Name: Methylprednisolone
SKU: 83-43-2

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Basic Information

Molecular Structure:
CAS No.:	83-43-2
Name:	Methylprednisolone

Formula:	C₂₂H₃₀O₅
Molecular Weight:	374.477
Synonyms:	Pregna-1,4-diene-3,20-dione,11b,17,21-trihydroxy-6a-methyl- (7CI,8CI);11b,17,21-Trihydroxy-6a-methylpregna-1,4-diene-3,20-dione;6a-Methyl-11b,17a,21b-trihydroxy-1,4-pregnadiene-3,20-dione;6a-Methylprednisolone;Besonia;Duralone;M-Prednisol;Medorol;Medralone;Medrol;Metastab;Metilbetasone;Metrisone;NSC 19987;Prednol;Promacortine;Suprametil;Urbason;Urbasone;Wyacort;Methylphenisolone;
EINECS:	201-476-4
Density:	1.28 g/cm³
Melting Point:	228-237 °C (dec.)
Boiling Point:	571.8 °C at 760 mmHg
Flash Point:	313.7 °C
Solubility:	0.12g/L(25 oC)
Appearance:	White to off-white crystalline powder
Hazard Symbols:	Xi
Risk Codes:	36/37/38
Safety:	22-36-26
PSA:	94.83000
LogP:	1.80360

Synthetic route

: 53-36-1
methylprednisolone acetate

: 83-43-2
Methylprednisolone

Conditions

Conditions	Yield
Hydrolysis;
With potassium hydroxide In methanol; dichloromethane at 10 - 15℃; for 0.333333h; Inert atmosphere;

: 117888-35-4
(20Ξ)-11β-hydroxy-6α-methyl-17,20;20,21-bis-methylenedioxy-pregna-1,4-dien-3-one

: 83-43-2
Methylprednisolone

Conditions

Conditions	Yield
With formic acid

: 53-36-1
methylprednisolone acetate

A: 83-43-2
Methylprednisolone

B: 86401-94-7
17α-acetoxy-11β,21-dihydroxy-6α-methyl-1,4-pregnadiene-3,20-dione

Conditions

Conditions	Yield
With aq. buffer In N,N-dimethyl-formamide at 25℃; Rate constant; Mechanism; pH dependence;

: 86401-94-7
17α-acetoxy-11β,21-dihydroxy-6α-methyl-1,4-pregnadiene-3,20-dione

A: 83-43-2
Methylprednisolone

B: 53-36-1
methylprednisolone acetate

Conditions

Conditions	Yield
With aq. buffer In N,N-dimethyl-formamide at 25℃; Rate constant; Mechanism; pH dependence;

: 2921-57-5
6α-methylprednisolone-21-hydrogen succinate

: 83-43-2
Methylprednisolone

Conditions

Conditions	Yield
With tetramethyl ammoniumhydroxide; tetrazolium blue In ethanol Rate constant; Ambient temperature; reaction of corticosteroids and their hemisuccinate esters with blue tetrazolium under USP assay conditions, hydrolysis of esters, effect of water content, kinetic study by HPLC;
With water In acetonitrile at 25℃; Rate constant;
In water at 25℃; Rate constant; rate constants for hydrolysis;

: 2921-57-5
6α-methylprednisolone-21-hydrogen succinate

A: 83-43-2
Methylprednisolone

B: 77074-42-1
6α-methylprednisolone 17-hemisuccinate

Conditions

Conditions	Yield
With aq. buffer In N,N-dimethyl-formamide at 25℃; Rate constant; Mechanism; pH dependence;

: 77074-42-1
6α-methylprednisolone 17-hemisuccinate

A: 83-43-2
Methylprednisolone

B: 2921-57-5
6α-methylprednisolone-21-hydrogen succinate

Conditions

Conditions	Yield
With aq. buffer In N,N-dimethyl-formamide at 25℃; Rate constant; Mechanism; pH dependence;

: 85847-50-3
6α-methylprednisolone 21-hemiadipate

: 83-43-2
Methylprednisolone

Conditions

Conditions	Yield
With water In acetonitrile at 25℃; Rate constant;

: 85847-51-4
6α-methylprednisolone 21-hemisuberate

: 83-43-2
Methylprednisolone

Conditions

Conditions	Yield
With water In acetonitrile at 25℃; Rate constant;

: 53-06-5, 10007-36-0, 15779-07-4, 35446-72-1, 104713-00-0
17,21-dihydroxy-pregn-4-ene-3,11,20-trione

: 83-43-2
Methylprednisolone

Conditions

Yield

Multi-step reaction with 9 steps
1: aqueous hydrochloric acid; chloroform
2: benzene; toluene-4-sulfonic acid
3: peroxybenzoic acid; benzene / Behandeln unter Ausschluss von Licht, Behandeln des Reaktionsprodukts mit Ameisensaeure und Erwaermen des danach isolierten Reaktionsprodukts mit wss.-methanol. Kalilauge
4: toluene-4-sulfonic acid
5: benzene; diethyl ether
6: pyridine; thionyl chloride / Erwaermen des Reaktionsprodukts mit Lithiumalanat in Aether und Benzol
7: acetone; toluene-4-sulfonic acid
8: acetic acid; tert-butyl alcohol; selenium dioxide
9: aqueous formic acid
View Scheme

Raw Materials

3386-04-7

77074-42-1

2921-57-5

53-06-5

53-36-1

Downstream Products

1625-39-4

359-80-8

53-36-1

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Consensus Reports

Reported in EPA TSCA Inventory.

Specification

1. Introduction of Methylprednisolone
Methylprednisolone is one kind of white to off-white crystalline powder. 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 belongs to the classes of Miscellaneous Biochemicals; Biochemistry; Hydroxyketosteroids; Steroids; Intermediates & Fine Chemicals; Pharmaceuticals. It is sparingly soluble in alcohol, in dioxane, and in methanol, slightly soluble in acetone, and in chloroform, and very slightly soluble in ether. It is practically insoluble in water.

The Classification Code of this chemical is Adrenal Cortex Hormones; Anti-Inflammatory Agents; Anti-inflammatory; Antiemetics; Autonomic Agents; Central Nervous System Agents; Drug / Therapeutic Agent; Gastrointestinal Agents; Glucocorticoid; Glucocorticoids; Hormones; Hormones, Hormone Substitutes, and Hormone Antagonists; Human Data; Immunosuppressant; Neuroprotective agents; Peripheral Nervous System Agents; Protective Agents.

2. Properties of Methylprednisolone
Physical properties about Methylprednisolone 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 Å²; (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.

3. Structure Descriptors of Methylprednisolone
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
(4)Canonical SMILES : CC1CC2C3CCC(C3(CC(C2C4(C1=CC(=O)C=C4)C)O)C)(C(=O)CO)O
(5)Isomeric 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

4. Toxicity of Methylprednisolone
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.

5. Physical Properties of Methylprednisolone

Physical Property	Value	Units	Temp (deg C)	Source
Melting Point	232.5	deg C		EXP
log P (octanol-water)	1.820	(none)		EST
Water Solubility	120	mg/L	25	EXP
Atmospheric OH Rate Constant	7.39E-11	cm3/molecule-sec	25	EST

6. 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. It can be used for Bio-Research.

7. Safety information of Methylprednisolone
Hazard Codes:

Xi
Risk Statements: 36/37/38
36/37/38: Irritating to eyes, respiratory system and skin.
Safety Statements: 22-36-26
22: Do not breathe dust.
36: Wear suitable protective clothing.
26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
WGK Germany: 2
RTECS: TU4146000
F: 8-10-23
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.

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Consensus Reports

Specification