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Methylprednisolone Hemisuccinate

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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

Methylprednisolone Hemisuccinate

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 Formula	C₂₆H₃₄O₈
Molecular Weight	474.5 g/mol
XLogP3	2.2
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	8
Rotatable Bond Count	7
Exact Mass	474.22536804 g/mol
Monoisotopic Mass	474.22536804 g/mol
Topological Polar Surface Area	138 Å²
Heavy Atom Count	34
Formal Charge	0
Complexity	981
Isotope Atom Count	0
Defined Atom Stereocenter Count	8
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Information

1 of 2
Drug Name	Methylprednisolone sodium succinate
Drug Label	SOLU-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 Ingredient	Methylprednisolone sodium succinate
Dosage Form	Injectable
Route	Injection
Strength	eq 2gm base/vial; eq 40mg base/vial; eq 125mg base/vial; eq 500mg base/vial; eq 1gm base/vial
Market Status	Prescription
Company	Mustafa Nevsat; Fresenius Kabi Usa

2 of 2
Drug Name	Methylprednisolone sodium succinate
Drug Label	SOLU-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 Ingredient	Methylprednisolone sodium succinate
Dosage Form	Injectable
Route	Injection
Strength	eq 2gm base/vial; eq 40mg base/vial; eq 125mg base/vial; eq 500mg base/vial; eq 1gm base/vial
Market Status	Prescription
Company	Mustafa 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.)