Methylprednisolone

Details

• Internal ID: dfbb3c80-cf01-4bdd-924f-d17f585dbae2
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Hydroxysteroids > 21-hydroxysteroids
• IUPAC Name: (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
• SMILES (Canonical): CC1CC2C3CCC(C3(CC(C2C4(C1=CC(=O)C=C4)C)O)C)(C(=O)CO)O
• SMILES (Isomeric): 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
• InChI: 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
• InChI Key: VHRSUDSXCMQTMA-PJHHCJLFSA-N
• Popularity: 61,531 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₃₀O₅
• Molecular Weight: 374.50 g/mol
• Exact Mass: 374.20932405 g/mol
• Topological Polar Surface Area (TPSA): 94.80 Ų
• XlogP: 1.90

Synonyms

• 83-43-2
• Medrol
• Medrone
• Metilprednisolone
• Urbason
• 6alpha-Methylprednisolone
• Metilbetasone
• Medrate
• Dopomedrol
• Medesone
• Mesopren
• Metastab
• Metrisone
• Noretona
• Promacortine
• Urbasone
• Besonia
• Moderin
• Solomet
• Wyacort
• Methylprednisolon
• Sieropresol
• Suprametil
• Esametone
• Firmacort
• Medixon
• Metrocort
• Metysolon
• Nirypan
• Reactenol
• Lemod
• Artisone-wyeth
• Medrol dosepak
• Methyleneprednisolone
• Medrol adt pak
• Predni N Tablinen
• Metilprednisolona
• delta(1)-6alpha-Methylhydrocortisone
• NSC-19987
• 1-Dehydro-6alpha-methylhydrocortisone
• Methylprednisolonum
• Medlone 21
• Metilprednisolone [DCIT]
• 6-alpha-Methylprednisolone
• Metipred
• Summicort
• Prednisolone, methyl-
• Summicort;
• Prednol- L
• Methylprednisolonum [INN-Latin]
• Metilprednisolona [INN-Spanish]
• U 7532
• Prednisolone, 6alpha-methyl-
• Depo-Medrol (acetate)
• CHEBI:6888
• HSDB 3127
• EINECS 201-476-4
• 11beta,17,21-Trihydroxy-6alpha-methylpregna-1,4-diene-3,20-dione
• 6alpha-Methyl-11beta,17alpha,21-triol-1,4-pregnadiene-3,20-dione
• UNII-X4W7ZR7023
• BRN 2340300
• MEPRDL
• A-Methapred
• 6-methyl-prednisolone
• DTXSID7023300
• delta(sup 1)-6-alpha-Methylhydrocortisone
• X4W7ZR7023
• (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
• J3.872E
• Methylprednisolone, 6-alpha
• medralone
• 11beta,17alpha,21-Trihydroxy-6alpha-methyl-1,4-pregnadiene-3,20-dione
• (6alpha,11beta)-11,17,21-Trihydroxy-6-methylpregna-1,4-diene-3,20-dione
• 6alpha-Methylprednisolone base
• MLS000028541
• MLS001148159
• DTXCID903300
• (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
• EC 201-476-4
• 4-08-00-03498 (Beilstein Handbook Reference)
• NSC19987
• Pregna-1,4-diene-3,20-dione, 11,17,21-trihydroxy-6-methyl-, (6alpha,11beta)-
• Methylprednisolone [USP:INN:BAN:JAN]
• Methylprednisolone [USAN:INN:BAN:JAN]
• SMR000058330
• 11-beta,17,21-Trihydroxy-6-alpha-methylpregna-1,4-diene-3,20-dione
• Pregna-1,4-diene-3,20-dione, 11beta,17,21-trihydroxy-6alpha-methyl-
• NEO-MEDROL COMPONENT METHYLPREDNISOLONE
• Pregna-1,4-diene-3,20-dione, 11,17,21-trihydroxy-6-methyl-, (6a,11b)-
• METHYLPREDNISOLONE COMPONENT OF NEO-MEDROL
• METHYLPREDNISOLONE (MART.)
• METHYLPREDNISOLONE [MART.]
• METHYLPREDNISOLONE (USP-RS)
• METHYLPREDNISOLONE [USP-RS]
• Pregna-1,4-diene-3,20-dione, 6-alpha-methyl-11-beta-17,21-trihydroxy-
• CAS-83-43-2
• METHYLPREDNISOLONE (EP MONOGRAPH)
• METHYLPREDNISOLONE [EP MONOGRAPH]
• METHYLPREDNISOLONE (USP MONOGRAPH)
• METHYLPREDNISOLONE [USP MONOGRAPH]
• 6 Methylprednisolone
• MLS002638721
• Prednisolone, 6.alpha.-methyl-
• Solpredone
• Duralone
• Meprolone
• Prednilen
• Radilem
• DepMedalone
• methylprenisolone
• Veriderm Medrol
• Caberdelta M
• Depo Moderin
• Depo-Nisolone
• Mega-Star
• Prednol-L
• Pregna-1,4-diene-3,20-dione, 11,17,21-trihydroxy-6-methyl-, (6.alpha.,11.beta.)-
• Predni-M-Tablinen
• .DELTA.1-6.alpha.-Methylhydrocortisone
• NCGC00016330-01
• Prestwick_622
• Medrol (TN)
• Metilbetasone Solubile
• Opera_ID_1576
• Prestwick0_000279
• Prestwick1_000279
• Prestwick2_000279
• Prestwick3_000279
• 6alpha-Methyl-11beta,17alpha,21-trihydroxy-1,4-pregnadiene-3,20-dione
• CHEMBL650
• D08PIQ
• 6.alpha.-Methylprednisolone
• SCHEMBL5084
• BSPBio_000158
• MLS002207191
• SPBio_002377
• METHYLPREDNISOLONE [MI]
• BPBio1_000174
• GTPL7088
• Solu-Medrol (sodium succinate)
• METHYLPREDNISOLONE [INN]
• METHYLPREDNISOLONE [JAN]
• METHYLPREDNISOLONE [HSDB]
• METHYLPREDNISOLONE [VANDF]
• VHRSUDSXCMQTMA-PJHHCJLFSA-N
• HMS1568H20
• HMS2090B13
• HMS2095H20
• HMS2230D16
• HMS3259J04
• HMS3712H20
• 6alpha-Methylprednisolone, >=98%
• METHYLPREDNISOLONE [WHO-DD]
• DRG-0050
• HY-B0260
• Tox21_110376
• Tox21_302018
• BDBM50103616
• LMST02030178
• Methylprednisolone (JP17/USP/INN)
• s1733
• 1-dehydro-6-alpha-methylhydrocortisone
• AKOS015969744
• Tox21_110376_1
• CCG-220279
• DB00959
• KS-1273
• METHYLPREDNISOLONE [GREEN BOOK]
• NC00691
• METHYLPREDNISOLONE [ORANGE BOOK]
• Methylprednisolone [USAN:BAN:INN:JAN]
• NCGC00022735-03
• NCGC00022735-06
• NCGC00255269-01
• NCI60_001657
• LS-118498
• M1665
• C16437
• D00407
• EN300-7414014
• A855290
• Q417222
• SR-01000003089
• Q-201395
• SR-01000003089-2
• BRD-K35240538-001-03-1
• BRD-K35240538-001-11-4
• BRD-K35240538-001-26-2
• 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
• 11?,17?,21-Trihydroxy-6?-methyl-1,4-pregnadiene-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-
• (6?,11?)-11,17,21-Trihydroxy-6-methylpregna-1,4-diene-3,20-dione
• (6a,11b)-11,17,21-Trihydroxy-6-methylpregna-1,4-diene-3,20-dione
• 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
• (6-alpha,11-beta)-11,17,21-Trihydroxy-6-methylpregna-1,4-diene-3,20-dione
• Methylprednisolone for system suitability A, EuropePharmacopoeia (EP) Reference Standard
• Methylprednisolone for system suitability, European Pharmacopoeia (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))-
• Pregna-1,4-diene-3,20-dione, 11,17,21-trihydroxy-6-methyl-,(6.alpha.,11.beta.)-
• Pregna-1,4-dieno-3,20-diona, 11,17,21-trihidroxi-6-metil-, (6alfa, 11beta)-
• (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

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
No predicted properties yet!

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL2034	P04150	Glucocorticoid receptor	11 nM	IC50	via CMAUP
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	39.8 nM; 50.1 nM; 50.1 nM; 50.1 nM	Potency; Potency; Potency; Potency	via Super-PRED; via Super-PRED; via CMAUP; via CMAUP
CHEMBL3401	O75469	Pregnane X receptor	12600 nM	EC50	PMID: 20966043
CHEMBL1293235	P02545	Prelamin-A/C	0.9 nM	Potency	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.76%	96.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	96.14%	100.00%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.48%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.43%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.06%	97.09%
CHEMBL1871	P10275	Androgen Receptor	89.19%	96.43%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	88.51%	82.69%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.89%	89.00%
CHEMBL226	P30542	Adenosine A1 receptor	86.23%	95.93%
CHEMBL221	P23219	Cyclooxygenase-1	85.13%	90.17%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	83.93%	96.77%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.84%	86.33%
CHEMBL253	P34972	Cannabinoid CB2 receptor	82.94%	97.25%
CHEMBL230	P35354	Cyclooxygenase-2	82.81%	89.63%
CHEMBL2581	P07339	Cathepsin D	82.68%	98.95%
CHEMBL4208	P20618	Proteasome component C5	82.17%	90.00%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	81.54%	95.50%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	80.13%	91.07%

Plants that contains it

• Apocynum venetum

Cross-Links

• PubChem: 6741
• NPASS: NPC144956
• ChEMBL: CHEMBL650