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Details

Stereochemistry ABSOLUTE
Molecular Formula C22H29ClO5
Molecular Weight 408.916
Optical Activity UNSPECIFIED
Defined Stereocenters 8 / 8
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BECLOMETHASONE

SMILES

[H][C@@]12C[C@H](C)[C@](O)(C(=O)CO)[C@@]1(C)C[C@H](O)[C@@]3(Cl)[C@@]2([H])CCC4=CC(=O)C=C[C@]34C

InChI

InChIKey=NBMKJKDGKREAPL-DVTGEIKXSA-N
InChI=1S/C22H29ClO5/c1-12-8-16-15-5-4-13-9-14(25)6-7-19(13,2)21(15,23)17(26)10-20(16,3)22(12,28)18(27)11-24/h6-7,9,12,15-17,24,26,28H,4-5,8,10-11H2,1-3H3/t12-,15-,16-,17-,19-,20-,21-,22-/m0/s1

HIDE SMILES / InChI

Molecular Formula C22H29ClO5
Molecular Weight 408.916
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 8 / 8
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Beclometasone dipropionate or beclomethasone dipropionate is sold under the brand name Qvar among others. Beclomethasone dipropionate is a corticosteroid demonstrating potent anti-inflammatory activity. The precise mechanism of corticosteroid action on asthma is not known. Corticosteroids have been shown to have multiple anti-inflammatory effects, inhibiting both inflammatory cells (e.g., mast cells, eosinophils, basophils, lymphocytes, macrophages, and neutrophils) and release of inflammatory mediators (e.g., histamine, eicosanoids, leukotrienes, and cytokines). These anti-inflammatory actions of corticosteroids may contribute to their efficacy in asthma. Beclomethasone dipropionate is a prodrug that is rapidly activated by hydrolysis to the active monoester, 17 monopropionate (17-BMP). Beclomethasone 17 monopropionate has been shown in vitro to exhibit a binding affinity for the human glucocorticoid receptor, which is approximately 13 times that of dexamethasone, 6 times that of triamcinolone acetonide, 1.5 times that of budesonide and 25 times that of beclomethasone dipropionate. The clinical significance of these findings is unknown. Studies in patients with asthma have shown a favorable ratio between topical anti-inflammatory activity and systemic corticosteroid effects with recommended doses of QVAR. Beclometasone dipropionate was first patented in 1962 and used medically in 1972. Common side effects with the inhaled form include respiratory infections, headaches, and throat inflammation. Serious side effects include an increased risk of infection, cataracts, Cushing’s syndrome, and severe allergic reactions. Long term use of the pill form may cause adrenal insufficiency. The pills may also cause mood or personality changes. The inhaled form is generally regarded as safe in pregnancy. Beclometasone is mainly a glucocorticoid.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
QVAR® 40

Cmax

ValueDoseCo-administeredAnalytePopulation
3103.4 pg/mL
160 μg single, respiratory
BECLOMETHASONE plasma
Homo sapiens
6635.1 pg/mL
320 μg single, respiratory
BECLOMETHASONE plasma
Homo sapiens
88 pg/mL
320 μg single, respiratory
BECLOMETHASONE plasma
Homo sapiens
181.95 pg/mL
320 μg single, nasal
BECLOMETHASONE plasma
Homo sapiens
262.65 pg/mL
320 μg single, nasal
BECLOMETHASONE 17-MONOPROPIONATE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
283.5 pg × h/mL
160 μg single, respiratory
BECLOMETHASONE plasma
Homo sapiens
623.6 pg × h/mL
320 μg single, respiratory
BECLOMETHASONE plasma
Homo sapiens
88.23 pg × h/mL
320 μg single, nasal
BECLOMETHASONE plasma
Homo sapiens
1661.53 pg × h/mL
320 μg single, nasal
BECLOMETHASONE 17-MONOPROPIONATE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
0.57 h
160 μg single, respiratory
BECLOMETHASONE plasma
Homo sapiens
0.92 h
320 μg single, respiratory
BECLOMETHASONE plasma
Homo sapiens
0.278 h
320 μg single, nasal
BECLOMETHASONE plasma
Homo sapiens
4.457 h
320 μg single, nasal
BECLOMETHASONE 17-MONOPROPIONATE plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
13%
BECLOMETHASONE plasma
Homo sapiens

Doses

AEs

Drug as perpetrator​

Drug as victim

PubMed

Sample Use Guides

In Vivo Use Guide
Administer QVAR (beclomethasone dipropionate HFA 40 ug) by the orally inhaled route only. Patients should prime QVAR by actuating into the air twice before using for the first time or if QVAR has not been used for over 10 days.
Route of Administration: Other
In Vitro Use Guide
Incubation of challenged rings (bronchial rings from nonatopic humans) for 3 h with 3 x 10(-6) M beclomethasone dipropionate (BDP) restored the relaxant effect, suggesting reversal of beta(2)-AR pathway dysfunction.
Substance Class Chemical
Record UNII
KGZ1SLC28Z
Record Status Validated (UNII)
Record Version