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83-43-2

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83-43-2 Usage

Chemical Properties

White to Off-White Crystalline Powder

Originator

Medrol,Upjohn,US,1957

Uses

Different sources of media describe the Uses of 83-43-2 differently. You can refer to the following data:
1. A glucocorticoid which displays anti-inflamatory and antioxidant properties and attenuates apoptosis in oligodendrocytes after injury. 6α-Methyl Prednisolone is neuroprotective.
2. A glucocorticoid

Definition

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

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.

Therapeutic Function

Glucocorticoid

General Description

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

Biological Activity

methylprednisolone is a synthetic glucocorticoid receptor agonist, used to achieve prompt suppression of inflammation.cllinical trials: in patients with acute spinal cord injury diagnosed in national acute spinal cord injury study (nascis) centers within 8 hours of injury, methylprednisolone treatment for 48 hours improved motor recovery at 6 weeks (p= 0.09) and 6 months (p= 0.07) after injury[6]. in patients with acute spinal-cord injury, methylprednisolone (30 mg/kg) followed by infusion at 5.4 mg/kg/hour for 23 hours improved neurologic recovery. among patients treated with methylprednisolone (30 mg/kg), mortality at 14 days was significantly increasedsecondary infection[7]. methylprednisolone has entered

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.

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.

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.

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).

in vitro

methylprednisolone (2-10 mg/kg) significantly inhibited tnf production. high doses of methylprednisolone (50 mg/kg) increased lps-induced il-10 levels. methylprednisolone (0.01-100 μg/ml) increased the biosynthesis of il-10 in lps-activated mouse peritoneal macrophages [1]. in wg patients and controls, methylprednisolone (mp) down-regulated the spontaneous and the staphylococcal enterotoxin b (seb)-induced release of chemokines from peripheral blood mononuclear cells (pbmc)[2]. treatment with 0.25 mm methylprednisolone inhibited acantholysis in skin cultures directly [3].

in vivo

methylprednisolone (30 mg/kg, i.v.) given immediately after sci reduced tnf-α expression by 55% (p<0.01) and nf-kb binding activity. methylprednisolone suppressed the post-traumatic inflammatory activity caused by tnf-alpha-nf-kb cascade[4]. intravenously administration of mp (30 mg/kg) reduced the number of ed1-positive cells by 82% in the rostral cord stump and 66% in the caudal stump. in the adult rat, mp administration shortly after spinal cord transection resulted in a long-term reduction of ed1-positive cells and spinal tissue loss, reduced dieback of vestibule spinal fibres, and a transient sprouting of vestibule spinal fibres near the lesion at 1 and 2 weeks post-lesion. mp treatment also significantly reduced the tissue loss in both cord stumps at 2, 4 and 8 week post-injury[5].

Drug interactions

Metabolism in the liver occurs primarily via the CYP3A4 enzyme to inactive metabolites, which are excreted in the urine Aldesleukin: avoid concomitant use. Antibacterials: metabolism accelerated by rifampicin; metabolism inhibited by erythromycin and possibly clarithromycin; concentration of isoniazid possibly reduced. Anticoagulants: efficacy of coumarins and phenindione may be altered. Antiepileptics: metabolism accelerated by carbamazepine, fosphenytoin, phenobarbital, phenytoin and primidone. Antifungals: increased risk of hypokalaemia with amphotericin - avoid; metabolism inhibited by ketoconazole and possibly itraconazole. Antivirals: concentration possibly increased by ritonavir. Ciclosporin: rare reports of convulsions in patients on ciclosporin and high-dose corticosteroids; levels of ciclosporin increased with high dose methylprednisolone. Cobicistat: concentration possibly increased by cobicistat. Diuretics: enhanced hypokalaemic effects of acetazolamide, loop diuretics and thiazide diuretics. Vaccines: high dose corticosteroids can impair immune response to vaccines; avoid with live vaccines.

Metabolism

Metabolism in the liver occurs primarily via the CYP3A4 enzyme to inactive metabolites, which are excreted in the urine

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.]

references

[1] marchant a, amraoui z, gueydan c, et al. methylprednisolone differentially regulates il‐10 and tumour necrosis factor (tnf) production during murine endotoxaemia[j]. clinical & experimental immunology, 1996, 106(1): 91-96.[2] torheim e a, yndestad a, bjerkeli v, et al. increased expression of chemokines in patients with wegener's granulomatosis modulating effects of methylprednisolone in vitro[j]. clinical & experimental immunology, 2005, 140(2): 376-383.[3] swanson d l, dahl m v. methylprednisolone inhibits pemphigus acantholysis in skin cultures[j]. journal of investigative dermatology, 1983, 81(3): 258-260.[4] xu j, fan g, chen s, et al. methylprednisolone inhibition of tnf-α expression and nf-kb activation after spinal cord injury in rats[j]. molecular brain research, 1998, 59(2): 135-142.[5] oudega m, vargas c g, weber a b, et al. [j]. european journal of neuroscience, 1999, 11(7): 2453-2464.long‐term effects of methylprednisolone following transection of adult rat spinal cord[6] bracken m b, shepard m j, holford t r, et al. administration of methylprednisolone for 24 or 48 hours or tirilazadmesylate for 48 hours in the treatment of acute spinal cord injury: results of the third national acute spinal cord injury randomized controlled trial[j]. jama, 1997, 277(20): 1597-1604.[7] bracken m b, shepard m j, collins w f, 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[j]. new england journal of medicine, 1990, 322(20): 1405-1411.

Check Digit Verification of cas no

The CAS Registry Mumber 83-43-2 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 8 and 3 respectively; the second part has 2 digits, 4 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 83-43:
(4*8)+(3*3)+(2*4)+(1*3)=52
52 % 10 = 2
So 83-43-2 is a valid CAS Registry Number.
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

83-43-2 Well-known Company Product Price

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  • (M1750000)  Methylprednisolone  European Pharmacopoeia (EP) Reference Standard

  • 83-43-2

  • M1750000

  • 1,880.19CNY

  • Detail
  • Sigma-Aldrich

  • (Y0001799)  MethylprednisoloneforsystemsuitabilityA  EuropePharmacopoeia (EP) Reference Standard

  • 83-43-2

  • Y0001799

  • 1,880.19CNY

  • Detail

83-43-2SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 13, 2017

Revision Date: Aug 13, 2017

1.Identification

1.1 GHS Product identifier

Product name 6α-methylprednisolone

1.2 Other means of identification

Product number -
Other names (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

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:83-43-2 SDS

83-43-2Synthetic route

methylprednisolone acetate
53-36-1

methylprednisolone acetate

Methylprednisolone
83-43-2

Methylprednisolone

Conditions
ConditionsYield
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
117888-35-4

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

Methylprednisolone
83-43-2

Methylprednisolone

Conditions
ConditionsYield
With formic acid
methylprednisolone acetate
53-36-1

methylprednisolone acetate

A

Methylprednisolone
83-43-2

Methylprednisolone

B

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

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

Conditions
ConditionsYield
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
86401-94-7

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

A

Methylprednisolone
83-43-2

Methylprednisolone

B

methylprednisolone acetate
53-36-1

methylprednisolone acetate

Conditions
ConditionsYield
With aq. buffer In N,N-dimethyl-formamide at 25℃; Rate constant; Mechanism; pH dependence;
6α-methylprednisolone-21-hydrogen succinate
2921-57-5

6α-methylprednisolone-21-hydrogen succinate

Methylprednisolone
83-43-2

Methylprednisolone

Conditions
ConditionsYield
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
2921-57-5

6α-methylprednisolone-21-hydrogen succinate

A

Methylprednisolone
83-43-2

Methylprednisolone

B

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

6α-methylprednisolone 17-hemisuccinate

Conditions
ConditionsYield
With aq. buffer In N,N-dimethyl-formamide at 25℃; Rate constant; Mechanism; pH dependence;
6α-methylprednisolone 17-hemisuccinate
77074-42-1

6α-methylprednisolone 17-hemisuccinate

A

Methylprednisolone
83-43-2

Methylprednisolone

B

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

6α-methylprednisolone-21-hydrogen succinate

Conditions
ConditionsYield
With aq. buffer In N,N-dimethyl-formamide at 25℃; Rate constant; Mechanism; pH dependence;
6α-methylprednisolone 21-hemiadipate
85847-50-3

6α-methylprednisolone 21-hemiadipate

Methylprednisolone
83-43-2

Methylprednisolone

Conditions
ConditionsYield
With water In acetonitrile at 25℃; Rate constant;
6α-methylprednisolone 21-hemisuberate
85847-51-4

6α-methylprednisolone 21-hemisuberate

Methylprednisolone
83-43-2

Methylprednisolone

Conditions
ConditionsYield
With water In acetonitrile at 25℃; Rate constant;
17,21-dihydroxy-pregn-4-ene-3,11,20-trione
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

Methylprednisolone
83-43-2

Methylprednisolone

Conditions
ConditionsYield
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
11β,21-dihydroxy-6α-methyl-pregna-4,17(20)c-dien-3-one
3386-04-7, 14423-17-7

11β,21-dihydroxy-6α-methyl-pregna-4,17(20)c-dien-3-one

Methylprednisolone
83-43-2

Methylprednisolone

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: Dehydrierung durch Septomyxa affinis und anschliessende Acetylierung
2: diacetoxy-phenyl-iodan; OsO4; tert-butyl alcohol / Reagens 4: Pyridin
3: Hydrolysis
View Scheme
21-acetoxy-11β-hydroxy-6α-methyl-pregna-1,4,17(20)c-trien-3-one
1968-76-9

21-acetoxy-11β-hydroxy-6α-methyl-pregna-1,4,17(20)c-trien-3-one

Methylprednisolone
83-43-2

Methylprednisolone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: diacetoxy-phenyl-iodan; OsO4; tert-butyl alcohol / Reagens 4: Pyridin
2: Hydrolysis
View Scheme
(20Ξ)-11β-hydroxy-6α-methyl-17,20;20,21-bis-methylenedioxy-pregn-4-en-3-one
123292-91-1

(20Ξ)-11β-hydroxy-6α-methyl-17,20;20,21-bis-methylenedioxy-pregn-4-en-3-one

Methylprednisolone
83-43-2

Methylprednisolone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: acetic acid; tert-butyl alcohol; selenium dioxide
2: aqueous formic acid
View Scheme
17α,20;20,21-bismethylenedioxypregn-4-ene-3,11-dione
3607-68-9

17α,20;20,21-bismethylenedioxypregn-4-ene-3,11-dione

Methylprednisolone
83-43-2

Methylprednisolone

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1: benzene; toluene-4-sulfonic acid
2: peroxybenzoic acid; benzene / Behandeln unter Ausschluss von Licht, Behandeln des Reaktionsprodukts mit Ameisensaeure und Erwaermen des danach isolierten Reaktionsprodukts mit wss.-methanol. Kalilauge
3: toluene-4-sulfonic acid
4: benzene; diethyl ether
5: pyridine; thionyl chloride / Erwaermen des Reaktionsprodukts mit Lithiumalanat in Aether und Benzol
6: acetone; toluene-4-sulfonic acid
7: acetic acid; tert-butyl alcohol; selenium dioxide
8: aqueous formic acid
View Scheme
(20Ξ)-17,20;20,21-bis-methylenedioxy-5α-pregnane-3,6,11-trione
55701-21-8

(20Ξ)-17,20;20,21-bis-methylenedioxy-5α-pregnane-3,6,11-trione

Methylprednisolone
83-43-2

Methylprednisolone

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: toluene-4-sulfonic acid
2: benzene; diethyl ether
3: pyridine; thionyl chloride / Erwaermen des Reaktionsprodukts mit Lithiumalanat in Aether und Benzol
4: acetone; toluene-4-sulfonic acid
5: acetic acid; tert-butyl alcohol; selenium dioxide
6: aqueous formic acid
View Scheme
(20Ξ)-3,3-ethanediyldioxy-6-methyl-17,20;20,21-bis-methylenedioxy-pregn-5-en-11β-ol

(20Ξ)-3,3-ethanediyldioxy-6-methyl-17,20;20,21-bis-methylenedioxy-pregn-5-en-11β-ol

Methylprednisolone
83-43-2

Methylprednisolone

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: acetone; toluene-4-sulfonic acid
2: acetic acid; tert-butyl alcohol; selenium dioxide
3: aqueous formic acid
View Scheme
6-methyl-11-oxo-3-pyrrolidino-pregna-3,5,17(20)c-trien-21-oic acid methyl ester
1968-77-0

6-methyl-11-oxo-3-pyrrolidino-pregna-3,5,17(20)c-trien-21-oic acid methyl ester

Methylprednisolone
83-43-2

Methylprednisolone

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: LiAlH4; diethyl ether / Behandeln des Reaktionsprodukts mit wss.-methanol.Alkalilauge
2: Dehydrierung durch Septomyxa affinis und anschliessende Acetylierung
3: diacetoxy-phenyl-iodan; OsO4; tert-butyl alcohol / Reagens 4: Pyridin
4: Hydrolysis
View Scheme
(8′S,9′S,10′R,13′S,14′S,17′R)-10′,13′-dimethyl-1′,2′,4′,7′,8′,9′,10′,12′,13′,14′,15′,16′-dodecahydro-11′H-trispiro[[1,3]dioxolane-2,3′-cyclopenta[a]phenanthrene-17′,4''-[1,3]dioxolane-5'',4'''-[1,3]dioxolan]-11′-one
52248-40-5

(8′S,9′S,10′R,13′S,14′S,17′R)-10′,13′-dimethyl-1′,2′,4′,7′,8′,9′,10′,12′,13′,14′,15′,16′-dodecahydro-11′H-trispiro[[1,3]dioxolane-2,3′-cyclopenta[a]phenanthrene-17′,4''-[1,3]dioxolane-5'',4'''-[1,3]dioxolan]-11′-one

Methylprednisolone
83-43-2

Methylprednisolone

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: peroxybenzoic acid; benzene / Behandeln unter Ausschluss von Licht, Behandeln des Reaktionsprodukts mit Ameisensaeure und Erwaermen des danach isolierten Reaktionsprodukts mit wss.-methanol. Kalilauge
2: toluene-4-sulfonic acid
3: benzene; diethyl ether
4: pyridine; thionyl chloride / Erwaermen des Reaktionsprodukts mit Lithiumalanat in Aether und Benzol
5: acetone; toluene-4-sulfonic acid
6: acetic acid; tert-butyl alcohol; selenium dioxide
7: aqueous formic acid
View Scheme
(20Ξ)-3,3-ethanediyldioxy-6β-hydroxy-6α-methyl-17,20;20,21-bis-methylenedioxy-5α-pregnan-11-one
123885-50-7

(20Ξ)-3,3-ethanediyldioxy-6β-hydroxy-6α-methyl-17,20;20,21-bis-methylenedioxy-5α-pregnan-11-one

Methylprednisolone
83-43-2

Methylprednisolone

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: pyridine; thionyl chloride / Erwaermen des Reaktionsprodukts mit Lithiumalanat in Aether und Benzol
2: acetone; toluene-4-sulfonic acid
3: acetic acid; tert-butyl alcohol; selenium dioxide
4: aqueous formic acid
View Scheme
(20Ξ)-3,3-ethanediyldioxy-17,20;20,21-bis-methylenedioxy-5α-pregnane-6,11-dione
107157-45-9

(20Ξ)-3,3-ethanediyldioxy-17,20;20,21-bis-methylenedioxy-5α-pregnane-6,11-dione

Methylprednisolone
83-43-2

Methylprednisolone

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: benzene; diethyl ether
2: pyridine; thionyl chloride / Erwaermen des Reaktionsprodukts mit Lithiumalanat in Aether und Benzol
3: acetone; toluene-4-sulfonic acid
4: acetic acid; tert-butyl alcohol; selenium dioxide
5: aqueous formic acid
View Scheme
HYCp45

HYCp45

A

C16H27NO11

C16H27NO11

B

Methylprednisolone
83-43-2

Methylprednisolone

Conditions
ConditionsYield
With sodium hydroxide In water-d2 at 37℃; pH=7.0;
C26H42O6

C26H42O6

Methylprednisolone
83-43-2

Methylprednisolone

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: sulfuric acid / tetrahydrofuran / pH 2 - 3
2.1: D-glucose; potassium dihydrogenphosphate / water; methanol / 50 h
3.1: iodine; calcium oxide / methanol; dichloromethane
3.2: 2 h / 45 - 50 °C
4.1: potassium hydroxide / methanol; dichloromethane / 0.33 h / 10 - 15 °C / Inert atmosphere
View Scheme
11β,17-dihydroxy-6α-methyl-pregn-4-ene-3,20-dione
7055-53-0

11β,17-dihydroxy-6α-methyl-pregn-4-ene-3,20-dione

Methylprednisolone
83-43-2

Methylprednisolone

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: D-glucose; potassium dihydrogenphosphate / water; methanol / 50 h
2.1: iodine; calcium oxide / methanol; dichloromethane
2.2: 2 h / 45 - 50 °C
3.1: potassium hydroxide / methanol; dichloromethane / 0.33 h / 10 - 15 °C / Inert atmosphere
View Scheme
17-hydroxy-pregn-4-ene-3,11,20-trione
1882-82-2

17-hydroxy-pregn-4-ene-3,11,20-trione

Methylprednisolone
83-43-2

Methylprednisolone

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1.1: trimethyloxosulfonium bromide; orthoformic acid triethyl ester / 5 h
2.1: sodium tetrahydroborate / tetrahydrofuran / 12 h
3.1: phthalic anhydride; dihydrogen peroxide / ethyl acetate / 6 h
4.1: magnesium / tetrahydrofuran / 4 h
5.1: sulfuric acid / tetrahydrofuran / pH 2 - 3
6.1: D-glucose; potassium dihydrogenphosphate / water; methanol / 50 h
7.1: iodine; calcium oxide / methanol; dichloromethane
7.2: 2 h / 45 - 50 °C
8.1: potassium hydroxide / methanol; dichloromethane / 0.33 h / 10 - 15 °C / Inert atmosphere
View Scheme
3,3;20,20-bis-ethanediyldioxy-17-hydroxy-pregn-5-en-11-one
74332-34-6

3,3;20,20-bis-ethanediyldioxy-17-hydroxy-pregn-5-en-11-one

Methylprednisolone
83-43-2

Methylprednisolone

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: sodium tetrahydroborate / tetrahydrofuran / 12 h
2.1: phthalic anhydride; dihydrogen peroxide / ethyl acetate / 6 h
3.1: magnesium / tetrahydrofuran / 4 h
4.1: sulfuric acid / tetrahydrofuran / pH 2 - 3
5.1: D-glucose; potassium dihydrogenphosphate / water; methanol / 50 h
6.1: iodine; calcium oxide / methanol; dichloromethane
6.2: 2 h / 45 - 50 °C
7.1: potassium hydroxide / methanol; dichloromethane / 0.33 h / 10 - 15 °C / Inert atmosphere
View Scheme
3,3;20,20-bis-ethanediyldioxy-pregn-5-ene-11β,17-diol
41870-77-3

3,3;20,20-bis-ethanediyldioxy-pregn-5-ene-11β,17-diol

Methylprednisolone
83-43-2

Methylprednisolone

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: phthalic anhydride; dihydrogen peroxide / ethyl acetate / 6 h
2.1: magnesium / tetrahydrofuran / 4 h
3.1: sulfuric acid / tetrahydrofuran / pH 2 - 3
4.1: D-glucose; potassium dihydrogenphosphate / water; methanol / 50 h
5.1: iodine; calcium oxide / methanol; dichloromethane
5.2: 2 h / 45 - 50 °C
6.1: potassium hydroxide / methanol; dichloromethane / 0.33 h / 10 - 15 °C / Inert atmosphere
View Scheme
C25H38O7

C25H38O7

Methylprednisolone
83-43-2

Methylprednisolone

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: magnesium / tetrahydrofuran / 4 h
2.1: sulfuric acid / tetrahydrofuran / pH 2 - 3
3.1: D-glucose; potassium dihydrogenphosphate / water; methanol / 50 h
4.1: iodine; calcium oxide / methanol; dichloromethane
4.2: 2 h / 45 - 50 °C
5.1: potassium hydroxide / methanol; dichloromethane / 0.33 h / 10 - 15 °C / Inert atmosphere
View Scheme
Methylprednisolone
83-43-2

Methylprednisolone

methanesulfonyl chloride
124-63-0

methanesulfonyl chloride

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 methanesulfonate
51474-81-8

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 methanesulfonate

Conditions
ConditionsYield
With pyridine at 0 - 10℃;95%
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃;81%
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃;
ethyl orthoacetate
58924-88-2

ethyl orthoacetate

Methylprednisolone
83-43-2

Methylprednisolone

A

6α-methylprednisolone 17α,21-ethyl orthoacetate

6α-methylprednisolone 17α,21-ethyl orthoacetate

B

17α,21-diacetoxy-11β-hydroxy-6α-methyl-1,4-pregnadiene-3,20-dione
86413-24-3

17α,21-diacetoxy-11β-hydroxy-6α-methyl-1,4-pregnadiene-3,20-dione

Conditions
ConditionsYield
With sodium carbonate; toluene-4-sulfonic acid In N-methyl-acetamide; water; ethyl acetateA 92.5%
B n/a
methyl orthovalerate
856317-97-0

methyl orthovalerate

Methylprednisolone
83-43-2

Methylprednisolone

A

6α-methylprednisolone 17α,21-methyl orthovalerate

6α-methylprednisolone 17α,21-methyl orthovalerate

B

11β,21-dihydroxy-6α-methyl-17α-valeroyloxy-1,4-pregnadiene-3,20-dione
86413-38-9

11β,21-dihydroxy-6α-methyl-17α-valeroyloxy-1,4-pregnadiene-3,20-dione

Conditions
ConditionsYield
With sodium carbonate; toluene-4-sulfonic acid In N-methyl-acetamide; water; ethyl acetateA n/a
B 91.7%
methyl orthoisovalerate

methyl orthoisovalerate

Methylprednisolone
83-43-2

Methylprednisolone

A

6α-methylprednisolone 17α,21-methyl orthoisovalerate

6α-methylprednisolone 17α,21-methyl orthoisovalerate

B

11β,21-dihydroxy-17α-isovaleryloxy-6α-methyl-1,4-pregnadiene-3,20-dione
86413-32-3

11β,21-dihydroxy-17α-isovaleryloxy-6α-methyl-1,4-pregnadiene-3,20-dione

Conditions
ConditionsYield
With sodium carbonate; toluene-4-sulfonic acid In N-methyl-acetamide; water; ethyl acetateA 82.8%
B n/a
3-sulfopropanoic acid
44826-45-1

3-sulfopropanoic acid

Methylprednisolone
83-43-2

Methylprednisolone

21-<<3-sulfo-1-oxopropyl>oxy>-11β,17-dihydroxy-6α-methylpregna-1,4-diene-3,20-dione

21-<<3-sulfo-1-oxopropyl>oxy>-11β,17-dihydroxy-6α-methylpregna-1,4-diene-3,20-dione

Conditions
ConditionsYield
With pyridine; dicyclohexyl-carbodiimide for 16h;70%
Methylprednisolone
83-43-2

Methylprednisolone

17α,21-dihydroxy-6α-methylpregna-1,4-diene-3,11,20-trione
111264-84-7, 91523-05-6

17α,21-dihydroxy-6α-methylpregna-1,4-diene-3,11,20-trione

Conditions
ConditionsYield
With pyridine; N-bromoacetamide
Methylprednisolone
83-43-2

Methylprednisolone

11β,17α-dihydroxy-6α-methyl-1,4-pregnadiene-3,20-dione
6870-94-6

11β,17α-dihydroxy-6α-methyl-1,4-pregnadiene-3,20-dione

Conditions
ConditionsYield
ueber mehrere Stufen;

83-43-2Relevant articles and documents

Kinetics of drug release from a hyaluronan-steroid conjugate investigated by NMR spectroscopy

Taglienti, Anna,Sequi, Paolo,Valentini, Massimiliano

, p. 245 - 249 (2009)

The methylprednisolone steroid ester of hyaluronan was hydrolyzed under physiological conditions in vitro, and the kinetics of drug release was investigated by NMR spectroscopy. Transverse relaxation times are correlated with the molecular rotational free

Method for reducing or preventing transplant rejection in the eye and intraocular implants for use therefor

-

, (2008/06/13)

Methods for reducing or preventing transplant rejection in the eye of an individual are described, comprising: a) performing an ocular transplant procedure; and b) implanting in the eye a bioerodible drug delivery system comprising an immunosuppressive agent and a bioerodible polymer.

High molecular weight prodrug derivatives of antiinflammatory drugs

-

, (2008/06/13)

Compounds of the formula 1, PS - O - A - (CH2)n- B - D (1), wherein PS-O represents an alkoxide residue of any of the free hydroxy groups of a polysaccharide (PS-OH) compound with molecular weight (Mw) of from 40,000 to 5,000,000 selected from dextran, carboxymethyl dextran, diethylaminoethyl dextran, starch, hydroxyet-hyl starch, alginates, glycogen, pullullan, agarose, cellulose, chitosan, chitin and carrageenan,A is a carbonyl group or absent,n is zero or a positive integer from 1 to 14,B is oxygen, a carbonyl group, NR wherein R is hydrogen or lower alkyl, or B is absent, and, D is (i) a group of the formula:, R1 - CO - (11), wherein R1-CO- represents the acyl residue of a carboxylic acid drug (R1-COOH) used in the treatment of inflammatory disorders; or (ii) a group of the formula:, R2 - O - (12), wherein R2-O- refers to the C-21 alkoxide residue of a known antiinflammatory steroid (R2-OH) or an alkoxide residue of any other drug or medicament containing a hydroxy functional group used in the treatment of inflammatory disorders; with the proviso that when A is absent, n is 0, and B is absent, then R1-CO- is different from the acyl residue of acetylsalicylic acid;, and non-toxic pharmaceutically acceptable acid addition salts thereof;, and non-toxic pharmaceutically acceptable cation salts thereof. Such compounds are biolabile prodrugs providing controlled release and prolonged duration of action of the parent active antiinflamma-tory agents locally at the administration site after intra-articular, intra-muscular, subcutaneous or extra-dural application while at the same time being highly stable in aqueous solution in the pH range 3--5. After oral administration of such prodrugs the parent drug is liberated selectively in the terminal ileum and the colon over an extended period of time.

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