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15-EPI BIMATOPROST

15-EPI Bimatoprost is a stereochemically distinct epimer of the parent drug, featuring inversion of configuration at the 15ฮฒ-hydroxyl position. This structural modification preserves the core cyclopentylprostaglandin scaffold but alters the spatial orientation of the lateral chain hydroxyl group, resulting in distinct chromatographic behavior while maintaining similar molecular interactions. The compound arises as a synthetic byproduct during API manufacturing processes involving asymmetric synthesis of the 15ฮฑ-hydroxyl stereocenter. Functions as a critical HPLC reference standard for quantifying epimeric impurity levels in bimatoprost formulations.

On Request
Molecular Formula C25H37NO4
Molecular Weight 415.6000
CAS Number N/A
PubChem CID 52193994 โ†—
Purity N/A
Product Type API Impurity
Parent Drug BIMATOPROST
Lead Time On Request
IUPAC Name (Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(E,3R)-3-hydroxy-5-phenylpent-1-enyl]cyclopentyl]-N-ethylhept-5-enamide

๐Ÿ“ Synonyms

1163135-92-9 Bimatoprost impurity A (5Z)-7-((1R,2R,3R,5S)-3,5-Dihydroxy-2-((1E,3R)-3-hydroxy-5-phenyl-1-penten-1-yl)cyclopentyl)-N-ethyl-5-heptenamide UNII-JY922N486Z JY922N486Z (5Z)-7-[(1R,2R,3R,5S)-3,5-Dihydroxy-2-[(1E,3R)-3-hydroxy-5-phenyl-1-penten-1-yl]cyclopentyl]-N-ethyl-5-heptenamide 5-Heptenamide, 7-((1R,2R,3R,5S)-3,5-dihydroxy-2-((1E,3R)-3-hydroxy-5-phenyl-1-penten-1-yl)cyclopentyl)-N-ethyl-, (5Z)- 7-((1R,2R,3R,5S)-3,5-Dihydroxy-2-((1E,3R)-3-hydroxy-5-phenyl-1-penten-1-yl)cyclopentyl)-N-ethyl-5-heptenamide, (5Z)- RefChem:199151 (15R)-Bimatoprost

๐Ÿ”ฌ Chemical Identifiers

CCNC(=O)CCC/C=C\C[C@H]1[C@H](C[C@H]([C@@H]1/C=C/[C@@H](CCC2=CC=CC=C2)O)O)O
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)/b8-3-,17-16+/t20-,21-,22-,23+,24-/m1/s1
AQOKCDNYWBIDND-ZPFRTTICSA-N

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