(1S,2R,8S,10S,11S,14R,15S,17S)-14,17-dihydroxy-14-(2-hydroxyacetyl)-2,8,15-trimethyltetracyclo[8.7.0.02,7.011,15]heptadeca-3,6-dien-5-one

• ChemBase ID: 835
• Molecular Formular: C22H30O5
• Molecular Mass: 374.4706
• Monoisotopic Mass: 374.20932406
• SMILES: O[C@]1([C@@]2([C@H]([C@H]3[C@H]([C@@H](O)C2)[C@@]2(C(=CC(=O)C=C2)[C@H](C3)C)C)CC1)C)C(=O)CO
• Canonical SMILES: OCC(=O)[C@@]1(O)CC[C@@H]2[C@]1(C)C[C@H](O)[C@H]1[C@H]2C[C@@H](C2=CC(=O)C=C[C@]12C)C
• 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
• InChIKey: VHRSUDSXCMQTMA-PJHHCJLFSA-N

NAMES AND DATABASE IDS

Names

• 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,^7.0^1^1,^1^5]heptadeca-3,6-dien-5-one; (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
• IUPAC Traditional name: methylprednisolone; (1S,2R,8S,10S,11S,14R,15S,17S)-14,17-dihydroxy-14-(2-hydroxyacetyl)-2,8,15-trimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-dien-5-one
• Brand Name: 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
• Synonyms: (6α,11β)-11,17,21-Trihydroxy-6-methylpregna-1,4-diene-3,20-dione; Medrate; 6α-Methyl Prednisolone; Medrol; Solu-Medrol; Medrone; 6α-Methylprednisolone; 11β,17α,21-Trihydroxy-6α-methyl-1,4-pregnadiene-3,20-dione; 6α-Methyl-11β,17α,21-trihydroxy-1,4-pregnadiene-3,20-dione; 11β,17α,21-Trihydroxy-6α-methyl-1,4-pregnadiene-3,20-dione; 6α-Methyl-11β,17α,21-trihydroxy-1,4-pregnadiene-3,20-dione; 6-α-METHYLPREDNISOLONE; Methyleneprednisolone; Methylprednisolon; Methylprednisolonum [INN-Latin]; Metilprednisolona [INN-Spanish]; Metilprednisolone [Dcit]; 6alpha-Methylprednisolone; Methylprednisolone; Methylprednisolone-gellan ester; 11β,17α,21-三羟基-6α-甲基-1,4-孕甾二烯-3,20-二酮; 6α-甲基-11β,17α,21-三羟基-1,4-孕甾二烯-3,20-二酮; 甲基强的松龙; 甲基泼尼松龙; 6α-甲基泼尼松龙

Database IDs

• CAS Number: 83-43-2
• EC Number: 201-476-4
• MDL Number: MFCD00010591
• Beilstein Number: 2340300
• PubChem SID: 160964298; 46504885; 24896564; 24870169
• PubChem CID: 6741

CALCULATED PROPERTIES

JChem

• Acid pKa: 12.584675
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 1.560009
• LogD (pH = 7.4): 1.5600061
• Log P: 1.560009
• Molar Refractivity: 103.0419 cm^3
• Polarizability: 39.87477 Å^3
• Polar Surface Area: 94.83 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.06
• LOG S: -3.54
• Solubility (Water): 1.09e-01 g/l

PROPERTIES

Physical Property

• Solubility: 120 mg/L; Acetone; Chloroform; chloroform/methanol (9:1): soluble50 mg/mL, clear, faintly yellow; DMSO
• Apperance: White to Off-White Solid
• Melting Point: 213-215°C (dec.); 228-237 °C
• Hydrophobicity(logP): 1.5

Safety Information

• Storage Condition: -20°C; -20°C Freezer; Room Temperature (15-30°C)
• RTECS: TU4146000
• German water hazard class: 2
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Pharmacology Properties

• Gene Information: rat ... Nr3c1(24413)
• Mechanism of Action: ACTH antagonist; ACTH secretion inhibitor; Calcium mobilizer; Causes protein catabolism; Glucocorticoid; Gluconeogenesis promoter; Glycogen deposition inhibitor; Phosphorus mobilizer

Product Information

• Purity: ≥98%; ≥98.0% (HPLC)
• Grade: VETRANAL™, analytical standard
• Salt Data: Free Base
• Application(s): Immunomodulator; Potent antiinflammatory agent
• Empirical Formula (Hill Notation): C22H30O5

DETAILS

MP Biomedicals - 02151671

Crystalline
m.p. 228-237°C

DrugBank - DB00959

• Drug Groups: approved
• Description: A prednisolone derivative with similar anti-inflammatory action. [PubChem]
• Indication: Adjunctive therapy for short-term administration in rheumatoid arthritis.
• Pharmacology: Methylprednisolone and its derivatives, methylprednisolone sodium succinate and methylprednisolone acetate, are synthetic glucocorticoids used as antiinflammatory or immunosuppressive agents.
• Toxicity: LD₅₀=2000 mg/kg (orally in rat)
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic
• Absorption: Oral bioavailability 80-99%
• Half Life: 1-3 hours
• Protein Binding: 78%
• References: 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: Wikipedia; RxList; Drugs.com

Selleck Chemicals - S1733

Research Area: Immunology , Inflammation
Biological Activity:
Methylprednisolone is a synthetic corticosteroid with anti-inflammatory and immunomodulating properties. Methylprednisolone binds to and activates specific nuclear receptors, resulting in altered gene expression and inhibition of proinflammatory cytokine production. This agent also decreases the number of circulating lymphocytes, induces cell differentiation, and stimulates apoptosis in sensitive tumor cell populations. [1, 2]

Sigma Aldrich - 46436

Legal Information
VETRANAL is a trademark of Sigma-Aldrich Co. LLC

Toronto Research Chemicals - M325934

A glucocorticoid.

REFERENCES

• 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
• http://en.wikipedia.org/wiki/Methylprednisolone
• Hall, E.D., et al.: J. Neurosurg., 76, 13 (1992)
• Hommes, O.R., et al.: Mult. Scler., 1, 327 (1992)
• Bracken, M.B., et al.: J. Neurosurg., 89, 699 (1992)
• Dammers, J.W.H.H., et al.: Brit. Med. J., 319, 884 (1999)