120373-24-2

Basic information

• Product Name: Isopropyl unoprostone
• Synonyms: RESCULA;UNOPROSTONE ISOPROPYL ESTER;isopropyl unoprostone;9ALPHA,11ALPHA-DIHYDROXY-15-OXO-20A,20B-DIHOMOPROST-5-EN-1-OIC ACID, ISOPROPYL ESTER;(5z)-7-((1r,2r,3r,5s)-3,5-dihydroxy-2-(3-oxodecyl)cyclopentyl)-5-heptenoic acid 1-methylethyl ester;13,14-dihydro-15-keto-20-ethyl-pgf;13,14-DIHYDRO-15-KETO-20-ETHYL PROSTAGLANDIN F2ALPHA ISOPROPYL ESTER;(5Z)-7-[(1R,2R,3R,5S)-3,5-Dihydroxy-2-(3-oxodecyl)cyclopenthyl]-5-heptenoic Acid Isopropyl Ester
• CAS NO: 120373-24-2
• Molecular Formula: C25H44O5
• Molecular Weight: 424.61
• EINECS: 1312995-182-4
• Product Categories: Prostaglandins;Prostaglandin;Intermediates & Fine Chemicals;Pharmaceuticals;Chiral Reagents
• Mol File: 120373-24-2.mol
• Article Data: 0

Chemical Properties

• Boiling Point: 546.3 °C at 760 mmHg
• Flash Point: 172.2 °C
• Appearance: /
• Density: 1.019 g/cm³
• Vapor Pressure: 3.27E-14mmHg at 25°C
• Refractive Index: 1.491
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly)
• PKA: 14.79±0.70(Predicted)
• CAS DataBase Reference: Isopropyl unoprostone(CAS DataBase Reference)
• NIST Chemistry Reference: Isopropyl unoprostone(120373-24-2)
• EPA Substance Registry System: Isopropyl unoprostone(120373-24-2)

Safety Data

• Hazardous Substances Data: 120373-24-2(Hazardous Substances Data)

Usage

Description

Isopropyl unoprostone, also known as unoprostone isopropyl ester or Rescula, is a novel prostaglandin derivative that has been clinically approved as a prodrug form of unoprostone, a free acid analog of prostaglandin F2α (PGF2α). It is a clear, colorless oil that is used primarily in the treatment of glaucoma and ocular hypertension.

Uses

Used in Ophthalmology:
Isopropyl unoprostone is used as an antiglaucoma agent for the treatment of ocular hypertension. It effectively reduces intraocular pressure without causing systemic effects, myosis, or mydriasis. Unlike other prostaglandin analogs such as PGF2α, it does not cause irritation in the outer segment of the eye or significant changes in aqueous protein concentration and corneal endothelial permeability. It is believed to act by increasing uveoscleral outflow or by decreasing episcleral venous pressure, resulting in ocular hypotension.
Isopropyl unoprostone is also used as a prodrug in the eye, with endogenous esterases within the eye releasing the free acid active form of the drug. It 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 PGF2α on FP receptors. The typical dose of Rescula (one drop of 0.12% solution) is nearly 100 times that of latanoprost, another prostaglandin analog used for the same purpose.

Originator

Ueno (Japan)

Hazard

A poison.

InChI:InChI=1/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