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2D Structure
Also known as: 2921-57-5, Methylprednisolone succinate, Methylprednisolone hydrogen succinate, Methylprednisolone hydrogen hemisuccinate, Methylprednisolone hemisuccinate [usp], 4-[2-[(6s,8s,9s,10r,11s,13s,14s,17r)-11,17-dihydroxy-6,10,13-trimethyl-3-oxo-7,8,9,11,12,14,15,16-octahydro-6h-cyclopenta[a]phenanthren-17-yl]-2-oxoethoxy]-4-oxobutanoic acid
Molecular Formula
C26H34O8
Molecular Weight
474.5  g/mol
InChI Key
IMBXEJJVJRTNOW-XYMSELFBSA-N
FDA UNII
5GMR90S4KN

A water-soluble ester of METHYLPREDNISOLONE used for cardiac, allergic, and hypoxic emergencies.
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
4-[2-[(6S,8S,9S,10R,11S,13S,14S,17R)-11,17-dihydroxy-6,10,13-trimethyl-3-oxo-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-yl]-2-oxoethoxy]-4-oxobutanoic acid
2.1.2 InChI
InChI=1S/C26H34O8/c1-14-10-16-17-7-9-26(33,20(29)13-34-22(32)5-4-21(30)31)25(17,3)12-19(28)23(16)24(2)8-6-15(27)11-18(14)24/h6,8,11,14,16-17,19,23,28,33H,4-5,7,9-10,12-13H2,1-3H3,(H,30,31)/t14-,16-,17-,19-,23+,24-,25-,26-/m0/s1
2.1.3 InChI Key
IMBXEJJVJRTNOW-XYMSELFBSA-N
2.1.4 Canonical SMILES
CC1CC2C3CCC(C3(CC(C2C4(C1=CC(=O)C=C4)C)O)C)(C(=O)COC(=O)CCC(=O)O)O
2.1.5 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)COC(=O)CCC(=O)O)O
2.2 Other Identifiers
2.2.1 UNII
5GMR90S4KN
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 6 Alpha-methylprednisolone Sodium Hemisuccinate

2. A-methapred

3. Hemisuccinate, Methylprednisolone

4. Methylprednisolone Hemisuccinate Monosodium Salt

5. Methylprednisolone Sodium Hemisuccinate

6. Methylprednisolone Sodium Succinate

7. Methylprednisolone Succinate

8. Sodium Hemisuccinate, Methylprednisolone

9. Sodium Succinate, Methylprednisolone

10. Solu-medrol

11. Solumedrol

12. Succinate, Methylprednisolone

13. Urbason-soluble

14. Urbasonsoluble

2.3.2 Depositor-Supplied Synonyms

1. 2921-57-5

2. Methylprednisolone Succinate

3. Methylprednisolone Hydrogen Succinate

4. Methylprednisolone Hydrogen Hemisuccinate

5. Methylprednisolone Hemisuccinate [usp]

6. 4-[2-[(6s,8s,9s,10r,11s,13s,14s,17r)-11,17-dihydroxy-6,10,13-trimethyl-3-oxo-7,8,9,11,12,14,15,16-octahydro-6h-cyclopenta[a]phenanthren-17-yl]-2-oxoethoxy]-4-oxobutanoic Acid

7. 5gmr90s4kn

8. 6alpha-methylprednisolone Hemisuccinate

9. 6alpha-methylprednisolone 21-hemisuccinate

10. Methylprednisolone Hemisuccinate (usp)

11. Ncgc00185763-01

12. Einecs 220-863-9

13. Unii-5gmr90s4kn

14. Ec 220-863-9

15. Schembl7915

16. 11beta,17,21-trihydroxy-6alpha-methylpregna-1,4-diene-3,20-dione 21-(hydrogen Succinate)

17. Pregna-1,4-diene-3,20-dione, 21-(3-carboxy-1-oxopropoxy)-11,17-dihydroxy-6-methyl-, (6alpha,11beta)-

18. Methylpredinisolone Hemisuccinate

19. Chembl1201265

20. Dtxsid80183466

21. 6-methylprednisolone Hemisuccinate

22. Chebi:135765

23. Methylprednisolone-sodium-succinate

24. Hy-b1900

25. Zinc3977781

26. Methylprednisolone Succinate (jp17)

27. S6588

28. 6-methylprednisolone-21-hemisuccinate

29. Akos015894899

30. Cs-8183

31. Db14644

32. Ncgc00185763-03

33. As-76484

34. Methylprednisolone Succinate [jan]

35. D05000

36. D97631

37. Methylprednisolone Hemisuccinate [usp-rs]

38. Methylprednisolone Hemisuccinate [who-dd]

39. 921m575

40. A819819

41. Methylprednisolone Hydrogen Succinate [mart.]

42. Methylprednisolone Hemisuccinate [usp Impurity]

43. Q27262132

44. Methylprednisolone Hemisuccinate [usp Monograph]

45. Methylprednisolone Hydrogen Succinate For Performance Test

46. Methylprednisolone Hydrogen Succinate For Peak Identification

47. 11beta,17,21-trihydroxy-6alpha-methyl-3,20-dioxopregna-1,4-dien-21-yl 3-carboxypropionate

48. 11beta,17,21-trihydroxy-6alpha-methylpregna-1,4-diene-3,20-dione 21-succinate

49. 4-(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-oxoethoxy)-4-oxobutanoic Acid

50. 4-[2-[(6s,8s,9s,10r,11s,13s,14s,17r)-11,17-dihydroxy-6,10,13-trimethyl-3-oxo-7,8,9,11,12,14,15,16-octahydro-6h-cyclopenta[a]phenanthren-17-yl]-2-oxo-ethoxy]-4-oxo-butanoic Acid

2.4 Create Date
2005-06-24
3 Chemical and Physical Properties
Molecular Weight 474.5 g/mol
Molecular Formula C26H34O8
XLogP32.2
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count8
Rotatable Bond Count7
Exact Mass474.22536804 g/mol
Monoisotopic Mass474.22536804 g/mol
Topological Polar Surface Area138 Ų
Heavy Atom Count34
Formal Charge0
Complexity981
Isotope Atom Count0
Defined Atom Stereocenter Count8
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Information
1 of 2  
Drug NameMethylprednisolone sodium succinate
Drug LabelSOLU-MEDROL Sterile Powder is an antiflammatory glucocorticoid, which contains methylprednisolone sodium succinate as the active ingredient. Methylprednisolone sodium succinate, USP, is the sodium succinate ester of methylprednisolone, and it occurs...
Active IngredientMethylprednisolone sodium succinate
Dosage FormInjectable
RouteInjection
Strengtheq 2gm base/vial; eq 40mg base/vial; eq 125mg base/vial; eq 500mg base/vial; eq 1gm base/vial
Market StatusPrescription
CompanyMustafa Nevsat; Fresenius Kabi Usa

2 of 2  
Drug NameMethylprednisolone sodium succinate
Drug LabelSOLU-MEDROL Sterile Powder is an antiflammatory glucocorticoid, which contains methylprednisolone sodium succinate as the active ingredient. Methylprednisolone sodium succinate, USP, is the sodium succinate ester of methylprednisolone, and it occurs...
Active IngredientMethylprednisolone sodium succinate
Dosage FormInjectable
RouteInjection
Strengtheq 2gm base/vial; eq 40mg base/vial; eq 125mg base/vial; eq 500mg base/vial; eq 1gm base/vial
Market StatusPrescription
CompanyMustafa Nevsat; Fresenius Kabi Usa

5 Pharmacology and Biochemistry
5.1 Pharmacology

Methylprednisolone sodium succinate (the sodium salt of methylprednisolone hemisuccinate) has the same metabolic and anti-inflammatory actions as methylprednisolone. When given parenterally and in equimolar quantities, the two compounds are equivalent in biologic activity.


5.2 MeSH Pharmacological Classification

Antineoplastic Agents, Hormonal

Antineoplastic agents that are used to treat hormone-sensitive tumors. Hormone-sensitive tumors may be hormone-dependent, hormone-responsive, or both. A hormone-dependent tumor regresses on removal of the hormonal stimulus, by surgery or pharmacological block. Hormone-responsive tumors may regress when pharmacologic amounts of hormones are administered regardless of whether previous signs of hormone sensitivity were observed. The major hormone-responsive cancers include carcinomas of the breast, prostate, and endometrium; lymphomas; and certain leukemias. (From AMA Drug Evaluations Annual 1994, p2079) (See all compounds classified as Antineoplastic Agents, Hormonal.)


Anti-Inflammatory Agents

Substances that reduce or suppress INFLAMMATION. (See all compounds classified as Anti-Inflammatory Agents.)


Neuroprotective Agents

Drugs intended to prevent damage to the brain or spinal cord from ischemia, stroke, convulsions, or trauma. Some must be administered before the event, but others may be effective for some time after. They act by a variety of mechanisms, but often directly or indirectly minimize the damage produced by endogenous excitatory amino acids. (See all compounds classified as Neuroprotective Agents.)


Glucocorticoids

A group of CORTICOSTEROIDS that affect carbohydrate metabolism (GLUCONEOGENESIS, liver glycogen deposition, elevation of BLOOD SUGAR), inhibit ADRENOCORTICOTROPIC HORMONE secretion, and possess pronounced anti-inflammatory activity. They also play a role in fat and protein metabolism, maintenance of arterial blood pressure, alteration of the connective tissue response to injury, reduction in the number of circulating lymphocytes, and functioning of the central nervous system. (See all compounds classified as Glucocorticoids.)