Welcome to DrugBank 4.0! If you prefer, you can still go back to version 3.0.
Identification
NameMethylprednisolone
Accession NumberDB00959  (APRD00342)
Typesmall molecule
Groupsapproved
Description

A prednisolone derivative with similar anti-inflammatory action. [PubChem]

Structure
Thumb
Synonyms
SynonymLanguageCode
(6α,11β)-11,17,21-trihydroxy-6-methylpregna-1,4-diene-3,20-dioneNot AvailableNot Available
1-dehydro-6α-methylhydrocortisoneNot AvailableNot Available
MethylprednisolonNot AvailableNot Available
MethylprednisolonumLatinINN
MetilprednisolonaSpanishINN
SaltsNot Available
Brand names
NameCompany
MedrateNot Available
MedrolNot Available
MedroneNot Available
MeproloneNot Available
SolometNot Available
Solu-MedrolNot Available
UrbasonNot Available
Brand mixtures
Brand NameIngredients
Depo-Medrol with LidocaineLidocaine Hydrochloride + Methylprednisolone Acetate
Medrol Acne LotionAluminum Chlorohydrate + Methylprednisolone Acetate + Sulfur
Methylprednisolone Sodium Succinate for InjectionMethylprednisolone + Water
Neo-MedrolMethylprednisolone Acetate + Neomycin Sulfate
Neo-Medrol Acne LotionAluminum Chlorohydrate + Methylprednisolone Acetate + Neomycin Sulfate + Sulfur
Categories
CAS number83-43-2
WeightAverage: 374.4706
Monoisotopic: 374.20932407
Chemical FormulaC22H30O5
InChI KeyInChIKey=VHRSUDSXCMQTMA-PJHHCJLFSA-N
InChI
InChI=1S/C22H30O5/c1-12-8-14-15-5-7-22(27,18(26)11-23)21(15,3)10-17(25)19(14)20(2)6-4-13(24)9-16(12)20/h4,6,9,12,14-15,17,19,23,25,27H,5,7-8,10-11H2,1-3H3/t12-,14-,15-,17-,19+,20-,21-,22-/m0/s1
IUPAC Name
(1S,2R,8S,10S,11S,14R,15S,17S)-14,17-dihydroxy-14-(2-hydroxyacetyl)-2,8,15-trimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,6-dien-5-one
SMILES
[H][C@@]12CC[C@](O)(C(=O)CO)[C@@]1(C)C[C@H](O)[C@@]1([H])[C@@]2([H])C[C@H](C)C2=CC(=O)C=C[C@]12C
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassLipids
ClassSteroids and Steroid Derivatives
SubclassGluco/mineralocorticoids, Progestogins and Derivatives
Direct parentGluco/mineralocorticoids, Progestogins and Derivatives
Alternative parentsKetosteroids; Hydroxysteroids; Cyclohexanols; Tertiary Alcohols; Ketones; Cyclic Alcohols and Derivatives; Enolates; Polyamines; Primary Alcohols; Aldehydes
Substituents3-keto-steroid; 11-hydroxy-steroid; 17-hydroxy-steroid; 20-keto-steroid; cyclohexanol; tertiary alcohol; cyclic alcohol; secondary alcohol; ketone; primary alcohol; enolate; polyamine; alcohol; carbonyl group; aldehyde
Classification descriptionThis compound belongs to the gluco/mineralocorticoids, progestogins and derivatives. These are steroids whose structure is based on an hydroxylated prostane moiety.
Pharmacology
IndicationAdjunctive therapy for short-term administration in rheumatoid arthritis.
PharmacodynamicsMethylprednisolone and its derivatives, methylprednisolone sodium succinate and methylprednisolone acetate, are synthetic glucocorticoids used as antiinflammatory or immunosuppressive agents.
Mechanism of actionUnbound glucocorticoids cross cell membranes and bind with high affinity to specific cytoplasmic receptors, modifying transcription and protein synthesis. By this mechanism, glucocorticoids can inhibit leukocyte infiltration at the site of inflammation, interfere with mediators of inflammatory response, and suppress humoral immune responses. The antiinflammatory actions of corticosteroids are thought to involve phospholipase A2 inhibitory proteins, lipocortins, which control the biosynthesis of potent mediators of inflammation such as prostaglandins and leukotrienes.
AbsorptionOral bioavailability 80-99%
Volume of distributionNot Available
Protein binding78%
Metabolism

Hepatic

Route of eliminationNot Available
Half life1-3 hours
ClearanceNot Available
ToxicityLD50=2000 mg/kg (orally in rat)
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 + 0.9911
Blood Brain Barrier + 0.9484
Caco-2 permeable - 0.6404
P-glycoprotein substrate Substrate 0.7812
P-glycoprotein inhibitor I Non-inhibitor 0.7489
P-glycoprotein inhibitor II Non-inhibitor 0.604
Renal organic cation transporter Non-inhibitor 0.769
CYP450 2C9 substrate Non-substrate 0.8415
CYP450 2D6 substrate Non-substrate 0.9115
CYP450 3A4 substrate Substrate 0.7582
CYP450 1A2 substrate Non-inhibitor 0.9473
CYP450 2C9 substrate Non-inhibitor 0.907
CYP450 2D6 substrate Non-inhibitor 0.9513
CYP450 2C19 substrate Non-inhibitor 0.9026
CYP450 3A4 substrate Non-inhibitor 0.8309
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9167
Ames test Non AMES toxic 0.9337
Carcinogenicity Non-carcinogens 0.9529
Biodegradation Not ready biodegradable 0.9492
Rat acute toxicity 2.0025 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.9459
hERG inhibition (predictor II) Non-inhibitor 0.5985
Pharmacoeconomics
Manufacturers
  • Pharmacia and upjohn co
  • Cadista pharmaceuticals inc
  • Duramed pharmaceuticals inc sub barr laboratories inc
  • Heather drug co inc
  • Par pharmaceutical inc
  • Sandoz inc
  • Vintage pharmaceuticals inc
  • Watson laboratories inc
  • Abbott laboratories hosp products div
  • Hemopharm usa corp
  • Hospira inc
  • Elkins sinn div ah robins co inc
  • Organon usa inc
  • Abraxis pharmaceutical products
  • App pharmaceuticals llc
  • Bedford laboratories
  • International medication systems ltd
  • Teva parenteral medicines inc
Packagers
Dosage forms
FormRouteStrength
PowderIntramuscular
PowderIntravenous
Powder, for solutionIntravenous
SuspensionIntramuscular
TabletOral
Prices
Unit descriptionCostUnit
Methylprednisolone powder96.25USDg
Methylprednisolone ac powdr40.09USDg
Methylprednisolone ss 1 gm vial31.2USDvial
Solu-medrol 1 gm vial24.43USDvial
Solu-medrol (pf) 500 mg vial20.9USDvial
MethylPREDNISolone (Pak) 21 4 mg tablet Disp Pack16.99USDdisp
Methylprednisolone 500 mg vial15.6USDvial
Solu-medrol 500 mg vial12.9USDvial
Depo-medrol 80 mg/ml vial11.67USDml
Methylprednisolone 125 mg vial10.0USDvial
Methylprednisolone 80 mg/ml vial9.12USDml
Depo-medrol 40 mg/ml vial6.41USDml
Solu-medrol (pf) 125 mg vial5.83USDvial
Methylprednisolone 40 mg/ml vial5.22USDml
Medrol 32 mg tablet5.13USDtablet
Methylprednisolone 32 mg tablet4.62USDtablet
Depo-medrol 20 mg/ml vial3.78USDml
Methylprednisolone 16 mg tablet3.17USDtablet
Methylprednisolone 40 mg vial3.0USDvial
A-methapred 40 mg vial2.36USDvial
Medrol 16 mg tablet2.28USDtablet
Medrol 8 mg tablet2.23USDtablet
Methylprednisolone 8 mg tablet1.74USDtablet
Methylprednisolone 4 mg tablet1.68USDtablet
Medrol 4 mg dosepak1.59USDeach
Medrol 4 mg tablet0.99USDtablet
Medrol 2 mg tablet0.84USDtablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
Statesolid
Experimental Properties
PropertyValueSource
melting point232.5 °CPhysProp
water solubility120 mg/L (at 25 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP1.5Not Available
logS-2.99ADME Research, USCD
Predicted Properties
PropertyValueSource
water solubility1.09e-01 g/lALOGPS
logP2.06ALOGPS
logP1.56ChemAxon
logS-3.5ALOGPS
pKa (strongest acidic)12.58ChemAxon
pKa (strongest basic)-2.9ChemAxon
physiological charge0ChemAxon
hydrogen acceptor count5ChemAxon
hydrogen donor count3ChemAxon
polar surface area94.83ChemAxon
rotatable bond count2ChemAxon
refractivity103.04ChemAxon
polarizability40.84ChemAxon
number of rings4ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterYesChemAxon
Veber's ruleNoChemAxon
MDDR-like ruleNoChemAxon
Spectra
SpectraNot Available
References
Synthesis Reference

Klaus Annen, Karl Petzoldt, Henry Laurent, Rudolf Wiechert, Helmut Hofmeister, “Novel 6.alpha.-methylprednisolone derivatives, their preparation, and their use.” U.S. Patent US4587236, issued March, 1973.

US4587236
General Reference
  1. Sloka JS, Stefanelli M: The mechanism of action of methylprednisolone in the treatment of multiple sclerosis. Mult Scler. 2005 Aug;11(4):425-32. Pubmed
External Links
ResourceLink
KEGG DrugD00407
PubChem Compound6741
PubChem Substance46504885
ChemSpider6485
ChEBI6888
ChEMBLCHEMBL650
Therapeutic Targets DatabaseDAP001040
PharmGKBPA450466
Drug Product Database2245406
RxListhttp://www.rxlist.com/cgi/generic/methprd.htm
Drugs.comhttp://www.drugs.com/methylprednisolone.html
WikipediaMethylprednisolone
ATC CodesNot Available
AHFS Codes
  • 68:04.00
PDB EntriesNot Available
FDA labelshow(244 KB)
MSDSshow(72.6 KB)
Interactions
Drug Interactions
Drug
Acetylsalicylic acidThe corticosteroid, methylprednisolone, may decrease the effect of the salicylate, acetylsalicylic acid.
AprepitantIncreases the effect and toxicity of methylprednisolone
ClarithromycinThe macrolide, clarithromycin, may increase the effect of corticosteroid, methylprednisolone.
ConivaptanCYP3A4 Inhibitors (Strong) may increase the serum concentration of Methylprednisolone. Consider methylprednisolone dose titration and/or adjustments in patients receiving strong CYP3A4 inhibitors (eg, azole antifungals, protease inhibitors) and monitor for increased steroid related adverse effects.
ErythromycinThe macrolide, erythromycin, may increase the effect of corticosteroid, methylprednisolone.
FosphenytoinThe enzyme inducer, fosphenytoin, may decrease the effect of the corticosteroid, methylprednisolone.
ItraconazoleThe imidazole, itraconazole, may increase the effect and toxicity of the corticosteroid, methylprednisolone.
KetoconazoleThe imidazole, ketoconazole, may increase the effect and toxicity of the corticosteroid, methylprednisolone.
MidodrineIncreased arterial pressure
PhenobarbitalThe barbiturate, phenobarbital, may decrease the effect of the corticosteroid, methylprednisolone.
PhenytoinThe enzyme inducer, phenytoin, may decrease the effect of the corticosteroid, methylprednisolone.
PrimidoneThe barbiturate, primidone, may decrease the effect of the corticosteroid, methylprednisolone.
PyridostigmineThe corticosteroid, methylprednisolone, may decrease the effect of the anticholinesterase, pyridostigmine.
QuinupristinThis combination presents an increased risk of toxicity
RifampicinThe enzyme inducer, rifampin, may decrease the effect of the corticosteroid, methylprednisolone.
TacrineTacrine and Methylprednisolone may independently exacerbate muscle weakness in myasthenia gravis patients. Monitor for additive muscle weakness effects.
TacrolimusMethylprednisone may increase the blood concentration of Tacrolimus. Monitor for changes in the therapeutic/toxic effects of Tacrolimus if Methylprednisone therapy is initiated, discontinued or altered.
TrastuzumabTrastuzumab may increase the risk of neutropenia and anemia. Monitor closely for signs and symptoms of adverse events.
VecuroniumVecuronium may increase the adverse neuromuscular effects of systemic corticosteroids, such as Methylprednisolone. Monitor for increased muscle weakness and signs of polyneuropathies and myopathy.
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. Owen HC, Miner JN, Ahmed SF, Farquharson C: The growth plate sparing effects of the selective glucocorticoid receptor modulator, AL-438. Mol Cell Endocrinol. 2007 Jan 29;264(1-2):164-70. Epub 2006 Dec 19. Pubmed
  2. Juruena MF, Cleare AJ, Papadopoulos AS, Poon L, Lightman S, Pariante CM: Different responses to dexamethasone and prednisolone in the same depressed patients. Psychopharmacology (Berl). 2006 Dec;189(2):225-35. Epub 2006 Oct 3. Pubmed
  3. Boivin MA, Ye D, Kennedy JC, Al-Sadi R, Shepela C, Ma TY: Mechanism of glucocorticoid regulation of the intestinal tight junction barrier. Am J Physiol Gastrointest Liver Physiol. 2007 Feb;292(2):G590-8. Epub 2006 Oct 26. Pubmed
  4. Quesnell RR, Han X, Schultz BD: Glucocorticoids stimulate ENaC upregulation in bovine mammary epithelium. Am J Physiol Cell Physiol. 2007 May;292(5):C1739-45. Epub 2007 Jan 24. Pubmed
  5. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed

1. Cytochrome P450 3A4

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate inhibitor

Components

Name UniProt ID Details
Cytochrome P450 3A4 P08684 Details

References:

  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

1. Multidrug resistance protein 1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Multidrug resistance protein 1 P08183 Details

References:

  1. Oka A, Oda M, Saitoh H, Nakayama A, Takada M, Aungst BJ: Secretory transport of methylprednisolone possibly mediated by P-glycoprotein in Caco-2 cells. Biol Pharm Bull. 2002 Mar;25(3):393-6. Pubmed
  2. Troutman MD, Thakker DR: Novel experimental parameters to quantify the modulation of absorptive and secretory transport of compounds by P-glycoprotein in cell culture models of intestinal epithelium. Pharm Res. 2003 Aug;20(8):1210-24. Pubmed
  3. Yates CR, Chang C, Kearbey JD, Yasuda K, Schuetz EG, Miller DD, Dalton JT, Swaan PW: Structural determinants of P-glycoprotein-mediated transport of glucocorticoids. Pharm Res. 2003 Nov;20(11):1794-803. Pubmed

Comments
Drug created on June 13, 2005 07:24 / Updated on January 11, 2014 08:39