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]
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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
CAS Number: 149820-74-6
TTD ID: D07EXV

Repurposed Drugs (RPD)

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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 Interaction Atlas (MIA)

MIA Detail

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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)

MEA Detail

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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.