A 15(S) isomer of latanoprost
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15(S)-Latanoprost

Item No. 16818

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(5Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3S)-3-hydroxy-5-phenylpentyl]cyclopentyl]-5-heptenoic acid, 1-methylethyl ester
CAS Number
145773-22-4
Synonyms
  • 15-epi Latanoprost
Molecular Formula
C26H40O5
Formula Weight
432.6
Purity
≥98%
Formulation (Request formulation change)
A 10 mg/ml solution in methyl acetate
Solubility(Learn about Variance in Solubility)
DMF: 100 mg/mlDMSO: 100 mg/mlDMSO:PBS (1:12): 80 µg/mlEthanol: 100 mg/ml
SMILES
O[C@@H]1[C@H](C/C=C\CCCC(OC(C)C)=O)[C@@H](CC[C@H](O)CCC2=CC=CC=C2)[C@H](O)C1
InChi Code
InChI=1S/C26H40O5/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/h3,5-8,10-11,19,21-25,27-29H,4,9,12-18H2,1-2H3/b8-3-/t21-,22-,23-,24+,25-/m1/s1
InChi Key
GGXICVAJURFBLW-SCTZCWPJSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

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    Product Description

    15(S)-Latanoprost is a 15(S) isomer of the FP receptor agonist latanoprost (Item No. 16812) in which the carbon 15 hydroxyl is inverted relative to latanoprost.1 Topical administration of 15(S)-latanoprost (3 µg/eye) reduces intraocular pressure (IOP) in cynomolgus monkeys and does not induce eye irritation in cats. The free acid form of 15(S)-latanoprost induces relaxation in isolated cat iris sphincter muscles (IC50 = 24 nM). 15(S)-Latanoprost is a potential impurity in commercial preparations of latanoprost.2

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

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

    2. Widomski, P., Baran, P., Golebiewski, P., et al. Validated liquid chromatographic method for analysis of the isomers of latanoprost. Acta Chromatagr. 20(2), 157-164 (2008).