A potential impurity of latanoprost
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15(R)-17-phenyl trinor Prostaglandin F isopropyl ester

Item No. 16825

Technical Information
Formal Name
9α,11α,15R-trihydroxy-17-phenyl-18,19,20-trinor-prosta-5Z,13E-dien-1-oic acid, isopropyl ester
CAS Number
130273-87-9
Synonyms
  • 15-epi Bimatoprost isopropyl ester
  • 15(R)-Bimatoprost isopropyl ester
  • 15(R)-17-phenyl trinor PGF isopropyl ester
Molecular Formula
C26H38O5
Formula Weight
Purity
≥98%
A 10 mg/ml solution in methyl acetate
DMF: 30 mg/mlDMSO: 25 mg/mlEthanol: 30 mg/mlPBS (pH 7.2): 1 mg/ml
SMILES
O[C@@H]1[C@H](C/C=C\CCCC(OC(C)C)=O)[C@@H](/C=C/[C@H](O)CCC2=CC=CC=C2)[C@H](O)C1
InChi Code
InChI=1S/C26H38O5/c1-19(2)31-26(30)13-9-4-3-8-12-22-23(25(29)18-24(22)28)17-16-21(27)15-14-20-10-6-5-7-11-20/h3,5-8,10-11,16-17,19,21-25,27-29H,4,9,12-15,18H2,1-2H3/b8-3-,17-16+/t21-,22-,23-,24+,25-/m1/s1
InChi Key
JGZRPRSJSQLFBO-DYZSFVSISA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    15(R)-17-phenyl trinor Prostaglandin F isopropyl ester (15(R)-17-phenyl trinor PGF isopropyl ester) is the latanoprost-related isomer containing both a double bond at 13,14 and an inverted (β) hydroxyl group at C-15. Similar to 15(S)-latanoprost, 15(R)-17-phenyl trinor PGF isopropyl ester is a potential impurity in most commercial preparations of the latanoprost bulk drug product. The IC50 values for the free acid forms of 15(S)-17-phenyl trinor PGF and 15(R)-17-phenyl trinor PGF 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 PGF caused a 1.9 mmHg reduction of IOP in normotensive cynomolgus monkeys.1

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Resul, B., Stjernschantz, J., No, K., et alPhenyl-substituted prostaglandins: Potent and selective antiglaucoma agents. J. Med. Chem. 36(2), 243-248 (1993).