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Join us! · InformexUSA 2012 · New Orleans, Louisiana · February 14-17, 2012 · Booth 2514

17-phenyl trinor Prostaglandin F ethyl amide

Cayman Chemical Item Number 16820

17-phenyl trinor PGF ethyl amide; Bimatoprost; 15(S)-Bimatoprost (CAS 155206-00-1)

17-phenyl trinor Prostaglandin F2α ethyl amide (CAS 155206-00-1)

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Description

17-phenyl trinor Prostaglandin F ethyl amide (17-phenyl trinor PGF ethyl amide) is sold under the Allergan trade name Bimatoprost and is an F-series PG analog which has been approved for use as an ocular hypotensive drug.1 Investigations in our lab have shown that 17-phenyl trinor PGF ethyl amide is converted by an amidase enzymatic activity in the bovine and human cornea to yield the corresponding free acid, with a conversion rate of about 40 µg/g corneal tissue/24 hours.2 The free acid, 17-phenyl trinor PGF, is a potent FP receptor agonist.3,4 In human and animal models of glaucoma, FP receptor agonist activity corresponds very closely with intraocular hypotensive activity.

1 Woodward, D.F., Krauss, A.H., Chen, J., et al. The pharmacology of Bimatoprost (Lumigan). Surv Ophthalmol 45 S337-S345 (2001).

2 Maxey, K.M., Johnson, J., Camras, C.B., et al. The hydrolysis of bimatoprost in corneal tissue generates a potent prostanoid FP receptor agonist. Surv Ophthalmol 47(4) 34-40 (2002).

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

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

Synonyms
  • 17-phenyl trinor PGF2α ethyl amide
  • Bimatoprost
  • 15(S)-Bimatoprost
Formal Name N-​ethyl-​9α,​11α,​15S-​trihydroxy-​17-​phenyl-​18,​19,​20-​trinor-​prosta-​5Z,​13E-​dien-​1-​amide
CAS Number 155206-00-1
Molecular Formula C25H37NO4
Formula Weight 415.6
Formulation A crystalline solid
Purity >97%
Stability 2 years
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere
SMILES
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CCNC(=O)​CCC/C=C\CC1C(O)​CC(O)​[C@@H]​1\C=C\C(O)​CCc1ccccc1

Background Reading

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

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

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

Maxey, K.M., Johnson, J., Camras, C.B., et al. The hydrolysis of bimatoprost in corneal tissue generates a potent prostanoid FP receptor agonist. Surv Ophthalmol 47(4) 34-40 (2002).

Sharif, N.A., Williams, G.W., and Kelly, C.R. Bimatoprost and its free acid are prostaglandin FP receptor agonists. Eur J Pharmacol 432 211-213 (2001).

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17-phenyl trinor Prostaglandin F2α ethyl amide is available in the following screening library:

Size Price Quantity Subtotal
1 mg $58.00 $0.00
5 mg $261.00 $0.00
10 mg $464.00 $0.00
50 mg $2,030.00 $0.00
Bulk Contact
Cart Total $0.00

This product is available in custom sizes and/or larger quantities.

Please contact our Sales Department for a quote or to purchase.

Pricing updated 2012-02-11. Prices are subject to change without notice.

To ask for assistance with one of our products please contact a Technical Support Scientist.

Warning This product is not for human or veterinary use.

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