Methylprednisone
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This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.
Explore a selection of our essential drug information below, or:
Identification
- Generic Name
- Methylprednisone
- DrugBank Accession Number
- DB12952
- Background
Methylprednisone has been used in trials studying the treatment of Leukemia, Rheumatoid Arthritis, Renal Transplantation, Kidney Transplantation, and Acute Lymphocytic Leukemia, among others.
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Structure
- Weight
- Average: 372.461
Monoisotopic: 372.193674002 - Chemical Formula
- C22H28O5
- Synonyms
- 6-alpha-methylprednisone
- External IDs
- NSC-63546
Pharmacology
- Indication
Not Available
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- Pharmacodynamics
Not Available
- Mechanism of action
- Not Available
- Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAbametapir The serum concentration of Methylprednisone can be increased when it is combined with Abametapir. Abatacept The metabolism of Methylprednisone can be increased when combined with Abatacept. Abemaciclib The metabolism of Abemaciclib can be decreased when combined with Methylprednisone. Acalabrutinib The metabolism of Acalabrutinib can be decreased when combined with Methylprednisone. Acenocoumarol The metabolism of Acenocoumarol can be decreased when combined with Methylprednisone. - Food Interactions
- Not Available
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as 21-hydroxysteroids. These are steroids carrying a hydroxyl group at the 21-position of the steroid backbone.
- Kingdom
- Organic compounds
- Super Class
- Lipids and lipid-like molecules
- Class
- Steroids and steroid derivatives
- Sub Class
- Hydroxysteroids
- Direct Parent
- 21-hydroxysteroids
- Alternative Parents
- Gluco/mineralocorticoids, progestogins and derivatives / 20-oxosteroids / 3-oxo delta-1,4-steroids / 17-hydroxysteroids / 11-oxosteroids / Delta-1,4-steroids / Tertiary alcohols / Alpha-hydroxy ketones / Cyclic ketones / Cyclic alcohols and derivatives show 3 more
- Substituents
- 11-oxosteroid / 17-hydroxysteroid / 20-oxosteroid / 21-hydroxysteroid / 3-oxo-delta-1,4-steroid / 3-oxosteroid / Alcohol / Aliphatic homopolycyclic compound / Alpha-hydroxy ketone / Carbonyl group show 13 more
- Molecular Framework
- Aliphatic homopolycyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- 621XR2W6OP
- CAS number
- 91523-05-6
- InChI Key
- SVYCRJXQZUCUND-PQXSVQADSA-N
- InChI
- InChI=1S/C22H28O5/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/h4,6,9,12,14-15,19,23,27H,5,7-8,10-11H2,1-3H3/t12-,14-,15-,19+,20-,21-,22-/m0/s1
- IUPAC Name
- (1R,3aS,3bS,5S,9aR,9bS,11aS)-1-hydroxy-1-(2-hydroxyacetyl)-5,9a,11a-trimethyl-1H,2H,3H,3aH,3bH,4H,5H,7H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthrene-7,10-dione
- SMILES
- C[C@H]1C[C@H]2[C@@H]3CC[C@](O)(C(=O)CO)[C@@]3(C)CC(=O)[C@@H]2[C@@]2(C)C=CC(=O)C=C12
References
- General References
- Not Available
- External Links
- PubChem Compound
- 124653
- PubChem Substance
- 347829094
- ChemSpider
- 110996
- ZINC
- ZINC000004744090
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample dataNot Available Completed Treatment Congenital Heart Disease (CHD) / Disorder of Fetus or Newborn 1 somestatus stop reason just information to hide Not Available Recruiting Not Available Children / Immunosuppressive Treatment / Lupus Nephritis / Steroid therapy 1 somestatus stop reason just information to hide Not Available Recruiting Not Available Immunoglobulin A Nephropathy / Immunosuppressive Treatment / Proteinuria in Nephrotic Range 1 somestatus stop reason just information to hide Not Available Recruiting Treatment Idiopathic Membranous Nephropathy / Mild Cognitive Impairment (MCI) 1 somestatus stop reason just information to hide 4 Completed Treatment Chronic Kidney Disease (CKD) / End Stage Renal Disease (ESRD) / Hemodialysis Treatment / Kidney Transplantation / Renal Replacement Therapies 1 somestatus stop reason just information to hide
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Not Available
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.0587 mg/mL ALOGPS logP 2.24 ALOGPS logP 1.95 Chemaxon logS -3.8 ALOGPS pKa (Strongest Acidic) 12.58 Chemaxon pKa (Strongest Basic) -3.3 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 5 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 91.67 Å2 Chemaxon Rotatable Bond Count 2 Chemaxon Refractivity 102.12 m3·mol-1 Chemaxon Polarizability 40.27 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 192.59933 predictedDeepCCS 1.0 (2019) [M-H]- 192.59933 predictedDeepCCS 1.0 (2019) [M+H]+ 194.74605 predictedDeepCCS 1.0 (2019) [M+H]+ 194.74605 predictedDeepCCS 1.0 (2019) [M+Na]+ 200.65938 predictedDeepCCS 1.0 (2019) [M+Na]+ 200.65938 predictedDeepCCS 1.0 (2019)
Enzymes
1. DetailsCytochrome P450 3A4
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Substrate
- General Function
- A cytochrome P450 monooxygenase involved in the metabolism of sterols, steroid hormones, retinoids and fatty acids (PubMed:10681376, PubMed:11093772, PubMed:11555828, PubMed:12865317, PubMed:14559847, PubMed:15373842, PubMed:15764715, PubMed:19965576, PubMed:20702771, PubMed:21490593, PubMed:21576599). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase). Catalyzes the hydroxylation of carbon-hydrogen bonds (PubMed:12865317, PubMed:14559847, PubMed:15373842, PubMed:15764715, PubMed:21490593, PubMed:21576599, PubMed:2732228). Exhibits high catalytic activity for the formation of hydroxyestrogens from estrone (E1) and 17beta-estradiol (E2), namely 2-hydroxy E1 and E2, as well as D-ring hydroxylated E1 and E2 at the C-16 position (PubMed:11555828, PubMed:12865317, PubMed:14559847). Plays a role in the metabolism of androgens, particularly in oxidative deactivation of testosterone (PubMed:15373842, PubMed:15764715, PubMed:22773874, PubMed:2732228). Metabolizes testosterone to less biologically active 2beta- and 6beta-hydroxytestosterones (PubMed:15373842, PubMed:15764715, PubMed:2732228). Contributes to the formation of hydroxycholesterols (oxysterols), particularly A-ring hydroxylated cholesterol at the C-4beta position, and side chain hydroxylated cholesterol at the C-25 position, likely contributing to cholesterol degradation and bile acid biosynthesis (PubMed:21576599). Catalyzes bisallylic hydroxylation of polyunsaturated fatty acids (PUFA) (PubMed:9435160). Catalyzes the epoxidation of double bonds of PUFA with a preference for the last double bond (PubMed:19965576). Metabolizes endocannabinoid arachidonoylethanolamide (anandamide) to 8,9-, 11,12-, and 14,15-epoxyeicosatrienoic acid ethanolamides (EpETrE-EAs), potentially modulating endocannabinoid system signaling (PubMed:20702771). Plays a role in the metabolism of retinoids. Displays high catalytic activity for oxidation of all-trans-retinol to all-trans-retinal, a rate-limiting step for the biosynthesis of all-trans-retinoic acid (atRA) (PubMed:10681376). Further metabolizes atRA toward 4-hydroxyretinoate and may play a role in hepatic atRA clearance (PubMed:11093772). Responsible for oxidative metabolism of xenobiotics. Acts as a 2-exo-monooxygenase for plant lipid 1,8-cineole (eucalyptol) (PubMed:11159812). Metabolizes the majority of the administered drugs. Catalyzes sulfoxidation of the anthelmintics albendazole and fenbendazole (PubMed:10759686). Hydroxylates antimalarial drug quinine (PubMed:8968357). Acts as a 1,4-cineole 2-exo-monooxygenase (PubMed:11695850). Also involved in vitamin D catabolism and calcium homeostasis. Catalyzes the inactivation of the active hormone calcitriol (1-alpha,25-dihydroxyvitamin D(3)) (PubMed:29461981)
- Specific Function
- 1,8-cineole 2-exo-monooxygenase activity
- Gene Name
- CYP3A4
- Uniprot ID
- P08684
- Uniprot Name
- Cytochrome P450 3A4
- Molecular Weight
- 57342.67 Da
References
- Hardy KW, Crocker JF, McLellan H, Goralski KB, Renton KW, Acott PD: Paradoxical cyclosporine A requirements in pediatric renal transplants receiving high-dose steroids. J Clin Pharmacol. 2005 Feb;45(2):161-7. doi: 10.1177/0091270004271403. [Article]
- Aria N, Kauffman CL: Important drug interactions and reactions in dermatology. Dermatol Clin. 2003 Jan;21(1):207-15, ix. [Article]
- DEPO-MEDROL® (methylprednisolone acetate injectable suspension USP) - Product Monograph [Link]
Drug created at October 21, 2016 01:33 / Updated at June 12, 2020 16:53