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Identification
Name Methylprednisolone
Accession Number DB00959 (APRD00342)
Type small molecule
Groups approved
Description

A prednisolone derivative with similar anti-inflammatory action. [PubChem]
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
6alpha-Methylprednisolone
Methyleneprednisolone
Methylprednisolon
Methylprednisolonum [INN-Latin]
Metilprednisolona [INN-Spanish]
Metilprednisolone [Dcit]
Salts Not Available
Brand names
Name Company
Artisone-Wyeth
Besonia
Dopomedrol
Esametone
Firmacort
Lemod
Medesone
Medixon
Medlone 21
Medrate
Medrol Adt Pak
Medrol Dosepak
Medrone
Mesopren
Metastab
Metilbetasone
Metrisone
Metrocort
Metysolon
Moderin
Nirypan
Noretona
Predni N Tablinen
Promacortine
Reactenol
Sieropresol
Solomet
Summicort
Suprametil
Urbason
Urbasone
Wyacort
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Brand mixtures
Brand Name Ingredients
Depo-Medrol with Lidocaine Lidocaine Hydrochloride + Methylprednisolone Acetate
Medrol Acne Lotion Aluminum Chlorohydrate + Methylprednisolone Acetate + Sulfur
Methylprednisolone Sodium Succinate for Injection Methylprednisolone + Water
Neo-Medrol Methylprednisolone Acetate + Neomycin Sulfate
Neo-Medrol Acne Lotion Aluminum Chlorohydrate + Methylprednisolone Acetate + Neomycin Sulfate + Sulfur
Categories
  • Anti-inflammatory Agents
  • Adrenergic Agents
  • Antiemetics
  • Neuroprotective Agents
  • Glucocorticoids
CAS number 83-43-2
Weight Average: 374.4706
Monoisotopic: 374.20932407
Chemical Formula C22H30O5
InChI Key InChIKey=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
Plain Text
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
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Steroids and Steroid Derivatives
Substructures
  • Steroids and Steroid Derivatives
  • Hydroxy Compounds
  • Alkanes and Alkenes
  • Alcohols and Polyols
  • Ketones
Pharmacology
Indication Adjunctive therapy for short-term administration in rheumatoid arthritis.
Pharmacodynamics Methylprednisolone and its derivatives, methylprednisolone sodium succinate and methylprednisolone acetate, are synthetic glucocorticoids used as antiinflammatory or immunosuppressive agents.
Mechanism of action Unbound 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.
Absorption Oral bioavailability 80-99%
Volume of distribution Not Available
Protein binding 78%
Metabolism Hepatic
Route of elimination Not Available
Half life 1-3 hours
Clearance Not Available
Toxicity LD50=2000 mg/kg (orally in rat)
Affected organisms
  • Humans and other mammals
Pathways Not Available
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
Form Route Strength
Powder Intramuscular
Powder Intravenous
Powder, for solution Intravenous
Suspension Intramuscular
Tablet Oral
Prices
Unit description Cost Unit
Methylprednisolone powder 96.25 USD g
Methylprednisolone ac powdr 40.09 USD g
Methylprednisolone ss 1 gm vial 31.2 USD vial
Solu-medrol 1 gm vial 24.43 USD vial
Solu-medrol (pf) 500 mg vial 20.9 USD vial
MethylPREDNISolone (Pak) 21 4 mg tablet Disp Pack 16.99 USD disp
Methylprednisolone 500 mg vial 15.6 USD vial
Solu-medrol 500 mg vial 12.9 USD vial
Depo-medrol 80 mg/ml vial 11.67 USD ml
Methylprednisolone 125 mg vial 10.0 USD vial
Methylprednisolone 80 mg/ml vial 9.12 USD ml
Depo-medrol 40 mg/ml vial 6.41 USD ml
Solu-medrol (pf) 125 mg vial 5.83 USD vial
Methylprednisolone 40 mg/ml vial 5.22 USD ml
Medrol 32 mg tablet 5.13 USD tablet
Methylprednisolone 32 mg tablet 4.62 USD tablet
Depo-medrol 20 mg/ml vial 3.78 USD ml
Methylprednisolone 16 mg tablet 3.17 USD tablet
Methylprednisolone 40 mg vial 3.0 USD vial
A-methapred 40 mg vial 2.36 USD vial
Medrol 16 mg tablet 2.28 USD tablet
Medrol 8 mg tablet 2.23 USD tablet
Methylprednisolone 8 mg tablet 1.74 USD tablet
Methylprednisolone 4 mg tablet 1.68 USD tablet
Medrol 4 mg dosepak 1.59 USD each
Medrol 4 mg tablet 0.99 USD tablet
Medrol 2 mg tablet 0.84 USD tablet
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DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents Not Available
Properties
State solid
Experimental Properties
Property Value Source
melting point 232.5 °C PhysProp
water solubility 120 mg/L (at 25 °C) YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP 1.5 Not Available
logS -2.99 ADME Research, USCD
Predicted Properties
Property Value Source
water solubility 1.09e-01 g/l ALOGPS
logP 2.06 ALOGPS
logP 1.56 ChemAxon
logS -3.5 ALOGPS
pKa (strongest acidic) 12.58 ChemAxon
pKa (strongest basic) -2.9 ChemAxon
physiological charge 0 ChemAxon
hydrogen acceptor count 5 ChemAxon
hydrogen donor count 3 ChemAxon
polar surface area 94.83 ChemAxon
rotatable bond count 2 ChemAxon
refractivity 103.04 ChemAxon
polarizability 40.84 ChemAxon
References
Synthesis Reference Not Available
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
Resource Link
KEGG Drug D00407 Link_out
PubChem Compound 6741 Link_out
PubChem Substance 46504885 Link_out
ChemSpider 6485 Link_out
ChEBI 6888 Link_out
ChEMBL 6888 Link_out
Therapeutic Targets Database DAP001040 Link_out
PharmGKB PA450466 Link_out
Drug Product Database 2245406 Link_out
RxList http://www.rxlist.com/cgi/generic/methprd.htm Link_out
Drugs.com http://www.drugs.com/methylprednisolone.html Link_out
Wikipedia http://en.wikipedia.org/wiki/Methylprednisolone Link_out
ATC Codes
  • D07AA01
  • D07AC14
  • D10AA02
  • H02AB04
AHFS Codes
  • 68:04.00
PDB Entries Not Available
FDA label show (244 KB)
MSDS show (72.6 KB)
Interactions
Drug Interactions
Drug Interaction
Acetylsalicylic acid The corticosteroid, methylprednisolone, may decrease the effect of the salicylate, acetylsalicylic acid.
Aprepitant Increases the effect and toxicity of methylprednisolone
Clarithromycin The macrolide, clarithromycin, may increase the effect of corticosteroid, methylprednisolone.
Conivaptan CYP3A4 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.
Erythromycin The macrolide, erythromycin, may increase the effect of corticosteroid, methylprednisolone.
Fosphenytoin The enzyme inducer, fosphenytoin, may decrease the effect of the corticosteroid, methylprednisolone.
Itraconazole The imidazole, itraconazole, may increase the effect and toxicity of the corticosteroid, methylprednisolone.
Ketoconazole The imidazole, ketoconazole, may increase the effect and toxicity of the corticosteroid, methylprednisolone.
Midodrine Increased arterial pressure
Phenobarbital The barbiturate, phenobarbital, may decrease the effect of the corticosteroid, methylprednisolone.
Phenytoin The enzyme inducer, phenytoin, may decrease the effect of the corticosteroid, methylprednisolone.
Primidone The barbiturate, primidone, may decrease the effect of the corticosteroid, methylprednisolone.
Pyridostigmine The corticosteroid, methylprednisolone, may decrease the effect of the anticholinesterase, pyridostigmine.
Quinupristin This combination presents an increased risk of toxicity
Rifampin The enzyme inducer, rifampin, may decrease the effect of the corticosteroid, methylprednisolone.
Tacrine Tacrine and Methylprednisolone may independently exacerbate muscle weakness in myasthenia gravis patients. Monitor for additive muscle weakness effects.
Tacrolimus Methylprednisone 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.
Trastuzumab Trastuzumab may increase the risk of neutropenia and anemia. Monitor closely for signs and symptoms of adverse events.
Vecuronium Vecuronium may increase the adverse neuromuscular effects of systemic corticosteroids, such as Methylprednisolone. Monitor for increased muscle weakness and signs of polyneuropathies and myopathy.
Food Interactions Not Available
Targets

1. Glucocorticoid receptor

Pharmacological action: yes
Actions: agonist

Receptor for glucocorticoids (GC). Has a dual mode of action:as a transcription factor that binds to glucocorticoid response elements (GRE) 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 growth hormone (GH) stimulation and could reveal an essential role of hepatic GR in the control of body growth

Organism class: human
UniProt ID: P04150 Link_out
Gene: NR3C1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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
Enzymes

1. Cytochrome P450 3A4

Actions: substrate, inhibitor

Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4- hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. The enzyme also hydroxylates etoposide

UniProt ID: P08684 Link_out
Gene: CYP3A4
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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
Transporters

1. Multidrug resistance protein 1

Actions: substrate

Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells

UniProt ID: P08183 Link_out
Gene: ABCB1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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 February 08, 2013 16:19