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Fluprednisolone

Fluprednisolone

Synopsis, Chemistry

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Also known as: 53-34-9, Alphadrol, Etadrol, Isopredon, Vladicort, 6alpha-fluoroprednisolone

Molecular Formula

C₂₁H₂₇FO₅

Molecular Weight

378.4 g/mol

InChI Key

MYYIMZRZXIQBGI-HVIRSNARSA-N

FDA UNII

9H05937G3X

A synthetic glucocorticoid with anti-inflammatory properties.

1 2D Structure

Fluprednisolone

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(6S,8S,9S,10R,11S,13S,14S,17R)-6-fluoro-11,17-dihydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-3-one

2.1.2 InChI

InChI=1S/C21H27FO5/c1-19-5-3-11(24)7-14(19)15(22)8-12-13-4-6-21(27,17(26)10-23)20(13,2)9-16(25)18(12)19/h3,5,7,12-13,15-16,18,23,25,27H,4,6,8-10H2,1-2H3/t12-,13-,15-,16-,18+,19-,20-,21-/m0/s1

2.1.3 InChI Key

MYYIMZRZXIQBGI-HVIRSNARSA-N

2.1.4 Canonical SMILES

CC12CC(C3C(C1CCC2(C(=O)CO)O)CC(C4=CC(=O)C=CC34C)F)O

2.1.5 Isomeric SMILES

C[C@]12C[C@@H]([C@H]3[C@H]([C@@H]1CC[C@@]2(C(=O)CO)O)C[C@@H](C4=CC(=O)C=C[C@]34C)F)O

2.2 Other Identifiers

2.2.1 UNII

9H05937G3X

2.3 Synonyms

2.3.1 Depositor-Supplied Synonyms

1. 53-34-9

2. Alphadrol

3. Etadrol

4. Isopredon

5. Vladicort

6. 6alpha-fluoroprednisolone

7. F. I. 6150

8. Nsc 47439

9. Nsc-47439

10. 6

11. A-fluoroprednisolone

12. Pregna-1,4-diene-3,20-dione, 6-fluoro-11,17,21-trihydroxy-, (6alpha,11beta)-

13. U 7800

14. U-7800

15. 6-alpha-fluoroprednisolone

16. (6s,8s,9s,10r,11s,13s,14s,17r)-6-fluoro-11,17-dihydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-7,8,9,11,12,14,15,16-octahydro-6h-cyclopenta[a]phenanthren-3-one

17. Chebi:34474

18. Nsc47439

19. 9h05937g3x

20. Ncgc00182067-02

21. B 673

22. Dsstox_cid_26067

23. Dsstox_rid_81317

24. Dsstox_gsid_46067

25. Fluprednisolonum

26. Cas-53-34-9

27. Prednisolone, 6alpha-fluoro-

28. Fluprednisolonum [inn-latin]

29. Hsdb 3335

30. 6.alpha.-fluoroprednisolone

31. Einecs 200-170-8

32. 6alpha-fluoro-1-dehydrohydrocortisone

33. Prednisolone, 6.alpha.-fluoro-

34. Fi 6150

35. Corticosterone, 1-dehydro-6alpha-fluoro-

36. Unii-9h05937g3x

37. Pregna-1,4-diene-3,20-dione, 6-fluoro-11,17,21-trihydroxy-, (6.alpha.,11.beta.)-

38. Alphadrol (tn)

39. Ncgc00159474-02

40. Fluprednisolone [usan:inn:ban:nf]

41. Corticosterone, 1-dehydro-6.alpha.-fluoro-

42. 6alpha-fluprednisolone

43. 6alpha-fluoro-1,4-pregnadiene-11beta,17alpha,21-triol-3,20-dione

44. 6alpha-fluoro-11beta,17,21-trihydroxypregna-1,4-diene-3,20-dione

45. Pregna-1,4-diene-3,20-dione, 6alpha-fluoro-11beta,17,21-trihydroxy-

46. Fluprednisolone [mi]

47. Fluprednisolone (usan/inn)

48. Schembl24232

49. 6- Alpha -fluoroprednisolone

50. Fluprednisolone [inn]

51. Fluprednisolone [hsdb]

52. Fluprednisolone [usan]

53. Fluprednisolone [mart.]

54. 6.alpha.-fluoro-11.beta.,17,21-trihydroxypregna-1,4-diene-3,20-dione

55. Chembl1200774

56. Dtxsid5046067

57. Fluprednisolone [who-dd]

58. Zinc3875362

59. Tox21_111698

60. Tox21_113143

61. Fluprednisolone [orange Book]

62. Nsc47439nsc 47439

63. Tox21_111698_1

64. Db09378

65. Ncgc00159474-03

66. Hy-107935

67. Cs-0030934

68. D04227

69. 053f349

70. Q732234

71. 6-alpha-fluoroprednisolone 100 Microg/ml In Acetonitrile

72. 6-alpha-fluoroprednisolone, Vetranal(tm), Analytical Standard

73. Pregna-1,20-dione, 6.alpha.-fluoro-11.beta.,17,21-trihydroxy-

74. 6.alpha.-fluoro-11.beta.,21-trihydroxypregna-1,4-diene-3,20-dione

75. 6alpha-fluoro-11beta,17alpha,21-trihydroxypregna-1,4-diene-3,20-dione

76. Pregna-1,20-dione, 6-fluoro-11,17,21-trihydroxy-, (6.alpha.,11.beta.)-

2.4 Create Date

2005-03-26

3 Chemical and Physical Properties

Molecular Formula	C₂₁H₂₇FO₅
Molecular Weight	378.4 g/mol
XLogP3	1.4
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	2
Exact Mass	378.18425212 g/mol
Monoisotopic Mass	378.18425212 g/mol
Topological Polar Surface Area	94.8 Å²
Heavy Atom Count	27
Formal Charge	0
Complexity	760
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 Therapeutic Uses

Anti-Inflammatory Agents, Steroidal; Glucocorticoids, Synthetic

National Library of Medicine's Medical Subject Headings online file (MeSH, 1999)

.../FLUPREDNISOLONE/ IS APPROX 2.5 TIMES AS POTENT AS PREDNISOLONE & 40 TIMES AS POTENT AS CORTISONE. HOWEVER, OCCASIONALLY IT DOES NOT APPEAR...ABLE TO CONTROL ALLERGIC OR INFLAMMATORY CONDITIONS THAT CAN BE CONTROLLED WITH OTHER GLUCOCORTICOIDS. FLUPREDNISOLONE ALSO HAS ERRATIC MINERALOCORTICOID ACTIVITY.

Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 898

...USEFUL IN TREATING INFLAMMATORY & ALLERGIC CONDITIONS & OTHER DISEASES THAT RESPOND TO GLUCOCORTICOIDS. IN ANTI-INFLAMMATORY EFFECT, 1.5 MG FLUPREDNISOLONE IS EQUIVALENT TO 20 MG HYDROCORTISONE.

American Medical Association, AMA Department of Drugs, AMA Drug Evaluations. 3rd ed. Littleton, Massachusetts: PSG Publishing Co., Inc., 1977., p. 519

MEDICATION (VET): Glucocorticoids have profound effects on nearly all cell types and organ systems, particularly immunologic and inflammatory activity. They may be used in either an anti-inflammatory or immunosuppressive capacity, depending on the dosage selected. Glucocorticoids are used for hypersensitivity dermatoses, contact dermatitis, immune-mediated diseases (eg, pemphigus, pemphigoid, lupus erythematosus), and neoplasia (eg, mast cell tumor, lymphoma). ... They may be administered PO, IV, IM, or SC. /Glucocorticoids/

Kahn, C.M. (Ed.); The Merck Veterinary Manual 9th ed. Merck & Co. Whitehouse Station, NJ. 2005, p. 2008

4.2 Drug Warning

SINCE ITS MINERALOCORTICOID EFFECTS ARE POORLY DEFINED, FLUPREDNISOLONE IS NOT RECOMMENDED FOR REPLACEMENT THERAPY IN ADRENOCORTICAL INSUFFICIENCY.

American Medical Association, AMA Department of Drugs, AMA Drug Evaluations. 3rd ed. Littleton, Massachusetts: PSG Publishing Co., Inc., 1977., p. 520

HYDROCORTISONE MAY INCR RENAL EXCRETION OF ASPIRIN & RESULT IN DECR SALICYLATE LEVELS DURING CONCURRENT THERAPY. ... ASPIRIN & HYDROCORTISONE MAY THEORETICALLY EXERT COMBINED DELETERIOUS EFFECTS ON GASTRIC MUCOSA... /HYDROCORTISONE/

Evaluations of Drug Interactions. 2nd ed. and supplements. Washington, DC: American Pharmaceutical Assn., 1976, 1978., p. 18

HYPERGLYCEMIC ACTION OF CORTISONE MAY OFFSET HYPOGLYCEMIC EFFECT OF CHLORPROPAMIDE... THERE IS POSSIBILITY THAT CONCURRENT ADMIN OF CHLORPROPAMIDE & CORTISONE MAY INCR LIKELIHOOD OF PPT GASTRIC ULCER, BUT THERE ARE NO CLINICAL REPORTS OF THIS...IN HUMANS. /CORTISONE/

Evaluations of Drug Interactions. 2nd ed. and supplements. Washington, DC: American Pharmaceutical Assn., 1976, 1978., p. 38

The immunosuppressive effects of glucocorticoids may result in activation of latent infection or exacerbation of intercurrent infections, including those caused by Candida, Mycobacterium, Toxoplasma, Strongyloides, Pneumocystis, Cryptococcus, Nocardia, or Ameba. Glucocorticoids should be used with great care in patients with known or suspected Strongyloides (threadworm) infection. In such patients, glucocorticoid-induced immunosuppression may lead to Strongyloides hyperinfection and dissemination with widespread larval migration, often accompanied by severe enterocolitis and potentially fatal gram-negative septicemia. /Corticosteroids/

McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2007., p. 3033

For more Drug Warnings (Complete) data for FLUPREDNISOLONE (29 total), please visit the HSDB record page.

5 Pharmacology and Biochemistry

5.1 MeSH Pharmacological Classification

Anti-Inflammatory Agents

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

5.2 Absorption, Distribution and Excretion

EXCELLENT CORRELATIONS WERE OBTAINED BETWEEN DISSOLUTION RATES OF SOLVATED & NON-SOLVATED PHASES OF FLUPREDNISOLONE & IN VIVO DISSOLUTION RATES OF PELLET IMPLANTS IN RATS.

The Chemical Society. Foreign Compound Metabolism in Mammals. Volume 2: A Review of the Literature Published Between 1970 and 1971. London: The Chemical Society, 1972., p. 423

CONJUGATED MOSTLY IN LIVER BUT ALSO IN KIDNEY /HUMAN, ORAL/.

American Society of Hospital Pharmacists. Data supplied on contract from American Hospital Formulary Service and other current ASHP sources., p. 1963

5.3 Mechanism of Action

Glucocorticoids are capable of suppressing the inflammatory process through numerous pathways. They interact with specific intracellular receptor proteins in target tissues to alter the expression of corticosteroid-responsive genes. Glucocorticoid-specific receptors in the cell cytoplasm bind with steroid ligands to form hormone-receptor complexes that eventually translocate to the cell nucleus. There these complexes bind to specific DNA sequences and alter their expression. The complexes may induce the transcription of mRNA leading to synthesis of new proteins. Such proteins include lipocortin, a protein known to inhibit PLA2a and thereby block the synthesis of prostaglandins, leukotrienes, and PAF. Glucocorticoids also inhibit the production of other mediators including AA metabolites such as COX, cytokines, the interleukins, adhesion molecules, and enzymes such as collagenase. /Glucocorticoids/

Kahn, C.M. (Ed.); The Merck Veterinary Manual 9th ed. Merck & Co. Whitehouse Station, NJ. 2005, p. 2128