Details of the Drug

General Information of Drug (ID: DMZU1TV)

Drug Name

SIBRAFIBAN

Synonyms

Sibrafiban; UNII-YUE443B0NF; Sibrafiban [USAN:INN:BAN]; YUE443B0NF; Ro 48-3657; 172927-65-0; Ro 48-3657/001; Ethyl (Z)-((1-(N-((p-hydroxyamidino)benzoyl)-L-alanyl)-4-piperidyl)oxy)acetate; Ro-48-3657; ((1-(2-((4-(amino(hydroxyimino)methyl)benzoyl)amino)-1-oxopropyl)-4-piperidinyl)oxy)acetic acid ethyl ester; Sibrafiban [INN]; Acetic acid, ((1-(2-((4-(amino(hydroxyimino)methyl)benzoyl)amino)-1-oxopropyl)-4-piperidinyl)oxy)-, ethyl ester, (S-(Z))-; Sibrafiban [USAN]; Sibrafiban [MART.]; Sibrafiban [WHO-DD]; Xubix

Indication

Disease Entry	ICD 11	Status	REF
Angina pectoris	BA40	Discontinued in Phase 3	[1]
Cardiovascular disease	BA00-BE2Z	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)

420.5

Logarithm of the Partition Coefficient (xlogp)

1

Rotatable Bond Count (rotbonds)

9

Hydrogen Bond Donor Count (hbonddonor)

3

Hydrogen Bond Acceptor Count (hbondacc)

7

Chemical Identifiers

Formula: C20H28N4O6
IUPAC Name: ethyl 2-[1-[(2S)-2-[[4-[(E)-N'-hydroxycarbamimidoyl]benzoyl]amino]propanoyl]piperidin-4-yl]oxyacetate
Canonical SMILES: CCOC(=O)COC1CCN(CC1)C(=O)[C@H](C)NC(=O)C2=CC=C(C=C2)/C(=N\\O)/N
InChI: InChI=1S/C20H28N4O6/c1-3-29-17(25)12-30-16-8-10-24(11-9-16)20(27)13(2)22-19(26)15-6-4-14(5-7-15)18(21)23-28/h4-7,13,16,28H,3,8-12H2,1-2H3,(H2,21,23)(H,22,26)/t13-/m0/s1
InChIKey: WBNUCLPUOSXSNJ-ZDUSSCGKSA-N

Cross-matching ID

PubChem CID: 5491394
CAS Number: 170094-62-9
TTD ID: D0N0BI

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]

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Molecular Interaction Atlas (MIA)

MIA Detail

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Molecular Expression Atlas of This Drug

The Studied Disease

Angina pectoris

ICD Disease Classification

BA40

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	Trusted, scientifically sound profiles of drug programs, clinical trials, safety reports, and company deals, written by scientists. Springer. 2015. Adis Insight (drug id 800006751)
2	Small molecules, big targets: drug discovery faces the protein-protein interaction challenge.Nat Rev Drug Discov. 2016 Aug;15(8):533-50.
3	Pharmacokinetics and pharmacodynamics of sibrafiban, an orally administered GP IIb/IIIa antagonist, following coadministration of aspirin and heparin. J Clin Pharmacol. 2000 May;40(5):488-95.