loteprednol

Also known as chloromethyl (8S,9S,10R,11S,13S,14S,17R)-11,17-dihydroxy-10,13-dimethyl-3-oxo-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-17-carboxylate, 17a-hydroxy-11b-hydroxy-3-oxoandrosta-1,4-diene-17-carboxylic acid chloromethyl ester

Loteprednol (formulated as the ester loteprednol etabonate) is a topical corticosteroid used to treat inflammations of the eye. It is marketed by Bausch and Lomb as Lotemax and Loterex.

Chemical data

Formula: C21H27ClO5
Molecular weight: 394.9 g/mol
IUPAC name: chloromethyl (8S,9S,10R,11S,13S,14S,17R)-11,17-dihydroxy-10,13-dimethyl-3-oxo-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-17-carboxylate
SMILES: C[C@]12C[C@@H]([C@H]3[C@H]([C@@H]1CC[C@@]2(C(=O)OCCl)O)CCC4=CC(=O)C=C[C@]34C)O
InChIKey: YPZVAYHNBBHPTO-MXRBDKCISA-N
XLogP: 2.6
Polar surface area: 83.8 Å²
H-bond donors: 2
H-bond acceptors: 5
Formal charge: 0

via PubChem

Wikidata facts

Mass: 394.154701644

Show 4 more facts

chemical formula: C₂₁H₂₇ClO₅
isomeric SMILES: C[C@]12C[C@@H]([C@H]3[C@H]([C@@H]1CC[C@@]2(C(=O)OCCl)O)CCC4=CC(=O)C=C[C@]34C)O
Commons category: Loteprednol
canonical SMILES: CC12CC(C3C(C1CCC2(C(=O)OCCl)O)CCC4=CC(=O)C=CC34C)O

Sources (2)

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Encyclopedic overview

12 sections

Contents

Medical uses
Contraindications
Adverse effects
Interactions
Pharmacology
Mechanism of action
Pharmacokinetics
Retrometabolic drug design
Chemistry
Chemical synthesis
References
Further reading

Loteprednol (formulated as the ester loteprednol etabonate) is a topical corticosteroid used to treat inflammations of the eye. It is marketed by Bausch and Lomb as Lotemax and Loterex.

It was patented in 1980 and approved for medical use in 1998. It is available as a generic medication.

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