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    Halobetasol Propionate

    ACTIVE PHARMA INGREDIENTS

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    2D Structure
    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 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

    2D Structure

    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]