An FP receptor agonist and a prodrug of latanoprost (free acid)
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Latanoprost

Item No. 16812

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
9α,11α,15R-trihydroxy-17-phenyl-18,19,20-trinor-prost-5Z-en-1-oic acid, isopropyl ester
CAS Number
130209-82-4
Synonyms
  • CAY530500
  • (+)-Latanoprost
  • 17-phenyl-13,14-dihydro trinor PGF2α isopropyl ester
  • 17-phenyl-13,14-dihydro trinor Prostaglandin F2α isopropyl ester
  • PhXA41
Molecular Formula
C26H40O5
Formula Weight
432.6
Purity
≥98%
Formulation
A 10 mg/ml solution in methyl acetate
Solubility(Learn about Variance in Solubility)
DMF: >100 mg/mlDMSO: >50 mg/mlEthanol: MiscibleEthanol:PBS (pH 7.2): 400 µg/mlH2O: 125 µg/mlPBS (pH 7.2): 50 µg/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+/m0/s1
InChi Key
GGXICVAJURFBLW-CEYXHVGTSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $63

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    5 mg

    $183

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    10 mg

    $242

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    50 mg

    $1,053

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    Product Description

    Latanoprost is a derivative of prostaglandin F2α (PGF2α; Item Nos. 16010 | 16020), an FP receptor agonist, and a prodrug of latanoprost (free acid) (Item No. 16811).1 It induces phosphoinositide turnover in isolated human ciliary muscle and human trabecular meshwork cells, HEK293 cells expressing human ocular FP receptors, mouse NIH3T3 fibroblasts, and rat A7r5 vascular smooth muscle cells (EC50s = 313, 564, 173, 142, and 110 nM, respectively). Topical ocular application of latanoprost (0.005% twice per day) reduces intraocular pressure (IOP), without affecting outflow facility or aqueous humor flow rates, in cynomolgus monkeys in a model of laser-induced glaucoma.2 Formulations containing latanoprost have been used in the treatment of open-angle glaucoma or ocular hypertension.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Sharif, N.A., Kelly, C.R., Crider, J.Y., et al. Ocular hypotensive FP prostaglandin (PG) analogs: PG receptor subtype binding affinities and selectivities, and agonist potencies at FP and other PG receptors in cultured cells. J. Ocul. Pharmacol. Ther. 19(6), 501-515 (2003).

    2. Serle, J.B., Podos, S.M., Kitazawa, Y., et al. A comparative study of latanoprost (Xalatan) and isopropyl unoprostone (Rescula) in normal and glaucomatous monkey eyes. Jpn. J. Ophthalmol. 42(2), 95-100 (1997).

    Product Citations

    Ota, T., Aihara, M., Narumiya, S., et al. The effects of prostaglandin analogues on IOP in prostanoid FP-receptor-deficient mice. Invest. Ophthalmol. Vis. Sci. 46(11), 4159-4163 (2005).