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CAS No.: | 83-43-2 |
---|---|
Name: | Methylprednisolone |
Article Data: | 19 |
Molecular Structure: | |
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 |
Conditions | Yield |
---|---|
Hydrolysis; | |
With potassium hydroxide In methanol; dichloromethane at 10 - 15℃; for 0.333333h; Inert atmosphere; |
(20Ξ)-11β-hydroxy-6α-methyl-17,20;20,21-bis-methylenedioxy-pregna-1,4-dien-3-one
Methylprednisolone
Conditions | Yield |
---|---|
With formic acid |
methylprednisolone acetate
A
Methylprednisolone
B
17α-acetoxy-11β,21-dihydroxy-6α-methyl-1,4-pregnadiene-3,20-dione
Conditions | Yield |
---|---|
With aq. buffer In N,N-dimethyl-formamide at 25℃; Rate constant; Mechanism; pH dependence; |
17α-acetoxy-11β,21-dihydroxy-6α-methyl-1,4-pregnadiene-3,20-dione
A
Methylprednisolone
B
methylprednisolone acetate
Conditions | Yield |
---|---|
With aq. buffer In N,N-dimethyl-formamide at 25℃; Rate constant; Mechanism; pH dependence; |
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; |
6α-methylprednisolone-21-hydrogen succinate
A
Methylprednisolone
B
6α-methylprednisolone 17-hemisuccinate
Conditions | Yield |
---|---|
With aq. buffer In N,N-dimethyl-formamide at 25℃; Rate constant; Mechanism; pH dependence; |
6α-methylprednisolone 17-hemisuccinate
A
Methylprednisolone
B
6α-methylprednisolone-21-hydrogen succinate
Conditions | Yield |
---|---|
With aq. buffer In N,N-dimethyl-formamide at 25℃; Rate constant; Mechanism; pH dependence; |
6α-methylprednisolone 21-hemiadipate
Methylprednisolone
Conditions | Yield |
---|---|
With water In acetonitrile at 25℃; Rate constant; |
6α-methylprednisolone 21-hemisuberate
Methylprednisolone
Conditions | Yield |
---|---|
With water In acetonitrile at 25℃; Rate constant; |
17,21-dihydroxy-pregn-4-ene-3,11,20-trione
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 |
Reported in EPA TSCA Inventory.
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 |