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Methylprednisolone

Names

[ CAS No. ]:
83-43-2

[ Name ]:
Methylprednisolone

[Synonym ]:
(6S,8S,9S,10R,11S,13S,14S,17R)-11,17-dihydroxy-17-(2-hydroxyacetyl)-6,10,13-trimethyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-3-one
MFCD00010591
EINECS 201-476-4
Methylprednisolone
6alpha-methylprednisolone

Biological Activity

[Description]:

Methylprednisolone is a synthetic corticosteroid with anti-inflammatory and immunomodulating properties.Target: Glucocorticoid ReceptorMethylprednisolone is typically used for its anti-inflammatory effects. Common uses include arthritis therapy and short-term treatment of bronchial inflammation or acute bronchitis due to various respiratory diseases. Methylprednisolone is used both in the treatment of acute periods and long-term management of autoimmune diseases, most notably systemic lupus erythematosus. It is also used for vestibular neuritis [1].After six months the patients who were treated with methylprednisolone within eight hours of their injury had significant improvement as compared with those given placebo in motor function (neurologic change scores of 16.0 and 11.2, respectively; P = 0.03) and sensation to pinprick (change scores of 11.4 and 6.6; P = 0.02) and touch (change scores, 8.9 and 4.3; P = 0.03). Benefit from methylprednisolone was seen in patients whose injuries were initially evaluated as neurologically complete, as well as in those believed to have incomplete lesions [2].

[Related Catalog]:

Signaling Pathways >> Autophagy >> Autophagy
Signaling Pathways >> GPCR/G Protein >> Glucocorticoid Receptor
Research Areas >> Inflammation/Immunology

[References]

[1]. Strupp, M., et al., Methylprednisolone, valacyclovir, or the combination for vestibular neuritis. N Engl J Med, 2004. 351(4): p. 354-61.

[2]. Bracken, M.B., et al., A randomized, controlled trial of methylprednisolone or naloxone in the treatment of acute spinal-cord injury. Results of the Second National Acute Spinal Cord Injury Study. N Engl J Med, 1990. 322(20): p. 1405-11.


[Related Small Molecules]

Hydrocortisone | Mifepristone | Corticosterone | Prednisone | (20S)-Protopanaxatriol | Fluticasone propionate | Triamcinolone | Cortisone | AL 082D06 | Glucocorticoid receptor agonist | Mapracorat | Ciclesonide | Beclometasone dipropionate | Clobetasol propionate | CORT-108297

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Boiling Point ]:
571.8±50.0 °C at 760 mmHg

[ Melting Point ]:
228-237°C (dec.)

[ Molecular Formula ]:
C22H30O5

[ Molecular Weight ]:
374.471

[ Flash Point ]:
313.7±26.6 °C

[ Exact Mass ]:
374.209320

[ PSA ]:
94.83000

[ LogP ]:
1.99

[ Vapour Pressure ]:
0.0±3.6 mmHg at 25°C

[ Index of Refraction ]:
1.603

[ Storage condition ]:
0-6°C

[ Water Solubility ]:
chloroform/methanol (9:1): 50 mg/mL, clear, faintly yellow

MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
TU4146000
CHEMICAL NAME :
Pregna-1,4-diene-3,20-dione, 6-alpha-methyl-11-beta-17,21-trihydroxy-
CAS REGISTRY NUMBER :
83-43-2
BEILSTEIN REFERENCE NO. :
2340300
LAST UPDATED :
199701
DATA ITEMS CITED :
9
MOLECULAR FORMULA :
C22-H30-O5
MOLECULAR WEIGHT :
374.52
WISWESSER LINE NOTATION :
L E5 B666 OV AHTTT&J A1 CQ E1 FV1Q FQ L1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Parenteral
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
2400 ug/kg
TOXIC EFFECTS :
Cardiac - change in rate Lungs, Thorax, or Respiration - respiratory depression Nutritional and Gross Metabolic - body temperature increase
REFERENCE :
BJANAD British Journal of Anesthesia. (Macmillan Press Ltd., Houndmills, Basingstoke, Hants. RG21 2XS, UK) V.1- 1923- Volume(issue)/page/year: 69,422,1992
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
60 mg/kg/3D-I
TOXIC EFFECTS :
Cardiac - pulse rate increase, without fall in BP Vascular - BP lowering not characterized in autonomic section Nutritional and Gross Metabolic - body temperature increase
REFERENCE :
AIMEAS Annals of Internal Medicine. (American College of Physicians, 4200 Pine St., Philadelphia, PA 19104) V.1- 1927- Volume(issue)/page/year: 99,282,1983
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
20 mg/kg/45M-C
TOXIC EFFECTS :
Cardiac - arrhythmias (including changes in conduction)
REFERENCE :
JRHUA9 Journal of Rheumatology. (920 Yonge St., Suite 608, Toronto, Ont., Canada) V.1- 1974- Volume(issue)/page/year: 13,477,1986
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
>4 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: 6,832,1982
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
2292 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: 6,832,1982 ** OTHER MULTIPLE DOSE TOXICITY DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
210 mg/kg/6W-I
TOXIC EFFECTS :
Kidney, Ureter, Bladder - other changes in urine composition Nutritional and Gross Metabolic - weight loss or decreased weight gain Nutritional and Gross Metabolic - changes in sodium
REFERENCE :
TXAPA9 Toxicology and Applied Pharmacology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1959- Volume(issue)/page/year: 1,305,1959 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOHS - National Occupational Hazard Survey (1974) NOHS Hazard Code - 84067 No. of Facilities: 33 (estimated) No. of Industries: 2 No. of Occupations: 1 No. of Employees: 272 (estimated) NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - 84067 No. of Facilities: 42 (estimated) No. of Industries: 1 No. of Occupations: 1 No. of Employees: 2047 (estimated) No. of Female Employees: 983 (estimated)

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Hazard Codes ]:
Xi

[ Risk Phrases ]:
R36/37/38

[ Safety Phrases ]:
S22-S36

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
2

[ RTECS ]:
TU4146000

Synthetic Route

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Related Compounds