A derivative of 17-phenyl trinor PGF2α ethyl amide
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17-phenyl trinor Prostaglandin F2α amide

Item No. 16821

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-heptenamide
CAS Number
155205-89-3
Synonyms
  • Bimatoprost amide
  • 17-phenyl trinor PGF2α amide
Molecular Formula
C23H33NO4
Formula Weight
387.5
Purity
≥98%
Formulation (Request formulation change)
A solution in ethanol
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 20 mg/mlEthanol: 20 mg/mlPBS (pH 7.2): 2 mg/ml
SMILES
O[C@@H]1[C@H](C/C=C\CCCC(N)=O)[C@@H](/C=C/[C@@H](O)CCC2=CC=CC=C2)[C@H](O)C1
InChi Code
InChI=1S/C23H33NO4/c24-23(28)11-7-2-1-6-10-19-20(22(27)16-21(19)26)15-14-18(25)13-12-17-8-4-3-5-9-17/h1,3-6,8-9,14-15,18-22,25-27H,2,7,10-13,16H2,(H2,24,28)/b6-1-,15-14+/t18-,19+,20+,21-,22+/m0/s1
InChi Key
RAGQWYIPCPFTJC-KDACTHKWSA-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

    17-phenyl trinor Prostaglandin F2α (17-phenyl trinor PGF2α) amide is a derivative of the FP receptor agonist 17-phenyl trinor PGF2α ethyl amide (bimatoprost; Item No. 16820) with an unsubstituted amide.1 As with bimatoprost and other prostaglandin amides, the amide of 17-phenyl trinor PGF2α amide may be hydrolyzed to the free acid form in human eyes.2,3,4 Like other amide isomers of F-type prostaglandins, 17-phenyl trinor PGF2α amide may have similar FP receptor activation and intraocular pressure (IOP) reduction activities.3 It has a lower hydrolysis rate in primary human corneas compared to isopropyl ester-protected prodrugs.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Bito, L.Z. Comparison of the ocular hypotensive efficacy of eicosanoids and related compounds. Exp. Eye Res. 38(2), 181-184 (1984).

    2. 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).

    3. Woodward, D.F., Krauss, A.H., Chen, J., et al. The pharmacology of bimatoprost (Lumigan™). Surv. Ophthalmol. 45(Suppl. 4), S337-S345 (2001).

    4. Maxey, K.M., Johnson, J., and LaBrecque, J. The hydrolysis of bimatoprost in corneal tissue generates a potent prostanoid FP receptor agonist. Surv. Ophthalmol. 47(Suppl. 1), S34-S40 (2002).

    Product Citations

    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).