Loteprednol

Loteprednol
Clinical data
Trade names	Lotemax
Other names	11β,17α,Dihydroxy-21-oxa-21-chloromethylpregna-1,4-diene-3,20-dione 17α-ethylcarbonate
AHFS/Drugs.com	Micromedex Detailed Consumer Information
Routes of; administration	Eye drops
Drug class	Corticosteroid; glucocorticoid
ATC code	S01BA14 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); US: ℞-only;
Pharmacokinetic data
Bioavailability	None
Protein binding	95%
Metabolism	Ester hydrolysis
Metabolites	Δ1-cortienic acid and its etabonate
Onset of action	≤2 hrs (allergic conjunctivitis)
Elimination half-life	2.8 hrs
Identifiers
	IUPAC name Chloromethyl 17-ethoxycarbonyloxy-11-hydroxy-10,13-dimethyl-3-oxo-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-17-carboxylate;
CAS Number	82034-46-6 ;
PubChem CID	444025;
IUPHAR/BPS	7085;
DrugBank	DB14596 ;
ChemSpider	392049 ;
UNII	YEH1EZ96K6;
KEGG	D01689 ;
ChEBI	CHEBI:31784 ;
ChEMBL	ChEMBL1200865 ;
CompTox Dashboard (EPA)	DTXSID2046468 ;
ECHA InfoCard	100.167.120
Chemical and physical data
Formula	C24H31ClO7
Molar mass	466.96 g·mol−1
3D model (JSmol)	Interactive image;
Melting point	220.5 to 223.5 °C (428.9 to 434.3 °F)
Solubility in water	0.0005 mg/mL (20 °C)
	SMILES CCOC(=O)O[C@@]1(CC[C@@H]2[C@@]1(C[C@@H]([C@H]3[C@H]2CCC4=CC(=O)C=C[C@]34C)O)C)C(=O)OCCl;
	InChI InChI=1S/C24H31ClO7/c1-4-30-21(29)32-24(20(28)31-13-25)10-8-17-16-6-5-14-11-15(26)7-9-22(14,2)19(16)18(27)12-23(17,24)3/h7,9,11,16-19,27H,4-6,8,10,12-13H2,1-3H3/t16-,17-,18-,19+,22-,23-,24-/m0/s1 ; Key:DMKSVUSAATWOCU-HROMYWEYSA-N ;
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Loteprednol (synthesized 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^[2] and Loterex.

It was patented in 1980 and approved for medical use in 1998.^[3] It is available as a generic medication.^[4]

^ "Prescription medicines: registration of new chemical entities in Australia, 2014". Therapeutic Goods Administration (TGA). 21 June 2022. Retrieved 10 April 2023.
^ Cite error: The named reference AC was invoked but never defined (see the help page).
^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 488. ISBN 9783527607495.
^ "First Generic Drug Approvals 2023". U.S. Food and Drug Administration (FDA). 30 May 2023. Archived from the original on 30 June 2023. Retrieved 30 June 2023.

[1] "Prescription medicines: registration of new chemical entities in Australia, 2014". Therapeutic Goods Administration (TGA). 21 June 2022. Retrieved 10 April 2023.

[AC-2] Cite error: The named reference AC was invoked but never defined (see the help page).

[Fis2006-3] Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 488. ISBN 9783527607495.

[4] "First Generic Drug Approvals 2023". U.S. Food and Drug Administration (FDA). 30 May 2023. Archived from the original on 30 June 2023. Retrieved 30 June 2023.

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Loteprednol

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