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(+)-Cloprostenol isopropyl ester

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(+)-Cloprostenol isopropyl ester Basic information

Product Name:
(+)-Cloprostenol isopropyl ester
Synonyms:
  • 5-Heptenoic acid,7-[(1R,2R,3R,5S)-2-[(1E,3R)-4-(3-chlorophenoxy)-3-hydroxy-1-butenyl]-3,5-dihydroxycyclopentyl]-, 1-methylethyl ester, (5Z)-
  • D-cloprostenol isopropyl ester
  • ISOPROPYL CLOPROSTENAT
  • Isopropyl Cloprostenate
  • (+)-Cloprostenol isopropyl ester
  • CPG 6112-95
  • 5-Heptenoic acid, 7-[(1R,2R,3R,5S)-2-[(1E,3R)-4-(3-chlorophenoxy)-3-hydroxy-1-buten-1-yl]-3,5-dihydroxycyclopentyl]-, 1-methylethyl ester, (5Z)-
  • (+)-16-m-chlorophenoxy tetranor Prostaglandin F2α isopropyl ester
CAS:
157283-66-4
MF:
C25H35ClO6
MW:
466.99
Mol File:
157283-66-4.mol
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(+)-Cloprostenol isopropyl ester Chemical Properties

Boiling point:
600.0±55.0 °C(Predicted)
Density 
1.227±0.06 g/cm3(Predicted)
storage temp. 
-20°C Freezer, Under inert atmosphere
solubility 
Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
form 
Oil
pka
13.41±0.20(Predicted)
color 
Colourless
InChIKey
OCNSAYQJDKJOLH-AHTXBMBWSA-N
SMILES
C(OC(C)C)(=O)CCC/C=C\C[C@H]1[C@@H](O)C[C@@H](O)[C@@H]1/C=C/[C@@H](O)COC1=CC=CC(Cl)=C1
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(+)-Cloprostenol isopropyl ester Usage And Synthesis

Description

(+)-Cloprostenol is a synthetic analog of prostaglandin F (PGF). It is an FP receptor agonist and a potent luteolytic agent in rats and hamsters. (+)-Cloprostenol is the optically active, 15(R) enantiomer of cloprostenol responsible for the majority of its biological activity. It is 200 times more potent than PGF in terminating pregnancy when given subcutaneously at a daily dose of 0.125 μg/kg in rats and hamsters, without the side effects associated with PGF. (+)-Cloprostenol was also shown to be a potent inhibitor of rat adipose precursor differentiation in primary cultures with an IC50 value of 3 x 10-12 M. (+)-Cloprostenol isopropyl ester is a more lipid soluble form of cloprostenol.

Uses

(+)-Cloprostenol isopropyl ester is an isopropyl ester derivative of Cloprostenol (C587300); an aryl-oxymethyl analog of prostaglandin F2α.

in vivo

Cloprostenol isopropyl ester (25 μg/kg; i.p.; daily, for 4 weeks; male mice) induces changes in the evolution of the spermatogenesis and spermiogenesis[1].
Cloprostenol isopropyl ester (1 μg, 30 μL; injected into the eye; for 2, 4 and 6 h) causes pupil constriction in the cat. Cloprostenol isopropyl ester has an efficacious ocular hypotensive in the lasered monkey[2].

Animal Model:Male mice (50–80 days)[1]
Dosage:25 μg/kg
Administration:Intraperitoneal injection; daily, for 4 weeks
Result:Stimulated the androgen synthesis in a time-dependent manner.

IC 50

FP

References

[1] GINETTE SERRERO  Nancy M L. Prostaglandin F2αReceptor (FP Receptor) Agonists Are Potent Adipose Differentiation Inhibitors for Primary Culture of Adipocyte Precursors in Defined Medium[J]. Biochemical and biophysical research communications, 1997, 233 1: Pages 200-202. DOI: 10.1006/bbrc.1997.6433

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