ABC00289UF

5,6 Trans Bimatoprost

5,6 Trans Bimatoprost is a geometric isomer of the parent drug Bimatoprost, characterized by a trans-configuration at the 5,6-double bond of the cyclopentyl ring. This structural variation introduces distinct stereochemical properties, affecting its conformational flexibility and interactions with prostaglandin receptors. The molecule retains the tetrahydrofuran ring and terminal butyric acid ester critical to the parent compound’s activity but exhibits altered hydrophobicity due to the trans-geometry. It arises as a synthetic byproduct during Bimatoprost production, necessitating its quantification as an API impurity. This compound serves as an HPLC reference standard for impurity profiling in quality control of Bimatoprost formulations.

On Request
Molecular Formula C25H37NO4
Molecular Weight 415.6000
CAS Number 1163135-95-2 βœ“ Verified
PubChem CID 6505201 β†—
Purity N/A
Product Type API Impurity
Parent Drug Bimatoprost
Lead Time On Request
IUPAC Name (E)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(E,3S)-3-hydroxy-5-phenylpent-1-enyl]cyclopentyl]-N-ethylhept-5-enamide
Official Reference Standards
Std Catalog # Quantity Price
USP 1071359 β†— 1 mL USD 730.00

πŸ“ Synonyms

1163135-95-2 RefChem:406403 (E)-N-ethyl-7-((1R,2R,3R,5S)-3,5-dihydroxy-2-((S,E)-3-hydroxy-5-phenylpent-1-en-1-yl)cyclopentyl)hept-5-enamide 810-193-0 (5E)-Bimatoprost 5,6-trans-Bimatoprost 5-Trans Bimatoprost 5-trans-Bimatoprost Bimatoprost Impurity V (E)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(E,3S)-3-hydroxy-5-phenylpent-1-enyl]cyclopentyl]-N-ethylhept-5-enamide

πŸ”¬ 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+/m0/s1
AQOKCDNYWBIDND-ABRBVVEGSA-N

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