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Chemistry

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Also known as: 3093-35-4, Halciderm, Halcimat, Halog, Halcinonida, Sq 18566
Molecular Formula
C24H32ClFO5
Molecular Weight
455.0  g/mol
InChI Key
MUQNGPZZQDCDFT-JNQJZLCISA-N
FDA UNII
SI86V6QNEG

Halcinonide
A glucocorticoid used topically in the treatment of DERMATITIS; ECZEMA; or PSORIASIS. It may cause skin irritation.
Halcinonide is a Corticosteroid. The mechanism of action of halcinonide is as a Corticosteroid Hormone Receptor Agonist.
1 2D Structure

Halcinonide

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(1S,2S,4R,8S,9S,11S,12R,13S)-8-(2-chloroacetyl)-12-fluoro-11-hydroxy-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/C24H32ClFO5/c1-20(2)30-19-10-16-15-6-5-13-9-14(27)7-8-21(13,3)23(15,26)17(28)11-22(16,4)24(19,31-20)18(29)12-25/h9,15-17,19,28H,5-8,10-12H2,1-4H3/t15-,16-,17-,19+,21-,22-,23-,24+/m0/s1
2.1.3 InChI Key
MUQNGPZZQDCDFT-JNQJZLCISA-N
2.1.4 Canonical SMILES
CC1(OC2CC3C4CCC5=CC(=O)CCC5(C4(C(CC3(C2(O1)C(=O)CCl)C)O)F)C)C
2.1.5 Isomeric SMILES
C[C@]12CCC(=O)C=C1CC[C@@H]3[C@@]2([C@H](C[C@]4([C@H]3C[C@@H]5[C@]4(OC(O5)(C)C)C(=O)CCl)C)O)F
2.2 Other Identifiers
2.2.1 UNII
SI86V6QNEG
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Alcinonide

2. Dermalog

3. Halciderm

4. Halcimat

5. Halog

6. Sq 18,566

7. Sq-18,566

8. Sq18,566

2.3.2 Depositor-Supplied Synonyms

1. 3093-35-4

2. Halciderm

3. Halcimat

4. Halog

5. Halcinonida

6. Sq 18566

7. Si86v6qneg

8. Halcort

9. Sq-18566

10. Nsc-758413

11. So-18566

12. Dsstox_cid_25375

13. Dsstox_rid_80836

14. Dsstox_gsid_45375

15. (1s,2s,4r,8s,9s,11s,12r,13s)-8-(2-chloroacetyl)-12-fluoro-11-hydroxy-6,6,9,13-tetramethyl-5,7-dioxapentacyclo[10.8.0.02,9.04,8.013,18]icos-17-en-16-one

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

17. Sq-18,566

18. Betacorton

19. Halcinonidum

20. Halog-e

21. Ascochrom

22. Volog

23. (1s,2s,4r,8s,9s,11s,12r,13s)-8-(2-chloroacetyl)-12-fluoro-11-hydroxy-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

24. Unii-si86v6qneg

25. Halcinonidum [inn-latin]

26. Halcinonida [inn-spanish]

27. Ncgc00016621-01

28. (11?,16?)-21-chloro-9-fluoro-11-hydroxy-16,17-[(1-methylethylidene)bis(oxy)]-pregn-4-ene-3,20-dione

29. Cas-3093-35-4

30. Einecs 221-439-6

31. Prestwick_1069

32. Halog (tn)

33. Brn 1358242

34. Halcinonide [usan:usp:inn:ban:jan]

35. Halcinonide [mi]

36. Prestwick0_000655

37. Prestwick1_000655

38. Prestwick2_000655

39. Prestwick3_000655

40. Halcinonide [inn]

41. Halcinonide [jan]

42. Halcinonide [usan]

43. Halcinonide [vandf]

44. Schembl4335

45. Halcinonide [mart.]

46. Bspbio_000689

47. Halcinonide [usp-rs]

48. Halcinonide [who-dd]

49. 5-19-06-00301 (beilstein Handbook Reference)

50. Mls002153935

51. Halcinonide (jan/usp/inn)

52. Spbio_002610

53. Bpbio1_000759

54. Chembl1200845

55. Dtxsid6045375

56. Chebi:31663

57. Halcinonide [orange Book]

58. Hms1570c11

59. Hms2097c11

60. Hms2230o07

61. Hms3714c11

62. Halcinonide [usp Monograph]

63. 21-chloro-9-fluoro-11.beta.,16.alpha.,17-trihydroxypregn-4-ene-3,20-dione Cyclic 16,17-acetal With Acetone

64. Hy-b0877

65. Pregn-4-ene-3,20-dione, 21-chloro-9-fluoro-11-hydroxy-16,17-((1-methylethylidene)bis(oxy))-, (11.beta.,16.alpha.)-

66. Zinc4213474

67. Tox21_110530

68. S4098

69. Akos015962797

70. Tox21_110530_1

71. Ac-1114

72. Ac-1774

73. Ccg-220655

74. Db06786

75. Nsc 758413

76. N6-(trifluoroacetyl)-l-lysyl-l-proline

77. Ncgc00179475-01

78. Ncgc00179475-03

79. 21-chloro-9-fluoro-11beta,16alpha,17-trihydroxypregn-4-ene-3,20-dione Cyclic 16,17-acetal With Acetone

80. As-74757

81. Pregn-4-ene-3,20-dione, 21-chloro-9-fluoro-11-hydroxy-16,17-((1-methylethylidene)bis(oxy))-, (11beta,16alpha)-

82. Smr001233277

83. So 18566

84. H1672

85. C74589

86. D01308

87. 093h354

88. Q425991

89. Q-201180

90. Brd-k81709173-001-03-8

91. Halcinonide, United States Pharmacopeia (usp) Reference Standard

92. (1s,2s,4r,8s,9s,11s,12r,13s)-8-(2-chloroacetyl)-12-fluoro-11-hydroxy-6,6,9,13-tetramethyl-5,7-dioxapentacyclo[10.8.0.0(2),?.0?,?.0(1)(3),(1)?]icos-17-en-16-one

93. (4as,4br,5s,6as,6bs,9ar,10as,10bs)-6b-(chloroacetyl)-4b-fluoro-5-hydroxy-4a,6a,8,8-tetramethyl-3,4,4a,4b,5,6,6a,6b,9a,10,10a,10b,11,12-tetradecahydro-2h-naphtho[2',1':4,5]indeno[1,2-d][1,3]dioxol-2-one

94. Pregn-4-ene-3,20-dione, 21-chloro-9-fluoro-11-beta,16-alpha,17-trihydroxy-, Cyclic16,17-acetal With Acetone

95. Pregn-4-ene-3,20-dione,21-chloro-9-fluoro-11-hydroxy-16,17-[(1-methylethylidene)bis(oxy)]-,(11b,16a)-

2.4 Create Date
2005-06-24
3 Chemical and Physical Properties
Molecular Weight 455.0 g/mol
Molecular Formula C24H32ClFO5
XLogP33.6
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count6
Rotatable Bond Count2
Exact Mass454.1922300 g/mol
Monoisotopic Mass454.1922300 g/mol
Topological Polar Surface Area72.8 Ų
Heavy Atom Count31
Formal Charge0
Complexity887
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 NameHalog
PubMed HealthHalcinonide (Topical application route)
Drug ClassesAdrenal Glucocorticoid, Corticosteroid, Strong
Drug LabelThe topical corticosteroids constitute a class of primarily synthetic steroids used as anti-inflammatory and antipruritic agents. The steroids in this class include halcinonide. Halcinonide is designated chemically as 21-Chloro-9-fluoro-11, 16, 1...
Active IngredientHalcinonide
Dosage FormOintment; Cream
RouteTopical
Strength0.1%
Market StatusPrescription
CompanyRanbaxy

2 of 2  
Drug NameHalog
PubMed HealthHalcinonide (Topical application route)
Drug ClassesAdrenal Glucocorticoid, Corticosteroid, Strong
Drug LabelThe topical corticosteroids constitute a class of primarily synthetic steroids used as anti-inflammatory and antipruritic agents. The steroids in this class include halcinonide. Halcinonide is designated chemically as 21-Chloro-9-fluoro-11, 16, 1...
Active IngredientHalcinonide
Dosage FormOintment; Cream
RouteTopical
Strength0.1%
Market StatusPrescription
CompanyRanbaxy

4.2 Drug Indication

Indicated for the relief of the inflammatory and pruritic manifestations of corticosteroid-responsive dermatoses.


FDA Label


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.)


5.2 FDA Pharmacological Classification
5.2.1 Active Moiety
HALCINONIDE
5.2.2 FDA UNII
SI86V6QNEG
5.2.3 Pharmacological Classes
Corticosteroid [EPC]; Corticosteroid Hormone Receptor Agonists [MoA]
5.3 ATC Code

D - Dermatologicals

D07 - Corticosteroids, dermatological preparations

D07A - Corticosteroids, plain

D07AD - Corticosteroids, very potent (group iv)

D07AD02 - Halcinonide


5.4 Mechanism of Action

The precise mechanism of action of topical corticosteroids is unclear. However they possess anti-inflammatory, antipruritic, and vasoconstrictive actions. New research indicates that halcinonide activates MBP (myelin basic protein) expression via smoothened receptor activation. This finding suggests that halcinonide could be used in the treatment of multiple sclerosis therapy as an alternative to Dexamethasone or Methylprednisolone.


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