouse LD50 subcutaneous 2900ug/kg (2.9mg/kg) BEHAVIORAL: ATAXIA European Journal of Biochemistry. Vol. 56, Pg. 35, 1975.