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Also known as: Ulobetasol propionate, 66852-54-8, Ultravate, Miracorten, Halobetasol (propionate), Bmy-30056
Molecular Formula
C25H31ClF2O5
Molecular Weight
485.0  g/mol
InChI Key
BDSYKGHYMJNPAB-LICBFIPMSA-N
FDA UNII
91A0K1TY3Z

Halobetasol
Halobetasol Propionate is the propionate salt form of halobetasol, a synthetic corticosteroid with anti-inflammatory, antipruritic, and vasoconstrictor activities. Halobetasol, a topical steroid, diffuses across cell membranes to interact with cytoplasmic corticosteroid receptors located in both the dermal and intradermal cells, thereby activating gene expression of anti-inflammatory proteins mediated via corticosteroid receptor response element. Specifically, this agent induces phospholipase A2 inhibitory proteins, which inhibit the release of arachidonic acid, thereby inhibiting the biosynthesis of potent mediators of inflammation, such as prostaglandins and leukotrienes. As a result, halobetasol reduces edema, erythema, and pruritus through its cutaneous effects on vascular dilation and permeability.
1 2D Structure

Halobetasol

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
[(6S,8S,9R,10S,11S,13S,14S,16S,17R)-17-(2-chloroacetyl)-6,9-difluoro-11-hydroxy-10,13,16-trimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl] propanoate
2.1.2 InChI
InChI=1S/C25H31ClF2O5/c1-5-21(32)33-25(20(31)12-26)13(2)8-15-16-10-18(27)17-9-14(29)6-7-22(17,3)24(16,28)19(30)11-23(15,25)4/h6-7,9,13,15-16,18-19,30H,5,8,10-12H2,1-4H3/t13-,15-,16-,18-,19-,22-,23-,24-,25-/m0/s1
2.1.3 InChI Key
BDSYKGHYMJNPAB-LICBFIPMSA-N
2.1.4 Canonical SMILES
CCC(=O)OC1(C(CC2C1(CC(C3(C2CC(C4=CC(=O)C=CC43C)F)F)O)C)C)C(=O)CCl
2.1.5 Isomeric SMILES
CCC(=O)O[C@@]1([C@H](C[C@@H]2[C@@]1(C[C@@H]([C@]3([C@H]2C[C@@H](C4=CC(=O)C=C[C@@]43C)F)F)O)C)C)C(=O)CCl
2.2 Other Identifiers
2.2.1 UNII
91A0K1TY3Z
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 6 Alpha-fluoroclobetasol 17-propionate

2. 6-fluoroclobetasol 17-propionate

3. Cgp 14 458

4. Cgp 14458

5. Cgp-14458

6. Halobetasol

7. Ulobetasol

8. Ultravate

2.3.2 Depositor-Supplied Synonyms

1. Ulobetasol Propionate

2. 66852-54-8

3. Ultravate

4. Miracorten

5. Halobetasol (propionate)

6. Bmy-30056

7. Jemdel

8. Cgp-14458

9. Cgp-14,458

10. 91a0k1ty3z

11. Unii-91a0k1ty3z

12. Halobetasol Propionate [usan]

13. Ultravate (tn)

14. Ncgc00167451-01

15. Halobetasol Propionate [usan:usp]

16. [(6s,8s,9r,10s,11s,13s,14s,16s,17r)-17-(2-chloroacetyl)-6,9-difluoro-11-hydroxy-10,13,16-trimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl] Propanoate

17. Bmy 30056

18. Bryhali

19. Halobetasol-propionate

20. Bmy-30056;cgp-14458;ulobetasol Propionate

21. Dsstox_cid_26636

22. Dsstox_rid_81782

23. Dsstox_gsid_46636

24. Schembl33858

25. Halobetasol Propionate (usp)

26. Chembl1200908

27. Dtxsid6046636

28. Chebi:135782

29. Halobetasol Propionate [mi]

30. (6s,8s,9r,10s,11s,13s,14s,16s,17r)-17-(2-chloroacetyl)-6,9-difluoro-11-hydroxy-10,13,16-trimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3h-cyclopenta[a]phenanthren-17-yl Propionate

31. Hy-b0878

32. Zinc3920028

33. Tox21_112455

34. Mfcd00866013

35. S4089

36. Halobetasol Propionate [vandf]

37. Ulobetasol Propionate [mart.]

38. Akos025310143

39. Ulobetasol Propionate [who-dd]

40. Ccg-269585

41. Cs-4305

42. Halobetasol Propionate [usp-rs]

43. Ncgc00373230-02

44. 21-chloro-6alpha,9-difluoro-11beta,17-dihydroxy-16beta-methylpregna-1,4-diene-3,20-dione 17-propionate

45. Cas-66852-54-8

46. Halobetasol Propionate [orange Book]

47. Halobetasol Propionate [usp Monograph]

48. D04409

49. Duobrii Component Halobetasol Propionate

50. Ab01566925_01

51. Idp-118 Component Halobetasol Propionate

52. 852h548

53. Halobetasol Propionate Component Of Duobrii

54. Sr-01000942239

55. Sr-01000942239-1

56. (6alpha,11beta,16beta)-21-chloro-6,9-difluoro-11-hydroxy-16-methyl-17-(1-oxopropoxy)pregna-1,4-diene-3,20-dione

57. 21-chloro-6.alpha.,9-difluoro-11.beta.,17-dihydroxy-16.beta.-methylpregna-1,4-diene-3,20-dione 17-propionate

58. Pregna-1,4-diene-3,20-dione, 21-chloro-6,9-difluoro-11-hydroxy-16-methyl-17-(1-oxopropoxy)-, (6.alpha.,11.beta.,16.beta.)-

59. Pregna-1,4-diene-3,20-dione, 21-chloro-6,9-difluoro-11-hydroxy-16-methyl-17-(1-oxopropoxy)-, (6alpha,11beta,16beta)-

2.4 Create Date
2006-07-28
3 Chemical and Physical Properties
Molecular Weight 485.0 g/mol
Molecular Formula C25H31ClF2O5
XLogP33.7
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count7
Rotatable Bond Count5
Exact Mass484.1828081 g/mol
Monoisotopic Mass484.1828081 g/mol
Topological Polar Surface Area80.7 Ų
Heavy Atom Count33
Formal Charge0
Complexity964
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 2  
Drug NameHalobetasol propionate
Drug LabelHalonate Halobetasol Propionate Ointment, 0.05% contains halobetasol propionate, a synthetic corticosteroid for topical dermatological use. The corticosteroids constitute a class of primarily synthetic steroids used topically as an anti-inflammatory...
Active IngredientHalobetasol propionate
Dosage FormOintment; Cream
RouteTopical
Strength0.05%
Market StatusPrescription
CompanyTaro; Fougera Pharms; Perrigo; G And W Labs; Perrigo Israel

2 of 2  
Drug NameHalobetasol propionate
Drug LabelHalonate Halobetasol Propionate Ointment, 0.05% contains halobetasol propionate, a synthetic corticosteroid for topical dermatological use. The corticosteroids constitute a class of primarily synthetic steroids used topically as an anti-inflammatory...
Active IngredientHalobetasol propionate
Dosage FormOintment; Cream
RouteTopical
Strength0.05%
Market StatusPrescription
CompanyTaro; Fougera Pharms; Perrigo; G And W Labs; Perrigo Israel

5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

Vasoconstrictor Agents

Drugs used to cause constriction of the blood vessels. (See all compounds classified as Vasoconstrictor Agents.)


5.2 FDA Pharmacological Classification
5.2.1 Pharmacological Classes
Corticosteroid [EPC]; Corticosteroid Hormone Receptor Agonists [MoA]

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24-Feb-2021
25-Oct-2024
KGS
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DOSAGE - CREAM;TOPICAL - 0.05% **Federal Regi...DOSAGE - CREAM;TOPICAL - 0.05% **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

USFDA APPLICATION NUMBER - 19967

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DOSAGE - OINTMENT;TOPICAL - 0.05% **Federal R...DOSAGE - OINTMENT;TOPICAL - 0.05% **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

USFDA APPLICATION NUMBER - 19968

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DOSAGE - AEROSOL, FOAM;TOPICAL - 0.05%

USFDA APPLICATION NUMBER - 210566

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