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Identification
NameMedrysone
Accession NumberDB00253  (APRD01091)
TypeSmall Molecule
GroupsApproved
DescriptionMedrysone is a corticosteroid used in ophthalmology. [Wikipedia]
Structure
Thumb
Synonyms
11beta-Hydroxy-6alpha-methylpregn-4-ene-3,20-dione
HMS
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Hmsdrops1 %ophthalmicAllergan Inc1969-12-312011-08-04Canada
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
UNIID2UFC189XF
CAS number2668-66-8
WeightAverage: 344.4877
Monoisotopic: 344.23514489
Chemical FormulaC22H32O3
InChI KeyInChIKey=GZENKSODFLBBHQ-ILSZZQPISA-N
InChI
InChI=1S/C22H32O3/c1-12-9-15-17-6-5-16(13(2)23)22(17,4)11-19(25)20(15)21(3)8-7-14(24)10-18(12)21/h10,12,15-17,19-20,25H,5-9,11H2,1-4H3/t12-,15-,16+,17-,19-,20+,21-,22+/m0/s1
IUPAC Name
(1S,2R,8S,10S,11S,14S,15S,17S)-14-acetyl-17-hydroxy-2,8,15-trimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-one
SMILES
[H][C@@]12CC[[email protected]](C(C)=O)[C@@]1(C)C[[email protected]](O)[C@@]1([H])[C@@]2([H])C[[email protected]](C)C2=CC(=O)CC[C@]12C
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as gluco/mineralocorticoids, progestogins and derivatives. These are steroids with a structure based on a hydroxylated prostane moiety.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassPregnane steroids
Direct ParentGluco/mineralocorticoids, progestogins and derivatives
Alternative Parents
Substituents
  • Progestogin-skeleton
  • 20-oxosteroid
  • 11-hydroxysteroid
  • 11-beta-hydroxysteroid
  • Oxosteroid
  • Hydroxysteroid
  • 3-oxosteroid
  • 3-oxo-delta-4-steroid
  • Delta-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 allergic conjunctivitis, vernal conjunctivitis, episcleritis, and epinephrine sensitivity.
PharmacodynamicsMedrysone is a topical anti-inflammatory corticoidsteroids for ophthalmic use. In patients with increased intraocular pressure and in those susceptible to a rise in intraocular pressure, there is less effect on pressure with medrysone than with dexamethasone or betamethasone. Corticoidsteroids inhibit the edema, fibrin deposition, capillary dilation, and phagocytic migration of the acute inflammatory response, as well as capillary proliferation, deposition of collagen, and scar formation.
Mechanism of actionThere is no generally accepted explanation for the mechanism of action of ocular corticosteroids. However, corticosteroids are thought to act by the induction of phospholipase A2 inhibitory proteins, collectively called lipocortins. It is postulated that these proteins control the biosynthesis of potent mediators of inflammation such as prostaglandins and leukotrienes by inhibiting the release of their common precursor, arachidonic acid. Arachidonic acid is released from membrane phospholipids by phospholipase A2. Initially, the drug binds to the glucocorticoid receptor in the cytosol. This migrates to the nucleus and binds to genetic elements which cause activation and repression of the involved genes in the inflammatory pathway.
Related Articles
AbsorptionRapidly absorbed following oral administration.
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
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+0.9705
Caco-2 permeable+0.8125
P-glycoprotein substrateSubstrate0.6825
P-glycoprotein inhibitor IInhibitor0.6076
P-glycoprotein inhibitor IINon-inhibitor0.7298
Renal organic cation transporterNon-inhibitor0.7757
CYP450 2C9 substrateNon-substrate0.7961
CYP450 2D6 substrateNon-substrate0.9127
CYP450 3A4 substrateSubstrate0.7688
CYP450 1A2 substrateNon-inhibitor0.9046
CYP450 2C9 inhibitorNon-inhibitor0.869
CYP450 2D6 inhibitorNon-inhibitor0.9491
CYP450 2C19 inhibitorNon-inhibitor0.9026
CYP450 3A4 inhibitorNon-inhibitor0.8309
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9052
Ames testNon AMES toxic0.9525
CarcinogenicityNon-carcinogens0.9338
BiodegradationNot ready biodegradable0.9822
Rat acute toxicity2.3015 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8934
hERG inhibition (predictor II)Non-inhibitor0.7724
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Allergan pharmaceutical
PackagersNot Available
Dosage forms
FormRouteStrength
Dropsophthalmic1 %
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point156.5 °CPhysProp
logP3.2Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0337 mg/mLALOGPS
logP3.06ALOGPS
logP3.13ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)19.14ChemAxon
pKa (Strongest Basic)-0.26ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area54.37 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity98.85 m3·mol-1ChemAxon
Polarizability39.92 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesS01BA08
AHFS Codes
  • 52:08.08
PDB EntriesNot Available
FDA labelDownload (149 KB)
MSDSDownload (48.5 KB)
Interactions
Drug Interactions
Drug
1,10-PhenanthrolineThe risk or severity of adverse effects can be increased when Medrysone is combined with 1,10-Phenanthroline.
Acetylsalicylic acidThe risk or severity of adverse effects can be increased when Acetylsalicylic acid is combined with Medrysone.
AldesleukinMedrysone may decrease the antineoplastic activities of Aldesleukin.
Aluminum hydroxideThe bioavailability of Medrysone can be decreased when combined with Aluminum hydroxide.
Aluminum phosphateThe bioavailability of Medrysone can be decreased when combined with Aluminum phosphate.
AmbenoniumThe risk or severity of adverse effects can be increased when Medrysone is combined with Ambenonium.
Aminosalicylic AcidThe risk or severity of adverse effects can be increased when Aminosalicylic Acid is combined with Medrysone.
AmiodaroneThe serum concentration of Medrysone can be increased when it is combined with Amiodarone.
Amphotericin BMedrysone may increase the hypokalemic activities of Amphotericin B.
AprepitantThe serum concentration of Medrysone can be increased when it is combined with Aprepitant.
AtazanavirThe serum concentration of Medrysone can be increased when it is combined with Atazanavir.
Atracurium besylateAtracurium besylate may increase the adverse neuromuscular activities of Medrysone.
BazedoxifeneThe serum concentration of Medrysone can be increased when it is combined with Bazedoxifene.
BendroflumethiazideMedrysone may increase the hypokalemic activities of Bendroflumethiazide.
Benzoic AcidThe therapeutic efficacy of Benzoic Acid can be decreased when used in combination with Medrysone.
Bismuth SubcitrateThe bioavailability of Medrysone can be decreased when combined with Bismuth Subcitrate.
BoceprevirThe serum concentration of Medrysone can be increased when it is combined with Boceprevir.
BumetanideMedrysone may increase the hypokalemic activities of Bumetanide.
CalcitriolThe therapeutic efficacy of Calcitriol can be decreased when used in combination with Medrysone.
Calcium carbonateThe bioavailability of Medrysone can be decreased when combined with Calcium carbonate.
CarbamazepineThe serum concentration of Medrysone can be decreased when it is combined with Carbamazepine.
CeritinibMedrysone may increase the hyperglycemic activities of Ceritinib.
CeritinibThe serum concentration of Medrysone can be increased when it is combined with Ceritinib.
ChlorothiazideMedrysone may increase the hypokalemic activities of Chlorothiazide.
ChlorotrianiseneThe serum concentration of Medrysone can be increased when it is combined with Chlorotrianisene.
ChlorthalidoneMedrysone may increase the hypokalemic activities of Chlorthalidone.
CholestyramineCholestyramine can cause a decrease in the absorption of Medrysone resulting in a reduced serum concentration and potentially a decrease in efficacy.
ClarithromycinThe serum concentration of Medrysone can be increased when it is combined with Clarithromycin.
CobicistatThe serum concentration of Medrysone can be increased when it is combined with Cobicistat.
ColesevelamColesevelam can cause a decrease in the absorption of Medrysone resulting in a reduced serum concentration and potentially a decrease in efficacy.
ColestipolColestipol can cause a decrease in the absorption of Medrysone resulting in a reduced serum concentration and potentially a decrease in efficacy.
Conjugated Equine EstrogensThe serum concentration of Medrysone 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 Medrysone.
CoumaphosThe risk or severity of adverse effects can be increased when Medrysone is combined with Coumaphos.
DarunavirThe serum concentration of Medrysone can be increased when it is combined with Darunavir.
DecamethoniumThe risk or severity of adverse effects can be increased when Medrysone is combined with Decamethonium.
DeferasiroxThe risk or severity of adverse effects can be increased when Medrysone is combined with Deferasirox.
DemecariumThe risk or severity of adverse effects can be increased when Medrysone is combined with Demecarium.
DichlorvosThe risk or severity of adverse effects can be increased when Medrysone is combined with Dichlorvos.
DienestrolThe serum concentration of Medrysone can be increased when it is combined with Dienestrol.
DiethylstilbestrolThe serum concentration of Medrysone can be increased when it is combined with Diethylstilbestrol.
DiflunisalThe risk or severity of adverse effects can be increased when Diflunisal is combined with Medrysone.
DihydrotestosteroneMedrysone may increase the fluid retaining activities of Dihydrotestosterone.
DonepezilThe risk or severity of adverse effects can be increased when Medrysone is combined with Donepezil.
EchothiophateThe risk or severity of adverse effects can be increased when Medrysone is combined with Echothiophate.
EdrophoniumThe risk or severity of adverse effects can be increased when Medrysone is combined with Edrophonium.
EnzalutamideThe serum concentration of Medrysone can be decreased when it is combined with Enzalutamide.
EstradiolThe serum concentration of Medrysone can be increased when it is combined with Estradiol.
EstriolThe serum concentration of Medrysone can be increased when it is combined with Estriol.
EstroneThe serum concentration of Medrysone can be increased when it is combined with Estrone.
Etacrynic acidMedrysone may increase the hypokalemic activities of Etacrynic acid.
Ethinyl EstradiolThe serum concentration of Medrysone can be increased when it is combined with Ethinyl Estradiol.
FenthionThe risk or severity of adverse effects can be increased when Medrysone is combined with Fenthion.
FluoxymesteroneMedrysone may increase the fluid retaining activities of Fluoxymesterone.
FosaprepitantThe serum concentration of Medrysone can be increased when it is combined with Fosaprepitant.
FosphenytoinThe serum concentration of Medrysone can be decreased when it is combined with Fosphenytoin.
FurosemideMedrysone may increase the hypokalemic activities of Furosemide.
GalantamineThe risk or severity of adverse effects can be increased when Medrysone is combined with Galantamine.
Gallamine TriethiodideThe risk or severity of adverse effects can be increased when Medrysone is combined with Gallamine Triethiodide.
GenisteinThe serum concentration of Medrysone can be increased when it is combined with Genistein.
Ginkgo bilobaThe risk or severity of adverse effects can be increased when Medrysone is combined with Ginkgo biloba.
Glycerol PhenylbutyrateThe therapeutic efficacy of Glycerol Phenylbutyrate can be decreased when used in combination with Medrysone.
HexestrolThe serum concentration of Medrysone can be increased when it is combined with Hexestrol.
Huperzine AThe risk or severity of adverse effects can be increased when Medrysone is combined with Huperzine A.
HyaluronidaseThe therapeutic efficacy of Hyaluronidase can be decreased when used in combination with Medrysone.
HydrochlorothiazideMedrysone may increase the hypokalemic activities of Hydrochlorothiazide.
HydroflumethiazideMedrysone may increase the hypokalemic activities of Hydroflumethiazide.
IdelalisibThe serum concentration of Medrysone can be increased when it is combined with Idelalisib.
IndacaterolIndacaterol may increase the hypokalemic activities of Medrysone.
IndapamideMedrysone may increase the hypokalemic activities of Indapamide.
IndinavirThe serum concentration of Medrysone can be increased when it is combined with Indinavir.
IsoflurophateThe risk or severity of adverse effects can be increased when Medrysone is combined with Isoflurophate.
IsoniazidThe serum concentration of Isoniazid can be decreased when it is combined with Medrysone.
ItraconazoleThe serum concentration of Medrysone can be increased when it is combined with Itraconazole.
KetoconazoleThe serum concentration of Medrysone can be increased when it is combined with Ketoconazole.
LopinavirThe serum concentration of Medrysone can be increased when it is combined with Lopinavir.
MagaldrateThe bioavailability of Medrysone can be decreased when combined with Magaldrate.
Magnesium carbonateThe bioavailability of Medrysone can be decreased when combined with Magnesium carbonate.
Magnesium hydroxideThe bioavailability of Medrysone can be decreased when combined with Magnesium hydroxide.
Magnesium oxideThe bioavailability of Medrysone can be decreased when combined with Magnesium oxide.
Magnesium TrisilicateThe bioavailability of Medrysone can be decreased when combined with Magnesium Trisilicate.
MalathionThe risk or severity of adverse effects can be increased when Medrysone is combined with Malathion.
MefloquineThe risk or severity of adverse effects can be increased when Medrysone is combined with Mefloquine.
MemantineThe risk or severity of adverse effects can be increased when Medrysone is combined with Memantine.
MesalazineThe risk or severity of adverse effects can be increased when Mesalazine is combined with Medrysone.
MestranolThe serum concentration of Medrysone can be increased when it is combined with Mestranol.
MethyclothiazideMedrysone may increase the hypokalemic activities of Methyclothiazide.
MethyltestosteroneMedrysone may increase the fluid retaining activities of Methyltestosterone.
MetolazoneMedrysone may increase the hypokalemic activities of Metolazone.
MifepristoneThe therapeutic efficacy of Medrysone can be decreased when used in combination with Mifepristone.
MinaprineThe risk or severity of adverse effects can be increased when Medrysone is combined with Minaprine.
MitotaneThe serum concentration of Medrysone can be decreased when it is combined with Mitotane.
MivacuriumMivacurium may increase the adverse neuromuscular activities of Medrysone.
NefazodoneThe serum concentration of Medrysone can be increased when it is combined with Nefazodone.
NelfinavirThe serum concentration of Medrysone can be increased when it is combined with Nelfinavir.
NeostigmineThe risk or severity of adverse effects can be increased when Medrysone is combined with Neostigmine.
NevirapineThe serum concentration of Medrysone can be decreased when it is combined with Nevirapine.
NicorandilThe risk or severity of adverse effects can be increased when Medrysone is combined with Nicorandil.
OxandroloneMedrysone may increase the fluid retaining activities of Oxandrolone.
OxymetholoneMedrysone may increase the fluid retaining activities of Oxymetholone.
PentobarbitalThe serum concentration of Medrysone can be decreased when it is combined with Pentobarbital.
PhenobarbitalThe serum concentration of Medrysone can be decreased when it is combined with Phenobarbital.
Phenylacetic acidThe therapeutic efficacy of Phenylacetic acid can be decreased when used in combination with Medrysone.
PhenytoinThe serum concentration of Medrysone can be decreased when it is combined with Phenytoin.
PhysostigmineThe risk or severity of adverse effects can be increased when Medrysone is combined with Physostigmine.
PiretanideMedrysone may increase the hypokalemic activities of Piretanide.
Polyestradiol phosphateThe serum concentration of Medrysone can be increased when it is combined with Polyestradiol phosphate.
PolythiazideMedrysone may increase the hypokalemic activities of Polythiazide.
PosaconazoleThe serum concentration of Medrysone can be increased when it is combined with Posaconazole.
PrimidoneThe serum concentration of Medrysone can be decreased when it is combined with Primidone.
PyridostigmineThe risk or severity of adverse effects can be increased when Medrysone is combined with Pyridostigmine.
QuinestrolThe serum concentration of Medrysone can be increased when it is combined with Quinestrol.
QuinethazoneMedrysone may increase the hypokalemic activities of Quinethazone.
Rabies vaccineThe risk or severity of adverse effects can be increased when Medrysone is combined with Rabies vaccine.
RapacuroniumRapacuronium may increase the adverse neuromuscular activities of Medrysone.
RifabutinThe serum concentration of Medrysone can be decreased when it is combined with Rifabutin.
RifampicinThe serum concentration of Medrysone can be decreased when it is combined with Rifampicin.
RifapentineThe serum concentration of Medrysone can be decreased when it is combined with Rifapentine.
RitonavirThe serum concentration of Medrysone can be increased when it is combined with Ritonavir.
RivastigmineThe risk or severity of adverse effects can be increased when Medrysone is combined with Rivastigmine.
Salicylic acidThe risk or severity of adverse effects can be increased when Salicylic acid is combined with Medrysone.
SaquinavirThe serum concentration of Medrysone can be increased when it is combined with Saquinavir.
Sodium phenylbutyrateThe therapeutic efficacy of Sodium phenylbutyrate can be decreased when used in combination with Medrysone.
StanozololMedrysone may increase the fluid retaining activities of Stanozolol.
Synthetic Conjugated Estrogens, AThe serum concentration of Medrysone can be increased when it is combined with Synthetic Conjugated Estrogens, A.
Synthetic Conjugated Estrogens, BThe serum concentration of Medrysone can be increased when it is combined with Synthetic Conjugated Estrogens, B.
TacrineThe risk or severity of adverse effects can be increased when Medrysone is combined with Tacrine.
TelaprevirThe serum concentration of Telaprevir can be decreased when it is combined with Medrysone.
TelaprevirThe serum concentration of Medrysone can be increased when it is combined with Telaprevir.
TelithromycinThe serum concentration of Medrysone can be increased when it is combined with Telithromycin.
TestosteroneMedrysone may increase the fluid retaining activities of Testosterone.
TiboloneThe serum concentration of Medrysone can be increased when it is combined with Tibolone.
TorasemideMedrysone may increase the hypokalemic activities of Torasemide.
TrichlorfonThe risk or severity of adverse effects can be increased when Medrysone is combined with Trichlorfon.
TrichlormethiazideMedrysone may increase the hypokalemic activities of Trichlormethiazide.
TubocurarineThe risk or severity of adverse effects can be increased when Medrysone is combined with Tubocurarine.
VoriconazoleThe serum concentration of Medrysone can be increased when it is combined with Voriconazole.
WarfarinMedrysone may increase the anticoagulant activities of Warfarin.
ZeranolThe serum concentration of Medrysone 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. Southren AL, Dominguez MO, Gordon GG, Wenk EJ, Hernandez MR, Dunn MW, Weinstein BI: Nuclear translocation of the cytoplasmic glucocorticoid receptor in the iris-ciliary body and adjacent corneoscleral tissue of the rabbit following topical administration of various glucocorticoids. A rapid screening method for glucocorticoid activity. Invest Ophthalmol Vis Sci. 1983 Feb;24(2):147-52. [PubMed:6336597 ]
  2. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Carriers

Kind
Protein
Organism
Human
Pharmacological action
unknown
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 ]
Comments
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23