2-[(3R,11S,17S,20S,25aS)-11-(4-carbamimidamidobutyl)-3-carbamoyl-20-(1H-indol-3-ylmethyl)-1,9,12,15,18,21-hexaoxo-docosahydro-1H-pyrrolo[2,1-g]1,2-dithia-5,8,11,14,17,20-hexaazacyclotricosan-17-yl]acetic acid

• ChemBase ID: 130446
• Molecular Formular: C35H49N11O9S2
• Molecular Mass: 831.96186
• Monoisotopic Mass: 831.3156142
• SMILES: NC(=O)[C@H]1CSSCCC(=O)N[C@H](CCCCNC(=N)N)C(=O)NCC(=O)N[C@H](CC(=O)O)C(=O)N[C@@H](Cc2c[nH]c3ccccc23)C(=O)N2CCC[C@H]2C(=O)N1
• Canonical SMILES: OC(=O)C[C@H]1NC(=O)CNC(=O)[C@@H](CCCCNC(=N)N)NC(=O)CCSSC[C@@H](NC(=O)[C@H]2N(C(=O)[C@@H](NC1=O)Cc1c[nH]c3c1cccc3)CCC2)C(=O)N
• InChI: InChI=1S/C35H49N11O9S2/c36-30(51)25-18-57-56-13-10-27(47)42-22(8-3-4-11-39-35(37)38)31(52)41-17-28(48)43-23(15-29(49)50)32(53)44-24(14-19-16-40-21-7-2-1-6-20(19)21)34(55)46-12-5-9-26(46)33(54)45-25/h1-2,6-7,16,22-26,40H,3-5,8-15,17-18H2,(H2,36,51)(H,41,52)(H,42,47)(H,43,48)(H,44,53)(H,45,54)(H,49,50)(H4,37,38,39)/t22-,23-,24-,25-,26-/m0/s1
• InChIKey: CZKPOZZJODAYPZ-LROMGURASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(3R,11S,17S,20S,25aS)-11-(4-carbamimidamidobutyl)-3-carbamoyl-20-(1H-indol-3-ylmethyl)-1,9,12,15,18,21-hexaoxo-docosahydro-1H-pyrrolo[2,1-g]1,2-dithia-5,8,11,14,17,20-hexaazacyclotricosan-17-yl]acetic acid
• IUPAC Traditional name: eptifibatide
• Brand Name: Integrilin
• Synonyms: Eptifibatide

Database IDs

• CAS Number: 188627-80-7
• PubChem SID: 162224725
• PubChem CID: 123610; 448812
• CHEBI ID: 291902
• ATC CODE: B01AC16
• CHEMBL: 1174
• Chemspider ID: 10482060
• DrugBank ID: DB00063
• KEGG ID: D06888
• Unique Ingredient Identifier: NA8320J834
• Wikipedia Title: Eptifibatide
• Medline Plus: a601210

CALCULATED PROPERTIES

• Acid pKa: 3.6680408
• H Acceptors: 12
• H Donor: 11
• LogD (pH = 5.5): -5.068173
• LogD (pH = 7.4): -5.0630093
• Log P: -5.063064
• Molar Refractivity: 219.8379 cm^3
• Polarizability: 82.15443 Å^3
• Polar Surface Area: 323.89 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

PROPERTIES

Pharmacology Properties

• Admin Routes: IV only
• Bioavailability: n/a
• Excretion: Renal
• Half Life: ~2.5 hours
• Protein Bound: ~25%
• Legal Status: POM (UK); Rx-only (US)
• Pregnancy Category: B (US)
• US Licence: Eptifibatide
• EU Licence: Integrilin