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| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 1201389
| ChEMBL = 1201389
| ChEBI = 31784
| synonyms = HGP 1
<!-- Chemical data -->
<!-- Chemical data -->
| C=24 | H=31 | Cl=1 | O=7
| C=24 | H=31 | Cl=1 | O=7
| molecular_weight = 466.951 g/mol
| molecular_weight = 466.951 g/mol
| 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
| StdInChI=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
| StdInChIKey = DMKSVUSAATWOCU-HROMYWEYSA-N
}}
}}



Revision as of 07:13, 15 June 2016

Loteprednol etabonate
Clinical data
Trade namesLotemax
Other namesHGP 1
AHFS/Drugs.comMicromedex Detailed Consumer Information
MedlinePlusa606003
Routes of
administration
Eye drops
ATC code
Legal status
Legal status
Identifiers
  • 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
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.167.120 Edit this at Wikidata
Chemical and physical data
FormulaC24H31ClO7
Molar mass466.951 g/mol g·mol−1
3D model (JSmol)
  • 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=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
 ☒NcheckY (what is this?)  (verify)

Loteprednol (as the ester loteprednol etabonate) is a corticosteroid used to treat inflammations of the eye. It is marketed by Bausch and Lomb as Lotemax.[1]

Medical uses

Ocular applications for this drug include the treatment of inflammation of the eye due to allergies, as well as chronic forms of keratitis (e.g. adenoviral and Thygeson's keratitis), vernal keratoconjunctivitis,[2] pingueculitis, and episcleritis.[citation needed]

Contraindications

As corticosteroids are immunosuppressive, loteprednol is contraindicated in patients with viral or fungal infections of the eye.[1][2]

Adverse effects

Common adverse effects include foreign body sensation in the eye, dry eye and epiphora (overflow of tears), chemosis (swelling of the conjunctiva), headache, and itching. Increased intraocular pressure, a side effect typical of corticosteroids, occurs in about 2% of patients.[1][2]

Interactions

The effect of drugs lowering intraocular pressure may be reduced. Loteprednol is not detectable in the bloodstream; so interactions with systemic drugs are highly unlikely.[1]

Physical and chemical properties

Chemical synthesis

[3]

See also

References

  1. ^ a b c d Haberfeld, H, ed. (2015). Austria-Codex (in German). Vienna: Österreichischer Apothekerverlag.
  2. ^ a b c Loteprednol Professional Drug Facts.
  3. ^ Druzgala, P.; Hochhaus, G.; Bodor, N. (1991). "Soft drugs—10. Blanching activity and receptor binding affinity of a new type of glucocorticoid: Loteprednol etabonate". J. Steroid Biochem. Mol. Biol. 38 (2): 149–54. doi:10.1016/0960-0760(91)90120-T. PMID 2004037.{{cite journal}}: CS1 maint: multiple names: authors list (link)

Further reading

  • Steward, R; et al. (November 1998). "Double-masked, placebo-controlled evaluation of loteprednol etabonate 0.5% for postoperative inflammation". J Cataract Surg. 24: 1480–1489.
  • Pavesio, CE; Decory, HH (2008). "Treatment of ocular inflammatory conditions with loteprednol etabonate". Br J Ophthalmol. 92 (4): 455–459. doi:10.1136/bjo.2007.132621. PMID 18245274.