An FP receptor agonist and active metabolite of latanoprost
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Latanoprost (free acid)

Item No. 16811

Technical Information
Formal Name
(5Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3R)-3-hydroxy-5-phenylpentyl]cyclopentyl]-5-heptenoic acid
CAS Number
41639-83-2
Synonyms
  • Lat-FA
  • PhXA-85
  • 17-phenyl-13,14-dihydro trinor Prostaglandin F
Molecular Formula
C23H34O5
Formula Weight
Purity
≥98%
Formulation
A 10 mg/ml solution in methyl acetate
DMF: 100 mg/mlDMSO: 100 mg/mlEthanol: 100 mg/mlPBS (pH 7.2): 0.8 mg/ml
SMILES
O[C@@H]1[C@H](C/C=C\CCCC(O)=O)[C@@H](CC[C@@H](O)CCC2=CC=CC=C2)[C@H](O)C1
InChi Code
InChI=1S/C23H34O5/c24-18(13-12-17-8-4-3-5-9-17)14-15-20-19(21(25)16-22(20)26)10-6-1-2-7-11-23(27)28/h1,3-6,8-9,18-22,24-26H,2,7,10-16H2,(H,27,28)/b6-1-/t18-,19+,20+,21-,22+/m0/s1
InChi Key
HNPFPERDNWXAGS-NFVOFSAMSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Latanoprost (free acid) is a derivative of prostaglandin F (PGF; Item Nos. 16010 | 16020), an FP receptor agonist, and an active metabolite of the prodrug latanoprost (Item No. 16812).1 It selectively binds to the FP receptor (Ki = 0.098 µM) over the EP1, EP2, EP3, and EP4 receptors (Kis = 2.06, 39.667, 7.519, and 75 µM, respectively), as well as the DP, IP, and TP receptors (Kis = ≥20, ≥90, and ≥60 µM, respectively). It induces phosphoinositide turnover in isolated human ciliary muscle and human trabecular meshwork cells, mouse NIH3T3 fibroblasts, and rat A7r5 vascular smooth muscle cells, which all endogenously express FP receptors (EC50s = 124, 35, 32, and 35 nM, respectively), as well as HEK293 cells expressing human ocular FP receptors (EC50 = 45.7 nM). It also increases intracellular calcium levels in hEP1-5/293-AEQ17 cells expressing EP1 receptors in an aequorin-based calcium assay (EC50 = 119 nM).2 Latanoprost (free acid) induces contraction of isolated cat iris sphincter smooth muscle (EC50 = 29.9 nM).3

    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 alOcular 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. Ungrin, M.D., Carrière, M.C., Denis, D., et alKey structural features of prostaglandin E2 and prostanoid analogs involved in binding and activation of the human EP1 prostanoid receptor. Mol. Pharmacol. 59(6), 1446-1456 (2001).

    3. Sharif, N.A., Kaddour-Djebbar, I., and Abdel-Latif, A.A. Cat iris sphincter smooth-muscle contraction: Comparison of FP-class prostaglandin analog agonist activities. J. Ocul. Pharmacol. Ther. 24(2), 152-163 (2008).