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Details

Stereochemistry ABSOLUTE
Molecular Formula C25H44O5
Molecular Weight 424.6139
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of UNOPROSTONE ISOPROPYL

SMILES

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

InChI

InChIKey=XXUPXHKCPIKWLR-JHUOEJJVSA-N
InChI=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

HIDE SMILES / InChI

Molecular Formula C25H44O5
Molecular Weight 424.6139
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 1
Optical Activity UNSPECIFIED

Description
Curator's Comment: Description was created based on several sources, including http://www.drugs.com/ppa/unoprostone.html http://www.drugbank.ca/drugs/DB06826 http://www.rxlist.com/rescula-drug.htm

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

Curator's Comment: R-Tech Ueno received the first marketing approval of unoprostone isopropyl in Japan in 1994 for the treatment of Glaucoma and Ocular Hypertension.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
RESCULA

Approved Use

Rescula (unoprostone isopropyl ophthalmic solution) 0.15% is indicated for the lowering of intraocular pressure in patients with open-angle glaucoma or ocular hypertension.

Launch Date

9.652608E11
Primary
RESCULA

Approved Use

Rescula (unoprostone isopropyl ophthalmic solution) 0.15% is indicated for the lowering of intraocular pressure in patients with open-angle glaucoma or ocular hypertension.

Launch Date

9.652608E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
1.5 ng/mL
1 drop 2 times / day multiple, ocular
dose: 1 drop
route of administration: Ocular
experiment type: MULTIPLE
co-administered:
UNOPROSTONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
14 min
1 drop 2 times / day multiple, ocular
dose: 1 drop
route of administration: Ocular
experiment type: MULTIPLE
co-administered:
UNOPROSTONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
0.15 % 2 times / day steady, ophthalmic
Recommended
Dose: 0.15 %, 2 times / day
Route: ophthalmic
Route: steady
Dose: 0.15 %, 2 times / day
Sources:
unhealthy, adult
n = 659
Health Status: unhealthy
Condition: glaucoma or ocular hypertension
Age Group: adult
Sex: unknown
Population Size: 659
Sources:
Disc. AE: Abnormal vision, Burning sensation...
AEs leading to
discontinuation/dose reduction:
Abnormal vision (1.1%)
Burning sensation (0.6%)
Instillation site burning (0.3%)
Conjunctivitis (0.5%)
Sensation of foreign body (0.6%)
Asthma (0.2%)
Chest pain (0.2%)
Insomnia (0.3%)
Rash (0.5%)
Sources:
0.15 % 2 times / day steady, ophthalmic
Recommended
Dose: 0.15 %, 2 times / day
Route: ophthalmic
Route: steady
Dose: 0.15 %, 2 times / day
Sources:
unhealthy, adult
n = 77
Health Status: unhealthy
Condition: intraocular pressure
Age Group: adult
Sex: unknown
Population Size: 77
Sources:
Disc. AE: Intraocular pressure increased...
AEs leading to
discontinuation/dose reduction:
Intraocular pressure increased (2 patients)
Sources:
AEs

AEs

AESignificanceDosePopulation
Asthma 0.2%
Disc. AE
0.15 % 2 times / day steady, ophthalmic
Recommended
Dose: 0.15 %, 2 times / day
Route: ophthalmic
Route: steady
Dose: 0.15 %, 2 times / day
Sources:
unhealthy, adult
n = 659
Health Status: unhealthy
Condition: glaucoma or ocular hypertension
Age Group: adult
Sex: unknown
Population Size: 659
Sources:
Chest pain 0.2%
Disc. AE
0.15 % 2 times / day steady, ophthalmic
Recommended
Dose: 0.15 %, 2 times / day
Route: ophthalmic
Route: steady
Dose: 0.15 %, 2 times / day
Sources:
unhealthy, adult
n = 659
Health Status: unhealthy
Condition: glaucoma or ocular hypertension
Age Group: adult
Sex: unknown
Population Size: 659
Sources:
Insomnia 0.3%
Disc. AE
0.15 % 2 times / day steady, ophthalmic
Recommended
Dose: 0.15 %, 2 times / day
Route: ophthalmic
Route: steady
Dose: 0.15 %, 2 times / day
Sources:
unhealthy, adult
n = 659
Health Status: unhealthy
Condition: glaucoma or ocular hypertension
Age Group: adult
Sex: unknown
Population Size: 659
Sources:
Instillation site burning 0.3%
Disc. AE
0.15 % 2 times / day steady, ophthalmic
Recommended
Dose: 0.15 %, 2 times / day
Route: ophthalmic
Route: steady
Dose: 0.15 %, 2 times / day
Sources:
unhealthy, adult
n = 659
Health Status: unhealthy
Condition: glaucoma or ocular hypertension
Age Group: adult
Sex: unknown
Population Size: 659
Sources:
Conjunctivitis 0.5%
Disc. AE
0.15 % 2 times / day steady, ophthalmic
Recommended
Dose: 0.15 %, 2 times / day
Route: ophthalmic
Route: steady
Dose: 0.15 %, 2 times / day
Sources:
unhealthy, adult
n = 659
Health Status: unhealthy
Condition: glaucoma or ocular hypertension
Age Group: adult
Sex: unknown
Population Size: 659
Sources:
Rash 0.5%
Disc. AE
0.15 % 2 times / day steady, ophthalmic
Recommended
Dose: 0.15 %, 2 times / day
Route: ophthalmic
Route: steady
Dose: 0.15 %, 2 times / day
Sources:
unhealthy, adult
n = 659
Health Status: unhealthy
Condition: glaucoma or ocular hypertension
Age Group: adult
Sex: unknown
Population Size: 659
Sources:
Burning sensation 0.6%
Disc. AE
0.15 % 2 times / day steady, ophthalmic
Recommended
Dose: 0.15 %, 2 times / day
Route: ophthalmic
Route: steady
Dose: 0.15 %, 2 times / day
Sources:
unhealthy, adult
n = 659
Health Status: unhealthy
Condition: glaucoma or ocular hypertension
Age Group: adult
Sex: unknown
Population Size: 659
Sources:
Sensation of foreign body 0.6%
Disc. AE
0.15 % 2 times / day steady, ophthalmic
Recommended
Dose: 0.15 %, 2 times / day
Route: ophthalmic
Route: steady
Dose: 0.15 %, 2 times / day
Sources:
unhealthy, adult
n = 659
Health Status: unhealthy
Condition: glaucoma or ocular hypertension
Age Group: adult
Sex: unknown
Population Size: 659
Sources:
Abnormal vision 1.1%
Disc. AE
0.15 % 2 times / day steady, ophthalmic
Recommended
Dose: 0.15 %, 2 times / day
Route: ophthalmic
Route: steady
Dose: 0.15 %, 2 times / day
Sources:
unhealthy, adult
n = 659
Health Status: unhealthy
Condition: glaucoma or ocular hypertension
Age Group: adult
Sex: unknown
Population Size: 659
Sources:
Intraocular pressure increased 2 patients
Disc. AE
0.15 % 2 times / day steady, ophthalmic
Recommended
Dose: 0.15 %, 2 times / day
Route: ophthalmic
Route: steady
Dose: 0.15 %, 2 times / day
Sources:
unhealthy, adult
n = 77
Health Status: unhealthy
Condition: intraocular pressure
Age Group: adult
Sex: unknown
Population Size: 77
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer





Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
yes
Drug as victim
PubMed

PubMed

TitleDatePubMed
Long-Term Protection of Genetically Ablated Rabbit Retinal Degeneration by Sustained Transscleral Unoprostone Delivery.
2016 Dec 1
Protective effects of sustained transscleral unoprostone delivery against retinal degeneration in S334ter rhodopsin mutant rats.
2016 Nov
Effect of topical isopropyl unoprostone on macular atrophy progression in eyes with exudative age-related macular degeneration.
2017 Mar
Patents

Patents

Sample Use Guides

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
Curator's Comment: 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.
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
Created
by admin
on Sat Dec 16 05:16:17 UTC 2023
Edited
by admin
on Sat Dec 16 05:16:17 UTC 2023
Record UNII
5M161S5O5P
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
UNOPROSTONE ISOPROPYL
MART.   ORANGE BOOK   VANDF   WHO-DD  
Common Name English
ISOPROPYL UNOPROSTONE
JAN  
Common Name English
UNOPROSTONE ISOPROPYL [VANDF]
Common Name English
Unoprostone isopropyl [WHO-DD]
Common Name English
UF-021
Code English
ISOPROPYL Z-7-((1R,2R,3R,5S)-3,5-DIHYDROXY-2-(3-OXODECYL)CYCLOPENTYL)HEPT-5-ENOATE, (+)-
Systematic Name English
UNOPROSTONE ISOPROPYL [MART.]
Common Name English
UNOPROSTONE ISOPROPYL [ORANGE BOOK]
Common Name English
RESCULA
Common Name English
UNOPROSTONE ISOPROPYL ESTER
MI  
Common Name English
ISOPROPYL UNOPROSTONE [JAN]
Common Name English
ISOPROPYL Z-7-((1R,2R,3R,5S)-3,5-DIHYDROXY-2-(3-OXODECYL)CYCLOPENTYL)HEPT-5-ENOATE, D-
Common Name English
UNOPROSTONE ISOPROPYL ESTER [MI]
Common Name English
Classification Tree Code System Code
EU-Orphan Drug EU/3/13/1146
Created by admin on Sat Dec 16 05:16:18 UTC 2023 , Edited by admin on Sat Dec 16 05:16:18 UTC 2023
NCI_THESAURUS C29705
Created by admin on Sat Dec 16 05:16:18 UTC 2023 , Edited by admin on Sat Dec 16 05:16:18 UTC 2023
FDA ORPHAN DRUG 314810
Created by admin on Sat Dec 16 05:16:18 UTC 2023 , Edited by admin on Sat Dec 16 05:16:18 UTC 2023
NCI_THESAURUS C78568
Created by admin on Sat Dec 16 05:16:18 UTC 2023 , Edited by admin on Sat Dec 16 05:16:18 UTC 2023
Code System Code Type Description
DRUG CENTRAL
2794
Created by admin on Sat Dec 16 05:16:18 UTC 2023 , Edited by admin on Sat Dec 16 05:16:18 UTC 2023
PRIMARY
EPA CompTox
DTXSID5049071
Created by admin on Sat Dec 16 05:16:18 UTC 2023 , Edited by admin on Sat Dec 16 05:16:18 UTC 2023
PRIMARY
PUBCHEM
5282175
Created by admin on Sat Dec 16 05:16:18 UTC 2023 , Edited by admin on Sat Dec 16 05:16:18 UTC 2023
PRIMARY
CHEBI
31731
Created by admin on Sat Dec 16 05:16:18 UTC 2023 , Edited by admin on Sat Dec 16 05:16:18 UTC 2023
PRIMARY
MERCK INDEX
m11304
Created by admin on Sat Dec 16 05:16:18 UTC 2023 , Edited by admin on Sat Dec 16 05:16:18 UTC 2023
PRIMARY Merck Index
WIKIPEDIA
Unoprostone isopropyl
Created by admin on Sat Dec 16 05:16:18 UTC 2023 , Edited by admin on Sat Dec 16 05:16:18 UTC 2023
PRIMARY
CAS
120373-24-2
Created by admin on Sat Dec 16 05:16:18 UTC 2023 , Edited by admin on Sat Dec 16 05:16:18 UTC 2023
PRIMARY
NCI_THESAURUS
C47778
Created by admin on Sat Dec 16 05:16:18 UTC 2023 , Edited by admin on Sat Dec 16 05:16:18 UTC 2023
PRIMARY
IUPHAR
8282
Created by admin on Sat Dec 16 05:16:18 UTC 2023 , Edited by admin on Sat Dec 16 05:16:18 UTC 2023
PRIMARY
MESH
C072630
Created by admin on Sat Dec 16 05:16:18 UTC 2023 , Edited by admin on Sat Dec 16 05:16:18 UTC 2023
PRIMARY
RXCUI
135313
Created by admin on Sat Dec 16 05:16:18 UTC 2023 , Edited by admin on Sat Dec 16 05:16:18 UTC 2023
PRIMARY RxNorm
DRUG BANK
DBSALT001760
Created by admin on Sat Dec 16 05:16:18 UTC 2023 , Edited by admin on Sat Dec 16 05:16:18 UTC 2023
PRIMARY
EVMPD
SUB15658MIG
Created by admin on Sat Dec 16 05:16:18 UTC 2023 , Edited by admin on Sat Dec 16 05:16:18 UTC 2023
PRIMARY
SMS_ID
100000077315
Created by admin on Sat Dec 16 05:16:18 UTC 2023 , Edited by admin on Sat Dec 16 05:16:18 UTC 2023
PRIMARY
ChEMBL
CHEMBL1200661
Created by admin on Sat Dec 16 05:16:18 UTC 2023 , Edited by admin on Sat Dec 16 05:16:18 UTC 2023
PRIMARY
FDA UNII
5M161S5O5P
Created by admin on Sat Dec 16 05:16:18 UTC 2023 , Edited by admin on Sat Dec 16 05:16:18 UTC 2023
PRIMARY
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METABOLITE ACTIVE -> PRODRUG
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ACTIVE MOIETY