| 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 |
| Salts |
Not Available |
| Brand names |
| Name |
Company |
| 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 |
|
| Diprolene |
|
| Diprolene AF |
|
| Diprosone |
|
| Flubenisolone |
|
| Hormezon |
|
| Lotrisone |
|
| Luxiqo |
|
| Maxivate |
|
| Methazon |
|
| Rinderon |
|
| Rinderon A |
|
| Uticort |
|
| Valisone |
|
| Valnac |
|
| Visubeta |
|
|
| Brand mixtures |
| Brand Name |
Ingredients |
| 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 |
|
| 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 |
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational
purposes only.
|
| Patents |
| Country |
Patent Number |
Approved |
Expires (estimated) |
| United States |
7078058 |
1997-05-24 |
2017-05-24 |
| United States |
6126920 |
1996-03-01 |
2016-03-01 |
|
| Properties |
|---|
| State |
solid |
| Experimental Properties |
| Property |
Value |
Source |
| melting point |
232 °C |
PhysProp |
| water solubility |
66.5 mg/L (at 25 °C) |
EPA |
| logP |
1.94 |
HANSCH,C ET AL. (1995) |
| logS |
-3.77 |
ADME Research, USCD |
|
| Predicted Properties |
|
| References |
|---|
| Synthesis Reference |
Not Available
|
| General Reference |
Not Available
|
| External Links |
|
| ATC Codes |
- A07EA04
- C05AA05
- D07AC01
- D07XC01
- H02AB01
- R01AD06
- R03BA04
- S01BA06
- S01CB04
- S02BA07
- S03BA03
|
| AHFS Codes |
|
| PDB Entries |
Not Available |
| FDA label |
show (37.5 KB)
|
| MSDS |
show (71.9 KB)
|
| Interactions |
|---|
| Drug Interactions |
| Drug |
Interaction |
| Acenocoumarol |
The corticosteroid, betamethasone, alters the anticoagulant effect, acenocoumarol. |
| Acetylsalicylic acid |
The corticosteroid, betamethasone, may decrease the effect of the salicylate, acetylsalicylic acid. |
| Ambenonium |
The corticosteroid, betamethasone, may decrease the effect of the anticholinesterase, ambenonium. |
| Amobarbital |
The barbiturate, amobarbital, may decrease the effect of the corticosteroid, betamethasone. |
| Anisindione |
The corticosteroid, betamethasone, alters the anticoagulant effect of anisindione. |
| Aprobarbital |
The barbiturate, aprobarbital, may decrease the effect of the corticosteroid, betamethasone. |
| Bismuth Subsalicylate |
The corticosteroid, betamethasone, may decrease the effect of the salicylate, bismuth subsalicylate. |
| Butabarbital |
The barbiturate, butabarbital, may decrease the effect of the corticosteroid, betamethasone. |
| Butalbital |
The barbiturate, butalbital, may decrease the effect of the corticosteroid, betamethasone. |
| Butethal |
The barbiturate, butethal, may decrease the effect of the corticosteroid, betamethasone. |
| Dicumarol |
The corticosteroid, betamethasone, alters the anticoagulant effect of dicumarol. |
| Dihydroquinidine barbiturate |
The barbiturate, dihydroquinidine barbiturate, may decrease the effect of the corticosteroid, betamethasone. |
| Edrophonium |
The corticosteroid, betamethasone, may decrease the effect of the anticholinesterase, edrophonium. |
| Ethotoin |
The enzyme inducer, ethotoin, may decrease the effect of the corticosteroid, betamethasone. |
| Fosphenytoin |
The enzyme inducer, fosphenytoin, may decrease the effect of the corticosteroid, betamethasone. |
| Heptabarbital |
The barbiturate, heptabarbital, may decrease the effect of the corticosteroid, betamethasone. |
| Hexobarbital |
The barbiturate, hexobarbital, may decrease the effect of the corticosteroid, betamethasone. |
| Magnesium salicylate |
The corticosteroid, betamethasone, may decrease the effect of magnesium salicylate. |
| Mephenytoin |
The enzyme inducer, mephenytoin, may decrease the effect of the corticosteroid, betamethasone. |
| Methohexital |
The barbiturate, methohexital, may decrease the effect of the corticosteroid, betamethasone. |
| Methylphenobarbital |
The barbiturate, methylphenobarbital, may decrease the effect of the corticosteroid, betamethasone. |
| Midodrine |
Increased arterial pressure |
| Pentobarbital |
The barbiturate, pentobarbital, may decrease the effect of the corticosteroid, betamethasone. |
| Phenobarbital |
The barbiturate, phenobarbital, may decrease the effect of the corticosteroid, betamethasone. |
| Phenytoin |
The enzyme inducer, phenytoin, may decrease the effect of the corticosteroid, betamethasone. |
| Primidone |
The barbiturate, primidone, may decrease the effect of the corticosteroid, betamethasone. |
| Pyridostigmine |
The corticosteroid, betamethasone, may decrease the effect of the anticholinesterase, pyridostigmine. |
| Quinidine barbiturate |
The barbiturate, quinidine barbiturate, may decrease the effect of the corticosteroid, betamethasone. |
| Rifampin |
The enzyme inducer, rifampin, may decrease the effect of the corticosteroid, betamethasone. |
| Salicylate-sodium |
The corticosteroid, betamethasone, may decrease the effect of the salicylate, salicylate-sodium. |
| Salsalate |
The corticosteroid, betamethasone, may decrease the effect of the salicylate, salsalate. |
| Secobarbital |
The barbiturate, secobarbital, may decrease the effect of the corticosteroid, betamethasone. |
| Tacrine |
Tacrine and Betamethasone may independently exacerbate muscle weakness in myasthenia gravis patients. Monitor for additive muscle weakness effects. |
| Talbutal |
The barbiturate, talbutal, may decrease the effect of the corticosteroid, betamethasone. |
| Trastuzumab |
Trastuzumab may increase the risk of neutropenia and anemia. Monitor closely for signs and symptoms of adverse events. |
| Trisalicylate-choline |
The corticosteroid, betamethasone, may decrease the effect of the salicylate, trisalicylate-choline. |
| Vecuronium |
Vecuronium may increase the adverse neuromuscular effects of systemic corticosteroids, such as Betamethasone. Monitor for increased muscle weakness and signs of polyneuropathies and myopathy. |
| Warfarin |
The corticosteroid, betamethasone, alters the anticoagulant effect of warfarin. |
|
| Food Interactions |
- Take with food to reduce irritation.
|
