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Identification
NameBetamethasone
Accession NumberDB00443  (APRD00513)
Typesmall molecule
Groupsapproved
Description

A glucocorticoid given orally, parenterally, by local injection, by inhalation, or applied topically in the management of various disorders in which corticosteroids are indicated. Its lack of mineralocorticoid properties makes betamethasone particularly suitable for treating cerebral edema and congenital adrenal hyperplasia. (From Martindale, The Extra Pharmacopoeia, 30th ed, p724)

Structure
Thumb
Synonyms
SynonymLanguageCode
16β-Methyl-1,4-pregnadiene-9α-fluoro-11β,17α,21-triol-3,20-dioneNot AvailableNot Available
9-Fluoro-16β-methylprednisoloneNot AvailableNot Available
9α-Fluoro-16β-methylprednisoloneNot AvailableNot Available
beta-Methasone alcoholNot AvailableNot Available
BetadexamethasoneNot AvailableNot Available
BetametasonaSpanishINN
BetamethasoneNot AvailableINN, BAN, USAN, JAN
BetamethasonumLatinINN
Betamethasonvalerat MikronNot AvailableNot Available
Salts
Name/CAS Structure Properties
Betamethasone dipropionate
Thumb Not applicable DBSALT000851
Betamethasone sodium phosphate
Thumb Not applicable DBSALT000850
Betamethasone valerate
Thumb Not applicable DBSALT000849
Brand names
NameCompany
BentelanDefiante
BetnovateGlaxoSmithKline
CelestamineSchering-Plough
CelestoneSchering-Plough
DIPROLENENot Available
DiprosoneSchering-Plough
FucibetLEO
LUXIQNot Available
ProcortNot Available
RinderonShionogi Seiyaku
Brand mixtures
Brand NameIngredients
Lotridermbetamethasone + clotrimazole
Lotrisonebetamethasone + clotrimazole
TACLONEXBetamethasone + Calcipotriol
TaclonexBetamethasone + Calcipotriol
Categories
CAS number378-44-9
WeightAverage: 392.4611
Monoisotopic: 392.199902243
Chemical FormulaC22H29FO5
InChI KeyUREBDLICKHMUKA-DVTGEIKXSA-N
InChI
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
IUPAC Name
(1R,2S,10S,11S,13S,14R,15S,17S)-1-fluoro-14,17-dihydroxy-14-(2-hydroxyacetyl)-2,13,15-trimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,6-dien-5-one
SMILES
[H][C@@]12C[C@H](C)[C@](O)(C(=O)CO)[C@@]1(C)C[C@H](O)[C@@]1(F)[C@@]2([H])CCC2=CC(=O)C=C[C@]12C
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassLipids
ClassSteroids and Steroid Derivatives
SubclassGluco/mineralocorticoids, Progestogins and Derivatives
Direct parentGluco/mineralocorticoids, Progestogins and Derivatives
Alternative parentsHydroxysteroids; Ketosteroids; Halogenated Steroids; Iridoids and Derivatives; Cyclohexanols; Tertiary Alcohols; Cyclic Alcohols and Derivatives; Ketones; Fluorohydrins; Polyamines; Enolates; Primary Alcohols; Organofluorides; Alkyl Fluorides; Aldehydes
Substituents3-keto-steroid; 20-keto-steroid; 9-halo-steroid; 17-hydroxy-steroid; 11-hydroxy-steroid; 11-noriridane monoterpene; monoterpene; cyclohexanol; tertiary alcohol; cyclic alcohol; secondary alcohol; ketone; halohydrin; fluorohydrin; polyamine; enolate; primary alcohol; alcohol; organofluoride; organohalogen; carbonyl group; alkyl halide; alkyl fluoride; aldehyde
Classification descriptionThis compound belongs to the gluco/mineralocorticoids, progestogins and derivatives. These are steroids whose structure is based on an hydroxylated prostane moiety.
Pharmacology
IndicationTopical use (cream, lotion and ointment): for relief of the inflammatory and pruritic manifestations of corticosteroid-responsive dermatoses
Topical use (foam): relief of the inflammatory and pruritic manifestations of corticosteroid-responsive dermatoses of the scalp
Systemic use: for the treatment of edocrine disorders, rheumatic disorders, collagen diseases, dermatological diseases, allergic states, ophthalmic diseases, respiratory diseases, hematologic disorders, neoplastic diseases, edematous states, gastrointestinal diseases, tuberculous meningitis and trichinosis.
PharmacodynamicsBetamethasone 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.
Mechanism of actionBetamethasone 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.
AbsorptionMinimal if applied topically.
Volume of distributionNot Available
Protein binding64%
Metabolism

Hepatic

Route of eliminationNot Available
Half life5.6 hours
ClearanceNot Available
ToxicitySymptoms of overdose include burning, itching, irritation, dryness, folliculitis, hypertrichosis, acneiform eruptions, hypopigmentation, perioral dermatitis, allergic contact dermatitis, maceration of the skin, secondary infection, skin atrophy, striae, and miliaria.
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 0.992
Blood Brain Barrier + 0.9781
Caco-2 permeable + 0.8304
P-glycoprotein substrate Substrate 0.7862
P-glycoprotein inhibitor I Non-inhibitor 0.8112
P-glycoprotein inhibitor II Non-inhibitor 0.8134
Renal organic cation transporter Non-inhibitor 0.7971
CYP450 2C9 substrate Non-substrate 0.8733
CYP450 2D6 substrate Non-substrate 0.9115
CYP450 3A4 substrate Substrate 0.7315
CYP450 1A2 substrate Non-inhibitor 0.938
CYP450 2C9 substrate Non-inhibitor 0.9106
CYP450 2D6 substrate Non-inhibitor 0.9231
CYP450 2C19 substrate Non-inhibitor 0.9247
CYP450 3A4 substrate Non-inhibitor 0.8308
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9169
Ames test Non AMES toxic 0.9132
Carcinogenicity Non-carcinogens 0.9399
Biodegradation Not ready biodegradable 1.0
Rat acute toxicity 2.1482 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.9558
hERG inhibition (predictor II) Inhibitor 0.5091
Pharmacoeconomics
Manufacturers
  • Schering corp sub schering plough corp
  • Parke davis div warner lambert co
  • Parke davis pharmaceutical research div warner lambert co
  • Altana inc
  • Glenmark generics inc usa
  • Perrigo new york inc
  • Taro pharmaceuticals usa inc
  • Tolmar inc
  • Schering corp
  • Savage laboratories inc div altana inc
  • Actavis mid atlantic llc
  • E fougera div altana inc
  • Pharmaderm div altana inc
  • Teva pharmaceuticals usa inc
  • Alpharma us pharmaceuticals division
  • Taro pharmaceuticals inc
  • Teva pharmaceuticals usa
  • Watson laboratories inc
  • Connectics corp
  • Tj roaco ltd
  • Pharmafair inc
  • Stat trade inc
Packagers
Dosage forms
FormRouteStrength
CreamTopical
EnemaTopical
LotionTopical
OintmentTopical
Prices
Unit descriptionCostUnit
Luxiq 0.12% Foam 100 gm Can325.17USDcan
Luxiq 0.12% Foam 50 gm Can174.7USDcan
Diprolene 0.05% Lotion 60ml Bottle148.19USDbottle
Diprolene 0.05% Ointment 50 gm Tube147.41USDtube
Diprolene AF 0.05% Cream 50 gm Tube147.02USDtube
Betamethasone Dipropionate Aug 0.05% Ointment 45 gm Tube118.42USDtube
Diprolene 0.05% Gel 50 gm Tube103.99USDtube
Betamethasone Dipropionate Aug 0.05% Lotion 60ml Bottle100.64USDbottle
Betamethasone Dipropionate Aug 0.05% Cream 50 gm Tube88.66USDtube
Betamethasone Dipropionate Aug 0.05% Gel 50 gm Tube88.26USDtube
Diprolene 0.05% Lotion 30ml Bottle78.79USDbottle
Betamethasone acetate powd78.03USDg
Diprolene 0.05% Ointment 15 gm Tube69.38USDtube
Diprolene AF 0.05% Cream 15 gm Tube69.38USDtube
Betamethasone Dipropionate Aug 0.05% Ointment 15 gm Tube58.83USDtube
Betamethasone sod phos powder56.61USDg
Diprolene 0.05% Gel 15 gm Tube49.99USDtube
Betamethasone dp powder48.96USDg
Betamethasone valerate powd47.89USDg
Maxivate 0.05% Cream 45 gm Tube44.99USDtube
Betamethasone Dipropionate 0.05% Lotion 60ml Bottle40.4USDbottle
Betamethasone Dipropionate Aug 0.05% Cream 15 gm Tube39.62USDtube
Betamethasone Dipropionate Aug 0.05% Gel 15 gm Tube39.46USDtube
Betamethasone Dipropionate 0.05% Ointment 45 gm Tube19.67USDtube
Betamethasone Dipropionate 0.05% Cream 45 gm Tube18.9USDtube
Betamethasone Valerate 0.1% Lotion 60ml Bottle16.99USDbottle
Betamethasone Valerate 0.1% Ointment 45 gm Tube15.87USDtube
Beta-Val 0.1% Lotion 60ml Bottle14.99USDbottle
Betamethasone Dipropionate 0.05% Ointment 15 gm Tube13.51USDtube
Betamethasone Dipropionate 0.05% Cream 15 gm Tube12.99USDtube
Betamethasone Valerate 0.1% Cream 45 gm Tube12.99USDtube
Beta-Val 0.1% Cream 45 gm Tube12.99USDtube
Betamethasone Valerate 0.1% Cream 15 gm Tube11.99USDtube
Betamethasone Valerate 0.1% Ointment 15 gm Tube11.99USDtube
Beta-Val 0.1% Cream 15 gm Tube11.99USDtube
Betnesol (5 mg/100Ml) 5 mg/enm Enema9.51USDenema
Celestone soluspan 6 mg/ml8.08USDml
Betamethasone ac-sp 6 mg/ml vial7.68USDml
Luxiq 0.12% foam5.01USDg
Diprolene af 0.05% cream4.19USDg
Lotrisone 1-0.05% Lotion2.89USDml
Lotrisone cream2.71USDg
Betamethasone dp aug 0.05% crm2.17USDg
Diprolene Glycol 0.05 % Glycol Cream0.54USDg
Diprolene Glycol 0.05 % Glycol Ointment0.54USDg
Ratio-Topilene 0.05 % Glycol Cream0.54USDg
Ratio-Topilene 0.05 % Glycol Ointment0.54USDg
Diprolene Glycol 0.05 % Glycol Lotion0.49USDg
Ratio-Topilene 0.05 % Glycol Lotion0.49USDg
Prevex B 0.1 % Occlusive Cream0.4USDg
Beta-val 0.1% cream0.32USDg
Ratio-Ectosone Regular 0.1 % Lotion0.3USDg
Ratio-Ectosone Mild 0.05 % Lotion0.23USDg
Diprosone 0.05 % Ointment0.23USDg
Ratio-Topisone 0.05 % Ointment0.23USDg
Diprosone 0.05 % Cream0.21USDg
Diprosone 0.05 % Lotion0.21USDg
Ratio-Topisone 0.05 % Cream0.21USDg
Ratio-Topisone 0.05 % Lotion0.21USDg
Betamethasone va 0.1% cream0.14USDg
Betaderm Regular 0.1 % Ointment0.1USDg
Ratio-Ectosone Regular 0.1 % Cream0.1USDg
Valisone Scalp 0.1 % Lotion0.1USDg
Betaderm Regular 0.1 % Cream0.09USDg
Ratio-Ectosone Scalp 0.1 % Lotion0.09USDg
Betaderm Mild 0.05 % Ointment0.07USDg
Betaderm Mild 0.05 % Cream0.06USDg
Ratio-Ectosone Mild 0.05 % Cream0.06USDg
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
CountryPatent NumberApprovedExpires (estimated)
United States70780581997-05-242017-05-24
United States61269201996-03-012016-03-01
Properties
Statesolid
Experimental Properties
PropertyValueSource
melting point232 °CU.S. Patent 3,164,618
water solubility66.5 mg/L (at 25 °C)EPA
logP1.94HANSCH,C ET AL. (1995)
logS-3.77ADME Research, USCD
Predicted Properties
PropertyValueSource
water solubility5.05e-02 g/lALOGPS
logP1.93ALOGPS
logP1.68ChemAxon
logS-3.9ALOGPS
pKa (strongest acidic)12.42ChemAxon
pKa (strongest basic)-3.3ChemAxon
physiological charge0ChemAxon
hydrogen acceptor count5ChemAxon
hydrogen donor count3ChemAxon
polar surface area94.83ChemAxon
rotatable bond count2ChemAxon
refractivity102.49ChemAxon
polarizability40.88ChemAxon
number of rings4ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterYesChemAxon
Veber's ruleNoChemAxon
MDDR-like ruleNoChemAxon
Spectra
SpectraNot Available
References
Synthesis Reference

Fernando AHUMADA AYALA, “SKIN-CARE PREPARATIONS CONTAINING MUPIROCIN AND BETAMETHASONE DIPROPIONATE.” U.S. Patent US20100063015, issued March 11, 2010.

US20100063015
General ReferenceNot Available
External Links
ResourceLink
KEGG DrugD00244
PubChem Compound9782
PubChem Substance46505155
ChemSpider9399
ChEBI3077
ChEMBLCHEMBL632
Therapeutic Targets DatabaseDAP001043
PharmGKBPA164754818
Drug Product Database716618
RxListhttp://www.rxlist.com/cgi/generic2/betamet.htm
Drugs.comhttp://www.drugs.com/cdi/betamethasone.html
WikipediaBetamethasone
ATC CodesA07EA04C05AA05D07AC01D07XC01H02AB01R01AD06R03BA04S01BA06S01CB04S02BA07S03BA03
AHFS Codes
  • 84:06.00
PDB EntriesNot Available
FDA labelshow(37.5 KB)
MSDSshow(71.9 KB)
Interactions
Drug Interactions
Drug
AcenocoumarolThe corticosteroid, betamethasone, alters the anticoagulant effect, acenocoumarol.
Acetylsalicylic acidThe corticosteroid, betamethasone, may decrease the effect of the salicylate, acetylsalicylic acid.
AmbenoniumThe corticosteroid, betamethasone, may decrease the effect of the anticholinesterase, ambenonium.
AmobarbitalThe barbiturate, amobarbital, may decrease the effect of the corticosteroid, betamethasone.
AnisindioneThe corticosteroid, betamethasone, alters the anticoagulant effect of anisindione.
AprobarbitalThe barbiturate, aprobarbital, may decrease the effect of the corticosteroid, betamethasone.
Bismuth SubsalicylateThe corticosteroid, betamethasone, may decrease the effect of the salicylate, bismuth subsalicylate.
ButabarbitalThe barbiturate, butabarbital, may decrease the effect of the corticosteroid, betamethasone.
ButalbitalThe barbiturate, butalbital, may decrease the effect of the corticosteroid, betamethasone.
ButethalThe barbiturate, butethal, may decrease the effect of the corticosteroid, betamethasone.
DicoumarolThe corticosteroid, betamethasone, alters the anticoagulant effect of dicumarol.
Dihydroquinidine barbiturateThe barbiturate, dihydroquinidine barbiturate, may decrease the effect of the corticosteroid, betamethasone.
EdrophoniumThe corticosteroid, betamethasone, may decrease the effect of the anticholinesterase, edrophonium.
EthotoinThe enzyme inducer, ethotoin, may decrease the effect of the corticosteroid, betamethasone.
FosphenytoinThe enzyme inducer, fosphenytoin, may decrease the effect of the corticosteroid, betamethasone.
HeptabarbitalThe barbiturate, heptabarbital, may decrease the effect of the corticosteroid, betamethasone.
HexobarbitalThe barbiturate, hexobarbital, may decrease the effect of the corticosteroid, betamethasone.
IndacaterolConcomitant therapy may increase the risk of hypokalemia via intracellular shunting. Monitor for adverse effects and especially for cardiovascular effects associated with hypokalemia.
Magnesium salicylateThe corticosteroid, betamethasone, may decrease the effect of magnesium salicylate.
MephenytoinThe enzyme inducer, mephenytoin, may decrease the effect of the corticosteroid, betamethasone.
MethohexitalThe barbiturate, methohexital, may decrease the effect of the corticosteroid, betamethasone.
MethylphenobarbitalThe barbiturate, methylphenobarbital, may decrease the effect of the corticosteroid, betamethasone.
MidodrineIncreased arterial pressure
PentobarbitalThe barbiturate, pentobarbital, may decrease the effect of the corticosteroid, betamethasone.
PhenobarbitalThe barbiturate, phenobarbital, may decrease the effect of the corticosteroid, betamethasone.
PhenytoinThe enzyme inducer, phenytoin, may decrease the effect of the corticosteroid, betamethasone.
PrimidoneThe barbiturate, primidone, may decrease the effect of the corticosteroid, betamethasone.
PyridostigmineThe corticosteroid, betamethasone, may decrease the effect of the anticholinesterase, pyridostigmine.
Quinidine barbiturateThe barbiturate, quinidine barbiturate, may decrease the effect of the corticosteroid, betamethasone.
RifampicinThe enzyme inducer, rifampin, may decrease the effect of the corticosteroid, betamethasone.
Salicylate-sodiumThe corticosteroid, betamethasone, may decrease the effect of the salicylate, salicylate-sodium.
SalsalateThe corticosteroid, betamethasone, may decrease the effect of the salicylate, salsalate.
SecobarbitalThe barbiturate, secobarbital, may decrease the effect of the corticosteroid, betamethasone.
TacrineTacrine and Betamethasone may independently exacerbate muscle weakness in myasthenia gravis patients. Monitor for additive muscle weakness effects.
TalbutalThe barbiturate, talbutal, may decrease the effect of the corticosteroid, betamethasone.
TrastuzumabTrastuzumab may increase the risk of neutropenia and anemia. Monitor closely for signs and symptoms of adverse events.
Trisalicylate-cholineThe corticosteroid, betamethasone, may decrease the effect of the salicylate, trisalicylate-choline.
VecuroniumVecuronium may increase the adverse neuromuscular effects of systemic corticosteroids, such as Betamethasone. Monitor for increased muscle weakness and signs of polyneuropathies and myopathy.
WarfarinThe corticosteroid, betamethasone, alters the anticoagulant effect of warfarin.
Food Interactions
  • Take with food to reduce irritation.

Targets

1. Glucocorticoid receptor

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: agonist

Components

Name UniProt ID Details
Glucocorticoid receptor P04150 Details

References:

  1. Tanigawa K, Nagase H, Ohmori K, Tanaka K, Miyake H, Kiniwa M, Ikizawa K: Species-specific differences in the glucocorticoid receptor transactivation function upon binding with betamethasone-esters. Int Immunopharmacol. 2002 Jun;2(7):941-50. Pubmed
  2. Aida K, Shi Q, Wang J, VandeBerg JL, McDonald T, Nathanielsz P, Wang XL: The effects of betamethasone (BM) on endothelial nitric oxide synthase (eNOS) expression in adult baboon femoral arterial endothelial cells. J Steroid Biochem Mol Biol. 2004 Aug;91(4-5):219-24. Pubmed
  3. Johnstone JF, Bocking AD, Unlugedik E, Challis JR: The effects of chorioamnionitis and betamethasone on 11beta hydroxysteroid dehydrogenase types 1 and 2 and the glucocorticoid receptor in preterm human placenta. J Soc Gynecol Investig. 2005 May;12(4):238-45. Pubmed
  4. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed

Enzymes

1. Cytochrome P450 3A4

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Cytochrome P450 3A4 P08684 Details

References:

  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

2. Cytochrome P450 19A1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate inducer

Components

Name UniProt ID Details
Cytochrome P450 19A1 P11511 Details

References:

  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

Transporters

1. Multidrug resistance protein 1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Multidrug resistance protein 1 P08183 Details

References:

  1. Yates CR, Chang C, Kearbey JD, Yasuda K, Schuetz EG, Miller DD, Dalton JT, Swaan PW: Structural determinants of P-glycoprotein-mediated transport of glucocorticoids. Pharm Res. 2003 Nov;20(11):1794-803. Pubmed

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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:10