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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 Thumb
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 Link_out
PubChem Compound 9782 Link_out
PubChem Substance 46505155 Link_out
ChemSpider 9399 Link_out
ChEBI 3077 Link_out
ChEMBL 3077 Link_out
Therapeutic Targets Database DAP001043 Link_out
PharmGKB PA448605 Link_out
Drug Product Database 716618 Link_out
RxList http://www.rxlist.com/cgi/generic2/betamet.htm Link_out
Drugs.com http://www.drugs.com/cdi/betamethasone.html Link_out
Wikipedia http://en.wikipedia.org/wiki/Betamethasone Link_out
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 Link_out
Gene: NR3C1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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

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:
  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

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:
  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

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:
  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

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.