Unoprostone isopropyl ester

Cayman Chemical Item Number 16681

13,14-dihydro-15-keto-20-ethyl Prostaglandin F isopropyl ester; Rescula (CAS 120373-24-2)

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Description

Unoprostone isopropyl ester (Rescula) is the clinically approved, prodrug form of unoprostone, which is a free acid analog of prostaglandin F (PGF). Both latanoprost and Rescula have been approved for the treatment of ocular hypertension. Both analogs of PGF are believed to act by increasing the rate of aqueous humor outflow through the uveoscleral pathway.1 Both drugs are believed to act as prodrugs, with endogenous esterases within the eye releasing the free acid active form of the drug. The typical does of Rescula (one drop of 0.12% solution) is nearly 100 times that of latanoprost.2 Rescula has very little activity on isolated DP or TP receptors, less than 0.0005% the activity of PGE2 on EP3 receptors, and about 3% of the activity of PGF on FP receptors.3

1. Taniguchi, T., Haque, M.S.R., Sugiyama, K., et al. Ocular hypotensive mechanism of topical isopropyl unoprostone, a novel prostaglandin metabolite-related drug, in rabbits. J Ocul Pharmacol 12 489-498 (1996).

2. Haria, M., and Spencer, C.M. Unoprostone (isopropyl unoprostone). Drugs Aging 9 213-218 (1996).

3. Goh, Y., and Kishino, J. Pharmacological characterization of prostaglandin-related ocular hypotensive agents. Jpn J Ophthamol 38 236-245 (1994).

Synonyms
  • 13,14-dihydro-15-keto-20-ethyl Prostaglandin F isopropyl ester
  • Rescula
Formal Name 9α,​11α-​dihydroxy-​13,​14-​dihydro-​15-​oxo-​20a,​20b-​dihomoprost-​5Z-​en-​1-​oic acid,​ isopropyl ester
CAS Number 120373-24-2
Molecular Formula C25H44O5
Formula Weight 424.6
Formulation A solution in methyl acetate
Purity ≥98%
Stability 2 years
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere
SMILES
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O[C@@H]​1[C@H]​(C/C=C\CCCC(OC(C)​C)​=O)​[C@@H]​(CCC(CCCCCCC)​=O)​[C@H]​(O)​C1
InCHI Code
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​1S/C25H44O5/c1-4-5-6-7-10-13-20(26)​16-17-22-21(23(27)​18-24(22)​28)​14-11-8-9-12-15-25(29)​30-19(2)​3/h8,11,19,21-24,27-28H,4-7,9-10,12-18H2,1-3H3/b11-8-/t21-,22-,23+,24-/m1/s1
InCHI Key
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XXUPXHKCPIKWLR-JHUOEJJVSA-N

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Unoprostone isopropyl ester is available in the following screening libraries:

Size Price Quantity Subtotal
1 mg $48.00 $0.00
5 mg $216.00 $0.00
10 mg $384.00 $0.00
50 mg $1,536.00 $0.00
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Related Products

Latanoprost
Latanoprost-d4
Latanoprost (free acid)
Lumula
Unoprostone
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