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Inhibitor Report for: Irinotecan

Irinotecan (CPT-11), an anticancer prodrug is a potent inhibitor of acetylcholinesterase but is rapidly catalyzed to its active metabolite SN-38 (7-ethyl-10-hydroxycamptothecin) a potent inhibitor of topoisomerase I. CPT-11 is hydrolysed by carboxylesterases in human pig and rabbit. Horse BChE hydrolyses 200 times faster CPT-11 than human BChE


General
Type Carbamate, Drug, Derivative of Irinotecan, Not A/B H target
Chemical_Nomenclature 7-ethyl-10-[4-(1-piperidino)-1-piperidino]carbonyloxycamptothecin)
Canonical SMILES CCC1=C2C=C(C=CC2=NC3=C1CN4C3=CC5=C(C4=O)COC(=O)C5(CC)O)OC(=O)N6CCC(CC6)N7CCCCC7
InChI InChI=1S/C33H38N4O6/c1-3-22-23-16-21(43-32(40)36-14-10-20(11-15-36)35-12-6-5-7-13-35)8-9-27(23)34-29-24(22)18-37-28(29)17-26-25(30(37)38)19-42-31(39)33(26,41)4-2/h8-9,16-17,20,41H,3-7,10-15,18-19H2,1-2H3/t33-/m0/s1
InChIKey UWKQSNNFCGGAFS-XIFFEERXSA-N
Other name(s) CPT-11 ; Camptosar ; Irinotecanum ; Biotecan
________________________________________________________________________________________________
MW|586.69
Formula|C33H38N4O6
CAS_number|97682-44-5
PubChem|60838
UniChem|UWKQSNNFCGGAFS-XIFFEERXSA-N
IUPHAR|6823
Wikipedia|Irinotecan

Target
Families | Irinotecan ligand of proteins in family: Carboxylesterase, Carb_B_Chordata, Carb_B_Bacteria
Stucture | 1 structure: 1U65: Torpedo acetylcholinesterase complex of the anticancer prodrug CPT-11 Irinotecan
Protein | rabit-1cxes

References:
Search PubMed for references concerning: Irinotecan

12 more
    Title: The crystal structure of the complex of the anticancer prodrug 7-ethyl-10-[4-(1-piperidino)-1-piperidino]-carbonyloxycamptothecin (CPT-11) with Torpedo californica acetylcholinesterase provides a molecular explanation for its cholinergic action
    Harel M, Hyatt JL, Brumshtein B, Morton CL, Yoon KJ, Wadkins RM, Silman I, Sussman JL, Potter PM
    Ref: Molecular Pharmacology, 67:1874, 2005 : PubMed

            

    Title: Gastrointestinal toxicity or irinotecan
    Hecht JR
    Ref: Oncology, 12:72, 1998 : PubMed

            

    Title: Pharmacology of irinotecan
    Kuhn JG
    Ref: Oncology, 12:39, 1998 : PubMed