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17-phenyl trinor Prostaglandin F2α isopropyl ester

Cayman Chemical Item Number 16824

Bimatoprost isopropyl ester; 17-phenyl trinor PGF2α isopropyl ester; 17-phenyl trinor PGF2α-iPr (CAS 130209-76-6)

17-phenyl trinor Prostaglandin F2α isopropyl ester (CAS 130209-76-6)

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Description

17-phenyl trinor PGF2α N-ethyl amide is an F-series prostaglandin analog which has been approved for use as an ocular hypotensive drug, sold under the Allergan trade name Bimatoprost.1 The N-ethyl amide prostaglandin prodrugs are converted to the active free acid more slowly than the analogous prostaglandin ester prodrugs such as latanoprost.2 This product is the isopropyl ester of the free acid prostaglandin which corresponds to Bimatoprost. The free acid, 17-phenyl trinor PGF2α, is a potent FP receptor agonist.3 In human and animal models of glaucoma, FP receptor agonist activity corresponds very closely with intraocular hypotensive activity. The 17-phenyl trinor PGF2α isopropyl ester derivative was examined for IOP-lowering activity during the development of latanoprost.4 At the dose of 3 μg/eye in the monkey, 17-phenyl trinor PGF2α isopropyl ester was the most potent analog tested in reducing IOP, lowering the IOP 1.3 mm Hg below the level achieved by latanoprost. However, this derivative was also significantly more irritating to the eye than latanoprost.4

1 Abramovitz, M., Adam, M., Boie, Y., et al. The utilization of recombinant prostanoid receptors to determine the affinities and selectivities of prostaglandins and related analogs. Biochim Biophys Acta 1483 285-293 (2000).

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

3 Resul, B., Stjernschantz, J., Selén, G., et al. Structure-activity relationships and receptor profiles of some ocular hypotensive prostanoids. Surv Ophthalmol 41 S47-S52 (1997).

4 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).

Synonyms
  • Bimatoprost isopropyl ester
  • 17-phenyl trinor PGF2α isopropyl ester
  • 17-phenyl trinor PGF2α-iPr
Formal Name 9α,​11α,​15S-​trihydroxy-​17-​phenyl-​18,​19,​20-​trinor-​prosta-​5Z,​13E-​dien-​1-​oic acid,​ isopropyl ester
CAS Number 130209-76-6
Molecular Formula C26H38O5
Formula Weight 430.6
Formulation A solution in ethanol
Purity >98%
Stability 1 year
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere
SMILES
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CC(C)​OC(=O)​CCC/C=C\CC1C(O)​CC(O)​[C@@H]​1\C=C\C(O)​CCc1ccccc1

Background Reading

Abramovitz, M., Adam, M., Boie, Y., et al. The utilization of recombinant prostanoid receptors to determine the affinities and selectivities of prostaglandins and related analogs. Biochim Biophys Acta 1483 285-293 (2000).

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

Resul, B., Stjernschantz, J., Selén, G., et al. Structure-activity relationships and receptor profiles of some ocular hypotensive prostanoids. Surv Ophthalmol 41 S47-S52 (1997).

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).

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17-phenyl trinor Prostaglandin F2α isopropyl ester is available in the following screening libraries:

Size Price Quantity Subtotal
1 mg $59.00 $0.00
5 mg $266.00 $0.00
10 mg $472.00 $0.00
50 mg $2,065.00 $0.00
Bulk Contact
Cart Total $0.00

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

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Pricing updated 2012-05-26. Prices are subject to change without notice.

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Warning This product is not for human or veterinary use.

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