Discuss This Drug

bivalirudin

CHEBI:CHEBI_59173

Definition

A synthetic peptide of 20 amino acids, comprising D-Phe, Pro, Arg, Pro, Gly, Gly, Gly, Gly, Asn, Gly, Asp, Phe, Glu, Glu, Ile, Pro, Glu, Glu, Tyr, and Leu in sequence. A congener of hirudin (a naturally occurring drug found in the saliva of the medicinal leech), it a specific and reversible inhibitor of thrombin, and is used as an anticoagulant.

Chemical Information

Molecular Formula
C98H138N24O33
Molecular Mass
2180.28530
Charge
0
SMILES
CC[C@H](C)[C@H](NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](Cc1ccccc1)NC(=O)[C@H](CC(O)=O)NC(=O)CNC(=O)[C@H](CC(N)=O)NC(=O)CNC(=O)CNC(=O)CNC(=O)CNC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCNC(N)=N)NC(=O)[C@@H]1CCCN1C(=O)[C@H](N)Cc1ccccc1)C(=O)N1CCC[C@H]1C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](Cc1ccc(O)cc1)C(=O)N[C@@H](CC(C)C)C(O)=O
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
InChIKey
OIRCOABEOLEUMC-GEJPAHFPSA-N

Alternative Names

  • bivalirudin
  • bivalirudina
  • bivalirudine
  • bivalirudinum
  • D-phenylalanyl-L-prolyl-L-arginyl-L-prolylglycylglycylglycylglycyl-L-asparaginylglycyl-L-alpha-aspartyl-L-phenylalanyl-L-alpha-glutamyl-L-alpha-glutamyl-L-isoleucyl-L-prolyl-L-alpha-glutamyl-L-alpha-glutamyl-L-tyrosyl-L-leucine
  • (2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-1-[(2S,3S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[2-[[(2S)-4-amino-2-[[2-[[2-[[2-[[2-[[(2S)-1-[(2S)-2-[[(2S)-1-[(2R)-2-amino-3-cyclohexylpropanoyl]pyrrolidine-2-carbonyl]amino]-5-carbamimidamidopentanoyl]pyrrolidine-2-carbonyl]amino]acetyl]amino]acetyl]amino]acetyl]amino]acetyl]amino]-4-oxobutanoyl]amino]acetyl]amino]-4-hydroxy-4-oxobutanoyl]amino]-3-cyclohexylpropanoyl]amino]-5-hydroxy-5-oxopentanoyl]amino]-5-hydroxy-5-oxopentanoyl]amino]-3-methylpentanoyl]pyrrolidine-2-carbonyl]amino]-5-hydroxy-5-oxopentanoyl]amino]-5-hydroxy-5-oxopentanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-methylpentanoic acid

Drug Classification

Important Medical Information

⚕️ This information is sourced from ChEBI (Chemical Entities of Biological Interest) database and is intended for educational purposes only.

  • Always consult with a healthcare professional before starting, stopping, or modifying any medication.
  • Side effects may vary and this list may not be comprehensive.
  • Drug interactions may occur with other medications.

Additional Identifiers

core#notation
CHEBI:59173
DRON_00010000
60819
oboInOwl#hasDbXref
PMID:29600024

Additional References

🔍 Click on any linked disease name to learn more about the conditions this medication is used to treat, or explore related drug classifications for more information about similar medications.

Additional Attributes

core#notation
CHEBI:59173
pharm_class_epc
Direct Thrombin Inhibitor [EPC]
pharm_class
Thrombin Inhibitors [MoA]
active_ingredient_strength
250 mg/1
nui
N0000009963
pharm_class_moa
Thrombin Inhibitors [MoA]
upc
0355150210107
22-rdf-syntax-ns#type
http://www.w3.org/2002/07/owl#Class
rxcui
1997015
package_marketing_start_date
06-JUL-12
manufacturer_name
Hainan Shuangcheng Pharmaceuticals Co., Ltd.
active_ingredient_name
BIVALIRUDIN
package_description
2500 g in 1 BAG (55463-0029-2)
unii
TN9BEX005G
spl_set_id
e574d04f-67b4-4a84-9d66-8c2d54f95120
package_ndc
72572-035-10
oboInOwl#hasOBONamespace
chebi_ontology
DRON_00010000
60819
oboInOwl#hasDbXref
PMID:29600024
generic_name
Bivalirudin
brand_name
Angiomax
brand_name_base
Angiomax
oboInOwl#id
CHEBI:59173
product_type
BULK INGREDIENT
marketing_category
BULK INGREDIENT
dosage_form
INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION
product_ndc
55463-0029
application_number
ANDA205962
RO_0000087
http://purl.obolibrary.org/obo/CHEBI_65232
oboInOwl#inSubset
http://purl.obolibrary.org/obo/chebi#3_STAR
listing_expiration_date
20241231
marketing_start_date
20191028
route
INTRACAVERNOUS
labeler_name
Ambiopharm, Inc.
spl_id
f817e680-9f50-4fee-9642-d1330e132fb8
has_treatment
http://purl.obolibrary.org/obo/DOID_9408
rdf-schema#domain
https://w3id.org/def/predibionto#has_side_effect29286
owl#annotatedSource
t252605
owl#someValuesFrom
t2996870