Details of the Drug

General Information of Drug (ID: DMBRYT8)

Drug Name
XEMILOFIBAN
Synonyms
Xemilofiban; Xemilofiban [INN]; 149820-74-6; UNII-P614JI3IYK; SC-54684A; SC 54684A; P614JI3IYK; SC-54684; CHEMBL76098; Ethyl-3S-((4-((4-(aminoiminomethyl)phenyl)amino)-1,4-dioxobutyl)amino)-4-pentynoate; C18H22N4O4; 4-Pentynoic acid, 3-((4-((4-(aminoiminomethyl)phenyl)amino)-1,4-dioxobutyl)amino)-, ethyl ester, (S)-; CS-551; AC1Q5MFX; AC1L1U8F; SCHEMBL50663; DTXSID60164410; ZINC1535967; BDBM50083460; KB-81502; LS-102305; ethyl(3s)-3-[3-[(p-amidinophenyl)carbamoyl]propionamido]-4-pentynoate
Indication
Disease Entry ICD 11 Status REF
Cardiovascular disease BA00-BE2Z Discontinued in Phase 3 [1]
Peripheral vascular disease BD4Z Discontinued in Phase 3 [2]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 358.4
Logarithm of the Partition Coefficient (xlogp) -0.4
Rotatable Bond Count (rotbonds) 10
Hydrogen Bond Donor Count (hbonddonor) 4
Hydrogen Bond Acceptor Count (hbondacc) 5
Chemical Identifiers
Formula
C18H22N4O4
IUPAC Name
ethyl (3S)-3-[[4-(4-carbamimidoylanilino)-4-oxobutanoyl]amino]pent-4-ynoate
Canonical SMILES
CCOC(=O)C[C@@H](C#C)NC(=O)CCC(=O)NC1=CC=C(C=C1)C(=N)N
InChI
InChI=1S/C18H22N4O4/c1-3-13(11-17(25)26-4-2)21-15(23)9-10-16(24)22-14-7-5-12(6-8-14)18(19)20/h1,5-8,13H,4,9-11H2,2H3,(H3,19,20)(H,21,23)(H,22,24)/t13-/m1/s1
InChIKey
ZHCINJQZDFCSEL-CYBMUJFWSA-N
Cross-matching ID
PubChem CID
60957
ChEBI ID
CHEMBL76098
CAS Number
149820-74-6
TTD ID
D07EXV
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Repurposed Drugs (RPD) Click to Jump to the Detailed RPD Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Glycoprotein IIb/IIIa receptor (GPIIb/IIIa) TT38RM1 ITA2B_HUMAN ; ITB3_HUMAN Modulator [3]
ITGB3 messenger RNA (ITGB3 mRNA) TTJA1ZO ITB3_HUMAN Inhibitor [4]
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Molecular Expression Atlas of This Drug

The Studied Disease Cardiovascular disease
ICD Disease Classification BA00-BE2Z
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Glycoprotein IIb/IIIa receptor (GPIIb/IIIa) DTT ITGA2B; ITGB3 7.83E-01 -0.11 -0.45
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

References

1 Small molecules, big targets: drug discovery faces the protein-protein interaction challenge.Nat Rev Drug Discov. 2016 Aug;15(8):533-50.
2 Trusted, scientifically sound profiles of drug programs, clinical trials, safety reports, and company deals, written by scientists. Springer. 2015. Adis Insight (drug id 800004434)
3 Glycoprotein IIb/IIIa receptor number and occupancy during chronic administration of an oral antagonist. J Pharmacol Exp Ther. 2000 Nov;295(2):670-6.
4 Potent, orally active GPIIb/IIIa antagonists containing a nipecotic acid subunit. Structure-activity studies leading to the discovery of RWJ-53308. J Med Chem. 1999 Dec 16;42(25):5254-65.