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Halcinonide

Halcinonide

Synopsis, 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

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 Formula	C₂₄H₃₂ClFO₅
Molecular Weight	455.0 g/mol
XLogP3	3.6
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	2
Exact Mass	454.1922300 g/mol
Monoisotopic Mass	454.1922300 g/mol
Topological Polar Surface Area	72.8 Å²
Heavy Atom Count	31
Formal Charge	0
Complexity	887
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	Halog
PubMed Health	Halcinonide (Topical application route)
Drug Classes	Adrenal Glucocorticoid, Corticosteroid, Strong
Drug Label	The 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 Ingredient	Halcinonide
Dosage Form	Ointment; Cream
Route	Topical
Strength	0.1%
Market Status	Prescription
Company	Ranbaxy

2 of 2
Drug Name	Halog
PubMed Health	Halcinonide (Topical application route)
Drug Classes	Adrenal Glucocorticoid, Corticosteroid, Strong
Drug Label	The 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 Ingredient	Halcinonide
Dosage Form	Ointment; Cream
Route	Topical
Strength	0.1%
Market Status	Prescription
Company	Ranbaxy

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.