Methylprednisolone

Iupac Name：(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

CAS No.: 83-43-2

Molecular Weight：374.47100

Modify Date.: 2022-11-02 11:27

Introduction: 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 lu View more+

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1. Names and Identifiers

1.1 Name: Methylprednisolone
1.2 Synonyms: (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 11Β,17α,21-Trihydroxy-6α-methyl-1,4-pregnadiene-3,20-dione 20-dione,11-beta,17,21-trihydroxy-6-alpha-methyl-pregna-4-diene-3 20-dione,11beta,17,21-trihydroxy-6alpha-methyl-pregna-4-diene-3 20-dione,6-alpha-methyl-11-beta-17,21-trihydroxy-pregna-4-diene-3 6alpha-methylprednisolone EINECS 201-476-4 Methyl Prednisolone Hydrogen succinate Impurity A Methylprednisolone Acetate EP Impurity B Methylprednisolone Hydrogen Succinate EP Impurity A Methylprednisolone Impurity A Methylprednisolone-d4 MFCD00010591

1.3 CAS No.: 83-43-2

1.4 CID: 6741

1.5 EINECS(EC#): 201-476-4

1.6 Molecular Formula: C22H30O5 (isomer)

1.7 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

1.8 InChkey: VHRSUDSXCMQTMA-PJHHCJLFSA-N

1.9 Canonical Smiles: CC1CC2C3CCC(C3(CC(C2C4(C1=CC(=O)C=C4)C)O)C)(C(=O)CO)O

1.10 Isomers Smiles: C[C@H]1C[C@H]2[C@@H]3CC[C@@]([C@]3(C[C@@H]([C@@H]2[C@@]4(C1=CC(=O)C=C4)C)O)C)(C(=O)CO)O

2. Properties

2.1 Density: 1.28

2.1 Melting point: 228-237°C (dec.)

2.1 Boiling point: 571.8ºC at 760 mmHg

2.1 Refractive index: 82 ° (C=1, Dioxane)

2.1 Flash Point: 571.8 °C at 760 mmHg

2.1 Precise Quality: 374.20900

2.1 PSA: 94.83000

2.1 logP: 1.80360

2.1 Solubility: chloroform/methanol (9:1): 50?mg/mL, clear, faintly yellow

2.2 Appearance: white to off-white crystalline powder

2.3 Chemical Properties: White to Off-White Crystalline Powder

2.4 Color/Form: Powder

2.5 pKa: 12.46±0.70(Predicted)

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

2.7 Spectral Properties: Specific optical rotation: +83 deg at 20 deg C/D (dioxane); max absorption (95% ethanol): 243 nm (alpha(m)= 14,875)

2.8 StorageTemp: 0-6°C

3. Use and Manufacturing

3.1 Definition: ChEBI: The 6alpha-stereoisomer of 6-methylprednisolone.

3.2 Purification Methods: Recrystallise medrol from EtOAc. The UV has max at in 95% EtOH 243nm ( 14,875). The 21-acetoxy derivative has m 205-208o (from EtOAc), and [] D +95o ( c 1, CHCl3). [Spero et al. J Am Chem Soc 78 6213 1956; Fried et al. J Am Chem Soc 81 1235 1959; 1H NMR: Slomp & McGarvey J Am Chem Soc 81 2200 1959, Beilstein 8 IV 3498.] Methylprednisolone Preparation Products And Raw materials Preparation Products

3.3 Usage: A glucocorticoid

4. Safety and Handling

4.1 Hazard Codes: Xi

4.1 Risk Statements: R36/37/38

4.1 Safety Statements: S22-S36

4.1 Exposure Standards and Regulations: The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl methylprednisolone approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act.
The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl methylprednisolone acetate approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act. /Methylprednisolone acetate/
The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl methylprednisolone sodium succinate approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act. /Methylprednisolone sodium succinate/
The Generic Animal Drug and Patent Restoration act requires that each sponsor of an approved animal drug must submit to the FDA certain information regarding patents held for the animal drug or its method of use. The Act requires that this information, as well as a list of all animal drug products approved for safety and effectiveness, be made available to the public. Methylprednisolone is included on this list.
Oral dosage form new animal drugs. Methylprednisolone tablets. ... For use in dogs and cats as an anti-inflammatory agent. ... Federal law restricts this drug to use by or on the order of a licensed veterinarian.
Implantation or injectable dosage form new animal drugs. Sterile methylprednisolone acetate suspension. ... Indications for use: Treatment of inflammation and related disorders in dogs, cats, and horses;1 treatment of allergic and dermatologic disorders in dogs and cats; and as supportive therapy to antibacterial treatment of severe infections in dogs and cats. ... Federal law restricts this drug to use by or on the order of a licensed veterinarian. /Methylprednisolone acetate/
A tolerance is established for negligible residues of methylprednisolone in milk at 10 parts per billion.

4.2 Octanol/Water Partition Coefficient: log Kow = 1.82 (est)

4.3 DisposalMethods: SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

4.4 RIDADR: NONH for all modes of transport

4.4 Safety Profile: Moderately toxic byintraperitoneal route. A steroid hormone.Human systemic effects include arrhythmias,blood pressure lowering, heart rate changes,increased body temperature, pulse rateincrease, respiratory depression. When heated to decomposition it emits acridsmoke and irritating fumes.

4.5 Formulations/Preparations: Oral: Tablets: 2 mg Medrol (scored), (Pfizer), 4 mg Medrol (scored), (Pfizer), Medrol Dosepak, (Pfizer), Meprolone Unipak, (Major), Methylprednisolone, (Barr), Methylprednisolone, (Par), Methylprednisolone, (Trigen); 8 mg Medrol (scored), (Pfizer), Methylprednisolone, (Par); 16 mg Medrol (scored), (Pfizer); 32 mg Medrol (scored), (Pfizer).
Parenteral: Injectable suspension: 20 mg/mL Depo-Medrol, (Pfizer); 40 mg/mL Depo-Medrol, (Pfizer), Methylprednisolone Acetate Injection, (Sicor), Methylprednisolone Acetate Injection, (Teva); 80 mg/mL Depo-Medrol, (Pfizer) Methylprednisolone Acetate Injection, (Sicor), Methylprednisolone Acetate Injection, (Teva). /Methylprednisolone acetate/
Parenteral: For injection: 40 mg (of methylprednisolone) A-methaPred ( with benzyl alcohol in Univial), (Hospira), Methylprednisolone Sodium Succinate Injection (with benzyl alcohol), (Abraxis) Solu-Medrol (with benzyl alcohol 8.8 mg in Act-O-Vial), (Pfizer); 125 mg (of methylprednisolone) A-methaPred (with benzyl alcohol in Univial), (Hospira), Methylprednisolone Sodium Succinate Injection (with benzyl alcohol), Abraxis Solu-Medrol (with benzyl alcohol 17.6 mg in Act-O-Vial), (Pfizer); 500 mg (of methylprednisolone) A-methaPred (with benzyl alcohol in Univial), (Hospira), A-methaPred ADD-Vantage, (Hospira) Solu-Medrol (with and without diluent containing benzyl alcohol 70.2 mg), (Pfizer); 1 g (of methylprednisolone) A-methaPred (with benzyl alcohol in Univial), (Hospira), A-methaPred ADD-Vantage, (Hospira), Methylprednisolone Sodium Succinate Injection (with benzyl alcohol), (Abraxis), Solu-Medrol (with benzyl alcohol 141 mg and with benzyl alcohol 66.8 mg in Act-O-Vial), (Pfizer); 2 g (of methylprednisolone) Solu-Medrol (with and without diluent containing benzyl alcohol 273 mg), (Pfizer). /Methylprednisolone sodium succinate/

4.6 WGK Germany: 2

4.6 RTECS: TU4146000

4.6 Report: Reported in EPA TSCA Inventory.

4.7 Safety: Moderately toxic by intraperitoneal route. A steroid hormone. Human systemic effects include arrhythmias, blood pressure lowering, heart rate changes, increased body temperature, pulse rate increase, respiratory depression. When heated to decomposition it emits acrid smoke and irritating fumes.

4.8 Specification

The Methylprednisolone?with cas registry number of 83-43-2 has?other registry numbers which are 121673-01-6 and 570-35-4. Its EINECS?registry number is 201-476-4. It belongs to the classes of Miscellaneous Biochemicals; Biochemistry; Hydroxyketosteroids; Steroids; Intermediates & Fine Chemicals; Pharmaceuticals. This chemical is also known as Promacortine, Reactenol, Sieropresol, Solomet, Solu-medrol, Summicort; Suprametil.Its systematic name is called (6alpha,11beta)-11,17,21-trihydroxy-6-methylpregna-1,4-diene-3,20-dione. And its IUPAC name is also called(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. It is white to off-white crystalline powder.

Physical properties about this chemical are:?(1)ACD/LogP: 1.99; (2) # of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.99; (4)ACD/LogD (pH 7.4): 1.99; (5)ACD/BCF (pH 5.5): 19.06; (6)ACD/BCF (pH 7.4): 19.06; (7)ACD/KOC (pH 5.5): 287.01; (8)ACD/KOC (pH 7.4): 287.01; (9)#H bond acceptors: 5; (10)#H bond donors: 3; (11)#Freely Rotating Bonds: 5; (12)Polar Surface Area: 61.83??²; (13)Index of Refraction: 1.602; (14)Molar Refractivity: 100.08 cm³; (15)Molar Volume: 291.4 cm³; (16)Surface Tension: 58.1 dyne/cm; (17)Density: 1.28 g/cm³; (18)Flash Point: 313.7 °C; (19)Enthalpy of Vaporization: 98.47 kJ/mol; (20)Boiling Point: 571.8 °C at 760 mmHg; (21)Vapour Pressure: 1.86E-15 mmHg at 25°C; (22)Refractive index: 82 ° (C=1, Dioxane); (23)Melting Point: 228-237°C.

Uses of?Methylprednisolone : this chemical can be used as a glucocorticoid. And it is used for rheumatoid arthritis, collagen diseases, allergic disease, ophthalmic disease, lymphatic leukemia, soft tissue inflammation and hemolytic anemia.

When you are using this chemical, please be cautious about it as the following:
Moderately toxic by intraperitoneal route. A steroid hormone. Human systemic effects include arrhythmias, blood pressure lowering, heart rate changes, increased body temperature, pulse rate increase, respiratory depression. When heated to decomposition it emits acrid smoke and irritating fumes.?Wear suitable protective clothing, gloves and eye/face protection when you are using it. Do not breathe dust.?In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.?Store it at?temperature of 0-6°C.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C\1\C=C/[C@]4(/C(=C/1)[C@@H](C)C[C@@H]2[C@@H]4[C@@H](O)C[C@@]3([C@@](O)(C(=O)CO)CC[C@@H]23)C)C;
(2)InChI: InChI=1/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;
(3)InChIKey: VHRSUDSXCMQTMA-PJHHCJLFBP

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
mouse	LD50	intraperitoneal	2292mg/kg (2292mg/kg)	?	Drugs in Japan Vol. 6, Pg. 832, 1982.
rat	LD50	oral	> 4gm/kg (4000mg/kg)	?	Drugs in Japan Vol. 6, Pg. 832, 1982.
women	TDLo	intravenous	20mg/kg/45M-C (20mg/kg)	CARDIAC: ARRHYTHMIAS (INCLUDING CHANGES IN CONDUCTION)	Journal of Rheumatology. Vol. 13, Pg. 477, 1986.
women	TDLo	intravenous	60mg/kg/3D-I (60mg/kg)	CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION	Annals of Internal Medicine. Vol. 99, Pg. 282, 1983.
women	TDLo	parenteral	2400ug/kg (2.4mg/kg)	CARDIAC: CHANGE IN RATE LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION	British Journal of Anesthesia. Vol. 69, Pg. 422, 1992.

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4.9 Toxicity

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)

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5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Reproductive toxicity, Category 1A

Specific target organ toxicity \u2013 repeated exposure, Category 2

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Danger
Hazard statement(s)	H373 May cause damage to organs through prolonged or repeated exposure
Precautionary statement(s)
Prevention	P201 Obtain special instructions before use. P202 Do not handle until all safety precautions have been read and understood. P280 Wear protective gloves/protective clothing/eye protection/face protection. P260 Do not breathe dust/fume/gas/mist/vapours/spray.
Response	P308+P313 IF exposed or concerned: Get medical advice/ attention. P314 Get medical advice/attention if you feel unwell.
Storage	P405 Store locked up.
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

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6. NMR Spectrum

13C NMR : Predict

1H NMR : Predict

Mass spectrum (electron ionization)

7. Synthesis Route

83-43-2Total: 2 Synthesis Route

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83-43-2 221 Suppliers

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Literatures:
Anderson; Conradi; Lambert Journal of Pharmaceutical Sciences, 1984 , vol. 73, # 5 p. 604 - 610
Yield: null

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83-43-2 221 Suppliers

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Literatures:
Anderson; Conradi; Lambert Journal of Pharmaceutical Sciences, 1984 , vol. 73, # 5 p. 604 - 610
Yield: null

8. Other Information

8.0 Merck: 14,6111

8.1 BRN: 2340300

8.2 Target: Value

8.3 Chemical Properties: White to Off-White Crystalline Powder

8.4 Originator: Medrol,Upjohn,US,1957

8.5 Uses: A glucocorticoid which displays anti-inflamatory and antioxidant properties and attenuates apoptosis in oligodendrocytes after injury. 6α-Methyl Prednisolone is neuroprotective.

8.6 Uses: A glucocorticoid

8.7 Definition: ChEBI: The 6alpha-stereoisomer of 6-methylprednisolone.

8.8 Manufacturing Process: The following process description is taken from US Patent 2,897,218. Six 100- ml portions of a medium in 250-ml Erlenmeyer flasks containing 1% glucose, 2% corn steep liquor (60% solids) and tap water was adjusted to a pH of 4.9. This medium was sterilized for 45 minutes at 15 psi pressure and inoculated with a one to two day growth of Septomyxa affinis ATCC 6737. The Erlenmeyer flasks were shaken at room temperature at about 24°C for a period of 3 days.
At the end of this period, this 600-ml volume was used as an inoculum for ten liters of the same glucose-corn steep liquor medium which in addition contained 10 ml of an antifoam (a mixture of lard oil and octadecanol). The fermentor was placed into the water bath, adjusted to 28°C, and the contents stirred (300 rpm) and aerated (0.5 liter air/10 liters beer). After 17 hours of incubation, when a good growth developed and the acidity rose to pH 6.7, 2 g of 6α-methylhydrocortisone plus 1 g of 3-ketobisnor-4-cholen-22-al, dissolved in 115 ml of dimethylformamide, was added and the incubation (conversion) carried out at the same temperature and aeration for 24 hours (final pH 7.9).
The mycelium (56 g dry weight) was filtered off and the steroidal material was extracted with methylene chloride, the methylene extracts evaporated to dryness, and the resulting residue chromatographed over a Florisil column. The column was packed with 200 g of Florisil and was developed with five 400-ml fractions each of methylene chloride, Skellysolve B-acetone mixtures of 9:1, 8:2, 7:3, 1:1, and methanol. The fraction eluted with Skellysolve Bacetone (7:3) weighed 1.545 g and on recrystallization from acetone gave, in three crops, 928 mg of product of MP 210° to 235°C. The sample prepared for analysis melted at 245° to 247°C.

8.9 Brand name: Medrol (Pharmacia & Upjohn).

8.10 Therapeutic Function: Glucocorticoid

8.11 General Description: Methylprednisolone, 11β,17,21-trihydroxy-6α-methyl-1,4-pregnadiene-3,20-dione, isavailable unmodified or as ester derivatives.
Methylprednisolone acetate, USP
Methylprednisolone sodium succinate, USP.

8.12 Mechanism of action: Methylprednisolone is an analog of prednisolone that exhibits a more prolonged effect than prednisolone and cortisone; it has practically no mineralocorticosteroid activity and is better tolerated.

8.13 Clinical Use: Adding a 6α-methyl group to prednisolone increases the glucocorticoid activity and effectively abolishes mineralocorticoid action. It has fivefold the glucocorticoid activity of hydrocortisone (prednisolone has fourfold the glucocorticoid activity) and none of its mineralocorticoid properties. It is used almost exclusively as a systemic product and is available as the free alcohol for oral administration and as various esters.

8.14 Safety Profile: Moderately toxic by intraperitoneal route. A steroid hormone. Human systemic effects include arrhythmias, blood pressure lowering, heart rate changes, increased body temperature, pulse rate increase, respiratory depression. When heated to decomposition it emits acrid smoke and irritating fumes.

8.15 Chemical Synthesis: Methylprednisolone, 11β,17α,21-trihydroxy-6α-methylpregna-1, 4-dien-3,20-dione (27.1.38), differs from prednisolone in the presence of a methyl group at position C6 of the steroid skeleton of the molecule. This seemingly simple difference in structure requires a different approach to synthesis. It is synthesized from hydrocortisone (27.1.8), the carbonyl group of which initially undergoes ketalization by ethylene glycol in the presence of traces of acid, during which the double bond at position C4– C5 is shifted to position C5– C6, giving the diethyleneketal 27.1.34. The product is oxidized to an epoxide (27.1.35) using perbenzoic acid. Next, the resulting epoxide is reacted with methylmagnesium bromide, and subsequent removal of the ketal protection by hydrogen reduction gives the 5-hydroxy-6-methyl derivative of dihydrocortisone 27.1.36. The resulting β-hydroxyketone is dehydrated using an alkaline, and then the resulting 6α-methylcortisone (27.1.37) undergoes microbiological dehydration at position C1–C2, giving the desired methylprednisolone (27.1.38).

8.16 Purification Methods: Recrystallise medrol from EtOAc. The UV has max at in 95% EtOH 243nm ( 14,875). The 21-acetoxy derivative has m 205-208o (from EtOAc), and [] D +95o ( c 1, CHCl3). [Spero et al. J Am Chem Soc 78 6213 1956; Fried et al. J Am Chem Soc 81 1235 1959; 1H NMR: Slomp & McGarvey J Am Chem Soc 81 2200 1959, Beilstein 8 IV 3498.]

9. Computational chemical data

Molecular Weight: 374.47100g/mol
Molecular Formula: C₂₂H₃₀O₅
Compound Is Canonicalized: True
XLogP3-AA: null
Exact Mass: 374.20932405
Monoisotopic Mass: 374.20932405
Complexity: 754
Rotatable Bond Count: 2
Hydrogen Bond Donor Count: 3
Hydrogen Bond Acceptor Count: 5
Topological Polar Surface Area: 94.8
Heavy Atom Count: 27
Defined Atom Stereocenter Count: 8
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADceB4OAAAAAAAAAAAAAAAAAAAAYAAAAAwYIAAAAAAAGDAAAAAGgAACAAAD1SggAICAAAAAgCIAqBSAAIAAAAgAAAICAFAAEgAEBIAAQAAQAAFgAAIAYPIzPDPgAAAAAAAAADAAAYAADAAAYAADAAAAA==

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