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Details

Stereochemistry ABSOLUTE
Molecular Formula C24H31FO6
Molecular Weight 434.4977
Optical Activity UNSPECIFIED
Defined Stereocenters 8 / 8
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BETAMETHASONE ACETATE

SMILES

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

InChI

InChIKey=AKUJBENLRBOFTD-QZIXMDIESA-N
InChI=1S/C24H31FO6/c1-13-9-18-17-6-5-15-10-16(27)7-8-21(15,3)23(17,25)19(28)11-22(18,4)24(13,30)20(29)12-31-14(2)26/h7-8,10,13,17-19,28,30H,5-6,9,11-12H2,1-4H3/t13-,17-,18-,19-,21-,22-,23-,24-/m0/s1

HIDE SMILES / InChI

Molecular Formula C24H31FO6
Molecular Weight 434.4977
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

Betamethasone and its derivatives, betamethasone sodium phosphate and betamethasone acetate, are synthetic glucocorticoids. Used for its antiinflammatory or immunosuppressive properties, betamethasone is combined with a mineralocorticoid to manage adrenal insufficiency and is used in the form of betamethasone benzoate, betamethasone dipropionate, or betamethasone valerate for the treatment of inflammation due to corticosteroid-responsive dermatoses. Betamethasone and clotrimazole are used together to treat cutaneous tinea infections. Betamethasone is a glucocorticoid receptor agonist. This leads to changes in genetic expression once this complex binds to the GRE. The antiinflammatory actions of corticosteroids are thought to involve lipocortins, phospholipase A2 inhibitory proteins which, through inhibition arachidonic acid, control the biosynthesis of prostaglandins and leukotrienes. The immune system is suppressed by corticosteroids due to a decrease in the function of the lymphatic system, a reduction in immunoglobulin and complement concentrations, the precipitation of lymphocytopenia, and interference with antigen-antibody binding. Betamethasone binds to plasma transcortin, and it becomes active when it is not bound to transcortin.Betamethasone is used for: treating certain conditions associated with decreased adrenal gland function. It is used to treat severe inflammation caused by certain conditions, including severe asthma, severe allergies, rheumatoid arthritis, ulcerative colitis, certain blood disorders, lupus, multiple sclerosis, and certain eye and skin conditions.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
1.3 nM [EC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
CELESTONE SOLUSPAN
Primary
CELESTONE SOLUSPAN
Primary
CELESTONE SOLUSPAN
Primary
CELESTONE SOLUSPAN
Palliative
CELESTONE SOLUSPAN
Primary
CELESTONE SOLUSPAN

Cmax

ValueDoseCo-administeredAnalytePopulation
76.8 ng/mL
6 mg single, oral
BETAMETHASONE plasma
Homo sapiens
67.6 ng/mL
6 mg single, intramuscular
BETAMETHASONE plasma
Homo sapiens
101 ng/mL
8 mg single, intravenous
BETAMETHASONE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
796 ng × h/mL
6 mg single, oral
BETAMETHASONE plasma
Homo sapiens
811 ng × h/mL
6 mg single, intramuscular
BETAMETHASONE plasma
Homo sapiens
46.3 μg × min/mL
8 mg single, intravenous
BETAMETHASONE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
13.9 h
6 mg single, oral
BETAMETHASONE plasma
Homo sapiens
10.2 h
6 mg single, intramuscular
BETAMETHASONE plasma
Homo sapiens
335 min
8 mg single, intravenous
BETAMETHASONE plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
36%
8 mg single, intravenous
BETAMETHASONE plasma
Homo sapiens

Doses

Drug as perpetrator​

Drug as victim

Tox targets

PubMed

Sample Use Guides

In Vivo Use Guide
The initial dosage of parenterally administered Betamethasone Sodium Phosphate and Betamethasone Acetate Injectable Suspension may vary from 0.25 to 9 mg per day depending on the specific disease entity being treated. However, in certain overwhelming, acute, life-threatening situations, administrations in dosages exceeding the usual dosages may be justified and may be in multiples of the oral dosages. In the treatment of acute exacerbations of multiple sclerosis, daily doses of 30 mg of betamethasone for a week followed by 12 mg every other day for 1 month are recommended.In pediatric patients, the initial dose of betamethasone may vary depending on the specific disease entity being treated. The range of initial doses is 0.02 to 0.3 mg/kg/day in three or four divided doses (0.6 to 9 mg/m2bsa/day).
Route of Administration: Parenteral
In Vitro Use Guide
Betamethasone (10(-6)M) significantly reduced both pH 6-induced bronchial response and CGRP-like immunoreactivity overflow in guinea-pig isolated perfused lung.
Substance Class Chemical
Record UNII
TI05AO53L7
Record Status Validated (UNII)
Record Version