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Identification
NameRimexolone
Accession NumberDB00896  (APRD01220)
TypeSmall Molecule
GroupsApproved
DescriptionRimexolone 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
Synonyms
Rimexolon
External Identifiers
  • Org 6216
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Vexolsuspension/ drops10 mg/mLophthalmicAlcon Laboratories, Inc1995-09-15Not applicableUs
Vexol Ophthalmic Suspension - 1%suspension1 %ophthalmicAlcon Canada Inc1997-01-222016-06-16Canada
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
UNIIO7M2E4264D
CAS number49697-38-3
WeightAverage: 370.533
Monoisotopic: 370.250794955
Chemical FormulaC24H34O3
InChI KeyQTTRZHGPGKRAFB-OOKHYKNYSA-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
(1S,2R,10S,11S,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
[H][C@@]12C[C@@H](C)[C@](C)(C(=O)CC)[C@@]1(C)C[[email protected]](O)[C@@]1([H])[C@@]2([H])CCC2=CC(=O)C=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
  • 3-oxo-delta-1,4-steroid
  • 3-oxosteroid
  • Hydroxysteroid
  • 11-beta-hydroxysteroid
  • 11-hydroxysteroid
  • Delta-1,4-steroid
  • Cyclic alcohol
  • Ketone
  • Secondary alcohol
  • Cyclic ketone
  • Organooxygen compound
  • Alcohol
  • Carbonyl group
  • Organic oxide
  • Hydrocarbon derivative
  • Organic oxygen compound
  • 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
Polarizability42.91 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
1,10-PhenanthrolineThe risk or severity of adverse effects can be increased when Rimexolone is combined with 1,10-Phenanthroline.
Acetylsalicylic acidThe risk or severity of adverse effects can be increased when Acetylsalicylic acid is combined with Rimexolone.
AldesleukinRimexolone may decrease the antineoplastic activities of Aldesleukin.
Aluminum hydroxideThe bioavailability of Rimexolone can be decreased when combined with Aluminum hydroxide.
Aluminum phosphateThe bioavailability of Rimexolone can be decreased when combined with Aluminum phosphate.
AmbenoniumThe risk or severity of adverse effects can be increased when Rimexolone is combined with Ambenonium.
Aminosalicylic AcidThe risk or severity of adverse effects can be increased when Aminosalicylic Acid is combined with Rimexolone.
AmiodaroneThe serum concentration of Rimexolone can be increased when it is combined with Amiodarone.
Amphotericin BRimexolone may increase the hypokalemic activities of Amphotericin B.
AprepitantThe serum concentration of Rimexolone can be increased when it is combined with Aprepitant.
AtazanavirThe serum concentration of Rimexolone can be increased when it is combined with Atazanavir.
Atracurium besylateAtracurium besylate may increase the adverse neuromuscular activities of Rimexolone.
BazedoxifeneThe serum concentration of Rimexolone can be increased when it is combined with Bazedoxifene.
BendroflumethiazideRimexolone may increase the hypokalemic activities of Bendroflumethiazide.
Benzoic AcidThe therapeutic efficacy of Benzoic Acid can be decreased when used in combination with Rimexolone.
Bismuth SubcitrateThe bioavailability of Rimexolone can be decreased when combined with Bismuth Subcitrate.
BoceprevirThe serum concentration of Rimexolone can be increased when it is combined with Boceprevir.
BumetanideRimexolone may increase the hypokalemic activities of Bumetanide.
CalcitriolThe therapeutic efficacy of Calcitriol can be decreased when used in combination with Rimexolone.
Calcium carbonateThe bioavailability of Rimexolone can be decreased when combined with Calcium carbonate.
CarbamazepineThe serum concentration of Rimexolone can be decreased when it is combined with Carbamazepine.
CeritinibRimexolone may increase the hyperglycemic activities of Ceritinib.
CeritinibThe serum concentration of Rimexolone can be increased when it is combined with Ceritinib.
ChlorothiazideRimexolone may increase the hypokalemic activities of Chlorothiazide.
ChlorotrianiseneThe serum concentration of Rimexolone can be increased when it is combined with Chlorotrianisene.
ChlorthalidoneRimexolone may increase the hypokalemic activities of Chlorthalidone.
CholestyramineCholestyramine can cause a decrease in the absorption of Rimexolone resulting in a reduced serum concentration and potentially a decrease in efficacy.
ClarithromycinThe serum concentration of Rimexolone can be increased when it is combined with Clarithromycin.
CobicistatThe serum concentration of Rimexolone can be increased when it is combined with Cobicistat.
ColesevelamColesevelam can cause a decrease in the absorption of Rimexolone resulting in a reduced serum concentration and potentially a decrease in efficacy.
ColestipolColestipol can cause a decrease in the absorption of Rimexolone resulting in a reduced serum concentration and potentially a decrease in efficacy.
Conjugated Equine EstrogensThe serum concentration of Rimexolone can be increased when it is combined with Conjugated Equine Estrogens.
Corticorelin ovine triflutateThe therapeutic efficacy of Corticorelin ovine triflutate can be decreased when used in combination with Rimexolone.
CoumaphosThe risk or severity of adverse effects can be increased when Rimexolone is combined with Coumaphos.
DarunavirThe serum concentration of Rimexolone can be increased when it is combined with Darunavir.
DecamethoniumThe risk or severity of adverse effects can be increased when Rimexolone is combined with Decamethonium.
DeferasiroxThe risk or severity of adverse effects can be increased when Rimexolone is combined with Deferasirox.
DemecariumThe risk or severity of adverse effects can be increased when Rimexolone is combined with Demecarium.
DichlorvosThe risk or severity of adverse effects can be increased when Rimexolone is combined with Dichlorvos.
DienestrolThe serum concentration of Rimexolone can be increased when it is combined with Dienestrol.
DiethylstilbestrolThe serum concentration of Rimexolone can be increased when it is combined with Diethylstilbestrol.
DiflunisalThe risk or severity of adverse effects can be increased when Diflunisal is combined with Rimexolone.
DihydrotestosteroneRimexolone may increase the fluid retaining activities of Dihydrotestosterone.
DonepezilThe risk or severity of adverse effects can be increased when Rimexolone is combined with Donepezil.
EchothiophateThe risk or severity of adverse effects can be increased when Rimexolone is combined with Echothiophate.
EdrophoniumThe risk or severity of adverse effects can be increased when Rimexolone is combined with Edrophonium.
EnzalutamideThe serum concentration of Rimexolone can be decreased when it is combined with Enzalutamide.
EstradiolThe serum concentration of Rimexolone can be increased when it is combined with Estradiol.
EstriolThe serum concentration of Rimexolone can be increased when it is combined with Estriol.
EstroneThe serum concentration of Rimexolone can be increased when it is combined with Estrone.
Etacrynic acidRimexolone may increase the hypokalemic activities of Etacrynic acid.
Ethinyl EstradiolThe serum concentration of Rimexolone can be increased when it is combined with Ethinyl Estradiol.
FenthionThe risk or severity of adverse effects can be increased when Rimexolone is combined with Fenthion.
FluoxymesteroneRimexolone may increase the fluid retaining activities of Fluoxymesterone.
FosaprepitantThe serum concentration of Rimexolone can be increased when it is combined with Fosaprepitant.
FosphenytoinThe serum concentration of Rimexolone can be decreased when it is combined with Fosphenytoin.
FurosemideRimexolone may increase the hypokalemic activities of Furosemide.
GalantamineThe risk or severity of adverse effects can be increased when Rimexolone is combined with Galantamine.
Gallamine TriethiodideThe risk or severity of adverse effects can be increased when Rimexolone is combined with Gallamine Triethiodide.
GenisteinThe serum concentration of Rimexolone can be increased when it is combined with Genistein.
Ginkgo bilobaThe risk or severity of adverse effects can be increased when Rimexolone is combined with Ginkgo biloba.
Glycerol PhenylbutyrateThe therapeutic efficacy of Glycerol Phenylbutyrate can be decreased when used in combination with Rimexolone.
HexestrolThe serum concentration of Rimexolone can be increased when it is combined with Hexestrol.
Huperzine AThe risk or severity of adverse effects can be increased when Rimexolone is combined with Huperzine A.
HyaluronidaseThe therapeutic efficacy of Hyaluronidase can be decreased when used in combination with Rimexolone.
HydrochlorothiazideRimexolone may increase the hypokalemic activities of Hydrochlorothiazide.
HydroflumethiazideRimexolone may increase the hypokalemic activities of Hydroflumethiazide.
IdelalisibThe serum concentration of Rimexolone can be increased when it is combined with Idelalisib.
IndacaterolIndacaterol may increase the hypokalemic activities of Rimexolone.
IndapamideRimexolone may increase the hypokalemic activities of Indapamide.
IndinavirThe serum concentration of Rimexolone can be increased when it is combined with Indinavir.
IsoflurophateThe risk or severity of adverse effects can be increased when Rimexolone is combined with Isoflurophate.
IsoniazidThe serum concentration of Isoniazid can be decreased when it is combined with Rimexolone.
ItraconazoleThe serum concentration of Rimexolone can be increased when it is combined with Itraconazole.
KetoconazoleThe serum concentration of Rimexolone can be increased when it is combined with Ketoconazole.
LopinavirThe serum concentration of Rimexolone can be increased when it is combined with Lopinavir.
MagaldrateThe bioavailability of Rimexolone can be decreased when combined with Magaldrate.
Magnesium carbonateThe bioavailability of Rimexolone can be decreased when combined with Magnesium carbonate.
Magnesium hydroxideThe bioavailability of Rimexolone can be decreased when combined with Magnesium hydroxide.
Magnesium oxideThe bioavailability of Rimexolone can be decreased when combined with Magnesium oxide.
Magnesium TrisilicateThe bioavailability of Rimexolone can be decreased when combined with Magnesium Trisilicate.
MalathionThe risk or severity of adverse effects can be increased when Rimexolone is combined with Malathion.
MefloquineThe risk or severity of adverse effects can be increased when Rimexolone is combined with Mefloquine.
MemantineThe risk or severity of adverse effects can be increased when Rimexolone is combined with Memantine.
MesalazineThe risk or severity of adverse effects can be increased when Mesalazine is combined with Rimexolone.
MestranolThe serum concentration of Rimexolone can be increased when it is combined with Mestranol.
MethyclothiazideRimexolone may increase the hypokalemic activities of Methyclothiazide.
MethyltestosteroneRimexolone may increase the fluid retaining activities of Methyltestosterone.
MetolazoneRimexolone may increase the hypokalemic activities of Metolazone.
MifepristoneThe therapeutic efficacy of Rimexolone can be decreased when used in combination with Mifepristone.
MinaprineThe risk or severity of adverse effects can be increased when Rimexolone is combined with Minaprine.
MitotaneThe serum concentration of Rimexolone can be decreased when it is combined with Mitotane.
MivacuriumMivacurium may increase the adverse neuromuscular activities of Rimexolone.
NefazodoneThe serum concentration of Rimexolone can be increased when it is combined with Nefazodone.
NelfinavirThe serum concentration of Rimexolone can be increased when it is combined with Nelfinavir.
NeostigmineThe risk or severity of adverse effects can be increased when Rimexolone is combined with Neostigmine.
NevirapineThe serum concentration of Rimexolone can be decreased when it is combined with Nevirapine.
NicorandilThe risk or severity of adverse effects can be increased when Rimexolone is combined with Nicorandil.
OxandroloneRimexolone may increase the fluid retaining activities of Oxandrolone.
OxymetholoneRimexolone may increase the fluid retaining activities of Oxymetholone.
PentobarbitalThe serum concentration of Rimexolone can be decreased when it is combined with Pentobarbital.
PhenobarbitalThe serum concentration of Rimexolone can be decreased when it is combined with Phenobarbital.
Phenylacetic acidThe therapeutic efficacy of Phenylacetic acid can be decreased when used in combination with Rimexolone.
PhenytoinThe serum concentration of Rimexolone can be decreased when it is combined with Phenytoin.
PhysostigmineThe risk or severity of adverse effects can be increased when Rimexolone is combined with Physostigmine.
PiretanideRimexolone may increase the hypokalemic activities of Piretanide.
Polyestradiol phosphateThe serum concentration of Rimexolone can be increased when it is combined with Polyestradiol phosphate.
PolythiazideRimexolone may increase the hypokalemic activities of Polythiazide.
PosaconazoleThe serum concentration of Rimexolone can be increased when it is combined with Posaconazole.
PrimidoneThe serum concentration of Rimexolone can be decreased when it is combined with Primidone.
PyridostigmineThe risk or severity of adverse effects can be increased when Rimexolone is combined with Pyridostigmine.
QuinestrolThe serum concentration of Rimexolone can be increased when it is combined with Quinestrol.
QuinethazoneRimexolone may increase the hypokalemic activities of Quinethazone.
Rabies vaccineThe risk or severity of adverse effects can be increased when Rimexolone is combined with Rabies vaccine.
RapacuroniumRapacuronium may increase the adverse neuromuscular activities of Rimexolone.
RifabutinThe serum concentration of Rimexolone can be decreased when it is combined with Rifabutin.
RifampicinThe serum concentration of Rimexolone can be decreased when it is combined with Rifampicin.
RifapentineThe serum concentration of Rimexolone can be decreased when it is combined with Rifapentine.
RitonavirThe serum concentration of Rimexolone can be increased when it is combined with Ritonavir.
RivastigmineThe risk or severity of adverse effects can be increased when Rimexolone is combined with Rivastigmine.
Salicylic acidThe risk or severity of adverse effects can be increased when Salicylic acid is combined with Rimexolone.
SaquinavirThe serum concentration of Rimexolone can be increased when it is combined with Saquinavir.
Sodium phenylbutyrateThe therapeutic efficacy of Sodium phenylbutyrate can be decreased when used in combination with Rimexolone.
StanozololRimexolone may increase the fluid retaining activities of Stanozolol.
Synthetic Conjugated Estrogens, AThe serum concentration of Rimexolone can be increased when it is combined with Synthetic Conjugated Estrogens, A.
Synthetic Conjugated Estrogens, BThe serum concentration of Rimexolone can be increased when it is combined with Synthetic Conjugated Estrogens, B.
TacrineThe risk or severity of adverse effects can be increased when Rimexolone is combined with Tacrine.
TelaprevirThe serum concentration of Telaprevir can be decreased when it is combined with Rimexolone.
TelaprevirThe serum concentration of Rimexolone can be increased when it is combined with Telaprevir.
TelithromycinThe serum concentration of Rimexolone can be increased when it is combined with Telithromycin.
TestosteroneRimexolone may increase the fluid retaining activities of Testosterone.
TiboloneThe serum concentration of Rimexolone can be increased when it is combined with Tibolone.
TorasemideRimexolone may increase the hypokalemic activities of Torasemide.
TrichlorfonThe risk or severity of adverse effects can be increased when Rimexolone is combined with Trichlorfon.
TrichlormethiazideRimexolone may increase the hypokalemic activities of Trichlormethiazide.
TubocurarineThe risk or severity of adverse effects can be increased when Rimexolone is combined with Tubocurarine.
VoriconazoleThe serum concentration of Rimexolone can be increased when it is combined with Voriconazole.
WarfarinRimexolone may increase the anticoagulant activities of Warfarin.
ZeranolThe serum concentration of Rimexolone can be increased when it is combined with Zeranol.
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 August 17, 2016 12:23