Rimexolone

Rimexolone is a glucocorticoid steroid used to treat inflammation in the eye.[1] It is marketed as a 1% eye drop suspension under the trade name Vexol by Alcon Laboratories, but was discontinued in the US and other countries.[2][3]

Rimexolone
Clinical data
Trade namesVexol
Other namesTrimexolone; Org 6216; 11β-Hydroxy-16α,17α,21-trimethylpregna-1,4-dien-3,20-dione
AHFS/Drugs.comMonograph
MedlinePlusa606003
Routes of
administration		Eye drops
ATC code
Pharmacokinetic data
Elimination half-lifeestimated 1–2 hours
Excretion>80% faeces
Identifiers
IUPAC name
  • (8S,9S,10R,11S,13S,14S,16R,17S)-11-Hydroxy-10,13,16,17-tetramethyl-17-propanoyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-3-one
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.211.227
Chemical and physical data
FormulaC24H34O3
Molar mass370.533 g·mol−1
3D model (JSmol)
SMILES
  • CCC(=O)[C@]1([C@@H](C[C@@H]2[C@@]1(C[C@@H]([C@H]3[C@H]2CCC4=CC(=O)C=C[C@]34C)O)C)C)C
InChI
  • InChI=1S/C24H34O3/c1-6-20(27)24(5)14(2)11-18-17-8-7-15-12-16(25)9-10-22(15,3)21(17)19(26)13-23(18,24)4/h9-10,12,14,17-19,21,26H,6-8,11,13H2,1-5H3/t14-,17+,18+,19+,21-,22+,23+,24-/m1/s1 N
  • Key:QTTRZHGPGKRAFB-OOKHYKNYSA-N N
 NY (what is this?)  (verify)

Medical uses

Rimexolone is used to treat inflammation after eye surgery, to treat anterior uveitis, conjunctivitis and keratitis.[2][3]

Contraindications

The substance is contraindicated in herpes simplex and most other viral eye infections, as well as mycobacterial, fungal and amoebal eye infections[2][3] because it only reduces the inflammation but does not act against such microorganisms.

Side effects

The most common adverse effects are blurred vision, tearing and other kinds of eye discomfort. Eye pain, eye oedema, headache, increased intraocular pressure and other side effects are seen in less than 1% of patients.[2][3]

Pharmacology

Pharmacodynamics
Further information: Glucocorticoid § Mechanism of action

As a glucocorticoid, rimexolone acts as an agonist of the glucocorticoid receptor.

Pharmacokinetics

A small amount of rimexolone is absorbed into the systemic circulation. On hourly treatment with the eye drops for a week, blood serum concentrations peaked at 150 pg/ml on average, with many patients remaining below the detection threshold of 80 pg/ml. The elimination half-life from the circulation is estimated at one to two hours; the substance is mainly (over 80%) excreted via the faeces.[2][3]

References
  1. Kavuncu S, Horoz H, Ardagil A, Erbil HH (August 2008). "Rimexolone 1% versus prednisolone acetate in preventing early postoperative inflammation after cataract surgery". Int Ophthalmol. 28 (4): 281–5. doi:10.1007/s10792-007-9131-0. PMID 17762913.
  2. Haberfeld, H, ed. (2015). Austria-Codex (in German). Vienna: Österreichischer Apothekerverlag. Vexol 1% (10 mg/ml)-Augentropfensuspension.
  3. Drugs.com: Monograph.


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