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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
External Identifiers Not Available
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Vexolsuspension/ drops10 mg/mLophthalmicAlcon Laboratories, Inc1995-09-152016-04-23Us
Vexol Ophthalmic Suspension - 1%suspension1 %ophthalmicAlcon Canada Inc1997-01-22Not applicableCanada
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
UNIIO7M2E4264D
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[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-3,6-dien-5-one
SMILES
CCC(=O)[C@@]1(C)[[email protected]](C)CC2C3CCC4=CC(=O)C=C[C@]4(C)C3[C@@H](O)C[C@]12C
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as 20-oxosteroids. These are steroid derivatives carrying a C=O group at the 20-position of the steroid skeleton.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassOxosteroids
Direct Parent20-oxosteroids
Alternative Parents
Substituents
  • 20-oxosteroid
  • Androgen-skeleton
  • Androstane-skeleton
  • 11-hydroxysteroid
  • 11-beta-hydroxysteroid
  • Hydroxysteroid
  • 3-oxosteroid
  • 3-oxo-delta-1,4-steroid
  • Delta-1,4-steroid
  • Cyclic alcohol
  • Cyclic ketone
  • Secondary alcohol
  • Ketone
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
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.
Related Articles
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
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9796
Caco-2 permeable+0.7879
P-glycoprotein substrateSubstrate0.7261
P-glycoprotein inhibitor IInhibitor0.616
P-glycoprotein inhibitor IIInhibitor0.5126
Renal organic cation transporterNon-inhibitor0.8022
CYP450 2C9 substrateNon-substrate0.8142
CYP450 2D6 substrateNon-substrate0.9195
CYP450 3A4 substrateSubstrate0.7631
CYP450 1A2 substrateNon-inhibitor0.9521
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-inhibitor0.6544
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7217
Ames testNon AMES toxic0.9396
CarcinogenicityNon-carcinogens0.9243
BiodegradationNot ready biodegradable0.9906
Rat acute toxicity2.1317 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8573
hERG inhibition (predictor II)Non-inhibitor0.7387
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Alcon laboratories inc
Packagers
Dosage forms
FormRouteStrength
Suspension/ dropsophthalmic10 mg/mL
Suspensionophthalmic1 %
Prices
Unit descriptionCostUnit
Vexol 1% Suspension 10ml Bottle74.08USD bottle
Vexol 1% Suspension 5ml Bottle48.29USD bottle
Vexol 1% eye drops7.14USD ml
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 Solubility0.0121 mg/mLALOGPS
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 Area54.37 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity109.07 m3·mol-1ChemAxon
Polarizability43.03 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesH02AB12S01BA13
AHFS Codes
  • 52:08.08
PDB EntriesNot Available
FDA labelDownload (108 KB)
MSDSDownload (248 KB)
Interactions
Drug Interactions
Drug
AldesleukinRimexolone may decrease the antineoplastic activities of Aldesleukin.
CeritinibRimexolone may increase the hyperglycemic activities of Ceritinib.
CorticorelinThe therapeutic efficacy of Corticorelin can be decreased when used in combination with Rimexolone.
DeferasiroxThe risk or severity of adverse effects can be increased when Rimexolone is combined with Deferasirox.
HyaluronidaseThe therapeutic efficacy of Hyaluronidase can be decreased when used in combination with Rimexolone.
InfliximabThe risk or severity of adverse effects can be increased when Infliximab is combined with Rimexolone.
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
agonist
General Function:
Zinc ion binding
Specific Function:
Receptor for glucocorticoids (GC). Has a dual mode of action: as a transcription factor that binds to glucocorticoid response elements (GRE), both for nuclear and mitochondrial DNA, and as a modulator of other transcription factors. Affects inflammatory responses, cellular proliferation and differentiation in target tissues. Could act as a coactivator for STAT5-dependent transcription upon grow...
Gene Name:
NR3C1
Uniprot ID:
P04150
Molecular Weight:
85658.57 Da
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:2386110 ]

Carriers

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
binder
General Function:
Steroid binding
Specific Function:
Major transport protein for glucocorticoids and progestins in the blood of almost all vertebrate species.
Gene Name:
SERPINA6
Uniprot ID:
P08185
Molecular Weight:
45140.49 Da
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:17139284 ]
  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:17016423 ]
  3. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Comments
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Drug created on June 13, 2005 07:24 / Updated on October 07, 2013 09:26