unoprostone

Also known as RSC021, 13,14-dihydro-15-keto-20-ethyl PGF2α, (5Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-(3-oxodecyl)cyclopentyl]hept-5-enoic acid, (+)-(Z)-7-((1R,2R,3R,5S)-3,5-dihydroxy-2-(3-oxodecyl)cyclopentyl)-5-heptenoic acid, 13,14-dihydro-15-keto-20-ethyl PGF2alpha

Unoprostone (INN) is a prostaglandin analogue. Its isopropyl ester, unoprostone isopropyl, was marketed under the trade name Rescula for the management of open-angle glaucoma and ocular hypertension.

Chemical data

Formula: C22H38O5
Molecular weight: 382.5 g/mol
IUPAC name: (Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-(3-oxodecyl)cyclopentyl]hept-5-enoic acid
SMILES: CCCCCCCC(=O)CC[C@H]1[C@@H](C[C@@H]([C@@H]1C/C=C\CCCC(=O)O)O)O
InChIKey: TVHAZVBUYQMHBC-SNHXEXRGSA-N
XLogP: 3.7
Polar surface area: 94.8 Å²
H-bond donors: 3
H-bond acceptors: 5
Formal charge: 0

via PubChem

Drug data · ChEMBL

Max clinical phase: Phase 2
Molecule type: Small molecule
Indications: glaucoma

via ChEMBL · EBI

Wikidata facts

Subclass of: prostaglandins
Mass: 382.271924
Has use: medication

Show 5 more facts

chemical formula: C₂₂H₃₈O₅
isomeric SMILES: CCCCCCCC(=O)CC[C@H]1[C@@H](C[C@@H]([C@@H]1C/C=C\CCCC(=O)O)O)O
canonical SMILES: CCCCCCCC(=O)CCC1C(CC(C1CC=CCCCC(=O)O)O)O
World Health Organisation international non-proprietary name: unoprostone
Commons category: Unoprostone

Sources (6)

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Encyclopedic overview

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Contents

References

Unoprostone (INN) is a prostaglandin analogue. Its isopropyl ester, unoprostone isopropyl, was marketed under the trade name Rescula for the management of open-angle glaucoma and ocular hypertension.

It was approved by the Food and Drug Administration in 2000.In 2009, Sucampo Pharmaceuticals acquired the rights to the drug in the U.S. and Canada.

Excerpted from Wikipedia’s “unoprostone” article, available under the CC BY-SA 4.0 licence.

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