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
Treatment of psoriasis with a new combination of calcipotriol and betamethasone dipropionate: a flow cytometric study.
2001
Clinical evaluation of human placental extract (placentrex) in radiation-induced oral mucositis.
2001
[Rupture of the Achilles tendon after local steroid injection. Case reports and consequences for treatment].
2001
Clinical experience with topical calcitriol (1,25-dihydroxyvitamin D3) in psoriasis.
2001 Apr
Efficacy and tolerance of topical calcitriol 3 microg g(-1) in psoriasis treatment: a review of our experience in Poland.
2001 Apr
[Analysis of selected parameters of maternal and fetal status during stimulation of fetal lung maturation].
2001 Apr
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
Painless thyroiditis induced by the cessation of betamethasone.
2001 Aug
Evaluation of the inhibitory activity of topical indomethacin, betamethasone valerate and emollients on UVL-induced inflammation by means of non-invasive measurements of the skin elasticity.
2001 Aug
Lichen planus-like eruption following autologous bone marrow transplantation for chronic myeloid leukaemia.
2001 Aug
Repeated prenatal corticosteroid administration delays astrocyte and capillary tight junction maturation in fetal sheep.
2001 Aug
Differentiation between dexamethasone and betamethasone in a mixture using multiple mass spectrometry.
2001 Aug 10
Comparative effects of calcipotriol and betamethasone 17-valerate solution in the treatment of seborrhoeic dermatitis of the scalp.
2001 Jan
Acute paronychia: comparative treatment with topical antibiotic alone or in combination with corticosteroid.
2001 Jan
Topical therapy with fluorinated and non-fluorinated corticosteroids in patients with atopic dermatitis.
2001 Jan
Systemic ketoconazole for yeast allergic patients with atopic dermatitis.
2001 Jan
Severe vulvovaginitis associated with intravaginal nystatin therapy.
2001 Jul
The interactive effects of endotoxin with prenatal glucocorticoids on short-term lung function in sheep.
2001 Jul
An evidence-based assessment of occlusal adjustment as a treatment for temporomandibular disorders.
2001 Jul
The effect of betamethasone versus dexamethasone on fetal biophysical parameters.
2001 Jul
Nonoperative treatment of an interosseous ganglion cyst.
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
Preliminary results of a pilot study investigating the potential of salivary cortisol measurements to detect occult adrenal suppression secondary to steroid nose drops.
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
Tacrolimus suppressed the production of cytokines involved in atopic dermatitis by direct stimulation of human PBMC system. (Comparison with steroids).
2001 Jun
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
Dermatitis during radiation for vulvar carcinoma: prevention and treatment with granulocyte-macrophage colony-stimulating factor impregnated gauze.
2001 May-Jun
Comparison of intramuscular betamethasone and oral prednisone in the prevention of relapse of acute asthma.
2001 May-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
Fetal monkey surfactants after intra-amniotic or maternal administration of betamethasone and thyroid hormone.
2001 Sep
Treatment of childhood phimosis with a moderately potent topical steroid.
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