methylprednisolone acetate

Names

[ CAS No. ]:
53-36-1

[ Name ]:
methylprednisolone acetate

[Synonym ]:
2-[(6S,8S,9S,10R,11S,13S,14S,17R)-11,17-Dihydroxy-6,10,13-trimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl]-2-oxoethylacetat
6-METHYLPREDNISOLONE ACETATE
(6α,11β)-11,17-Dihydroxy-6-methyl-3,20-dioxopregna-1,4-dien-21-yl acetate
Methylprednisolone acetate
21-Acetoxy-11b,17-dihydroxy-6a-methylpregna-1,4-diene-3,20-dione
(6a,11b)-21-(Acetyloxy)-11,17-dihydroxy-6-methylpregna-1,4-diene-3,20-dione
6a-Methylprednisolone 21-Acetate
CH3CO2CH(CH3)CH2OCH3
Depo-methylprednisolone
MFCD00144786
EINECS 200-171-3
Pregna-1,4-diene-3,20-dione, 21-(acetyloxy)-11,17-dihydroxy-6-methyl-, (6α,11β)-
2-[(6S,8S,9S,10R,11S,13S,14S,17R)-11,17-dihydroxy-6,10,13-trimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl]-2-oxoethyl acetate
acétate de 2-[(6S,8S,9S,10R,11S,13S,14S,17R)-11,17-dihydroxy-6,10,13-triméthyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodécahydro-3H-cyclopenta[a]phénanthrén-17-yl]-2-oxoéthyle
6α-Methyl Prednisolone 21-Acetate
6α-Methylprednisolone 21-acetate
Solsolona
Pregna-1,4-diene-3,20-dione, 11β,17,21-trihydroxy-6α-methyl-, 21-acetate (8CI)

Biological Activity

[Description]:

Methylprednisolone acetate, a prednisolone derivative, is a corticosteroid hormone. Methylprednisolone acetate can relieve pain and swelling that occurs with arthritis and other joint disorders in vivo[1][2].

[Related Catalog]:

Research Areas >> Inflammation/Immunology

Signaling Pathways >> GPCR/G Protein >> Glucocorticoid Receptor

[In Vivo]

Methylprednisolone acetate (30 mg/kg, intramuscular injection; additional oral doses of 13 mg/kg for 10 consecutive days）combines with LPS induces typical features of early AVN of the femoral head[2]. Animal Model: A mouse model of osteonecrotic femoral head induced by methylprednisolone and liposaccharide[2] Dosage: 30 mg/kg; 13 mg/kg for 10 consecutive days Administration: 30 mg/kg, intramuscular injection; additional oral doses of 13 mg/kg for 10 consecutive days Result: Lead to chondrocyte degeneration and fibrocartilage expression after 7 weeks. Increased the density of CD31 and VEGF-R2 markers in the femoral head.

[References]

[1]. Ha Thi -Ngan Le, et al. A mouse model of osteonecrotic femoral head induced by methylprednisolone and liposaccharide. Biomedical Research and Therapy volume 3, Article number: 12 (2016)

[2]. Luis M Franco,et al. Immune regulation by glucocorticoids can be linked to cell type-dependent transcriptional responses. J Exp Med. 2019 Feb 4;216(2):384-406.

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Boiling Point ]:
582.5±50.0 °C at 760 mmHg

[ Melting Point ]:
206ºC

[ Molecular Formula ]:
C₂₄H₃₂O₆

[ Molecular Weight ]:
416.507

[ Flash Point ]:
196.5±23.6 °C

[ Exact Mass ]:
416.219879

[ PSA ]:
100.90000

[ LogP ]:
3.08

[ Vapour Pressure ]:
0.0±3.7 mmHg at 25°C

[ Index of Refraction ]:
1.580

[ Storage condition ]:
Refrigerator

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: TU4154050

CHEMICAL NAME :: Pregna-1,4-diene-3,20-dione, 11-beta,17,21-trihydroxy-6-alpha-methyl-, 21-acetate

CAS REGISTRY NUMBER :: 53-36-1

LAST UPDATED :: 199706

DATA ITEMS CITED :: 11

MOLECULAR FORMULA :: C24-H32-O6

MOLECULAR WEIGHT :: 416.56

WISWESSER LINE NOTATION :: L E5 B666 OV AHTTT&J A1 CQ E1 FV1OV1 FQ L1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >10 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: -,1182,1990

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 265 mg/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Gastrointestinal - other changes Nutritional and Gross Metabolic - weight loss or decreased weight gain

REFERENCE :: JTSCDR Journal of Toxicological Sciences. (Japanese Soc. of Toxicological Sciences, 4th Floor, Gakkai Center Bldg., 4-16, Yayoi 2-chome, Bunkyo-ku, Tokyo 113, Japan) V.1- 1976- Volume(issue)/page/year: 10(Suppl 1),1,1985

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >1409 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: -,1182,1990

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1320 mg/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Gastrointestinal - other changes Nutritional and Gross Metabolic - weight loss or decreased weight gain

REFERENCE :: JTSCDR Journal of Toxicological Sciences. (Japanese Soc. of Toxicological Sciences, 4th Floor, Gakkai Center Bldg., 4-16, Yayoi 2-chome, Bunkyo-ku, Tokyo 113, Japan) V.1- 1976- Volume(issue)/page/year: 10(Suppl 1),1,1985 ** OTHER MULTIPLE DOSE TOXICITY DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 45500 ug/kg/13W-C

TOXIC EFFECTS :: Endocrine - other changes Blood - normocytic anemia Blood - changes in serum composition (e.g. TP, bilirubin, cholesterol)

REFERENCE :: JTSCDR Journal of Toxicological Sciences. (Japanese Soc. of Toxicological Sciences, 4th Floor, Gakkai Center Bldg., 4-16, Yayoi 2-chome, Bunkyo-ku, Tokyo 113, Japan) V.1- 1976- Volume(issue)/page/year: 10(Suppl 1),11,1985 ** REPRODUCTIVE DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intramuscular

DOSE :: 330 mg/kg

SEX/DURATION :: female 10 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Effects on Embryo or Fetus - fetal death Reproductive - Specific Developmental Abnormalities - eye/ear

REFERENCE :: TXAPA9 Toxicology and Applied Pharmacology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1959- Volume(issue)/page/year: 56,23,1980

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intramuscular

DOSE :: 330 mg/kg

SEX/DURATION :: female 10 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue)

REFERENCE :: TXAPA9 Toxicology and Applied Pharmacology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1959- Volume(issue)/page/year: 56,23,1980

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intramuscular

DOSE :: 1800 ug/kg

SEX/DURATION :: female 7-18 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Effects on Newborn - viability index (e.g., # alive at day 4 per # born alive)

REFERENCE :: ANREAK Anatomical Record. (Alan R. Liss, Inc., 41 E. 11th St., New York, NY 10003) V.1- 1906/08- Volume(issue)/page/year: 193,598,1979

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intramuscular

DOSE :: 1200 ug/kg

SEX/DURATION :: female 7-18 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - Central Nervous System Reproductive - Specific Developmental Abnormalities - musculoskeletal system

REFERENCE :: ANREAK Anatomical Record. (Alan R. Liss, Inc., 41 E. 11th St., New York, NY 10003) V.1- 1906/08- Volume(issue)/page/year: 193,598,1979 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOHS - National Occupational Hazard Survey (1974) NOHS Hazard Code - M1854 No. of Facilities: 202 (estimated) No. of Industries: 1 No. of Occupations: 2 No. of Employees: 426 (estimated) NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - M1854 No. of Facilities: 81 (estimated) No. of Industries: 1 No. of Occupations: 6 No. of Employees: 2381 (estimated) No. of Female Employees: 1905 (estimated)

Safety Information

[ Symbol ]:

GHS08

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H361

[ Precautionary Statements ]:
P201-P308 + P313

[ Hazard Codes ]:
Xn

[ Risk Phrases ]:
63-62

[ Safety Phrases ]:
S24/25

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Articles

Achyranthes bidentata extract exerts osteoprotective effects on steroid-induced osteonecrosis of the femoral head in rats by regulating RANKL/RANK/OPG signaling.

J. Transl. Med. 12 , 334, (2014)

Steroid-induced osteonecrosis of the femoral head (steroid-induced ONFH) presents great challenges due to the various effects of steroids on multi-system pathways involved into osteoblast differentiat...

Cholesterol- and lanolin-rich diets may protect against steroid-induced osteonecrosis in rabbits.

Acta Orthop. 84(6) , 593-7, (2013)

It remains controversial how hypercholesterolemia influences the development of steroid-induced osteonecrosis (ON). We investigated the role of hypercholesterolemia induced by a cholesterol-rich diet ...

Notes from the field: Department of Defense response to a multistate outbreak of fungal meningitis--United States, October 2012.

MMWR Morb. Mortal. Wkly. Rep. 62(38) , 800-1, (2013)

On October 1, 2012, the Department of Defense (DoD) learned of a multistate outbreak of fungal meningitis in persons who received injections of methylprednisolone acetate (MPA) from a single compoundi...