Beclomethasone dipropionate monohydrateProduct ingredient for Beclomethasone dipropionate

Name
Beclomethasone dipropionate monohydrate
Drug Entry
Beclomethasone dipropionate

Beclomethasone dipropionate is a second-generation10 synthetic corticosteroid and diester of beclomethasone, which is structurally similar to dexamethasone.11 It is a prodrug of an active metabolite beclomethasone 17-monopropionate (17-BMP)1 which acts on the glucocorticoid receptor to mediates its therapeutic action. Beclomethasone dipropionate itself posesses weak glucocorticoid receptor binding affinity and is rapidly converted into 17-BMP upon administration.1 Formulations for oral inhalation, intranasal, and topical use are available for beclomethasone dipropionate. Beclomethasone dipropionate became first available in a pressurized metered-dose inhaler in 1972 and later in a dry powder inhaler and an aqueous nasal spray.1 Due to its anti-inflammatory, antipruritic, and anti-allergy properties, beclomethasone dipropionate is used in various inflammatory conditions, such as asthma, allergic rhinitis, and dermatoses to reduce symptoms. When inhaled, it is proposed that beclomethasone dipropionate remains active locally in the lung without causing significant side effects associated with systemic corticosteroids.8 Compared to earlier corticosteroids such as dexamethasone and prednisolone, beclomethasone dipropionate is reported to be less irritating to the nasal mucosa with a longer duration of action when administered intranasally.3

Accession Number
DBSALT001373
Structure
Synonyms
Beclometasone dipropionate monohydrate
UNII
4H7L9AI22I
CAS Number
77011-63-3
Weight
Average: 539.06
Monoisotopic: 538.2333459
Chemical Formula
C28H39ClO8
InChI Key
QHQJZIXSVLFOHD-LYRZEVDOSA-N
InChI
InChI=1S/C28H37ClO7.H2O/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;1H2/t16-,19-,20-,21-,25-,26-,27-,28-;/m0./s1
IUPAC Name
2-[(1R,2S,10S,11S,13S,14R,15S,17S)-1-chloro-17-hydroxy-2,13,15-trimethyl-5-oxo-14-(propanoyloxy)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-3,6-dien-14-yl]-2-oxoethyl propanoate hydrate
SMILES
O.[H][C@]1(C)C[C@@]2([H])[C@]3([H])CCC4=CC(=O)C=C[C@]4(C)[C@@]3(Cl)[C@@]([H])(O)C[C@]2(C)[C@@]1(OC(=O)CC)C(=O)COC(=O)CC
ChemSpider
10482269
Predicted Properties
PropertyValueSource
Water Solubility0.00208 mg/mLALOGPS
logP3.69ALOGPS
logP4.43Chemaxon
logS-5.4ALOGPS
pKa (Strongest Acidic)13.85Chemaxon
pKa (Strongest Basic)-3.3Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area106.97 Å2Chemaxon
Rotatable Bond Count8Chemaxon
Refractivity134.79 m3·mol-1Chemaxon
Polarizability54.79 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon