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Chemistry

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Also known as: Fludroxycortide, Flurandrenolone, 1524-88-5, Cordran, Fluorandrenolone, Haelan
Molecular Formula
C24H33FO6
Molecular Weight
436.5  g/mol
InChI Key
POPFMWWJOGLOIF-XWCQMRHXSA-N
FDA UNII
8EUL29XUQT

Flurandrenolone
A corticosteroid used topically in the treatment of various skin disorders. It is usually employed as a cream or an ointment, and is also used as a polyethylene tape with an adhesive. (From Martindale, The Extra Pharmacopoeia, 30th ed, p733)
Flurandrenolide is a Corticosteroid. The mechanism of action of flurandrenolide is as a Corticosteroid Hormone Receptor Agonist.
1 2D Structure

Flurandrenolone

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(1S,2S,4R,8S,9S,11S,12S,13R,19S)-19-fluoro-11-hydroxy-8-(2-hydroxyacetyl)-6,6,9,13-tetramethyl-5,7-dioxapentacyclo[10.8.0.02,9.04,8.013,18]icos-17-en-16-one
2.1.2 InChI
InChI=1S/C24H33FO6/c1-21(2)30-19-9-14-13-8-16(25)15-7-12(27)5-6-22(15,3)20(13)17(28)10-23(14,4)24(19,31-21)18(29)11-26/h7,13-14,16-17,19-20,26,28H,5-6,8-11H2,1-4H3/t13-,14-,16-,17-,19+,20+,22-,23-,24+/m0/s1
2.1.3 InChI Key
POPFMWWJOGLOIF-XWCQMRHXSA-N
2.1.4 Canonical SMILES
CC1(OC2CC3C4CC(C5=CC(=O)CCC5(C4C(CC3(C2(O1)C(=O)CO)C)O)C)F)C
2.1.5 Isomeric SMILES
C[C@]12CCC(=O)C=C1[C@H](C[C@@H]3[C@@H]2[C@H](C[C@]4([C@H]3C[C@@H]5[C@]4(OC(O5)(C)C)C(=O)CO)C)O)F
2.2 Other Identifiers
2.2.1 UNII
8EUL29XUQT
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Cordran

2. Flurandrenolone

3. Haelan

2.3.2 Depositor-Supplied Synonyms

1. Fludroxycortide

2. Flurandrenolone

3. 1524-88-5

4. Cordran

5. Fluorandrenolone

6. Haelan

7. Fludroxicortidum

8. Flurandrenolone Acetonide

9. Fluorandrenolone Acetonide

10. Fludrossicortide [dcit]

11. Fludroxycortidum [inn-latin]

12. Fludroxicortida [inn-spanish]

13. Drenison

14. Drocort

15. Sermaka

16. Haldrone-f

17. Alondra-f

18. Fludroxicortide

19. Fludroxycortide [inn]

20. 8eul29xuqt

21. Mls000069556

22. Mls001148136

23. Nsc-757869

24. Fludroxicortida

25. Smr000058825

26. Floudroxycortide

27. Fludrossicortide

28. Fludroxycortidum

29. Cordran Sp

30. Flurandrenolide 100 Microg/ml In Acetonitrile

31. Flurandrenolide [usan]

32. L 33379

33. Dsstox_cid_27434

34. Dsstox_rid_82344

35. Dsstox_gsid_47434

36. (2s,6ar,6bs,7s,8as,8bs,11ar,12as,12bs)-2-fluoro-7-hydroxy-8b-(2-hydroxyacetyl)-6a,8a,10,10-tetramethyl-5,6,6a,6b,7,8,8a,8b,11a,12,12a,12b-dodecahydro-1h-naphtho[2',1':4,5]indeno[1,2-d][1,3]dioxol-4(2h)-one

37. Hsdb 3084

38. Flurandrenolide (usp)

39. Cordran (tn)

40. Einecs 216-196-8

41. Unii-8eul29xuqt

42. Fludroxycortide (jan/inn)

43. Fludroxycortid

44. Flurandrenolide [usan:usp]

45. Acetonide Of 6alpha-fluoro-16alpha-hydroxyhydrocortisone

46. 6alpha-fluoro-16alpha-hydroxyhydrocortisone 16,17-acetonide

47. Ncgc00016586-01

48. (6?,11?,16?)-6-fluoro-11,21-dihydroxy-16,17-[(1-methylethylidene)bis(oxy)]-pregn-4-ene-3,20-dione

49. Cas-1524-88-5

50. Prestwick_1065

51. 6alpha-fluoro-11beta,16alpha,17,21-tetrahydroxyprogesterone Cyclic 16,17-acetal With Acetone

52. 6alpha-fluoro-11beta,16alpha,17,21-tetrahydroxypregn-4-ene-3,20-dione, Cyclic 16,17-acetal With Acetone

53. Pregn-4-ene-3,20-dione, 6-fluoro-11,21-dihydroxy-16,17-((1-methylethylidene)bis(oxy))-, (6alpha,11beta,16alpha)-

54. Pregn-4-ene-3,20-dione, 6alpha-fluoro-11beta,16alpha,17,21-tetrahydroxy-, Cyclic 16,17-acetal With Acetone

55. Opera_id_1618

56. Prestwick0_000645

57. Prestwick1_000645

58. Prestwick2_000645

59. Prestwick3_000645

60. Schembl4694

61. Flurandrenolide [mi]

62. Bspbio_000649

63. Fludroxycortide [jan]

64. Pregn-4-ene-3,20-dione, 6-alpha-fluoro-11-beta,16-alpha,17,21-tetrahydroxy-, Cyclic 16,17-acetal With Acetone

65. Flurandrenolide [hsdb]

66. Spbio_002570

67. Flurandrenolide [vandf]

68. Bpbio1_000715

69. Chebi:5127

70. Gtpl7606

71. Fludroxycortide [mart.]

72. Chembl1201012

73. Dtxsid2047434

74. Fludroxycortide [who-dd]

75. Flurandrenolide [usp-rs]

76. Hms1570a11

77. Hms2097a11

78. Hms2233c04

79. Hms3714a11

80. 6.alpha.-fluoro-11.beta.,16.alpha.,17,21-tetrahydroxypregn-4-ene-3,20-dione, Cyclic 16,17-acetal With Acetone

81. Hy-b1013

82. Pregn-4-ene-3,20-dione, 6-fluoro-11,21-dihydroxy-16,17-((1-methylethylidene)bis(oxy))-, (6.alpha.,11.beta.,16.alpha.)-

83. Zinc4097308

84. Tox21_110509

85. Tox21_302611

86. Flurandrenolide [orange Book]

87. Tox21_110509_1

88. Ccg-220645

89. Cs-4526

90. Db00846

91. Flurandrenolide [usp Monograph]

92. Nsc 757869

93. Ncgc00023234-03

94. Ncgc00023234-05

95. Ncgc00256709-01

96. Cordran-n Component Flurandrenolide

97. Flurandrenolide Component Of Cordran-n

98. D00328

99. 524f885

100. Sr-01000003119

101. Q5462632

102. Sr-01000003119-3

103. W-108052

104. Brd-k00824317-001-03-0

105. (1s,2s,4r,8s,9s,11s,12s,13r,19s)-19-fluoro-11-hydroxy-8-(2-hydroxyacetyl)-6,6,9,13-tetramethyl-5,7-dioxapentacyclo[10.8.0.0^{2,9}.0^{4,8}.0^{13,18}]icos-17-en-16-one

106. (1s,2s,4r,8s,9s,11s,12s,13r,19s)-19-fluoro-11-hydroxy-8-(2-hydroxyacetyl)-6,6,9,13-tetramethyl-5,7-dioxapentacyclo[10.8.0.02,9.04,8.013,18]icos-17-en-16-one

107. (4r,8s,9s,11s,13r,19s)-19-fluoro-11-hydroxy-8-(2-hydroxyacetyl)-6,6,9,13-tetramethyl-5,7-dioxapentacyclo[10.8.0.02,9.04,8.013,18]icos-17-en-16-one

2.4 Create Date
2005-06-24
3 Chemical and Physical Properties
Molecular Weight 436.5 g/mol
Molecular Formula C24H33FO6
XLogP31.4
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count7
Rotatable Bond Count2
Exact Mass436.22611693 g/mol
Monoisotopic Mass436.22611693 g/mol
Topological Polar Surface Area93.1 Ų
Heavy Atom Count31
Formal Charge0
Complexity868
Isotope Atom Count0
Defined Atom Stereocenter Count9
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 4  
Drug NameCordran
PubMed HealthFlurandrenolide (On the skin)
Drug ClassesCorticosteroid, Strong
Drug LabelCordran Tape (Flurandrenolide Tape, USP) is a transparent, inconspicuous, plastic surgical tape, impervious to moisture. It contains Cordran (Flurandrenolide, USP), a potent corticosteroid for topical use. Flurandrenolide occurs as white to off-white...
Active IngredientFlurandrenolide
Dosage FormLotion; Tape
RouteTopical
Strength0.05%; 0.004mg/sq cm
Market StatusPrescription
CompanyWatson Pharms; Aqua Pharms

2 of 4  
Drug NameCordran sp
PubMed HealthFlurandrenolide (On the skin)
Drug ClassesCorticosteroid, Strong
Active IngredientFlurandrenolide
Dosage FormCream
RouteTopical
Strength0.05%; 0.025%
Market StatusPrescription
CompanyAqua Pharms

3 of 4  
Drug NameCordran
PubMed HealthFlurandrenolide (On the skin)
Drug ClassesCorticosteroid, Strong
Drug LabelCordran Tape (Flurandrenolide Tape, USP) is a transparent, inconspicuous, plastic surgical tape, impervious to moisture. It contains Cordran (Flurandrenolide, USP), a potent corticosteroid for topical use. Flurandrenolide occurs as white to off-white...
Active IngredientFlurandrenolide
Dosage FormLotion; Tape
RouteTopical
Strength0.05%; 0.004mg/sq cm
Market StatusPrescription
CompanyWatson Pharms; Aqua Pharms

4 of 4  
Drug NameCordran sp
PubMed HealthFlurandrenolide (On the skin)
Drug ClassesCorticosteroid, Strong
Active IngredientFlurandrenolide
Dosage FormCream
RouteTopical
Strength0.05%; 0.025%
Market StatusPrescription
CompanyAqua Pharms

4.2 Therapeutic Uses

Glucocorticoids, Synthetic; Glucocorticoids, Topical

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


Topical corticosteroids of low to medium potency are indicated in the treatment of corticosteroid-responsive dermatologic disorders /mild to moderate atopic dermatitis; contact dermatitis; mild nummular dermatitis; seborrheic dermatitis (facial and intertriginous areas); other mild to moderate forms of dermatitis; other mild to moderate inflammatory dermatoses; intertrigo; lichen planus (facial and intertriginous areas); discoid lupus erythematosus (facial and intertriginous areas); polymorphous light eruption; anogenital pruritus; pruritus senilis; psoriasis (facial and intertriginous areas); xerosis (inflammatory phase/. Occlusive dressings also may be required for chronic or severe cases of lichen simplex chronicus, psoriasis, eczema, atopic dermatitis, or chronic hand eczema. The more potent topical corticosteroids and/or occlusive dressings may be required for conditions such as discoid lupus erythematosus, lichen planus, granuloma annulare, psoriatic plaques, and psoriasis affecting the palms, soles, elbows, or knees. /Corticosteroids (topical); Included in US product labeling/

Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2007., p. 918


Flurandrenolide shares the actions of the other topical corticosteroids and is used for the relief of the inflammatory manifestations of corticosteroid-responsive dermatoses.

McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2007., p. 3531


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


4.3 Drug Warning

VET: AVOID COVERING OVER 5-10% OF BODY SURFACE, ESP IN PREGNANT ANIMALS.

Rossoff, I.S. Handbook of Veterinary Drugs. New York: Springer Publishing Company, 1974., p. 225


The following may occur more frequently with occlusive dressings: Maceration of the skin, Secondary infection, Skin atrophy, Striae Miliaria. /Topical corticosteroids/

Prescribing Information for Cordran (Flurandrenolide); Aqua Pharmaceuticals; 2006. Available from, as of November 18, 2007: https://www.aquapharm.com/prod_cordran.html


The following local adverse reactions are reported infrequently with topical corticosteroids but may occur more frequently with the use of occlusive dressings. These reactions are listed in an approximate decreasing order of occurrence: Burning, Itching, Irritation, Dryness, Folliculitis, Hypertrichosis, Acneform eruptions, Hypopigmentation, Perioral dermatitis, Allergic contact dermatitis. /Topical corticosteroids/

Prescribing Information for Cordran (Flurandrenolide); Aqua Pharmaceuticals; 2006. Available from, as of November 18, 2007: https://www.aquapharm.com/prod_cordran.html


Pediatric patients may demonstrate greater susceptibility to topical corticosteroid-induced HPA axis suppression and Cushing's syndrome than do mature patients because of a larger skin surface area to body weight ratio. Hypothalamic-pituitary-adrenal (HPA) axis suppression, Cushing's syndrome, and intracranial hypertension have been reported in pediatric patients receiving topical corticosteroids. Manifestations of adrenal suppression in pediatric patients include linear growth retardation, delayed weight gain, low plasma cortisol levels, and absence of response to ACTH stimulation. Manifestations of intracranial hypertension include bulging fontanelles, headaches, and bilateral papilledema. Administration of topical corticosteroids to pediatric patients should be limited to the least amount compatible with an effective therapeutic regimen. Chronic corticosteroid therapy may interfere with the growth and development of pediatric patients. /Topical corticosteroids/

Prescribing Information for Cordran (Flurandrenolide); Aqua Pharmaceuticals; 2006. Available from, as of November 18, 2007: https://www.aquapharm.com/prod_cordran.html


For more Drug Warnings (Complete) data for FLURANDRENOLIDE (36 total), please visit the HSDB record page.


4.4 Drug Indication

For relief of the inflammatory and pruritic manifestations of corticosteroid-responsive dermatoses, particularly dry, scaling localized lesions


5 Pharmacology and Biochemistry
5.1 Pharmacology

Flurandrenolide is primarily effective because of its anti-inflammatory, antipruritic, and vasoconstrictive actions.


5.2 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.)


5.3 FDA Pharmacological Classification
5.3.1 Active Moiety
FLURANDRENOLIDE
5.3.2 FDA UNII
8EUL29XUQT
5.3.3 Pharmacological Classes
Corticosteroid [EPC]; Corticosteroid Hormone Receptor Agonists [MoA]
5.4 ATC Code

D - Dermatologicals

D07 - Corticosteroids, dermatological preparations

D07A - Corticosteroids, plain

D07AC - Corticosteroids, potent (group iii)

D07AC07 - Fludroxycortide


5.5 Absorption, Distribution and Excretion

Absorption

Once absorbed through the skin, topical corticosteroids are handled through pharmacokinetic pathways similar to those of systemically administered corticosteroids


Route of Elimination

Topical corticosteroids can be absorbed from normal intact skin. They are metabolized primarily in the liver and then excreted in the kidneys. Some of the topical corticosteroids and their metabolites are also excreted into the bile.


Topical corticosteroids can be absorbed from normal intact skin. Inflammation and/or other disease processes in the skin increase percutaneous absorption. ... Once absorbed through the skin, topical corticosteroids are handled through pharmacokinetic pathways similar to systemically administered corticosteroids. Corticosteroids are bound to plasma proteins in varying degrees. They are metabolized primarily in the liver and then excreted in the kidneys. Some of the topical corticosteroids and their metabolites are also excreted into the bile. /Topical corticosteroids/

Prescribing Information for Cordran (Flurandrenolide); Aqua Pharmaceuticals; 2006. Available from, as of November 18, 2007: https://www.aquapharm.com/prod_cordran.html


5.6 Metabolism/Metabolites

Primarily hepatic


/Topical corticosteroids/ are metabolized primarily in the liver and then excreted in the kidneys. Some of the topical corticosteroids and their metabolites are also excreted into the bile. /Topical corticosteroids/

Prescribing Information for Cordran (Flurandrenolide); Aqua Pharmaceuticals; 2006. Available from, as of November 18, 2007: https://www.aquapharm.com/prod_cordran.html


5.7 Mechanism of Action

Flurandrenolide is a topical corticosteroid. It is normally applied to a plastic tape called Cordran. Cordran is primarily effective because of its anti-inflammatory, antipruritic, and vasoconstrictive actions. Flurandrenolide, which is slowly released from the Cordran tape, binds to the cytosolic glucocorticoid receptor. After binding the receptor the newly formed receptor-ligand complex translocates itself into the cell nucleus, where it binds to many glucocorticoid response elements (GRE) in the promoter region of the target genes. The DNA bound receptor then interacts with basic transcription factors, causing the increase in expression of specific target genes. The anti-inflammatory actions of corticosteroids are thought to involve lipocortins, phospholipase A2 inhibitory proteins which, through inhibition arachidonic acid, control the biosynthesis of prostaglandins and leukotrienes. Specifically glucocorticoids induce lipocortin-1 (annexin-1) synthesis, which then binds to cell membranes preventing the phospholipase A2 from coming into contact with its substrate arachidonic acid. This leads to diminished eicosanoid production. Cyclooxygenase (both COX-1 and COX-2) expression is also suppressed, potentiating the effect. In another words, the two main products in inflammation Prostaglandins and Leukotrienes are inhibited by the action of Glucocorticoids. Glucocorticoids also stimulate the lipocortin-1 escaping to the extracellular space, where it binds to the leukocyte membrane receptors and inhibits various inflammatory events: epithelial adhesion, emigration, chemotaxis, phagocytosis, respiratory burst and the release of various inflammatory mediators (lysosomal enzymes, cytokines, tissue plasminogen activator, chemokines etc.) from neutrophils, macrophages and mastocytes. Additionally the immune system is suppressed by corticosteroids due to a decrease in the function of the lymphatic system, a reduction in immunoglobulin and complement concentrations, the precipitation of lymphocytopenia, and interference with antigen-antibody binding. Like other glucocorticoid agents Fluocinolone acetonide acts as a physiological antagonist to insulin by decreasing glycogenesis (formation of glycogen). It also promotes the breakdown of lipids (lipolysis), and proteins, leading to the mobilization of extrahepatic amino acids and ketone bodies. This leads to increased circulating glucose concentrations (in the blood). There is also decreased glycogen formation in the liver.


The mechanism of the anti-inflammatory effect of topical corticosteroids is not completely understood. Various laboratory methods, including vasoconstrictor assays, are used to compare and predict potencies and/or clinical efficacies of the topical corticosteroids. There is some evidence to suggest that a recognizable correlation exists between vasoconstrictor potency and therapeutic efficacy in man. Corticosteroids with antiinflammatory activity may stabilize cellular and lysosomal membranes. There is also the suggestion that the effect on the membranes of lysosomes prevents the release of proteolytic enzymes and, thus, plays a part in reducing inflammation. /Topical corticosteroids/

Prescribing Information for Cordran (Flurandrenolide); Aqua Pharmaceuticals; 2006. Available from, as of November 18, 2007: https://www.aquapharm.com/prod_cordran.html


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


Corticosteroids diffuse across cell membranes and complex with specific cytoplasmic receptors. These complexes then enter the cell nucleus, bind to DNA (chromatin), and stimulate transcription of messenger RNA (mRNA) and subsequent protein synthesis of various inhibitory enzymes responsible for the anti-inflammatory effects of topical corticosteroids. These anti-inflammatory effects include inhibition of early processes such as edema, fibrin deposition, capillary dilatation, movement of phagocttes into the area, and phagocytic activities. Later processes, such as capillary production, collagen deposition, and keloid formation also are inhibited by corticosteroids. The overall actions of topical corticosteroids are catabolic. /Corticosteroids (topical)/

Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2007., p. 919


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DOSAGE - LOTION;TOPICAL - 0.05%

USFDA APPLICATION NUMBER - 13790

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DOSAGE - TAPE;TOPICAL - 0.004MG/SQ CM

USFDA APPLICATION NUMBER - 16455

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