CAS 83-43-2|Firmacort|Metrisone|Metrocort|Lemod|Solomet|Medixon|Predni N Tablinen|Mesopren|6alpha-Methylprednisolone|Methyleneprednisolone|Besonia|Promacortine|Metastab|Medrol Dosepak|Urbason|methyl...

General Information

Structure

Molecular Formula

C₂₂H₃₀O₅

Molecular Mass

374.4706

Exact Mass

374.20932406

Charge

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

Canonic 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

Isomeric 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

Calculated Properties

JChem

Acid pKa

12.584675

H Acceptors

H Donor

LogD (pH = 5.5)

1.560009

LogD (pH = 7.4)

1.5600061

Log P

1.560009

Molar Refractivity

103.0419

Polarizability

39.87477

Polar Surface Area

94.83

Rotatable Bonds

Lipinski's Rule of Five

true

ALOGPS 2.1

Log P

2.06

LOG S

-3.54

Solubility (Water)

1.09e-01 g/l

Data Source

Names and Identifiers

Brand Name

FirmacortMetrisoneMetrocortLemodSolometMedixonPredni N TablinenMesoprenBesoniaPromacortineMetastabMedrol DosepakUrbasonNirypanReactenolModerinMedroneArtisone-WyethWyacortEsametoneMedesoneMedlone 21Medrol Adt PakSummicortMetilbetasoneMetysolonMedrateSieropresolSuprametilUrbasoneDopomedrolNoretona

Synonyms

6alpha-MethylprednisoloneMethyleneprednisoloneMetilprednisolona [INN-Spanish]MethylprednisolonMethylprednisolonum [INN-Latin]MethylprednisoloneMetilprednisolone [Dcit]11β,17α,21-Trihydroxy-6α-methyl-1,4-pregnadiene-3,20-dioneMedrolMedrone6α-Methyl-11β,17α,21-trihydroxy-1,4-pregnadiene-3,20-dione6-α-METHYLPREDNISOLONE11β,17α,21-三羟基-6α-甲基-1,4-孕甾二烯-3,20-二酮6α-Methylprednisolone6α-甲基泼尼松龙甲基泼尼松龙甲基强的松龙6α-甲基-11β,17α,21-三羟基-1,4-孕甾二烯-3,20-二酮Solu-MedrolMedrate6α-Methyl Prednisolone(6α,11β)-11,17,21-Trihydroxy-6-methylpregna-1,4-diene-3,20-dione6α-Methyl-11β,17α,21-trihydroxy-1,4-pregnadiene-3,20-dione11β,17α,21-Trihydroxy-6α-methyl-1,4-pregnadiene-3,20-dioneMethylprednisolone-gellan ester

IUPAC Traditional name

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

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 (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

Names and Identifiers

Registration numbers

CAS Number

83-43-2

PubChem SID

465048851609642982489656424870169

EC Number

PubChem CID

MDL Number

Beilstein Number

Registration numbers

Properties

Physical Property

Product Information

Pharmacology Properties

Gene Information

rat ... Nr3c1(24413)

Properties

Related Proteins

No Data Available

Click here to submit data

Molecular Spectra

No Data Available

Click here to submit data

Molecule Details

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]

MP Biomedicals

02151671

Crystalline
m.p. 228-237°C

Sigma Aldrich

46436

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

TRC

M325934

A glucocorticoid.

Molecule Details

References

PubChem Literature

From Data Sources

• 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

• Dammers, J.W.H.H., et al.: Brit. Med. J., 319, 884 (1999)

• Hommes, O.R., et al.: Mult. Scler., 1, 327 (1992)

• Bracken, M.B., et al.: J. Neurosurg., 89, 699 (1992)

• Hall, E.D., et al.: J. Neurosurg., 76, 13 (1992)

References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

Brand Name

Synonyms

IUPAC Traditional name

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

IUPAC name

Registration numbers

CAS Number

83-43-2

PubChem SID

465048851609642982489656424870169

EC Number

PubChem CID

MDL Number

Beilstein Number

References

PubChem Literature

From Data Sources

• 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

• Dammers, J.W.H.H., et al.: Brit. Med. J., 319, 884 (1999)

• Hommes, O.R., et al.: Mult. Scler., 1, 327 (1992)

• Bracken, M.B., et al.: J. Neurosurg., 89, 699 (1992)

• Hall, E.D., et al.: J. Neurosurg., 76, 13 (1992)

Bioactivity

PubChem BioAssay

Properties

Physical Property

Product Information

Pharmacology Properties

Gene Information

rat ... Nr3c1(24413)

Molecule Details

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

MP Biomedicals

02151671

Crystalline
m.p. 228-237°C

Sigma Aldrich

46436

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

TRC

M325934

A glucocorticoid.

Molecule

ID:835