Compound: methylprednisolone
SMILES: O=C1C=C2[C@]([C@H]3[C@@H](O)C[C@@]4([C@@](O)(C(=O)CO)CC[C@H]4[C@@H]3C[C@@H]2C)C)(C)C=C1
InChIKey: VHRSUDSXCMQTMA-PJHHCJLFSA-N
Synonyms: methylprednisolone, 83-43-2, Medrone, Medrate, Urbason, 6alpha-Methylprednisolone, Metilbetasone, Promacortine, Metastab, Metrisone, Wyacort, Dopomedrol, Medesone, Noretona, Suprametil, Besonia, Moderin, Solomet, Artisone-wyeth, Methylprednisolon, Sieropresol, Esametone, Firmacort, Metrocort, Metysolon, Medlone 21, delta(1)-6alpha-Methylhydrocortisone, NSC-19987, 1-Dehydro-6alpha-methylhydrocortisone, Methylprednisolonum, Summicort, 11beta,17,21-Trihydroxy-6alpha-methylpregna-1,4-diene-3,20-dione, 6alpha-Methyl-11beta,17alpha,21-triol-1,4-pregnadiene-3,20-dione, 11beta,17alpha,21-Trihydroxy-6alpha-methyl-1,4-pregnadiene-3,20-dione, J3.872E, CHEBI:6888, (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, DTXSID7023300, X4W7ZR7023, (6alpha,11beta)-11,17,21-Trihydroxy-6-methylpregna-1,4-diene-3,20-dione, DTXCID903300, NSC19987, Pregna-1,4-diene-3,20-dione, 11beta,17,21-trihydroxy-6alpha-methyl-, Pregna-1,4-diene-3,20-dione, 11,17,21-trihydroxy-6-methyl-, (6alpha,11beta)-, Metipred, Solpredone, Duralone, Meprolone, Prednilen, Radilem, DepMedalone, Methylprednisole, Medrol Tablets, Veriderm Medrol, Caberdelta M, Depo Moderin, Depo-Nisolone, Methylpred DP, Mega-Star, Predni-M-Tablinen, (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, 6 Methylprednisolone, Metilbetasone Solubile, RefChem:6034, Methylprednisolene Tablets, 201-476-4, Adlone, Emmetipi, Metypresol, Medrol, Metilprednisolone, Urbasone, Mesopren, Methyleneprednisolone, 6-alpha-Methylprednisolone, Metilprednisolona, Metilprednisolone [DCIT], Methylprednisolonum [INN-Latin], Metilprednisolona [INN-Spanish], Medrol dosepak, Medrol adt pak, 6-methyl-prednisolone, (6S,8S,9S,10R,11S,13S,14S,17R)-11,17-dihydroxy-17-(2-hydroxyacetyl)-6,10,13-trimethyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-3-one, Prednisolone, methyl-, Methylprednisolone, 6-alpha, Methylprednisolone (Standard), MLS000028541, MLS001148159, Medixon, Nirypan, Reactenol, Lemod, U 7532, MEPRDL, Predni N Tablinen, SMR000058330, Prednol- L, Depo-Medrol (acetate), (6a,11b)-11,17,21-Trihydroxy-6-methylpregna-1,4-diene-3,20-dione, 6a-methylprednisolone, MFCD00010591, CAS-83-43-2, 6?-Methyl Prednisolone, Prednisolone, 6alpha-methyl-, HSDB 3127, MLS002638721, EINECS 201-476-4, 6alpha-methyl prednisolone, Prednisolone, 6.alpha.-methyl-, BRN 2340300, delta(sup 1)-6-alpha-Methylhydrocortisone, UNII-X4W7ZR7023, .DELTA.1-6.alpha.-Methylhydrocortisone, NCGC00016330-01, Prestwick_622, Medrol (TN), Methylprednisolone CRS, 6a-methyl prednisolone, Methylprednisolone [USP:INN:BAN:JAN], 6-|A-Methylprednisolone, Opera_ID_1576, Prestwick0_000279, Prestwick1_000279, Prestwick2_000279, Prestwick3_000279, 11-beta,17,21-Trihydroxy-6-alpha-methylpregna-1,4-diene-3,20-dione, CHEMBL650, EC 201-476-4, Pregna-1,4-diene-3,20-dione, 11,17,21-trihydroxy-6-methyl-, (6a,11b)-, 6-alpha-methyl prednisolone, 6.alpha.-Methylprednisolone, SCHEMBL5084, BSPBio_000158, 4-08-00-03498 (Beilstein Handbook Reference), MLS002207191, orb134664, Methylprednisolone-gellan ester, SPBio_002377, METHYLPREDNISOLONE [MI], BPBio1_000174, GTPL7088, METHYLPREDNISOLONE [INN], METHYLPREDNISOLONE [JAN], HY-B0260R, METHYLPREDNISOLONE [HSDB], METHYLPREDNISOLONE [VANDF], MSK2229, GLXC-23447, HMS1568H20, HMS2090B13, HMS2095H20, HMS2230D16, HMS3259J04, HMS3712H20, METHYLPREDNISOLONE [MART.], 6alpha-Methylprednisolone, >=98%, METHYLPREDNISOLONE [USP-RS], METHYLPREDNISOLONE [WHO-DD], HY-B0260, Tox21_110376, Tox21_302018, BDBM50103616, EBC-11062, LMST02030178, Methylprednisolone (JP17/USP/INN), MSK2229-100A, s1733, 6-alpha-Methylprednisolone(U 7532), 6alpha-Methyl-11beta,17alpha,21-trihydroxy-1,4-pregnadiene-3,20-dione, AKOS015969744, MSK2229-1000A, Pregna-1,4-diene-3,20-dione, 6-alpha-methyl-11-beta-17,21-trihydroxy-, Tox21_110376_1, CCG-220279, DB00959, FM25546, KS-1273, METHYLPREDNISOLONE [GREEN BOOK], NC00691, METHYLPREDNISOLONE [ORANGE BOOK], METHYLPREDNISOLONE [EP MONOGRAPH], NCGC00022735-03, NCGC00022735-06, NCGC00255269-01, (1R,3aS,3bS,5S,9aR,9bS,10S,11aS)-1,10-dihydroxy-1-(2-hydroxyacetyl)-5,9a,11a-trimethyl-1H,2H,3H,3aH,3bH,4H,5H,7H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-7-one, METHYLPREDNISOLONE [USP MONOGRAPH], NCI60_001657, CS-0694768, M1665, NS00000345, NEO-MEDROL COMPONENT METHYLPREDNISOLONE, C16437, D00407, Methylprednisolone for system suitability A CRS, EN300-7414014, Q417222, SR-01000003089, SR-01000003089-2, BRD-K35240538-001-03-1, BRD-K35240538-001-11-4, BRD-K35240538-001-26-2, Methylprednisolone Solution in Acetonitrile, 100ug/mL, Methylprednisolone Solution in Acetonitrile, 1000ug/mL, 6-alpha-Methylprednisolone 100 microg/mL in Acetonitrile, METHYLPREDNISOLONE ACETATE IMPURITY B [EP IMPURITY], 6alpha-Methylprednisolone, VETRANAL(TM), analytical standard, 1,4-pregnadien-6alpha-methyl-11beta, 17, 21-triol-3, 20-dione, 11beta,17,21-trihydroxy-6alpha-methyl-1,4-pregnadiene-3,20-dione, Methylprednisolone, British Pharmacopoeia (BP) Reference Standard, Methylprednisolone, European Pharmacopoeia (EP) Reference Standard, Pregna-1,20-dione, 11.beta.,17,21-trihydroxy-6.alpha.-methyl-, Pregna-1,20-dione, 6.alpha.-methyl-11.beta.-17,21-trihydroxy-, 11beta,17alpha,21-Trihydroxy-6alpha-methylpregna-1,4-diene-3,20-dione, METHYLPREDNISOLONE HYDROGEN SUCCINATE IMPURITY A [EP IMPURITY], Methylprednisolone, United States Pharmacopeia (USP) Reference Standard, Methylprednisolone for system suitability A, EuropePharmacopoeia (EP) Reference Standard, Methylprednisolone, Pharmaceutical Secondary Standard; Certified Reference Material, Pregna-1,20-dione, 11,17,21-trihydroxy-6-methyl-, (6.alpha.,11.beta.)-, Pregna-1,4-diene-3,20-dione, 11,17,21-trihydroxy-6-methyl-, (6I+/-,11I(2))-, Methylprednisolone; Methylprednisolone Hydrogen Succinate EP Impurity A; Methylprednisolone Acetate EP Impurity B
Theoretical properties:
molecular_formula: C22H30O5
molecular_weight: 374.5 g/mol
exact_mass: 374.20932405 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 3
hydrogen_bond_acceptor_count: 5
rotatable_bond_count: 2
heavy_atom_count: 27
topological_polar_surface_area: 94.8 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: Crystals
color: Crystals
odor: Odorless
Descriptions:
{"pubchem": "6alpha-methylprednisolone is the 6alpha-stereoisomer of 6-methylprednisolone. It has a role as an anti-inflammatory drug, a xenobiotic, an adrenergic agent, an antiemetic, a neuroprotective agent and an environmental contaminant. It is a primary alpha-hydroxy ketone, a tertiary alpha-hydroxy ketone and a 6-methylprednisolone.", "chebi": "The 6\u03b1-stereoisomer of  6-methylprednisolone.", "chembl": "METHYLPREDNISOLONE is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.", "wikipedia": "Methylprednisolone, sold under the brand name Medrol among others, is a synthetic glucocorticoid, primarily prescribed for its anti-inflammatory and immunosuppressive effects. It is either used at low doses for chronic illnesses or used at high doses during acute flares. Methylprednisolone and its derivatives can be administered orally or parenterally.\nRegardless of the route of administration, methylprednisolone integrates systemically as exhibited by its effectiveness to quickly reduce inflammation during acute flares. It is associated with many adverse reactions that require tapering off the drug as soon as the disease is under control. Serious side effects include iatrogenic Cushing's syndrome, hypertension, osteoporosis, diabetes, infection, psychosis, and skin atrophy.\nChemically, methylprednisolone is a synthetic pregnane steroid hormone derived from hydrocortisone and prednisolone. It belongs to a class of synthetic glucocorticoids and more generally, corticosteroids. It acts as a mineralocorticoid and glucocorticoid receptor agonist. In comparison to other exogenous glucocorticoids, methylprednisolone has a higher affinity to glucocorticoid receptors than to mineralocorticoid receptors.\nGlucocorticoid's name was derived after the discovery of their involvement in regulating carbohydrate metabolism. The cellular functions of glucocorticoids, such as methylprednisolone, are now understood to regulate homeostasis, metabolism, development, cognition, and inflammation. They play a critical role in adapting and responding to environmental, physical, and emotional stress.\nMethylprednisolone was first synthesized and manufactured by The Upjohn Company (now Viatris) and approved for use by the Food and Drug Administration (FDA) in the United States in October 1957. In 2023, it was the 135th most commonly prescribed medication in the United States, with more than 4 million prescriptions. It is on the World Health Organization's List of Essential Medicines."}