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Bimatoprost isopropyl ester;Isopropyl (5Z)-7-{(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxy-5-phenyl-1-penten-1-yl]cyclopentyl}-5-heptenoate(CAS: 130209-76-6)

Bimatoprost isopropyl ester;Isopropyl (5Z)-7-{(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxy-5-phenyl-1-penten-1-yl]cyclopentyl}-5-heptenoate
CAS Number
Origin Country
China China

Product Description

Bimatoprost isopropyl ester (17-phenyl trinor PGF₂α isopropyl ester) is a synthetic prostaglandin F‑series analog. It is the isopropyl ester prodrug of bimatoprost, and its active form—the free acid 17‑phenyl trinor PGF₂α—is a potent FP receptor agonist. It should be noted that its C‑15 stereoisomer, 15(R)‑bimatoprost isopropyl ester, is a related isomer and potential impurity of latanoprost. The IC50 values for the free acid forms of 15(S)-17-phenyl trinor PGF2α and 15(R)-17-phenyl trinor PGF2α were determined to be 0.71 nM and 30 nM, respectively, in a FP receptor binding assay using the cat iris sphincter muscle.1 A 3 μg dose of 15(R)-17-phenyl trinor PGF2α caused a 1.9 mmHg reduction of IOP in normotensive cynomolgus monkeys.

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Basic Information

Molecular Formula
C26H38O5
Molecular Weight
430.59 g/mol

Chemical Identifiers

SMILES
CC(C)OC(=O)CCCC=CCC1C(CC(C1C=CC(CCC2=CC=CC=C2)O)O)O
InChIKey
JGZRPRSJSQLFBO-FWPUOYPASA-N

Database References

MDL Number
MFCD00902150

FAQ

Isopropyl (5Z)-7-{(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxy-5-phenyl-1-penten-1-yl]cyclopentyl}-5-heptenoate (CAS: 130209-76-6) is a crystalline compound with a molecular weight of approximately 442.48 g/mol. It has a low solubility in water but is soluble in organic solvents like ethanol and acetone. Chemically, it is relatively stable but can react with strong bases and acids. It is typically used in research and pharmaceutical applications due to its unique structural features.
Isopropyl (5Z)-7-{(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxy-5-phenyl-1-penten-1-yl]cyclopentyl}-5-heptenoate (CAS: 130209-76-6) is synthesized through a multi-step process involving the synthesis of the cyclopentenone intermediate, followed by condensation with an isopropyl derivative. The reaction is typically catalyzed by palladium complexes and proceeds with high selectivity and yield. Detailed synthetic procedures are available in the literature.
Isopropyl (5Z)-7-{(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxy-5-phenyl-1-penten-1-yl]cyclopentyl}-5-heptenoate (CAS: 130209-76-6) is primarily used in the pharmaceutical industry for the development of novel drug candidates. It is also explored in organic synthesis, particularly for the construction of complex molecules. Additionally, it may have potential applications in the synthesis of new materials and sensors.
When handling Isopropyl (5Z)-7-{(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxy-5-phenyl-1-penten-1-yl]cyclopentyl}-5-heptenoate (CAS: 130209-76-6), use appropriate personal protective equipment (PPE) such as gloves, safety goggles, and a lab coat. Store it in a cool, dry place away from direct sunlight and heat sources. Handle in a well-ventilated area or fume hood to minimize inhalation risks. In case of a spill, follow standard safety protocols and consult the material safety data sheet (MSDS) for specific instructions.

Safety Notice

Please verify product specifications and safety data before use. Contact the supplier for detailed safety information.

Always follow proper handling procedures

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