Beclomethasone
Basic information
- CAS
4419-39-0- Standard SMILES
C[C@H]1C[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@]4(C)[C@@]3(Cl)[C@@H](O)C[C@]2(C)[C@@]1(O)C(=O)CO- InChIKey
NBMKJKDGKREAPL-DVTGEIKXSA-N- Molecular formula
- C22H29ClO5
- Average molar mass
- 408.9 g/mol
- Monoisotopic mass
- 408.1703517
Overview
Beclomethasone is a 17alpha-hydroxy steroid that is prednisolone in which the hydrogens at the 9alpha and 16beta positions are substituted by a chlorine and a methyl group, respectively. It has a role as an anti-inflammatory drug and an anti-asthmatic drug. It is a primary alpha-hydroxy ketone, a tertiary alpha-hydroxy ketone, a glucocorticoid, a 17alpha-hydroxy steroid, a 21-hydroxy steroid, an 11beta-hydroxy steroid, a 20-oxo steroid, a corticosteroid, a 3-oxo-Delta(1),Delta(4)-steroid and a chlorinated steroid. It is functionally related to a prednisolone. It derives from a hydride of a pregnane.
Names & identifiers
- Preferred name
- Beclomethasone
- IUPAC
- (8S,9R,10S,11S,13S,14S,16S,17R)-9-chloro-11,17-dihydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-3-one
- English name
- BECLOMETHASONE
- Molecular formula
- C22H29ClO5
- Molecular weight
- 408.92
Names & synonyms
beclomethasoneBeclometasone4419-39-0BeclometasonaBeclometasonum9-Chloro-11beta,17,21-trihydroxy-16beta-methylpregna-1,4-diene-3,20-dioneBeclometasonDTXSID5040750KGZ1SLC28ZBMJ 5800(8S,9R,10S,11S,13S,14S,16S,17R)-9-chloro-11,17-dihydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-3-oneCHEBI:3001
Show more names
BecLBecolventomethasoneChloro methimazoleBecloMethasone SolutionBeclomethasone - 98% minBeclomethasone - 95% minBECLOMETHASONE USP/EP/BP
DTXCID3020750(11beta,16beta)-9-chloro-11,17,21-trihydroxy-16-methylpregna-1,4-diene-3,20-dioneAscocortonylBecodiskViarinJunik(8S,9R,10S,11S,13S,14S,16S,17R)-9-chloro-11,17-dihydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-6,7,8,11,12,14,15,16-octahydrocyclopenta(a)phenanthren-3-oneRefChem:54431
Properties
Computed structural properties
- XLogP
- 2.2
- Topological polar surface area
- 94.8 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 2
- Heavy atoms
- 28
- Formal charge
- 0
- Complexity
- 805
Experimental & physicochemical properties
Human DrugsAntiasthmatic and medicines for chronic obstructive pulmonary disease
Endocrine DisruptorsPotential endocrine disrupting compound
Collision Cross Section189.2 Ų [M+H]+ [CCS Type: TW]
Physicochemical properties
- Melting point
- 217 · 217- 222°C (dec.)
- Boiling point
- 600.2 · 600.2±55.0 °C(Predicted)
- Density
- 1.35 · 1.35±0.1 g/cm3(Predicted)
- storage temp.
- 2 · 2-8°C
- solubility
- Dioxane (Sparingly, Sonicated), DMSO (Sparingly), Ethyl Acetate (Slightly), Methane
- form
- Solid
- pka
- 12.17 · 12.17±0.70(Predicted)
- color
- White to Pale Beige
- Merck
- 13 · 13,1020
- Stability
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Danger
H317 (31.2%): May cause an allergic skin reaction [Warning Sensitization, Skin]
P203, P260, P261, P272, P280, P302+P352, P318, P319, P321, P333+P317, P362+P364, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 32 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory InformationREACH registered substance: Beclometasone (EC: 224-585-9)
Other Safety InformationIMAP assessments - Pregna-1,4-diene-3,20-dione, 9-chloro-11,17,21-trihydroxy-16-methyl-, (11.beta.,16.beta.)-: Human health tier I assessment
Hazard Classes and CategoriesSkin Sens. 1 (31.2%)
Toxicology
Drug Induced Liver Injury
Drug-Induced Liver Injury Severity and Toxicity (DILIst)
beclomethasone
DILI Negative
Topical,Respiratory (inhalation)
DOI:10.1016/j.drudis.2019.09.022
Safety data
- PPE
- Eyeshields, Gloves, type N95 (US)
- wgk
- 3
- hs_code
- 29372900
- Signal word
- Warning
- Symbol(GHS)
- GHS08
Chemistry & industry
Pharmacology
ATC Code
A07EA07
R - Respiratory system
D - Dermatologicals
R - Respiratory system
A - Alimentary tract and metabolism
QD - Dermatologicals
FDA Pharmacological Classification
KGZ1SLC28Z
BECLOMETHASONE
Established Pharmacologic Class [EPC] - Corticosteroid
Mechanisms of Action [MoA] - Corticosteroid Hormone Receptor Agonists
Beclomethasone is a Corticosteroid. The mechanism of action of beclomethasone is as a Corticosteroid Hormone Receptor Agonist.
MeSH Pharmacological Classification
Substances that reduce or suppress INFLAMMATION.
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.
Drugs that are used to treat asthma.
Uses & manufacturing
UsesUse (kg; approx.) in Germany (2009): >50
Applications
DescriptionBeclomethasone dipropionate is claimed to exert a topical effect on the lungs without significant systemic activity. It is used by inhalation, generally from a metered aerosol, for the prophylaxis of the symptoms of asthma.
UsesBeclomethasone has been used in MSMS (mass spectrometry) methods for the analysis of β-agonists, corticosteroids, chloramphenicol and penicillins. It has also been used to find the differential response of glucocorticoids in larval regeneration model.
Related reactions
2 records
Compound notes
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