DrugBank: Betamethasone (DB00443)

targets (1) enzymes (2) transporters (1)

Identification

Name

Betamethasone

Accession Number

DB00443 (APRD00513)

Type

small molecule

Groups

approved

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

Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure

Synonyms

Not Available

Brand names

Alphatrex
Bebate
Becort
Bedifos
Beta-Methasone
Beta-Methasone Alcohol
Beta-Val
Betacorlan
Betacortril
Betaderm
Betadexamethasone
Betafluorene
Betamamallet
Betametasona [INN-Spanish]
Betametasone [DCIT]
Betamethasone [Usan:Ban:Inn:Jan]
Betamethasone Alcohol
Betamethasone Base
Betamethasone Cream
Betamethasone Dipropionate
Betamethasone Sodium Phosphate
Betamethasone Valearate
Betamethasone Valerate
Betamethasonum [INN-Latin]
Betamethasonvalerat Mikron
Betamethazone
Betapredol
Betasolon
Betatrex
Betnelan
Betsolan
Celestene
Celestone
Celestone Syrup and Tablets
Cidoten
Dermabet
Desacort-Beta
Diproderm
Diprolene
Diprolene AF
Diprosone
Flubenisolone
Hormezon
Lotrisone
Luxiq
Luxiqo
Maxivate
Methazon
Rinderon
Rinderon A
Uticort
Valisone
Valnac
Visubeta

Brand name mixtures

Lotrisone (betamethasone + clotrimazole)

Categories

Anti-Asthmatic Agents
Anti-inflammatory Agents
Immunosuppressive Agents
Glucocorticoids
Corticosteroid
Anti-inflammatory Agents, Steroidal

CAS number

378-44-9

Weight

Average: 392.4611
Monoisotopic: 392.199902243

Chemical Formula

C₂₂H₂₉FO₅

InChI Key

InChIKey=UREBDLICKHMUKA-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

Plain Text

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

Plain Text

Mass Spec

Not Available

Taxonomy

Kingdom

Organic

Classes

Steroids and Steroid Derivatives

Substructures

Steroids and Steroid Derivatives
Hydroxy Compounds
Alkanes and Alkenes
Alkyl Halides
Alcohols and Polyols
Ketones

Pharmacology

Indication

Topical 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.

Pharmacodynamics

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.

Mechanism of action

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.

Absorption

Minimal if applied topically.

Volume of distribution

Not Available

Protein binding

64%

Metabolism

Hepatic

Route of elimination

Not Available

Half life

5.6 hours

Clearance

Not Available

Toxicity

Symptoms 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

Pathways

Not Available

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

Form	Route	Strength
Cream	Topical
Enema	Topical
Lotion	Topical
Ointment	Topical

Prices

Unit description	Cost	Unit
Luxiq 0.12% Foam 100 gm Can	325.17 USD	can
Luxiq 0.12% Foam 50 gm Can	174.7 USD	can
Diprolene 0.05% Lotion 60ml Bottle	148.19 USD	bottle
Diprolene 0.05% Ointment 50 gm Tube	147.41 USD	tube
Diprolene AF 0.05% Cream 50 gm Tube	147.02 USD	tube
Betamethasone Dipropionate Aug 0.05% Ointment 45 gm Tube	118.42 USD	tube
Diprolene 0.05% Gel 50 gm Tube	103.99 USD	tube
Betamethasone Dipropionate Aug 0.05% Lotion 60ml Bottle	100.64 USD	bottle
Betamethasone Dipropionate Aug 0.05% Cream 50 gm Tube	88.66 USD	tube
Betamethasone Dipropionate Aug 0.05% Gel 50 gm Tube	88.26 USD	tube
Diprolene 0.05% Lotion 30ml Bottle	78.79 USD	bottle
Betamethasone acetate powd	78.03 USD	g
Diprolene 0.05% Ointment 15 gm Tube	69.38 USD	tube
Diprolene AF 0.05% Cream 15 gm Tube	69.38 USD	tube
Betamethasone Dipropionate Aug 0.05% Ointment 15 gm Tube	58.83 USD	tube
Betamethasone sod phos powder	56.61 USD	g
Diprolene 0.05% Gel 15 gm Tube	49.99 USD	tube
Betamethasone dp powder	48.96 USD	g
Betamethasone valerate powd	47.89 USD	g
Maxivate 0.05% Cream 45 gm Tube	44.99 USD	tube
Betamethasone Dipropionate 0.05% Lotion 60ml Bottle	40.4 USD	bottle
Betamethasone Dipropionate Aug 0.05% Cream 15 gm Tube	39.62 USD	tube
Betamethasone Dipropionate Aug 0.05% Gel 15 gm Tube	39.46 USD	tube
Betamethasone Dipropionate 0.05% Ointment 45 gm Tube	19.67 USD	tube
Betamethasone Dipropionate 0.05% Cream 45 gm Tube	18.9 USD	tube
Betamethasone Valerate 0.1% Lotion 60ml Bottle	16.99 USD	bottle
Betamethasone Valerate 0.1% Ointment 45 gm Tube	15.87 USD	tube
Beta-Val 0.1% Lotion 60ml Bottle	14.99 USD	bottle
Betamethasone Dipropionate 0.05% Ointment 15 gm Tube	13.51 USD	tube
Betamethasone Dipropionate 0.05% Cream 15 gm Tube	12.99 USD	tube
Betamethasone Valerate 0.1% Cream 45 gm Tube	12.99 USD	tube
Beta-Val 0.1% Cream 45 gm Tube	12.99 USD	tube
Betamethasone Valerate 0.1% Cream 15 gm Tube	11.99 USD	tube
Betamethasone Valerate 0.1% Ointment 15 gm Tube	11.99 USD	tube
Beta-Val 0.1% Cream 15 gm Tube	11.99 USD	tube
Betnesol (5 mg/100Ml) 5 mg/enm Enema	9.51 USD	enema
Celestone soluspan 6 mg/ml	8.08 USD	ml
Betamethasone ac-sp 6 mg/ml vial	7.68 USD	ml
Luxiq 0.12% foam	5.01 USD	g
Diprolene af 0.05% cream	4.19 USD	g
Lotrisone 1-0.05% Lotion	2.89 USD	ml
Lotrisone cream	2.71 USD	g
Betamethasone dp aug 0.05% crm	2.17 USD	g
Diprolene Glycol 0.05 % Glycol Cream	0.54 USD	g
Diprolene Glycol 0.05 % Glycol Ointment	0.54 USD	g
Ratio-Topilene 0.05 % Glycol Cream	0.54 USD	g
Ratio-Topilene 0.05 % Glycol Ointment	0.54 USD	g
Diprolene Glycol 0.05 % Glycol Lotion	0.49 USD	g
Ratio-Topilene 0.05 % Glycol Lotion	0.49 USD	g
Prevex B 0.1 % Occlusive Cream	0.4 USD	g
Beta-val 0.1% cream	0.32 USD	g
Ratio-Ectosone Regular 0.1 % Lotion	0.3 USD	g
Ratio-Ectosone Mild 0.05 % Lotion	0.23 USD	g
Diprosone 0.05 % Ointment	0.23 USD	g
Ratio-Topisone 0.05 % Ointment	0.23 USD	g
Diprosone 0.05 % Cream	0.21 USD	g
Diprosone 0.05 % Lotion	0.21 USD	g
Ratio-Topisone 0.05 % Cream	0.21 USD	g
Ratio-Topisone 0.05 % Lotion	0.21 USD	g
Betamethasone va 0.1% cream	0.14 USD	g
Betaderm Regular 0.1 % Ointment	0.1 USD	g
Ratio-Ectosone Regular 0.1 % Cream	0.1 USD	g
Valisone Scalp 0.1 % Lotion	0.1 USD	g
Betaderm Regular 0.1 % Cream	0.09 USD	g
Ratio-Ectosone Scalp 0.1 % Lotion	0.09 USD	g
Betaderm Mild 0.05 % Ointment	0.07 USD	g
Betaderm Mild 0.05 % Cream	0.06 USD	g
Ratio-Ectosone Mild 0.05 % Cream	0.06 USD	g

Patents

Country	Patent Number	Approved	Expires
United States	7078058	1997-05-24	2017-05-24
United States	6126920	1996-03-01	2016-03-01

Properties

State

solid

Melting point

231-234oC

Experimental Properties

Property	Value	Source
water solubility	Insoluble	PhysProp
logP	1.1	PhysProp
logS	-3.77 [ADME Research, USCD]	PhysProp

Predicted Properties

Property	Value	Source
water solubility	5.05e-02 g/l	ALOGPS
logP	1.93	ALOGPS
logP	1.68	ChemAxon Molconvert
logS	-3.89	ALOGPS
pKa	13.48	ChemAxon Molconvert
hydrogen acceptor count	5	ChemAxon Molconvert
hydrogen donor count	3	ChemAxon Molconvert
polar surface area	94.83	ChemAxon Molconvert
rotatable bond count	2	ChemAxon Molconvert
refractivity	102.49	ChemAxon Molconvert
polarizability	40.88	ChemAxon Molconvert

References

Synthesis Reference

Not Available

General Reference

Not Available

External Links

Resource	Link
KEGG Drug	D00244
PubChem Compound	9782
PubChem Substance	46505155
ChemSpider	9399
ChEBI	3077
ChEMBL	3077
Therapeutic Targets Database	DAP001043
PharmGKB	PA448605
Drug Product Database	716618
RxList	http://www.rxlist.com/cgi/generic2/betamet.htm
Drugs.com	http://www.drugs.com/cdi/betamethasone.html
Wikipedia	http://en.wikipedia.org/wiki/Betamethasone

ATC Codes

A07EA04
C05AA05
D07AC01
D07XC01
H02AB01
R01AD06
R03BA04
S01BA06
S01CB04
S02BA07
S03BA03

AHFS Codes

84:06.00

PDB Entries

Not Available

FDA label

show (37.5 KB)

MSDS

show (71.9 KB)

Interactions

Drug Interactions

Not Available

Food Interactions

Take with food to reduce irritation.

Targets
1. Glucocorticoid receptor Pharmacological action: yes Actions: agonist Receptor for glucocorticoids (GC). Has a dual mode of action:as a transcription factor that binds to glucocorticoid response elements (GRE) and as a modulator of other transcription factors. Affects inflammatory responses, cellular proliferation and differentiation in target tissues. Could act as a coactivator for STAT5-dependent transcription upon growth hormone (GH) stimulation and could reveal an essential role of hepatic GR in the control of body growth Organism class: human UniProt ID: P04150 Gene: NR3C1 Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References: 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 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 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 Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed

Targets

1. Glucocorticoid receptor

Pharmacological action: yes
Actions: agonist

Receptor for glucocorticoids (GC). Has a dual mode of action:as a transcription factor that binds to glucocorticoid response elements (GRE) and as a modulator of other transcription factors. Affects inflammatory responses, cellular proliferation and differentiation in target tissues. Could act as a coactivator for STAT5-dependent transcription upon growth hormone (GH) stimulation and could reveal an essential role of hepatic GR in the control of body growth

Organism class: human
UniProt ID: P04150 Link_out

Gene: NR3C1 Link_out

Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:

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
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
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
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 Actions: inhibitor Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4- hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. The enzyme also hydroxylates etoposide UniProt ID: P08684 Gene: CYP3A4 Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References: 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 Actions: substrate, inducer Catalyzes the formation of aromatic C18 estrogens from C19 androgens UniProt ID: P11511 Gene: CYP19A1 Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References: 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

Enzymes

1. Cytochrome P450 3A4

Actions: inhibitor

Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4- hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. The enzyme also hydroxylates etoposide

UniProt ID: P08684 Link_out

Gene: CYP3A4
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:

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

Actions: substrate, inducer

Catalyzes the formation of aromatic C18 estrogens from C19 androgens

UniProt ID: P11511 Link_out

Gene: CYP19A1 Link_out

Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:

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 Actions: substrate Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells UniProt ID: P08183 Gene: ABCB1 Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References: 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

Transporters

1. Multidrug resistance protein 1

Actions: substrate

Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells

UniProt ID: P08183 Link_out

Gene: ABCB1 Link_out

Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:

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

Comments

Drug created on June 13, 2005 07:24 / Updated on April 19, 2011 15:04

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.