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This article needs additional citations for verification. Please help improve this article by adding citations to reliable sources. Unsourced material may be challenged and removed. (January 2007) |
Methylprednisolone
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Systematic (IUPAC) name |
(1S,2R,8S,10S,11S,14R,15S,17S)-14,17-dihydroxy-14-(2-hydroxyacetyl)-2,8,15-trimethyltetracyclo[8.7.0.02,7.011,15]heptadeca-3,6-dien-5-one |
Clinical data |
Trade names |
Medrol, Meprolone |
AHFS/Drugs.com |
monograph |
MedlinePlus |
a682795 |
Licence data |
US FDA:link |
Pregnancy cat. |
A (AU) C (US) |
Legal status |
POM (UK) ℞-only (US) |
Routes |
IV, IM, IV Infusion, Oral, Rectal, Topical |
Pharmacokinetic data |
Protein binding |
78% |
Metabolism |
liver primarily, kidney, tissues; CYP450: 3A4 substrate |
Half-life |
urine; Half-life: 18-26h (biological) |
Identifiers |
CAS number |
83-43-2 Y |
ATC code |
D07AA01 D07AC14, D10AA02, H02AB04 |
PubChem |
CID 6741 |
DrugBank |
DB00959 |
ChemSpider |
6485 Y |
UNII |
X4W7ZR7023 Y |
KEGG |
D00407 Y |
ChEBI |
CHEBI:6888 Y |
ChEMBL |
CHEMBL650 Y |
Synonyms |
(6α, 11β)-11,17,21-trihydroxy-6-methyl-pregna-1,4-diene-3,20-dione |
Chemical data |
Formula |
C22H30O5 |
Mol. mass |
374.471 g/mol |
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
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InChI
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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 Y
Key:VHRSUDSXCMQTMA-PJHHCJLFSA-N Y
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Y (what is this?) (verify)
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Methylprednisolone is a synthetic glucocorticoid or corticosteroid drug. It is marketed in the USA and Canada under the brand names Medrol and Solu-Medrol.[1] It is also available as a generic drug.
It is a variant of prednisolone, methylated at carbon 6 of the B ring.
Contents
- 1 Uses
- 2 Side effects
- 3 Additional images
- 4 See also
- 5 References
- 6 External links
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Uses [edit]
Like most adrenocortical steroids, methylprednisolone is typically used for its anti-inflammatory effects. However, glucocorticoids have a wide range of effects, including changes to metabolism and immune responses. The list of medical conditions for which methylprednisolone is prescribed is rather long, and is similar to other corticosteroids such as prednisolone. Common uses include arthritis therapy and short-term treatment of bronchial inflammation or acute bronchitis due to various respiratory diseases. It is used both in the treatment of acute periods and long-term management of autoimmune diseases, most notably systemic lupus erythematosus. It is also used as a treatment for multiple sclerosis.
Methylprednisolone is also prescribed for nonpenetrating spinal cord injuries. It has been shown that a dose of 30 mg/kg IV followed by IV drip at 5.4 mg/kg/hr for 23 hours improves sensory and motor recovery if given within eight hours of the injury.[citation needed]
It is also used for vestibular neuritis.[2]
Side effects [edit]
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This section does not cite any references or sources. Please help improve this section by adding citations to reliable sources. Unsourced material may be challenged and removed. (March 2011) |
Long-term use of methylprednisolone, as with all corticosteroids, can be associated with hyperglycemia, decreased resistance to infection, swelling of face, weight gain, congestive cardiac insufficiency, fluid and sodium retention, edema, hypertension, increased eye pressure, glaucoma, osteoporosis and psychosis, especially when used at high dosage.[3][4] The most serious side effect occurs after the adrenal glands cease natural production of cortisol, which methylprednisolone will replace. Abrupt cessation of the drug after this occurs can result in a condition known as Addisonian crisis, which can be fatal. To prevent this, the drug is usually prescribed with a tapering dosage, including a pre-dosed "dose pack" detailing a specific number of tablets to take at designated times over a several-day period. Pharmacists sometimes advise that this drug can cause sleeplessness and "down" moods.
Individuals on methylprednisolone therapy should assiduously avoid exposure to measles and chicken pox as contracting these viral infections while on high dose corticosteroids can result in a potentially fatal viral course. Any accidental exposure to these viral infections by individuals uncertain of their immunity to chicken pox or measles should be reported immediately as prophylactic immunoglobulin therapy may be administered. Additionally, the administration of live, attenuated vaccines is contraindicated for individuals taking immunosuppressive doses of methylprednisolone. The exception to this rule is patients receiving complete corticosteroid replacement therapy, e.g., for Addison's disease, who may follow standard immunization protocols.
Additional images [edit]
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4mg Methylprednisolone tablets by Sandoz
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Medrol
32mg Methylprednisolone tablets by Pfizer
See also [edit]
- Guanacastepene A - also composed as C22H30O5
- Prednisone - also a corticosteroid
- Dexamethasone - also a corticosteroid
References [edit]
- ^ Methylprednisolone - Compound Summary PubChem
- ^ Strupp M, Zingler VC, Arbusow V, Niklas D, Maag KP, Dieterich M, Bense S, Theil D, Jahn K, Brandt T (July 2004). "Methylprednisolone, valacyclovir, or the combination for vestibular neuritis" (PDF). N. Engl. J. Med. 351 (4): 354–61. doi:10.1056/NEJMoa033280. PMID 15269315.
- ^ "SOLU-MEDROL (methylprednisolone sodium succinate) injection, powder, for solution". National Institutes of Health. Retrieved 24 August 2012.
- ^ "Medrol (Methylprednisolone - Tablets by Pfizer)". Sfatul Medicului. Retrieved 14 April 2013.
External links [edit]
- Medrol Prescribing Information Pfizer
- U.S. National Library of Medicine: Drug Information Portal - Methylprednisolone
- "methylprednisolone" at medicinenet.com
Corticosteroids – glucocorticoids and mineralocorticoids (H02)
(also A07EA, C05AA, D07, D10AA, R01AD, R03BA, S01BA, S02B, and S03B)
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Mineralocorticoids
(3-one, 4-ene,
no FG at 16) |
- Pregnenedione: ALDOSTERONE
- 11-DEOXYCORTICOSTERONE
- HALOGENATED AT 9: Fludrocortisone
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Glucocorticoids
(3-one, 4-ene,
11-FG,
17-hydroxy) |
Pregnene
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|
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Pregnenedione
(+20-one)
|
- HYDROCORTISONE/CORTISOL# (Hydrocortisone aceponate
- Hydrocortisone buteprate
- Hydrocortisone butyrate)
- Budesonide
- Ciclesonide
- Deflazacort
- Medrysone
- Tixocortol
- HALOGENATED AT 6: Cloprednol
- HALOGENATED, WITH FG AT 16: Halcinonide
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Pregnadiene (+1-ene)
|
- Rimexolone
- HALOGENATED, WITH FG AT 16: Flunisolide
- Triamcinolone
- Amcinonide
- Fluocinolone acetonide (Fluocinonide)
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Pregnadienediol
(+21-hydroxy)
|
- Prednisone (Meprednisone)
- HALOGENATED AT 9: Fluorometholone
- HALOGENATED, WITH FG AT 16: Fluocortolone (Clocortolone
- Diflucortolone
- Fluocortin)
- Desoximetasone
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|
Pregnadienetriol
(+11-hydroxy)
|
- Prednisolone# (Methylprednisolone
- Methylprednisolone aceponate
- Prednicarbate
- Prednylidene)
- Desonide
- HALOGENATED: Fluprednisolone (Difluprednate
- Fluperolone)
- HALOGENATED, WITH FG AT 16: Dexamethasone#
- Betamethasone (Clobetasol
- Clobetasone
- Diflorasone
- Halometasone
- Ulobetasol)
- Beclometasone
- Paramethasone
- Alclometasone
- Fluclorolone acetonide
- Flumetasone
- Fluprednidene
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Pregnatriene
(+2-ene)
|
|
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Androstene
|
- HALOGENATED, WITH FG AT 16: Fluticasone (Fluticasone propionate
- Fluticasone furoate)
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Other/ungrouped
|
- HALOGENATED: Loteprednol
- HALOGENATED, WITH FG AT 16: Fludroxycortide
- Formocortal
- Mometasone furoate
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Aldosterone antagonists |
- Spironolactone
- Eplerenone
- Potassium canrenoate
- Canrenone
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Synthesis modifiers |
- Trilostane
- Carbenoxolone
- Aminoglutethimide
- Metyrapone
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- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
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noco (d)/cong/tumr, sysi/epon
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proc, drug (A10/H1/H2/H3/H5)
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|
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Glucocorticoids
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Receptor |
|
|
Enzyme
(inhibitors) |
20,22-Desmolase
|
- 22-ABC
- 3,3′-Dimethoxybenzidine
- 3-Methoxybenzidine
- Aminoglutethimide
- Cyanoketone
- Danazol
- Etomidate
- Mitotane
- Trilostane
|
|
17α-Hydroxylase,
17,20-Lyase
|
- 22-ABC
- 22-Oxime
- Abiraterone
- Bifonazole
- Clotrimazole
- Cyanoketone
- Cyproterone
- Danazol
- Econazole
- Galeterone
- Gestrinone
- Isoconazole
- Ketoconazole
- L-39
- Liarozole
- LY-207,320
- MDL-27,302
- Miconazole
- Mifepristone
- Orteronel
- Pioglitazone
- Rosiglitazone
- Spironolactone
- Stanozolol
- SU-10,603
- TGF-β
- Tioconazole
- Troglitazone
- VN/87-1
- YM116
|
|
3β-HSD
|
- 4-MA
- Azastene
- Cyanoketone
- Danazol
- Epostane
- Genistein
- Gestrinone
- Metyrapone
- Norethisterone
- Oxymetholone
- Pioglitazone
- Rosiglitazone
- Trilostane
- Troglitazone
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|
21-Hydroxylase
|
- Aminoglutethimide
- Amphenone B
- Bifonazole
- Clotrimazole
- Diazepam
- Econazole
- Genistein
- Isoconazole
- Ketoconazole
- Metyrapone
- Miconazole
- Midazolam
- Tioconazole
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|
11β-Hydroxylase
|
- Aminoglutethimide
- Canrenone
- Etomidate
- Fadrozole
- FETO
- Ketoconazole
- Metomidate
- Metyrapone
- Mitotane
- Potassium canrenoate
- Spironolactone
- Trilostane
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|
18-Hydroxylase
|
- Aminoglutethimide
- Canrenone
- FAD286
- Fadrozole
- Ketoconazole
- LCI699
- Metyrapone
- Mespirenone
- Potassium canrenoate
- Spironolactone
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|
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Other |
Endogenous
|
- Glucocorticoids: Corticosterone
- Cortisone
- Cortodoxone/Deoxycortisol
- Hydrocortisone/Cortisol
- Antiglucocorticoids: 17-Hydroxyprogesterone
- Deoxycorticosterone
- Pregnenolone
- Progesterone
- Precursors: Cholesterol
- 22R-Hydroxycholesterol
- 20α,22R-Dihydroxycholesterol
- Pregnenolone
- 17-Hydroxypregnenolone
- 17-Hydroxyprogesterone
- Progesterone
- Deoxycorticosterone
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Indirect
|
- ACTH/Corticotropin
- CRH
- DHEA
- DHEA sulfate
- Plasma proteins (Transcortin, Albumin)
- Vasopressin
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Procedures
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- Adrenalectomy
- Hypophysectomy
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