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Details

Stereochemistry ABSOLUTE
Molecular Formula C22H38O5
Molecular Weight 382.5341
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of UNOPROSTONE

SMILES

CCCCCCCC(=O)CC[C@H]1[C@H](O)C[C@H](O)[C@@H]1C\C=C/CCCC(O)=O

InChI

InChIKey=TVHAZVBUYQMHBC-SNHXEXRGSA-N
InChI=1S/C22H38O5/c1-2-3-4-5-8-11-17(23)14-15-19-18(20(24)16-21(19)25)12-9-6-7-10-13-22(26)27/h6,9,18-21,24-25H,2-5,7-8,10-16H2,1H3,(H,26,27)/b9-6-/t18-,19-,20+,21-/m1/s1

HIDE SMILES / InChI

Molecular Formula C22H38O5
Molecular Weight 382.5341
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 1
Optical Activity UNSPECIFIED

Description

Unoprostone Isopropyl is a synthetic docosanoid and a structural analogue of an inactive biosynthetic cyclic derivative of arachidonic acid, 13,14-dihydro-15-keto-prostaglandin F 2a. Although the mechanism of action is unknown, unoprostone isopropyl is believed to reduce elevated intraocular pressure by increasing the outflow of aqueous humor through the trabecular meshwork. Unoprostone isopropyl (UI) may have a local effect on Big Potassium channels and ClC-2 chloride channels, but the exact mechanism is unknown at this time. Unoprostone is used for the management of open-angle glaucoma and ocular hypertension. The therapeutic efficacy of Unoprostone can be decreased when used in combination with Celecoxib, Diclofenac, Diflunisal, Etodolac and some other drugs. Unoprostone isopropyl ophthalmic solution may gradually increase the pigmentation of the iris, cause pigment changes (darkening) to periorbital pigmented tissues and eyelashes, exacerbate active intraocular inflammation (e.g., uveitis), and cause macular edema. In clinical studies, the most common ocular adverse reactions with use of Rescula were burning/stinging, burning/stinging upon drug instillation, dry eyes, itching, increased length of eyelashes, and injection. These were reported in approximately 10–25% of patients. Ocular adverse reactions occurring in approximately 5–10% of patients were abnormal vision, eyelid disorder, foreign body sensation, and lacrimation disorder. Other adverse reactions occurred more rarely.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
3280.0 nM [EC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
RESCULA
Primary
RESCULA

Cmax

ValueDoseCo-administeredAnalytePopulation
1.5 ng/mL
1 drop 2 times / day multiple, ocular
UNOPROSTONE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
14 min
1 drop 2 times / day multiple, ocular
UNOPROSTONE plasma
Homo sapiens

Doses

AEs

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer





Drug as perpetrator​

Drug as victim

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
Unoprostone isopropyl ophthalmic solution, 1.5 mg/mL. One drop in the affected eye(s) twice daily.
Route of Administration: Topical
In Vitro Use Guide
The porcine retinal arterioles dilated in response to Unoprostone Isopropyl in a dose-dependent (100 pM-10 uM) manner. The highest concentration (10 uM) elicited about 30% of the maximal dilation.
Substance Class Chemical
Record UNII
6X4F561V3W
Record Status Validated (UNII)
Record Version