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
- External Links
- ChemSpider
- 10482269
- Predicted Properties
Property Value Source Water Solubility 0.00208 mg/mL ALOGPS logP 3.69 ALOGPS logP 4.43 Chemaxon logS -5.4 ALOGPS pKa (Strongest Acidic) 13.85 Chemaxon pKa (Strongest Basic) -3.3 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 5 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 106.97 Å2 Chemaxon Rotatable Bond Count 8 Chemaxon Refractivity 134.79 m3·mol-1 Chemaxon Polarizability 54.79 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 1 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon