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

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
Case report: sexual intercourse as potential treatment for intractable hiccups.
2000 Aug
Treatment of psoriasis with a new combination of calcipotriol and betamethasone dipropionate: a flow cytometric study.
2001
Effects of endogenous and exogenous glucocorticoids on liver differentiation.
2001
Clinical experience with topical calcitriol (1,25-dihydroxyvitamin D3) in psoriasis.
2001 Apr
[Analysis of selected parameters of maternal and fetal status during stimulation of fetal lung maturation].
2001 Apr
[Dyshidrosis and acral purpura during polymorphic dermatitis in pregnancy: 2 cases].
2001 Apr
Orbital mass following injection with depot corticosteroids.
2001 Apr
Chromatographic analysis of phenethylamine-antihistamine combinations using C8, C18 or cyano columns and micellar sodium dodecyl sulfate-pentanol mixtures.
2001 Apr
Determination of apparent association constants of steroid-cyclodextrin inclusion complexes using a modification of the Hummel-Dreyer method.
2001 Apr 13
Action of glucocorticoids to antagonise cisplatin-induced acute and delayed emesis in the ferret.
2001 Apr 13
A topical steroid without an antibiotic cures external otitis efficiently: a study in an animal model.
2001 Aug
Single versus repeated-course antenatal corticosteroids: outcomes in singleton and multiple-gestation pregnancies.
2001 Aug
Differentiation between dexamethasone and betamethasone in a mixture using multiple mass spectrometry.
2001 Aug 10
Placebo-controlled, blinded comparison of antenatal betamethasone on mouse liver development.
2001 Feb
Bias shown in study of better care for patients with skin disease?
2001 Feb
Betamethasone alteration of the one-hour glucose challenge test in pregnancy.
2001 Feb
Two cases of severe bronchopneumonia due to influenza A (H3N2) virus: detection of influenza virus gene using reverse transcription polymerase chain reaction.
2001 Jan
Surfactant levels after reversible tracheal occlusion and prenatal steroids in experimental diaphragmatic hernia.
2001 Jan
Antenatal betamethasone treatment reduces synaptophysin immunoreactivity in presynaptic terminals in the fetal sheep brain.
2001 Jan 19
Repeated prenatal corticosteroid administration delays myelination of the corpus callosum in fetal sheep.
2001 Jul
Correlation between different gene expression assays designed to measure trans-activation potencies of systemic glucocorticoids.
2001 Jul
Valsalva retinopathy-like hemorrhage associated with combined trabeculotomy-trabeculectomy in a patient with developmental glaucoma.
2001 Jul-Aug
Tocolytic magnesium sulfate toxicity and unexpected neonatal death.
2001 Jun
Deleterious effects of local corticosteroid injections on the Achilles tendon of rats.
2001 Jun
Inhibitory effects of anti-inflammatory drugs on interleukin-6 bioactivity.
2001 Jun
A prospective, randomized trial comparing the efficacy of dexamethasone and betamethasone for the treatment of antepartum HELLP (hemolysis, elevated liver enzymes, and low platelet count) syndrome.
2001 Jun
Treatment of de Quervain's disease:role of conservative management.
2001 Jun
Glucocorticoid modulation of cardiovascular and autonomic function in preterm lambs: role of ANG II.
2001 Mar
Investigation of some commercially available spacer devices for the delivery of glucocorticoid steroids from a pMDI.
2001 May
[Pemphigoid gestationis: treatment by topical class I corticosteroid].
2001 May
High injection pressure during intralesional injection of corticosteroids into capillary hemangiomas.
2001 May
Comparison of intramuscular betamethasone and oral prednisone in the prevention of relapse of acute asthma.
2001 May-Jun
Antenatal corticosteroids-too much of a good thing?
2001 Oct 3
Manipulation under anesthesia for frozen shoulder with and without steroid injection.
2001 Sep
Fetal monkey surfactants after intra-amniotic or maternal administration of betamethasone and thyroid hormone.
2001 Sep
Programming effects in sheep of prenatal growth restriction and glucocorticoid exposure.
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.
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.
Systematic 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 Oct 22 00:48:43 UTC 2019 , Edited by admin on Tue Oct 22 00:48:43 UTC 2019
CFR 21 CFR 524.1044D
Created by admin on Tue Oct 22 00:48:43 UTC 2019 , Edited by admin on Tue Oct 22 00:48:43 UTC 2019
CFR 21 CFR 524.1044I
Created by admin on Tue Oct 22 00:48:43 UTC 2019 , Edited by admin on Tue Oct 22 00:48:43 UTC 2019
WHO-ATC R03BA04
Created by admin on Tue Oct 22 00:48:43 UTC 2019 , Edited by admin on Tue Oct 22 00:48:43 UTC 2019
CFR 21 CFR 524.1044B
Created by admin on Tue Oct 22 00:48:43 UTC 2019 , Edited by admin on Tue Oct 22 00:48:43 UTC 2019
WHO-VATC QA07EA04
Created by admin on Tue Oct 22 00:48:43 UTC 2019 , Edited by admin on Tue Oct 22 00:48:43 UTC 2019
WHO-ATC D07AC01
Created by admin on Tue Oct 22 00:48:43 UTC 2019 , Edited by admin on Tue Oct 22 00:48:43 UTC 2019
FDA ORPHAN DRUG 492415
Created by admin on Tue Oct 22 00:48:43 UTC 2019 , Edited by admin on Tue Oct 22 00:48:43 UTC 2019
NDF-RT N0000175576
Created by admin on Tue Oct 22 00:48:43 UTC 2019 , Edited by admin on Tue Oct 22 00:48:43 UTC 2019
WHO-VATC QD07BC01
Created by admin on Tue Oct 22 00:48:43 UTC 2019 , Edited by admin on Tue Oct 22 00:48:43 UTC 2019
WHO-ATC D07CC01
Created by admin on Tue Oct 22 00:48:43 UTC 2019 , Edited by admin on Tue Oct 22 00:48:43 UTC 2019
WHO-ATC S01BB04
Created by admin on Tue Oct 22 00:48:43 UTC 2019 , Edited by admin on Tue Oct 22 00:48:43 UTC 2019
WHO-VATC QD07CC01
Created by admin on Tue Oct 22 00:48:43 UTC 2019 , Edited by admin on Tue Oct 22 00:48:43 UTC 2019
NDF-RT N0000175450
Created by admin on Tue Oct 22 00:48:43 UTC 2019 , Edited by admin on Tue Oct 22 00:48:43 UTC 2019
WHO-VATC QR03BA04
Created by admin on Tue Oct 22 00:48:43 UTC 2019 , Edited by admin on Tue Oct 22 00:48:43 UTC 2019
WHO-ATC S01CA05
Created by admin on Tue Oct 22 00:48:43 UTC 2019 , Edited by admin on Tue Oct 22 00:48:43 UTC 2019
WHO-VATC QS02CA90
Created by admin on Tue Oct 22 00:48:43 UTC 2019 , Edited by admin on Tue Oct 22 00:48:43 UTC 2019
WHO-ATC S01CB04
Created by admin on Tue Oct 22 00:48:43 UTC 2019 , Edited by admin on Tue Oct 22 00:48:43 UTC 2019
WHO-ATC A07EA04
Created by admin on Tue Oct 22 00:48:43 UTC 2019 , Edited by admin on Tue Oct 22 00:48:43 UTC 2019
WHO-ESSENTIAL MEDICINES LIST 13.3
Created by admin on Tue Oct 22 00:48:43 UTC 2019 , Edited by admin on Tue Oct 22 00:48:43 UTC 2019
WHO-VATC QS01BA06
Created by admin on Tue Oct 22 00:48:43 UTC 2019 , Edited by admin on Tue Oct 22 00:48:43 UTC 2019
WHO-ATC H02AB01
Created by admin on Tue Oct 22 00:48:43 UTC 2019 , Edited by admin on Tue Oct 22 00:48:43 UTC 2019
WHO-ATC S01BA06
Created by admin on Tue Oct 22 00:48:43 UTC 2019 , Edited by admin on Tue Oct 22 00:48:43 UTC 2019
CFR 21 CFR 524.1044G
Created by admin on Tue Oct 22 00:48:43 UTC 2019 , Edited by admin on Tue Oct 22 00:48:43 UTC 2019
WHO-VATC QD07XC01
Created by admin on Tue Oct 22 00:48:43 UTC 2019 , Edited by admin on Tue Oct 22 00:48:43 UTC 2019
WHO-VATC QS01CB04
Created by admin on Tue Oct 22 00:48:43 UTC 2019 , Edited by admin on Tue Oct 22 00:48:43 UTC 2019
WHO-VATC QH02AB01
Created by admin on Tue Oct 22 00:48:43 UTC 2019 , Edited by admin on Tue Oct 22 00:48:43 UTC 2019
CFR 21 CFR 524.1044F
Created by admin on Tue Oct 22 00:48:43 UTC 2019 , Edited by admin on Tue Oct 22 00:48:43 UTC 2019
WHO-ATC R01AD06
Created by admin on Tue Oct 22 00:48:43 UTC 2019 , Edited by admin on Tue Oct 22 00:48:43 UTC 2019
WHO-ATC D07XC01
Created by admin on Tue Oct 22 00:48:43 UTC 2019 , Edited by admin on Tue Oct 22 00:48:43 UTC 2019
WHO-VATC QC05AA05
Created by admin on Tue Oct 22 00:48:43 UTC 2019 , Edited by admin on Tue Oct 22 00:48:43 UTC 2019
NCI_THESAURUS C521
Created by admin on Tue Oct 22 00:48:43 UTC 2019 , Edited by admin on Tue Oct 22 00:48:43 UTC 2019
WHO-ATC S02BA07
Created by admin on Tue Oct 22 00:48:43 UTC 2019 , Edited by admin on Tue Oct 22 00:48:43 UTC 2019
WHO-VATC QS03CA06
Created by admin on Tue Oct 22 00:48:43 UTC 2019 , Edited by admin on Tue Oct 22 00:48:43 UTC 2019
WHO-ATC D07BC01
Created by admin on Tue Oct 22 00:48:43 UTC 2019 , Edited by admin on Tue Oct 22 00:48:43 UTC 2019
LIVERTOX 100
Created by admin on Tue Oct 22 00:48:43 UTC 2019 , Edited by admin on Tue Oct 22 00:48:43 UTC 2019
WHO-VATC QS01BB04
Created by admin on Tue Oct 22 00:48:43 UTC 2019 , Edited by admin on Tue Oct 22 00:48:43 UTC 2019
WHO-ATC S03CA06
Created by admin on Tue Oct 22 00:48:43 UTC 2019 , Edited by admin on Tue Oct 22 00:48:43 UTC 2019
WHO-ATC S03BA03
Created by admin on Tue Oct 22 00:48:43 UTC 2019 , Edited by admin on Tue Oct 22 00:48:43 UTC 2019
WHO-VATC QD07AC01
Created by admin on Tue Oct 22 00:48:43 UTC 2019 , Edited by admin on Tue Oct 22 00:48:43 UTC 2019
WHO-VATC QS01CA05
Created by admin on Tue Oct 22 00:48:43 UTC 2019 , Edited by admin on Tue Oct 22 00:48:43 UTC 2019
WHO-ATC C05AA05
Created by admin on Tue Oct 22 00:48:43 UTC 2019 , Edited by admin on Tue Oct 22 00:48:43 UTC 2019
WHO-VATC QR01AD06
Created by admin on Tue Oct 22 00:48:43 UTC 2019 , Edited by admin on Tue Oct 22 00:48:43 UTC 2019
WHO-VATC QS02BA07
Created by admin on Tue Oct 22 00:48:43 UTC 2019 , Edited by admin on Tue Oct 22 00:48:43 UTC 2019
Code System Code Type Description
RXCUI
1514
Created by admin on Tue Oct 22 00:48:43 UTC 2019 , Edited by admin on Tue Oct 22 00:48:43 UTC 2019
PRIMARY RxNorm
MERCK INDEX
M2452
Created by admin on Tue Oct 22 00:48:43 UTC 2019 , Edited by admin on Tue Oct 22 00:48:43 UTC 2019
PRIMARY Merck Index
MESH
D001623
Created by admin on Tue Oct 22 00:48:43 UTC 2019 , Edited by admin on Tue Oct 22 00:48:43 UTC 2019
PRIMARY
ChEMBL
CHEMBL632
Created by admin on Tue Oct 22 00:48:43 UTC 2019 , Edited by admin on Tue Oct 22 00:48:43 UTC 2019
PRIMARY
EVMPD
SUB05797MIG
Created by admin on Tue Oct 22 00:48:43 UTC 2019 , Edited by admin on Tue Oct 22 00:48:43 UTC 2019
PRIMARY
NCI_THESAURUS
C303
Created by admin on Tue Oct 22 00:48:43 UTC 2019 , Edited by admin on Tue Oct 22 00:48:43 UTC 2019
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
BETAMETHASONE
Created by admin on Tue Oct 22 00:48:43 UTC 2019 , Edited by admin on Tue Oct 22 00:48:43 UTC 2019
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 Oct 22 00:48:43 UTC 2019 , Edited by admin on Tue Oct 22 00:48:43 UTC 2019
PRIMARY
EPA CompTox
378-44-9
Created by admin on Tue Oct 22 00:48:43 UTC 2019 , Edited by admin on Tue Oct 22 00:48:43 UTC 2019
PRIMARY
HSDB
378-44-9
Created by admin on Tue Oct 22 00:48:43 UTC 2019 , Edited by admin on Tue Oct 22 00:48:43 UTC 2019
PRIMARY
LactMed
378-44-9
Created by admin on Tue Oct 22 00:48:43 UTC 2019 , Edited by admin on Tue Oct 22 00:48:43 UTC 2019
PRIMARY
PUBCHEM
9782
Created by admin on Tue Oct 22 00:48:43 UTC 2019 , Edited by admin on Tue Oct 22 00:48:43 UTC 2019
PRIMARY
INN
1045
Created by admin on Tue Oct 22 00:48:43 UTC 2019 , Edited by admin on Tue Oct 22 00:48:43 UTC 2019
PRIMARY
CAS
378-44-9
Created by admin on Tue Oct 22 00:48:43 UTC 2019 , Edited by admin on Tue Oct 22 00:48:43 UTC 2019
PRIMARY
DRUG BANK
DB00443
Created by admin on Tue Oct 22 00:48:43 UTC 2019 , Edited by admin on Tue Oct 22 00:48:43 UTC 2019
PRIMARY
ECHA (EC/EINECS)
206-825-4
Created by admin on Tue Oct 22 00:48:43 UTC 2019 , Edited by admin on Tue Oct 22 00:48:43 UTC 2019
PRIMARY
IUPHAR
7061
Created by admin on Tue Oct 22 00:48:43 UTC 2019 , Edited by admin on Tue Oct 22 00:48:43 UTC 2019
PRIMARY