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    Chemistry

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    Also known as: Beclometasone dipropionate, 5534-09-8, Beclovent, Beconase, Vancenase, Sanasthmax
    Molecular Formula
    C28H37ClO7
    Molecular Weight
    521.0  g/mol
    InChI Key
    KUVIULQEHSCUHY-XYWKZLDCSA-N
    FDA UNII
    5B307S63B2
    Beclomethasone Dipropionate
    An anti-inflammatory, synthetic glucocorticoid. It is used topically as an anti-inflammatory agent and in aerosol form for the treatment of ASTHMA.
    1 2D Structure

    Beclomethasone Dipropionate

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    [2-[(8S,9R,10S,11S,13S,14S,16S,17R)-9-chloro-11-hydroxy-10,13,16-trimethyl-3-oxo-17-propanoyloxy-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl]-2-oxoethyl] propanoate
    2.1.2 InChI
    InChI=1S/C28H37ClO7/c1-6-23(33)35-15-22(32)28(36-24(34)7-2)16(3)12-20-19-9-8-17-13-18(30)10-11-25(17,4)27(19,29)21(31)14-26(20,28)5/h10-11,13,16,19-21,31H,6-9,12,14-15H2,1-5H3/t16-,19-,20-,21-,25-,26-,27-,28-/m0/s1
    2.1.3 InChI Key
    KUVIULQEHSCUHY-XYWKZLDCSA-N
    2.1.4 Canonical SMILES
    CCC(=O)OCC(=O)C1(C(CC2C1(CC(C3(C2CCC4=CC(=O)C=CC43C)Cl)O)C)C)OC(=O)CC
    2.1.5 Isomeric SMILES
    CCC(=O)OCC(=O)[C@]1([C@H](C[C@@H]2[C@@]1(C[C@@H]([C@]3([C@H]2CCC4=CC(=O)C=C[C@@]43C)Cl)O)C)C)OC(=O)CC
    2.2 Other Identifiers
    2.2.1 UNII
    5B307S63B2
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Aerobec

    2. Aerobec Forte

    3. Aldecin

    4. Apo-beclomethasone

    5. Ascocortonyl

    6. Asmabec Clickhaler

    7. Beclamet

    8. Beclazone

    9. Beclazone Easy Breathe

    10. Beclo Asma

    11. Beclo Azu

    12. Beclocort

    13. Becloforte

    14. Beclomet

    15. Beclometasone

    16. Beclomethasone

    17. Beclorhinol

    18. Becloturmant

    19. Beclovent

    20. Becodisk

    21. Becodisks

    22. Beconase

    23. Beconase Aq

    24. Becotide

    25. Bemedrex Easyhaler

    26. Bronchocort

    27. Dipropionate, Beclomethasone

    28. Ecobec

    29. Filair

    30. Filair Forte

    31. Junik

    32. Nasobec Aqueous

    33. Prolair

    34. Propaderm

    35. Qvar

    36. Respocort

    37. Sanasthmax

    38. Sanasthmyl

    39. Vancenase

    40. Vanceril

    41. Ventolair

    42. Viarin

    2.3.2 Depositor-Supplied Synonyms

    1. Beclometasone Dipropionate

    2. 5534-09-8

    3. Beclovent

    4. Beconase

    5. Vancenase

    6. Sanasthmax

    7. Beclazone

    8. Beclomet

    9. Vanceril

    10. Becloforte

    11. Beclorhinol

    12. Entyderma

    13. Korbutone

    14. Propaderm

    15. Sanasthmyl

    16. Aerobec

    17. Aldecin

    18. Qvar

    19. Beclacin

    20. Ventolair

    21. Viarox

    22. Propaderm Forte

    23. Rino-clenil

    24. Inalone R

    25. Clenil-a

    26. Beclometasone 17,21-dipropionate

    27. Qnasl

    28. Becotide

    29. Sch 18020w

    30. Beconase Aq

    31. Beclate

    32. Becodisks

    33. Benconase

    34. Chebi:3002

    35. (11beta,16beta)-9-chloro-11-hydroxy-16-methyl-17,21-bis(1-oxopropoxy)pregna-1,4-diene-3,20-dione

    36. Inalone O

    37. Sch 8020w

    38. Sgx-201

    39. Sgx-202

    40. Sgx-203

    41. Sch-18020w

    42. 9-chloro-11beta,17,21-trihydroxy-16beta-methylpregna-1,4-diene-3,20-dione 17,21-dipropionate

    43. 9-chloro-11beta-hydroxy-16beta-methylpregna-1,4-diene-3,20-dione 17,21-dipropionate

    44. 5b307s63b2

    45. Nsc-755901

    46. Becloturmant

    47. Respocort

    48. Belchlorhinol

    49. Sanasthymyl

    50. Anceron

    51. Becloval

    52. [2-[(8s,9r,10s,11s,13s,14s,16s,17r)-9-chloro-11-hydroxy-10,13,16-trimethyl-3-oxo-17-propanoyloxy-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl]-2-oxoethyl] Propanoate

    53. Pregna-1,4-diene-3,20-dione, 9-chloro-11-hydroxy-16-methyl-17,21-bis(1-oxopropoxy)-, (11.beta.,16.beta.)-

    54. Viarex

    55. Vancenase Aq

    56. Alanase

    57. Aldecina

    58. Aldecine

    59. Atomase

    60. Rhinosol

    61. Turbinal

    62. Clenil

    63. Spir

    64. Beclocort Nasel

    65. Beclomet Nasal

    66. Rhino Clenil

    67. (8s,9r,10s,11s,13s,14s,16s,17r)-9-chloro-11-hydroxy-10,13,16-trimethyl-3-oxo-17-[2-(propionyloxy)acetyl]-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3h-cyclopenta[a]phenanthren-17-yl Propionate

    68. 9-chloro-11.beta.,17,21-trihydroxy-16.beta.-methylpregna-1,4-diene-3,20-dione 17,21-dipropionate

    69. 9-chloro-16beta-methyl-11beta,17,21-trihydroxypregna-1,4-diene-3,20-dione 17,21-dipropionate

    70. Qvar 80

    71. Vanceril Double Strength

    72. Beconasol

    73. Inalone

    74. Menaderm

    75. Qvar 40

    76. Orbec

    77. Beclovent (tn)

    78. Ncgc00094596-03

    79. Beclomethasone Dipropionate [usan]

    80. Vanceril (tn)

    81. Beclazone 250

    82. Prestwick_990

    83. Einecs 226-886-0

    84. Kw-053

    85. Mfcd00135613

    86. Nasobec

    87. Orbeshield

    88. Topster

    89. Qnasl (tn)

    90. Clenil A

    91. Beclometasone Dipropionato

    92. Prestwick0_000855

    93. Prestwick1_000855

    94. Prestwick2_000855

    95. Prestwick3_000855

    96. Beclomethasone-dipropionate

    97. Schembl6890

    98. Dsstox_cid_28656

    99. Dsstox_rid_82926

    100. Propionic Acid Beclomethasone

    101. Dsstox_gsid_48730

    102. Bspbio_000869

    103. Mls002154034

    104. Spbio_002790

    105. Bpbio1_000957

    106. Gtpl5894

    107. Chembl1200500

    108. Dtxsid3048730

    109. Unii-5b307s63b2

    110. Beclomethasone Dipropionate (usp)

    111. Hms1570l11

    112. Hms2097l11

    113. Hms2235o23

    114. Hms3259h03

    115. Hms3714l11

    116. Beclometasone Dipropionate (jp17)

    117. Beclomethasone Dipropionate Anhydrous

    118. Zinc3938744

    119. Tox21_113168

    120. Hy-13571a

    121. S3078

    122. Akos015951275

    123. Ac-2159

    124. Ccg-220855

    125. Cs-1503

    126. Db00394

    127. Nc00610

    128. Nsc 755901

    129. Beclometasone Dipropionate [jan]

    130. Beclomethasone Dipropionate [mi]

    131. Beclomethasone Dipropionate [usan:usp]

    132. Ncgc00179392-01

    133. (11beta,16beta)-9-chloro-11-hydroxy-16-methyl-3,20-dioxopregna-1,4-diene-17,21-diyl Dipropanoate

    134. Cpd001233361

    135. Pregna-1,4-diene-3,20-dione, 9-chloro-11-hydroxy-16-methyl-17,21-bis(1-oxopropoxy)-, (11beta,16beta)-

    136. Pregna-1,4-diene-3,20-dione, 9-chloro-16-beta-methyl-11-beta,17,21-trihydroxy-, 17,21-dipropionate

    137. Smr001233361

    138. Beclometasone Dipropionate [who-dd]

    139. Beclometasone Dipropionate [who-ip]

    140. Beclometasone Dipropionate Anhydrous

    141. Beclomethasone 17,21-dipropionate

    142. Beclomethasone Dipropionate [vandf]

    143. Cas-5534-09-8

    144. Beclometasone Dipropionate, Anhydrous

    145. Beclomethasone 17,21-diproprionate

    146. Beclomethasone Dipropionate [usp-rs]

    147. Betamethasone Dipropionate Impurity E

    148. B4464

    149. C07813

    150. D00689

    151. D89082

    152. Beclometasone Dipropionate [ep Monograph]

    153. Beclometasoni Dipropionas [who-ip Latin]

    154. Beclomethasone Dipropionate [orange Book]

    155. 534b098

    156. Beclomethasone Dipropionate [usp Impurity]

    157. Beclomethasone Dipropionate [usp Monograph]

    158. Q421475

    159. Trimbow Component Beclomethasone Dipropionate

    160. Brd-k97810537-001-03-7

    161. Brd-k97810537-001-13-6

    162. Beclometasone Dipropionate, Anhydrous [ep Impurity]

    163. Beclomethasone Dipropionate, Analytical Standard, For Drug Analysis

    164. Beclometasone (beclomethasone) Dipropionate, British Pharmacopoeia (bp) Assay Standard

    165. Beclomethasone Dipropionate, Anhydrous, European Pharmacopoeia (ep) Reference Standard

    166. Beclomethasone Dipropionate, Pharmaceutical Secondary Standard; Certified Reference Material

    167. Beclomethasone Dipropionate, United States Pharmacopeia (usp) Reference Standard

    168. [(8s,9r,10s,11s,13s,14s,16s,17r)-9-chloro-11-hydroxy-10,13,16-trimethyl-3-oxo-17-(2-propanoyloxyacetyl)-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl] Propanoate

    169. 2-[(1r,2s,10s,11s,13s,14r,15s,17s)-1-chloro-17-hydroxy-2,13,15-trimethyl-5-oxo-14-(propanoyloxy)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,6-dien-14-yl]-2-oxoethyl Propanoate

    170. 9alpha-chloro-16beta-methyl-3,20-dioxo-1,4-pregnadiene-11beta,17,21-triol 17,21-dipropionate

    171. Beclometasone Dipropionate For Peak Identification, European Pharmacopoeia (ep) Reference Standard

    172. Beclometasone Dipropionate For System Suitability, European Pharmacopoeia (ep) Reference Standard

    2.4 Create Date
    2005-06-24
    3 Chemical and Physical Properties
    Molecular Weight 521.0 g/mol
    Molecular Formula C28H37ClO7
    XLogP33
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count7
    Rotatable Bond Count8
    Exact Mass520.2227812 g/mol
    Monoisotopic Mass520.2227812 g/mol
    Topological Polar Surface Area107 Ų
    Heavy Atom Count36
    Formal Charge0
    Complexity1050
    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 4  
    Drug NameQnasl
    PubMed HealthBeclomethasone
    Drug ClassesAnti-Inflammatory
    Drug LabelBeclomethasone dipropionate USP, the active component of QNASL Nasal Aerosol, is an anti-inflammatory steroid having the chemical name 9-chloro-11,17,21-trihydroxy-16-methylpregna-1,4-diene-3,20-dione 17, 21-dipropionate and the following chemica...
    Active IngredientBeclomethasone dipropionate
    Dosage FormAerosol, metered
    RouteNasal
    Strength0.08mg/actuation
    Market StatusPrescription
    CompanyTeva Branded Pharm

    2 of 4  
    Drug NameQvar 40
    Active IngredientBeclomethasone dipropionate
    Dosage FormAerosol, metered
    RouteInhalation
    Strength0.04mg/inh
    Market StatusPrescription
    CompanyTeva Branded Pharm

    3 of 4  
    Drug NameQnasl
    PubMed HealthBeclomethasone
    Drug ClassesAnti-Inflammatory
    Drug LabelBeclomethasone dipropionate USP, the active component of QNASL Nasal Aerosol, is an anti-inflammatory steroid having the chemical name 9-chloro-11,17,21-trihydroxy-16-methylpregna-1,4-diene-3,20-dione 17, 21-dipropionate and the following chemica...
    Active IngredientBeclomethasone dipropionate
    Dosage FormAerosol, metered
    RouteNasal
    Strength0.08mg/actuation
    Market StatusPrescription
    CompanyTeva Branded Pharm

    4 of 4  
    Drug NameQvar 40
    Active IngredientBeclomethasone dipropionate
    Dosage FormAerosol, metered
    RouteInhalation
    Strength0.04mg/inh
    Market StatusPrescription
    CompanyTeva Branded Pharm

    4.2 Drug Indication

    Indicated for oral inhalation use in the maintenance treatment of asthma as prophylactic therapy in patients 5 years of age and older. The aerosol form of beclomethasone diproprionate is not indicated for the relief of acute bronchospasm. Indicated for intranasal use to relieve the symptoms of seasonal or perennial allergic and nonallergic (vasomotor) rhinitis and prevent the recurrence of nasal polyps following surgical removal. Indicated for the relief of the inflammatory and pruritic manifestations of corticosteroid-responsive dermatoses in patients 13 years of age and older. Corticosteroid-responsive dermatoses include psoriasis, contact dermatitis (dermatitis venenata), atopic dermatitis (infantile eczema, allergic dermatitis), neurodermatitis (lichen simplex chronicus, lichen planus, eczema, eczematous dermatitis), intertrigo, dyshidroses (pompholyx), seborrheic dermatitis, exfoliative dermatitis, solar dermatitis, stasis dermatitis, and anogenital and senile pruritus.

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Inflammatory conditions, including asthma, dermatoses, and allergic rhinitis, involve the activation of cascades by inflammatory mediators. Inflammation is a primary defense mechanism and the homeostatic response of the immune system; however, a prolonged inflammatory response in certain disorders may lead to tissue damage, pain, and swelling. Beclomethasone dipropionate works by attenuating the inflammatory responses associated with asthma, allergic rhinitis, nasal polyps, and corticosteroid-responsive dermatoses. It suppresses the actions of inflammatory cells, such as mast cells, eosinophils, basophils, lymphocytes, macrophages, and neutrophils. It also inhibits the release of inflammatory mediators, such as histamine, eicosanoids, leukotrienes, and cytokines. Beclomethasone dipropionate is reported to exhibit potent topical activity while possessing low systemic effects. Beclomethasone dipropionate is a corticosteroid drug with anti-inflammatory and vasoconstrictive effects used to treat chronic inflammatory processes such as asthma, allergic rhinitis, corticosteroid-responsive dermatoses. When inhaled, it improves lung function, decreases airway hyper-reactivity, and reduces the severity of asthmatic symptoms. Although inhaled corticosteroids, including beclomethasone dipropionate, are reported to mainly act locally in the lungs, systemic effects such as disruption of hypothalamic-pituitary-adrenal (HPA) axis function, bone turnover, osteoporosis, and growth suppression may still be observed with chronic use or high dose administration. There were varying findings from clinical studies examining the effect of beclomethasone dipropionate on growth suppression in pediatric patients. It was shown to suppress the hypothalamo-pituitary-adrenal (HPA) axis in a dose-dependent manner. HPA axis is a central hormonal response system to stress and activation of HPA axis leads to the production of endogenous steroid hormone production. Long-term use of high-dose systemic corticosteroids, including those inhaled, was often associated with signs and symptoms of adrenal insufficiency when exposed to stress conditions, such as trauma, surgery, or infections. As corticosteroids work by suppressing the immune system, there may be an increased risk for developing infections. Cases of _Candida albicans_ infection of the mouth and throat have been reported with inhaled beclomethasone dipropionate therapy.

    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.)

    Anti-Asthmatic Agents

    Drugs that are used to treat asthma. (See all compounds classified as Anti-Asthmatic Agents.)

    5.3 FDA Pharmacological Classification
    5.3.1 Pharmacological Classes
    Corticosteroid [EPC]; Corticosteroid Hormone Receptor Agonists [MoA]
    5.4 Absorption, Distribution and Excretion

    Absorption

    Following oral inhalation of 320 mcg of beclomethasone dipropionate (BDP), the Cmax was 88 pg/mL and it was reached after 0.5 at post-administration. The mean Cmax of the major and most active metabolite, beclomethasone-17-monopropionate (17-BMP), was 1419 pg/mL at 0.7 hour post-dosing. In another pharmacokinetic study, the AUC of BDP and 17-BMP were 6660 and 6185 pgxh/mL, respectively. The Cmax was 35356 pg/mL for BDP and 2633 pg/mL for 17-BMP, and and the median time to reach these concentrations (Tmax) was 0.2 hours. In the same study, the AUC of 17-BMP following oral and intranasal administration were 10158 and 3660 pgxh/mL, respectively. The Cmax of 17-BMP following oral and intranasal administration were 703 and 310 pg/mL, respectively, and the Tmax was 4 hours. The total bioavailability of 17-BMP following oral and intranasal administration were 41% and 44%, respectively.

    Route of Elimination

    Regardless of the route of administration, beclomethasone dipropionate and its metabolites are predominantly excreted in the feces, with less than 10% of the drug and its metabolites being excreted in the urine.

    Volume of Distribution

    Following intravenous administration, the steady-state volume of distribution was 20 L for beclomethasone dipropionate and 424 L for the active metabolite, beclomethasone-17-monopropionate.

    Clearance

    Following intravenous administration, the clearance of beclomethasone dipropionate and 17-BMP were 150 L/h and 120 L/h, respectively.

    5.5 Metabolism/Metabolites

    During absorption, beclomethasone dipropionate is undergoes rapid and extensive hydrolysis mediated by esterases CYP3A to form beclomethasone-17-monopropionate (17-BMP), beclomethasone-21-monopropionate (21-BMP), and beclomethasone (BOH). 17-BMP is the major active metabolite with the most potent anti-inflammatory activity. About 95% of the total beclomethasone dipropionate administered via oral inhalation undergoes presystemic conversion to form 17-BMP in the lung.

    5.6 Biological Half-Life

    Following intravenous administration, the half life of beclomethasone dipropionate was 0.5 hours while the half life of the active metabolite 17-BMP was 2.7 hours. Following oral and intranasal administration, the half life of 17-BMP was 8.8 and 5.7 hours, respectively.

    5.7 Mechanism of Action

    Beclomethasone dipropionate is a corticosteroid and prodrug that is rapidly activated by hydrolysis to the active monoester, 17 monopropionate (17-BMP), which mediates anti-inflammatory actions. 17-BMP has been shown _in vitro_ to exhibit a binding affinity for the human glucocorticoid receptor which is approximately 13 times that of dexamethasone and 25 times that of beclomethasone dipropionate. Upon binding of the ligand, the glucocorticoid receptors dimerize and translocate into the nucleus, where they subsequently bind to glucocorticoid response elements (GRE) on glucocorticoid-responsive genes, leading to changes in transcription. There are several proposed mechanisms for the anti-inflammatory action of corticosteroids. Corticosteroids may work by increasing the transcription of genes coding for anti-inflammatory proteins, including lipocortin-1 and interleukin-10. Corticosteroids were also shown to inhibit the expression of multiple genes that encode pro-inflammatory factors, such as cytokines, chemokines, and adhesion molecules, that are activated during the chronic inflammatory process. This is thought to be due to the direct inhibitory interaction between activated glucocorticoid receptors and activated pro-inflammatory transcription factors, such as nuclear factor-kappa B and activator protein-1. Chronic inflammation is often characterized by enhanced expression of these transcription factors that bind to and activate coactivator molecules, which then acetylate core histones to switch on gene transcription to further amplify the inflammatory process. Corticosteroids suppress the multiple inflammatory gene expression by promoting histone deacetylation, resulting in tighter coiling of DNA and reduced access of transcription factors to their binding sites.

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    19-Jan-2021
    28-Oct-2024
    KGS
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