(5E)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxy-5-phenylpent-1-en-1-yl]cyclopentyl]-N-ethylhept-5-enamide

• ChemBase ID: 126156
• Molecular Formular: C25H37NO4
• Molecular Mass: 415.56558
• Monoisotopic Mass: 415.27225867
• SMILES: O=C(NCC)CCC/C=C/C[C@H]1[C@@H](O)C[C@@H](O)[C@@H]1C=C[C@@H](O)CCc1ccccc1
• Canonical SMILES: CCNC(=O)CCC/C=C/C[C@H]1[C@@H](O)C[C@H]([C@@H]1C=C[C@H](CCc1ccccc1)O)O
• InChI: InChI=1S/C25H37NO4/c1-2-26-25(30)13-9-4-3-8-12-21-22(24(29)18-23(21)28)17-16-20(27)15-14-19-10-6-5-7-11-19/h3,5-8,10-11,16-17,20-24,27-29H,2,4,9,12-15,18H2,1H3,(H,26,30)/t20-,21+,22+,23-,24+/m0/s1
• InChIKey: AQOKCDNYWBIDND-UDIRQSBCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (5E)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxy-5-phenylpent-1-en-1-yl]cyclopentyl]-N-ethylhept-5-enamide; 7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3S)-3-hydroxy-5-phenylpent-1-en-1-yl]cyclopentyl]-N-ethylhept-5-enamide
• IUPAC Traditional name: (5E)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxy-5-phenylpent-1-en-1-yl]cyclopentyl]-N-ethylhept-5-enamide; 7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3S)-3-hydroxy-5-phenylpent-1-en-1-yl]cyclopentyl]-N-ethylhept-5-enamide
• Brand Name: Lumigan
• Synonyms: Bimatoprost; 17-Phenyl-tri-norprostaglandin F2α-ethyl amide; (5E)-7-[(1R,2R,3R,5S)-3,5-Dihydroxy-2-[(1E,3S)-3-hydroxy-5-phenyl-1-penten-1-yl]cyclopentyl]-N-ethyl-5-heptenamide; 5-trans-Bimatoprost; (5E)-Bimatoprost; Bimatoprost

Database IDs

• CAS Number: 1163135-95-2; 155206-00-1
• MDL Number: MFCD03411999
• PubChem SID: 162220497
• PubChem CID: 5311027; 66509082
• CHEBI ID: 51230
• ATC CODE: S01EE03
• CHEMBL: 1200963
• Chemspider ID: 4470565
• DailyMed ID: 46098
• DrugBank ID: DB00905
• IUPHAR ligand ID: 1958
• Unique Ingredient Identifier: QXS94885MZ
• Wikipedia Title: Bimatoprost
• Medline Plus: a602030

CALCULATED PROPERTIES

• Acid pKa: 14.34702
• H Acceptors: 4
• H Donor: 4
• LogD (pH = 5.5): 2.6292617
• LogD (pH = 7.4): 2.6292624
• Log P: 2.6292624
• Molar Refractivity: 122.8312 cm^3
• Polarizability: 47.097137 Å^3
• Polar Surface Area: 89.79 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: solid

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Pharmacology Properties

• Admin Routes: Topical (eye drops)
• Legal Status: Rx-only (US)
• Pregnancy Category: C (US)

Product Information

• Purity: ≥95%
• Empirical Formula (Hill Notation): C25H37NO4

DETAILS

Sigma Aldrich - P6740

Application
Potent FP prostanoid receptor agonist used in animal models for glaucoma.

Toronto Research Chemicals - B386810

The trans-isomer used in the improved process for the production and purification of Bimatoprost (B386800).