U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C22H29FO5
Molecular Weight 392.4611
Optical Activity UNSPECIFIED
Defined Stereocenters 8 / 8
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BETAMETHASONE

SMILES

C[C@H]1C[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O)C[C@]2(C)[C@@]1(O)C(=O)CO

InChI

InChIKey=UREBDLICKHMUKA-DVTGEIKXSA-N
InChI=1S/C22H29FO5/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 C22H29FO5
Molecular Weight 392.4611
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry
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

Targets

Primary TargetPharmacologyConditionPotency
1.3 nM [EC50]
Conditions
PubMed

PubMed

TitleDatePubMed
Treatment of psoriasis with a new combination of calcipotriol and betamethasone dipropionate: a flow cytometric study.
2001
A topical steroid without an antibiotic cures external otitis efficiently: a study in an animal model.
2001 Aug
Severe oral manifestations of chronic graft-vs.-host disease.
2001 Aug
The delivery of topical nasal sprays and drops to the middle meatus: a semiquantitative analysis.
2001 Aug
Single versus repeated-course antenatal corticosteroids: outcomes in singleton and multiple-gestation pregnancies.
2001 Aug
Most patients overdose on topical nasal corticosteroid drops: an accurate delivery device is required.
2001 Aug
Infantile acute hemorrhagic edema of the skin.
2001 Aug
Multiple courses of antenatal betamethasone and cognitive development of mice offspring.
2001 Aug
Differentiation between dexamethasone and betamethasone in a mixture using multiple mass spectrometry.
2001 Aug 10
Tocolytic magnesium sulfate toxicity and unexpected neonatal death.
2001 Jun
Lumbar facet joint synovial cyst: percutaneous treatment with steroid injections and distention--clinical and imaging follow-up in 12 patients.
2001 Oct
Use of antenatal steroids to counteract the negative effects of tracheal occlusion in the fetal lamb model.
2001 Oct
Antenatal corticosteroids-too much of a good thing?
2001 Oct 3
Single vs weekly courses of antenatal corticosteroids for women at risk of preterm delivery: A randomized controlled trial.
2001 Oct 3
Growth and development of children to 4 years of age after repeated antenatal steroid administration.
2001 Sep
Repeated antenatal corticosteroid treatments. Do they reduce neonatal morbidity?
2001 Sep
Effects of antiinflammatory drugs on migration of the rabbit corneal epithelium.
2001 Sep
Manipulation under anesthesia for frozen shoulder with and without steroid injection.
2001 Sep
Multiple courses of antenatal steroids: risks and benefits.
2001 Sep
Patents

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
Created
by admin
on Tue Mar 06 10:30:12 UTC 2018
Edited
by admin
on Tue Mar 06 10:30:12 UTC 2018
Record UNII
9842X06Q6M
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
BETAMETHASONE
EP   HSDB   INN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD   WHO-IP  
INN   USAN  
Official Name English
DEXAMETHASONE SPECIFIED IMPURITY B [EP]
Common Name English
VISUBETA
Code English
FLOSTERON
Common Name English
BETAMETHASONE [WHO-DD]
Common Name English
BETAMETHASONE [VANDF]
Common Name English
FLUBENISOLONE
Common Name English
BETAMETHASONE [JAN]
Common Name English
BETAMETHASONE ACETATE IMPURITY A [EP]
Common Name English
DEXAMETHASONE IMPURITY B [EP]
Common Name English
SCH-4831
Code English
BETAMETHASONE DIPROPIONATE IMPURITY A
Common Name English
BETAMETHASONE [HSDB]
Common Name English
BETAMETHASONE [EP]
Common Name English
RINDERON
Brand Name English
BETAMETHASONUM [WHO-IP LATIN]
Common Name English
SCH 4831
Code English
BETAMETHASONE [WHO-IP]
Common Name English
BETAMETHASONE [MART.]
Common Name English
CELESTONE
Brand Name English
BETAMETHASONE [MI]
Common Name English
BETAMETHASONE [USP-RS]
Common Name English
BETAMETHASONE [USAN]
Common Name English
NSC-39470
Code English
DESACORT-BETA
Common Name English
BETAMETHASONE [INN]
Common Name English
CELESTENE
Common Name English
PREGNA-1,4-DIENE-3,20-DIONE, 9-FLUORO-11,17,21-TRIHYDROXY-16-METHYL-, (11.BETA.,16.BETA.)-
Systematic Name English
9-FLUORO-11.BETA.,17,21-TRIHYDROXY-16.BETA.-METHYLPREGNA-1,4-DIENE-3,20-DIONE.
Common Name English
BETAMETHASONE [USP]
Common Name English
BETAMETHASONE [ORANGE BOOK]
Common Name English
Classification Tree Code System Code
WHO-VATC QS03BA03
Created by admin on Tue Mar 06 10:30:12 UTC 2018 , Edited by admin on Tue Mar 06 10:30:12 UTC 2018
CFR 21 CFR 524.1044D
Created by admin on Tue Mar 06 10:30:12 UTC 2018 , Edited by admin on Tue Mar 06 10:30:12 UTC 2018
CFR 21 CFR 524.1044I
Created by admin on Tue Mar 06 10:30:12 UTC 2018 , Edited by admin on Tue Mar 06 10:30:12 UTC 2018
WHO-ATC R03BA04
Created by admin on Tue Mar 06 10:30:12 UTC 2018 , Edited by admin on Tue Mar 06 10:30:12 UTC 2018
CFR 21 CFR 524.1044B
Created by admin on Tue Mar 06 10:30:12 UTC 2018 , Edited by admin on Tue Mar 06 10:30:12 UTC 2018
WHO-VATC QA07EA04
Created by admin on Tue Mar 06 10:30:12 UTC 2018 , Edited by admin on Tue Mar 06 10:30:12 UTC 2018
WHO-ATC D07AC01
Created by admin on Tue Mar 06 10:30:12 UTC 2018 , Edited by admin on Tue Mar 06 10:30:12 UTC 2018
NDF-RT N0000175576
Created by admin on Tue Mar 06 10:30:12 UTC 2018 , Edited by admin on Tue Mar 06 10:30:12 UTC 2018
WHO-VATC QD07BC01
Created by admin on Tue Mar 06 10:30:12 UTC 2018 , Edited by admin on Tue Mar 06 10:30:12 UTC 2018
WHO-ATC D07CC01
Created by admin on Tue Mar 06 10:30:12 UTC 2018 , Edited by admin on Tue Mar 06 10:30:12 UTC 2018
WHO-ATC S01BB04
Created by admin on Tue Mar 06 10:30:12 UTC 2018 , Edited by admin on Tue Mar 06 10:30:12 UTC 2018
WHO-VATC QD07CC01
Created by admin on Tue Mar 06 10:30:12 UTC 2018 , Edited by admin on Tue Mar 06 10:30:12 UTC 2018
NDF-RT N0000175450
Created by admin on Tue Mar 06 10:30:12 UTC 2018 , Edited by admin on Tue Mar 06 10:30:12 UTC 2018
WHO-VATC QR03BA04
Created by admin on Tue Mar 06 10:30:12 UTC 2018 , Edited by admin on Tue Mar 06 10:30:12 UTC 2018
WHO-ATC S01CA05
Created by admin on Tue Mar 06 10:30:12 UTC 2018 , Edited by admin on Tue Mar 06 10:30:12 UTC 2018
WHO-VATC QS02CA90
Created by admin on Tue Mar 06 10:30:12 UTC 2018 , Edited by admin on Tue Mar 06 10:30:12 UTC 2018
WHO-ATC S01CB04
Created by admin on Tue Mar 06 10:30:12 UTC 2018 , Edited by admin on Tue Mar 06 10:30:12 UTC 2018
WHO-ATC A07EA04
Created by admin on Tue Mar 06 10:30:12 UTC 2018 , Edited by admin on Tue Mar 06 10:30:12 UTC 2018
WHO-ESSENTIAL MEDICINES LIST 13.3
Created by admin on Tue Mar 06 10:30:12 UTC 2018 , Edited by admin on Tue Mar 06 10:30:12 UTC 2018
WHO-VATC QS01BA06
Created by admin on Tue Mar 06 10:30:12 UTC 2018 , Edited by admin on Tue Mar 06 10:30:12 UTC 2018
WHO-ATC H02AB01
Created by admin on Tue Mar 06 10:30:12 UTC 2018 , Edited by admin on Tue Mar 06 10:30:12 UTC 2018
WHO-ATC S01BA06
Created by admin on Tue Mar 06 10:30:12 UTC 2018 , Edited by admin on Tue Mar 06 10:30:12 UTC 2018
CFR 21 CFR 524.1044G
Created by admin on Tue Mar 06 10:30:12 UTC 2018 , Edited by admin on Tue Mar 06 10:30:12 UTC 2018
WHO-VATC QD07XC01
Created by admin on Tue Mar 06 10:30:12 UTC 2018 , Edited by admin on Tue Mar 06 10:30:12 UTC 2018
WHO-VATC QS01CB04
Created by admin on Tue Mar 06 10:30:12 UTC 2018 , Edited by admin on Tue Mar 06 10:30:12 UTC 2018
WHO-VATC QH02AB01
Created by admin on Tue Mar 06 10:30:12 UTC 2018 , Edited by admin on Tue Mar 06 10:30:12 UTC 2018
CFR 21 CFR 524.1044F
Created by admin on Tue Mar 06 10:30:12 UTC 2018 , Edited by admin on Tue Mar 06 10:30:12 UTC 2018
WHO-ATC R01AD06
Created by admin on Tue Mar 06 10:30:12 UTC 2018 , Edited by admin on Tue Mar 06 10:30:12 UTC 2018
WHO-ATC D07XC01
Created by admin on Tue Mar 06 10:30:12 UTC 2018 , Edited by admin on Tue Mar 06 10:30:12 UTC 2018
WHO-VATC QC05AA05
Created by admin on Tue Mar 06 10:30:12 UTC 2018 , Edited by admin on Tue Mar 06 10:30:12 UTC 2018
WHO-ATC S02BA07
Created by admin on Tue Mar 06 10:30:12 UTC 2018 , Edited by admin on Tue Mar 06 10:30:12 UTC 2018
WHO-VATC QS03CA06
Created by admin on Tue Mar 06 10:30:12 UTC 2018 , Edited by admin on Tue Mar 06 10:30:12 UTC 2018
WHO-ATC D07BC01
Created by admin on Tue Mar 06 10:30:12 UTC 2018 , Edited by admin on Tue Mar 06 10:30:12 UTC 2018
LIVERTOX 100
Created by admin on Tue Mar 06 10:30:12 UTC 2018 , Edited by admin on Tue Mar 06 10:30:12 UTC 2018
WHO-VATC QS01BB04
Created by admin on Tue Mar 06 10:30:12 UTC 2018 , Edited by admin on Tue Mar 06 10:30:12 UTC 2018
WHO-ATC S03CA06
Created by admin on Tue Mar 06 10:30:12 UTC 2018 , Edited by admin on Tue Mar 06 10:30:12 UTC 2018
WHO-ATC S03BA03
Created by admin on Tue Mar 06 10:30:12 UTC 2018 , Edited by admin on Tue Mar 06 10:30:12 UTC 2018
WHO-VATC QD07AC01
Created by admin on Tue Mar 06 10:30:12 UTC 2018 , Edited by admin on Tue Mar 06 10:30:12 UTC 2018
WHO-VATC QS01CA05
Created by admin on Tue Mar 06 10:30:12 UTC 2018 , Edited by admin on Tue Mar 06 10:30:12 UTC 2018
WHO-ATC C05AA05
Created by admin on Tue Mar 06 10:30:12 UTC 2018 , Edited by admin on Tue Mar 06 10:30:12 UTC 2018
WHO-VATC QR01AD06
Created by admin on Tue Mar 06 10:30:12 UTC 2018 , Edited by admin on Tue Mar 06 10:30:12 UTC 2018
WHO-VATC QS02BA07
Created by admin on Tue Mar 06 10:30:12 UTC 2018 , Edited by admin on Tue Mar 06 10:30:12 UTC 2018
Code System Code Type Description
RXCUI
1514
Created by admin on Tue Mar 06 10:30:12 UTC 2018 , Edited by admin on Tue Mar 06 10:30:12 UTC 2018
PRIMARY RxNorm
MERCK INDEX
M2452
Created by admin on Tue Mar 06 10:30:12 UTC 2018 , Edited by admin on Tue Mar 06 10:30:12 UTC 2018
PRIMARY Merck Index
MESH
D001623
Created by admin on Tue Mar 06 10:30:12 UTC 2018 , Edited by admin on Tue Mar 06 10:30:12 UTC 2018
PRIMARY
ChEMBL
CHEMBL632
Created by admin on Tue Mar 06 10:30:12 UTC 2018 , Edited by admin on Tue Mar 06 10:30:12 UTC 2018
PRIMARY
EVMPD
SUB05797MIG
Created by admin on Tue Mar 06 10:30:12 UTC 2018 , Edited by admin on Tue Mar 06 10:30:12 UTC 2018
PRIMARY
NCI_THESAURUS
C303
Created by admin on Tue Mar 06 10:30:12 UTC 2018 , Edited by admin on Tue Mar 06 10:30:12 UTC 2018
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
BETAMETHASONE
Created by admin on Tue Mar 06 10:30:12 UTC 2018 , Edited by admin on Tue Mar 06 10:30:12 UTC 2018
PRIMARY Description: A white or creamy white powder; odourless. Solubility: Practically insoluble in water; sparingly soluble in ethanol (~750 g/l) TS. Category: Adrenoglucocorticoid. Storage: Betamethasone should be kept in a tightly closed container, protected from light. Definition: Betamethasone contains not less than 96.0% and not more than 104.0% of C22H29FO5 calculated with reference to the dried substance.
WIKIPEDIA
BETAMETHASONE
Created by admin on Tue Mar 06 10:30:12 UTC 2018 , Edited by admin on Tue Mar 06 10:30:12 UTC 2018
PRIMARY
EPA CompTox
378-44-9
Created by admin on Tue Mar 06 10:30:12 UTC 2018 , Edited by admin on Tue Mar 06 10:30:12 UTC 2018
PRIMARY
HSDB
378-44-9
Created by admin on Tue Mar 06 10:30:12 UTC 2018 , Edited by admin on Tue Mar 06 10:30:12 UTC 2018
PRIMARY
LactMed
378-44-9
Created by admin on Tue Mar 06 10:30:12 UTC 2018 , Edited by admin on Tue Mar 06 10:30:12 UTC 2018
PRIMARY
PUBCHEM
9782
Created by admin on Tue Mar 06 10:30:12 UTC 2018 , Edited by admin on Tue Mar 06 10:30:12 UTC 2018
PRIMARY SWITZERF
INN
1045
Created by admin on Tue Mar 06 10:30:12 UTC 2018 , Edited by admin on Tue Mar 06 10:30:12 UTC 2018
PRIMARY
CAS
378-44-9
Created by admin on Tue Mar 06 10:30:12 UTC 2018 , Edited by admin on Tue Mar 06 10:30:12 UTC 2018
PRIMARY
DRUG BANK
DB00443
Created by admin on Tue Mar 06 10:30:12 UTC 2018 , Edited by admin on Tue Mar 06 10:30:12 UTC 2018
PRIMARY
ECHA (EC/EINECS)
206-825-4
Created by admin on Tue Mar 06 10:30:12 UTC 2018 , Edited by admin on Tue Mar 06 10:30:12 UTC 2018
PRIMARY
IUPHAR
7061
Created by admin on Tue Mar 06 10:30:12 UTC 2018 , Edited by admin on Tue Mar 06 10:30:12 UTC 2018
PRIMARY
Related Record Type Details
BASIS OF STRENGTH->SUBSTANCE
ASSAY (UV)
EP
BINDER -> LIGAND
BINDING
Related Record Type Details
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
PARENT -> IMPURITY
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
PARENT -> IMPURITY
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
Genotoxic
Related Record Type Details
ACTIVE MOIETY
http://apps.who.int/phint/pdf/b/Jb.6.1.56.pdf
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC