bivalirudin   Click here for help

GtoPdb Ligand ID: 6470

Synonyms: Angiomax®
Approved drug
bivalirudin is an approved drug (FDA (2000))
Comment: Bivalirudin is a peptide congener of hirudin, the naturally occurring anticoagulant found in the saliva of the medicinal leech Hirudo medicinalis.
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View more information in the IUPHAR Pharmacology Education Project: bivalirudin

2D Structure
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SMILES / InChI / InChIKey
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Canonical SMILES CCC(C(C(=O)N1CCCC1C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)O)CC(C)C)Cc1ccc(cc1)O)CCC(=O)O)CCC(=O)O)NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(CC(=O)O)NC(=O)CNC(=O)C(NC(=O)CNC(=O)CNC(=O)CNC(=O)CNC(=O)C1CCCN1C(=O)C(NC(=O)C1CCCN1C(=O)C(Cc1ccccc1)N)CCCNC(=N)N)CC(=O)N)Cc1ccccc1)CCC(=O)O)CCC(=O)O)C
Isomeric SMILES CC[C@@H]([C@@H](C(=O)N1CCC[C@H]1C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)O)CC(C)C)Cc1ccc(cc1)O)CCC(=O)O)CCC(=O)O)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H](CC(=O)O)NC(=O)CNC(=O)[C@@H](NC(=O)CNC(=O)CNC(=O)CNC(=O)CNC(=O)[C@@H]1CCCN1C(=O)[C@@H](NC(=O)[C@@H]1CCCN1C(=O)[C@@H](Cc1ccccc1)N)CCCNC(=N)N)CC(=O)N)Cc1ccccc1)CCC(=O)O)CCC(=O)O)C
InChI InChI=1S/C98H138N24O33/c1-5-52(4)82(96(153)122-39-15-23-70(122)92(149)114-60(30-34-79(134)135)85(142)111-59(29-33-78(132)133)86(143)116-64(43-55-24-26-56(123)27-25-55)89(146)118-67(97(154)155)40-51(2)3)119-87(144)61(31-35-80(136)137)112-84(141)58(28-32-77(130)131)113-88(145)63(42-54-18-10-7-11-19-54)117-90(147)66(45-81(138)139)110-76(129)50-107-83(140)65(44-71(100)124)109-75(128)49-106-73(126)47-104-72(125)46-105-74(127)48-108-91(148)68-21-13-38-121(68)95(152)62(20-12-36-103-98(101)102)115-93(150)69-22-14-37-120(69)94(151)57(99)41-53-16-8-6-9-17-53/h6-11,16-19,24-27,51-52,57-70,82,123H,5,12-15,20-23,28-50,99H2,1-4H3,(H2,100,124)(H,104,125)(H,105,127)(H,106,126)(H,107,140)(H,108,148)(H,109,128)(H,110,129)(H,111,142)(H,112,141)(H,113,145)(H,114,149)(H,115,150)(H,116,143)(H,117,147)(H,118,146)(H,119,144)(H,130,131)(H,132,133)(H,134,135)(H,136,137)(H,138,139)(H,154,155)(H4,101,102,103)/t52-,57+,58-,59-,60-,61-,62-,63-,64-,65-,66-,67-,68-,69-,70-,82-/m0/s1
InChI Key OIRCOABEOLEUMC-GEJPAHFPSA-N
Classification Click here for help
Compound class Peptide or derivative
Approved drug? Yes (FDA (2000))
IUPAC Name Click here for help
(4S)-4-[(2S)-2-[(2S)-2-[(2S)-2-{2-[(2S)-2-(2-{2-[2-(2-{[(2S)-1-[(2S)-2-{[(2S)-1-[(2R)-2-amino-3-phenylpropanoyl]pyrrolidin-2-yl]formamido}-5-carbamimidamidopentanoyl]pyrrolidin-2-yl]formamido}acetamido)acetamido]acetamido}acetamido)-3-carbamoylpropanamido]acetamido}-3-carboxypropanamido]-3-phenylpropanamido]-4-carboxybutanamido]-4-{[(2S,3S)-1-[(2S)-2-{[(1S)-3-carboxy-1-{[(1S)-3-carboxy-1-{[(1S)-1-{[(1S)-1-carboxy-3-methylbutyl]carbamoyl}-2-(4-hydroxyphenyl)ethyl]carbamoyl}propyl]carbamoyl}propyl]carbamoyl}pyrrolidin-1-yl]-3-methyl-1-oxopentan-2-yl]carbamoyl}butanoic acid
International Nonproprietary Names Click here for help
INN number INN
7282 bivalirudin
Synonyms Click here for help
Angiomax®
Database Links Click here for help
Specialist databases
Reactome Drug Reactome logo R-ALL-9603269
Reactome Reaction Reactome logo R-HSA-9603302
Other databases
CAS Registry No. 128270-60-0 (source: PubChem)
ChEBI CHEBI:59173
ChEMBL Ligand CHEMBL2103749
DrugBank Ligand DB00006
DrugCentral Ligand 385
GtoPdb PubChem SID 178103084
PubChem CID 16129704
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Search UniChem for chemical match using the InChIKey OIRCOABEOLEUMC-GEJPAHFPSA-N
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Wikipedia Bivalirudin