View source for Rimexolone

{{Short description|Pharmaceutical drug}}
{{Drugbox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 464382584
| IUPAC_name = (8''S'',9''S'',10''R'',11''S'',13''S'',14''S'',16''R'',17''S'')-11-Hydroxy-10,13,16,17-tetramethyl-17-propanoyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-3-one
| image = Rimexolone structure.png
<!--Clinical data-->
| tradename = Vexol
| Drugs.com = {{drugs.com|monograph|rimexolone}}
| MedlinePlus = a606003
| pregnancy_US = C <!-- A / B            / C / D / X -->
| pregnancy_category =  
| legal_status =  
| routes_of_administration = Eye drops
<!--Pharmacokinetic data-->
| bioavailability = 
| protein_bound = 
| metabolism = 
| elimination_half-life = estimated 1–2 hours
| excretion = >80% faeces
<!--Identifiers-->
| IUPHAR_ligand = 7099
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 49697-38-3
| ATC_prefix = H02
| ATC_suffix = AB12
| ATC_supplemental =  {{ATC|S01|BA13}}
| PubChem = 5311412
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB00896
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 4470902
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = O7M2E4264D
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D05729
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 1200617
<!--Chemical data-->
| C=24 | H=34 | O=3
| 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
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = QTTRZHGPGKRAFB-OOKHYKNYSA-N
| synonyms = Trimexolone; Org 6216; 11β-Hydroxy-16α,17α,21-trimethylpregna-1,4-dien-3,20-dione
}}

'''Rimexolone''' is a [[glucocorticoid]] [[steroid]] used to treat [[inflammation]] in the [[human eye|eye]].<ref name="pmid17762913">{{cite journal |vauthors=Kavuncu S, Horoz H, Ardagil A, Erbil HH |title=Rimexolone 1% versus prednisolone acetate in preventing early postoperative inflammation after cataract surgery |journal=Int Ophthalmol |volume=28 |issue=4 |pages=281–5 |date=August 2008 |pmid=17762913 |doi=10.1007/s10792-007-9131-0|s2cid=20772101 }}</ref> It is marketed as a 1% [[eye drop]] suspension under the trade name '''Vexol''' by [[Alcon|Alcon Laboratories]], but was discontinued in the US and other countries.<ref name="AC">{{cite book|title=Austria-Codex|at=Vexol 1% (10 mg/ml)-Augentropfensuspension|editor=Haberfeld, H|publisher=Österreichischer Apothekerverlag|location=Vienna|year=2015|language=German}}</ref><ref name="Drugs.com">[[Drugs.com]]: {{drugs.com|monograph|rimexolone}}.</ref>

==Medical uses==
Rimexolone is used to treat inflammation after [[eye surgery]], to treat [[anterior uveitis]], [[conjunctivitis]] and [[keratitis]].<ref name="AC" /><ref name="Drugs.com" />

==Contraindications==
The substance is contraindicated in [[herpes simplex]] and most other viral eye infections, as well as [[mycobacterial]], [[fungal]] and [[amoeba]]l eye infections<ref name="AC" /><ref name="Drugs.com" /> because it only reduces the inflammation but does not act against such microorganisms.

==Side effects==
The most common adverse effects are blurred vision, [[Lacrimation|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.<ref name="AC" /><ref name="Drugs.com" />

==Pharmacology==

===Pharmacodynamics===
{{See|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&nbsp;[[picogram|pg]]/ml on average, with many patients remaining below the detection threshold of 80&nbsp;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.<ref name="AC" /><ref name="Drugs.com" />

==References==
{{Reflist}}

{{Glucocorticoids and antiglucocorticoids}}
{{Glucocorticoid receptor modulators}}
{{Xenobiotic-sensing receptor modulators}}

[[Category:Alcohols]]
[[Category:CYP3A4 inducers]]
[[Category:Diketones]]
[[Category:Glucocorticoids]]
[[Category:Pregnanes]]