Potent FP receptor agonist
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17-phenyl trinor Prostaglandin F2α

Item No. 16810

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(5Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxy-5-phenyl-1-penten-1-yl]cyclopentyl]-5-heptenoic acid
CAS Number
38344-08-0
Synonyms
  • Bimatoprost (free acid)
  • 17-phenyl trinor PGF2α
Molecular Formula
C23H32O5
Formula Weight
388.5
Purity
≥98%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: >100 mg/mlDMSO: >100 mg/mlEthanol: >100 mg/mlPBS (pH 7.2): >800 µg/ml
SMILES
O[C@@H]1[C@H](C/C=C\CCCC(O)=O)[C@@H](/C=C/[C@@H](O)CCC2=CC=CC=C2)[C@H](O)C1
InChi Code
InChI=1S/C23H32O5/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/h1,3-6,8-9,14-15,18-22,24-26H,2,7,10-13,16H2,(H,27,28)/b6-1-,15-14+/t18-,19+,20+,21-,22+/m0/s1
InChi Key
YFHHIZGZVLHBQZ-KDACTHKWSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    1 mg

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    10 mg

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    25 mg

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    Product Description

    17-phenyl trinor Prostaglandin F2α (17-phenyl trinor PGF2α) is a metabolically stable analog of PGF2α and is a potent agonist for the FP receptor. It binds to the FP receptor on ovine luteal cells with a relative potency of 756% compared to that of PGF2α.1 At the rat recombinant FP receptor expressed in CHO cells bimatoprost inhibits PGF2α binding with a Ki of 1.1 nM.2 The isopropyl ester of 17-phenyl trinor PGF2α ethyl amide is slightly better than PGF2α isopropyl ester in reducing the intraocular pressure in the cat eye without any irritation.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Balapure, A.K., Rexroad, C.E., Jr., Kawada, K., et al. Structural requirements for prostaglandin analog interaction with the ovine corpus luteum prostaglandin F2α receptor. Biochem. Pharmacol. 38(14), 2375-2381 (1989).

    2. Lake, S., Gullberg, H., Wahlqvist, J., et al. Cloning of the rat and human prostaglandin F2α receptors and the expression of the rat prostaglandin F2α receptor. FEBS Lett. 355(3), 317-325 (1994).

    3. Stjernschantz, J., and Resul, B. Phenyl substituted prostaglandin analogs for glaucoma treatment. Drugs Future 17(8), 691-704 (1992).

    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).

    Sharif, N.A., Kelly, C.R., and Williams, G.W. Bimatoprost (Lumiganr) is an agonist at the cloned human ocular FP prostaglandin receptor: Real-time FLIPR-based intracellular Ca2+ mobilization studies. Prostaglandis Leukot. Essent. Fatty Acids 68(1), 27-33 (2003).

    Woodward, D.F., Krauss, A.H.P., Chen, J., et al. Pharmacological characterization of a novel antiglaucoma agent, bimatoprost (AGN 192024). J. Pharmacol. Exp. Ther. 305(2), 772-785 (2003).

    Hellberg, M.R., Ke, T.-L., Haggard, K., et al. The hydrolysis of the prostaglandin analog prodrug bimatoprost to 17-phenyl-trinor PGF2α by human and rabbit ocular tissue. J. Ocul. Pharmacol. Ther. 19(2), 97-103 (2003).