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Identification
NameRimexolone
Accession NumberDB00896  (APRD01220)
Typesmall molecule
Groupsapproved
Description

Rimexolone is a glucocorticoid steroid used to treat inflammation in the eye. It is marketed as a 1% eye drop solution under the trade name Vexol

Structure
Thumb
SynonymsNot Available
SaltsNot Available
Brand names
NameCompany
VexolAlcon incorporated
Brand mixturesNot Available
CategoriesNot Available
CAS number49697-38-3
WeightAverage: 370.525
Monoisotopic: 370.250794954
Chemical FormulaC24H34O3
InChI KeyInChIKey=QTTRZHGPGKRAFB-PAIWTFDUSA-N
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
IUPAC Name
(2R,13R,14S,15S,17S)-17-hydroxy-2,13,14,15-tetramethyl-14-propanoyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,6-dien-5-one
SMILES
CCC(=O)[C@@]1(C)[C@H](C)CC2C3CCC4=CC(=O)C=C[C@]4(C)C3[C@@H](O)C[C@]12C
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassLipids
ClassSteroids and Steroid Derivatives
SubclassAndrogens and Derivatives
Direct parentAndrogens and Derivatives
Alternative parentsHydroxysteroids; Ketosteroids; Iridoids and Derivatives; Cyclohexanols; Cyclic Alcohols and Derivatives; Ketones; Enolates; Polyamines
Substituentsmonoterpene; 11-noriridane monoterpene; cyclohexanol; cyclic alcohol; ketone; secondary alcohol; enolate; polyamine; alcohol; carbonyl group
Classification descriptionThis compound belongs to the androgens and derivatives. These are hydroxylated C19 steroid hormones. They are known to favour the development of masculine characteristics. They also show profound effects on scalp and body hair in humans.
Pharmacology
IndicationFor the treatment of postoperative inflammation following ocular surgery and in the treatment of anterior uveitis.
PharmacodynamicsRimexolone is a glucocorticoid corticosteroid for systemic use. Corticosteroids suppress the inflammatory response to a variety of inciting agents of a mechanical, chemical, or immunological nature. They inhibit edema, cellular infiltration, capillary dilatation, fibroblastic proliferation, deposition of collagen and scar formation associated with inflammation.
Mechanism of actionRimexolone is a glucocorticoid receptor agonist. The antiinflammatory actions of corticosteroids are thought to involve lipocortins, phospholipase A2 inhibitory proteins which, through inhibition of arachidonic acid, control the biosynthesis of prostaglandins and leukotrienes. By binding to the glucocorticoid receptor, this drug ultimately leads to changes in genetic transcription involving the lipocortins and prostaglandins.
AbsorptionSystemically absorbed.
Volume of distributionNot Available
Protein bindingNot Available
Metabolism

Undergoes extensive metabolism. Following intravenous administration of radiolabeled rimexolone in rats, more than 80% of the dose was excreted in the feces as rimexolone and metabolites. Metabolites have been shown to be either less active than rimexolone or inactive in human glucocorticoid receptor binding assays.

Route of eliminationFollowing IV administration of radio-labelled rimexolone to rats, greater than 80% of the dose is excreted via the feces as rimexolone and metabolites.
Half lifeThe serum half-life of rimexolone could not be reliably estimated due to the large number of samples below the quantitation limit of the assay (80 pg/mL). However, based on the time required to reach steady-state, the half-life appears to be short (1-2 hours).
ClearanceNot Available
ToxicitySymptoms of overdose include retinal toxicity, glaucoma, and subcapsular cataract.
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 1.0
Blood Brain Barrier + 0.9796
Caco-2 permeable + 0.7879
P-glycoprotein substrate Substrate 0.7261
P-glycoprotein inhibitor I Inhibitor 0.616
P-glycoprotein inhibitor II Inhibitor 0.5126
Renal organic cation transporter Non-inhibitor 0.8022
CYP450 2C9 substrate Non-substrate 0.8142
CYP450 2D6 substrate Non-substrate 0.9195
CYP450 3A4 substrate Substrate 0.7631
CYP450 1A2 substrate Non-inhibitor 0.9521
CYP450 2C9 substrate Non-inhibitor 0.9071
CYP450 2D6 substrate Non-inhibitor 0.9231
CYP450 2C19 substrate Non-inhibitor 0.9025
CYP450 3A4 substrate Non-inhibitor 0.6544
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.7217
Ames test Non AMES toxic 0.9396
Carcinogenicity Non-carcinogens 0.9243
Biodegradation Not ready biodegradable 0.9906
Rat acute toxicity 2.1317 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.8573
hERG inhibition (predictor II) Non-inhibitor 0.7387
Pharmacoeconomics
Manufacturers
  • Alcon laboratories inc
Packagers
Dosage forms
FormRouteStrength
SuspensionOphthalmic
Prices
Unit descriptionCostUnit
Vexol 1% Suspension 10ml Bottle74.08USDbottle
Vexol 1% Suspension 5ml Bottle48.29USDbottle
Vexol 1% eye drops7.14USDml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
Statesolid
Experimental Properties
PropertyValueSource
water solubilityInsolubleNot Available
logP4.2Not Available
Predicted Properties
PropertyValueSource
water solubility1.21e-02 g/lALOGPS
logP3.64ALOGPS
logP4.38ChemAxon
logS-4.5ALOGPS
pKa (strongest acidic)18.76ChemAxon
pKa (strongest basic)-0.21ChemAxon
physiological charge0ChemAxon
hydrogen acceptor count3ChemAxon
hydrogen donor count1ChemAxon
polar surface area54.37ChemAxon
rotatable bond count2ChemAxon
refractivity109.07ChemAxon
polarizability43.03ChemAxon
number of rings4ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterYesChemAxon
Veber's ruleNoChemAxon
MDDR-like ruleNoChemAxon
Spectra
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
External Links
ResourceLink
KEGG DrugD05729
PubChem Compound39507
PubChem Substance46504820
ChemSpider36120
Therapeutic Targets DatabaseDAP000420
PharmGKBPA164752251
Drug Product Database2163691
RxListhttp://www.rxlist.com/cgi/generic3/rimexol.htm
Drugs.comhttp://www.drugs.com/cdi/rimexolone.html
WikipediaRimexolone
ATC CodesH02AB12S01BA13
AHFS Codes
  • 52:08.08
PDB EntriesNot Available
FDA labelshow(108 KB)
MSDSshow(248 KB)
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

1. Glucocorticoid receptor

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: agonist

Components

Name UniProt ID Details
Glucocorticoid receptor P04150 Details

References:

  1. Hochhaus G, Moellmann HW: Binding affinities of rimexolone (ORG 6216), flunisolide and their putative metabolites for the glucocorticoid receptor of human synovial tissue. Agents Actions. 1990 Jun;30(3-4):377-80. Pubmed

1. Corticosteroid-binding globulin

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: binder

Components

Name UniProt ID Details
Corticosteroid-binding globulin P08185 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
  3. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed

Comments
Drug created on June 13, 2005 07:24 / Updated on October 07, 2013 09:26