Betamethasone
From DrugPedia: A Wikipedia for Drug discovery
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| + | [http://crdd.osdd.net/raghava/hmrbase/test_extract.php?db=arun&table=nphormonet&id=1021&show=SHOW-3D Show 3-D Structure] | ||
| + | {{Drugbox | ||
| + | | IUPAC_name = (8S,9R,10S,11S,13S,14S,16S,17R)-9-fluoro-11,17-dihydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-3-one | ||
| + | | CAS_number = 378-44-9 | ||
| + | | CAS_supplemental = | ||
| + | | ATC_suffix = EA04 | ||
| + | | ATC_supplemental = {{ATC|C05|AA05}} {{ATC|D07|AC01}} {{ATC|D07|XC01}} {{ATC|H02|AB01}} {{ATC|R01|AD06}} {{ATC|R03|BA04}} {{ATC|S01|BA06}} {{ATC|S01|CB04}} {{ATC|S02|BA07}} {{ATC|S03|BA03}} | ||
| + | | PubChem = 123917 | ||
| + | | ChemSpiderID = 9382 | ||
| + | | chemical_formula =C<sub>2</sub><sub>2</sub>H<sub>2</sub><sub>9</sub>FO<sub>5</sub> | ||
| + | | molecular_weight = 392.46 | ||
| + | | smiles = CC1CC2C3CCC4=CC(=O)C=CC4(C3(C(CC2(C1(C(=O)CO)O)C)O)F)C | ||
| + | | synonyms = Betamethazone | ||
| + | | density = | ||
| + | | melting_point = 232(EXP) | ||
| + | | boiling_point = | ||
| + | | solubility = 66.5(EXP) at 25<sup>o</sup>C | ||
| + | | specific_rotation = | ||
| + | | sec_combustion = | ||
| + | | bioavailability = | ||
| + | | protein_bound = | ||
| + | | metabolism = [[hepatic]] [[CYP3A4]] | ||
| + | | elimination_half-life = 5.6 hours | ||
| + | | pregnancy_category= | ||
| + | | dependency_liability = | ||
| + | | routes_of_administration =oral or topical | ||
| + | }} | ||
==Description== | ==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) | + | 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). |
| + | |||
| + | '''Betamethasone''' is a moderately potent [[glucocorticoid]] [[steroid]] with [[anti-inflammatory]] and [[immunosuppressant|immunosuppressive]] properties. Unlike other drugs with these effects, betamethasone does not cause water retention. It is applied as a [[topical]] cream, ointment, foam, lotion or gel to treat [[pruritus|itching]] (e.g. from [[eczema]]). Betamethasone sodium phosphate is sometimes prescribed as an [[intramuscular injection]] (I.M) for itching from various ailments including allergic reactions to [[poison ivy]] and similar plants. | ||
| + | |||
| + | The compound is available as a number of [[ester]] derivatives: [[propionate|Dipropionate]] (branded as Diprosone, Diprolene and others), Sodium Phosphate and [[Valerate]] (branded as Betnovate, Celestone and others). <!-- which OH is esterified? --> In the United States and Canada, Betamethasone is mixed with [[Clotrimazole]] and sold as Lotrisone. | ||
| + | |||
==General Properties== | ==General Properties== | ||
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66.5(EXP) at 25C | 66.5(EXP) at 25C | ||
| + | == Indications == | ||
| + | Betamethasone is a [[corticosteroid]] used to stimulate fetal lung maturation, and to decrease the incidence and mortality from intracranial hemorrhage in premature infants. | ||
| + | |||
| + | It is also used as a topical cream to relieve skin irritation. The tablet form, available in Japan, eradicates eczematous rash within 24 hours, far more rapidly than the ointment. | ||
| + | |||
| + | 0.05% Betamethasone cream appears effective in treating [[phimosis]] in boys, and often averts the need for [[circumcision]]. | ||
| + | |||
| + | Betamethasone sodium phosphate is used orally and via [[injection]] with the same indications as other [[steroids]]. | ||
| + | |||
| + | Betamethasone Dipropionate and Salicylic Acid can be used as a treatment for Local Psoriasis. | ||
| + | == Fetal risk == | ||
| + | As it crosses the placenta, which is required for its beneficial effects, it may also be associated with complications, such as [[hypoglycemia]] and [[Neutrophil leucocytosis|leucocytosis]] in newborns exposed [[in utero]]. | ||
| + | ==Notes== | ||
| + | While betamethasone is commonly applied topically to treat skin inflammation, persistent application of large quantities may result in a more severe rebound inflammation when the medication is withdrawn, sometimes called "Betnovate face". | ||
| + | [[File:Betnovateonitemntcream.JPG|thumb|A tube of 'Betnovate ointment' cream and it's box.]] | ||
==External Links== | ==External Links== | ||
*[http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=9782]Pubchem | *[http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=9782]Pubchem | ||
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*[http://www.drugbank.ca/drugs/DB00443]Drugbank | *[http://www.drugbank.ca/drugs/DB00443]Drugbank | ||
| - | [[ | + | [[Category:Hormones]] |
| + | [[Category:Steroids]] | ||
| + | [[Category:Organofluorides]] | ||
Current revision
|
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| Betamethasone
| |
| Systematic (IUPAC) name | |
| (8S,9R,10S,11S,13S,14S,16S,17R)-9-fluoro-11,17-dihydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-3-one | |
| Identifiers | |
| CAS number | |
| ATC code | ? |
| PubChem | |
| ChemSpider | |
| Chemical data | |
| Formula | C22H29FO5 |
| Mol. mass | 392.46 |
| SMILES | & |
| Synonyms | Betamethazone |
| Physical data | |
| Melt. point | 232(EXP) °C |
| Solubility in water | 66.5(EXP) at 25oC mg/mL |
| Pharmacokinetic data | |
| Bioavailability | ? |
| Metabolism | hepatic CYP3A4 |
| Half life | 5.6 hours |
| Excretion | ? |
| Therapeutic considerations | |
| Pregnancy cat. |
? |
| Legal status | |
| Routes | oral or topical |
Contents |
[edit] 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).
Betamethasone is a moderately potent glucocorticoid steroid with anti-inflammatory and immunosuppressive properties. Unlike other drugs with these effects, betamethasone does not cause water retention. It is applied as a topical cream, ointment, foam, lotion or gel to treat itching (e.g. from eczema). Betamethasone sodium phosphate is sometimes prescribed as an intramuscular injection (I.M) for itching from various ailments including allergic reactions to poison ivy and similar plants.
The compound is available as a number of ester derivatives: Dipropionate (branded as Diprosone, Diprolene and others), Sodium Phosphate and Valerate (branded as Betnovate, Celestone and others). In the United States and Canada, Betamethasone is mixed with Clotrimazole and sold as Lotrisone.
[edit] General Properties
*Molecular Weight
392.46
*Molecular Formula
C22H29FO5
*IUPAC NAME
(8S,9R,10S,11S,13S,14S,16S,17R)-9-fluoro-11,17-dihydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-3-one
*Canonical Smiles
CC1CC2C3CCC4=CC(=O)C=CC4(C3(C(CC2(C1(C(=O)CO)O)C)O)F)C
*Isomeric Smiles
C[C@H]1C[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@@]4([C@]3([C@H](C[C@@]2([C@]1(C(=O)CO)O)C)O)F)C
[edit] PhysioChemical Properties
*Melting Point
232(EXP)
*LogP
1.94(EXP)
*Water Solubility
66.5(EXP) at 25C
[edit] Indications
Betamethasone is a corticosteroid used to stimulate fetal lung maturation, and to decrease the incidence and mortality from intracranial hemorrhage in premature infants.
It is also used as a topical cream to relieve skin irritation. The tablet form, available in Japan, eradicates eczematous rash within 24 hours, far more rapidly than the ointment.
0.05% Betamethasone cream appears effective in treating phimosis in boys, and often averts the need for circumcision.
Betamethasone sodium phosphate is used orally and via injection with the same indications as other steroids.
Betamethasone Dipropionate and Salicylic Acid can be used as a treatment for Local Psoriasis.
[edit] Fetal risk
As it crosses the placenta, which is required for its beneficial effects, it may also be associated with complications, such as hypoglycemia and leucocytosis in newborns exposed in utero.
[edit] Notes
While betamethasone is commonly applied topically to treat skin inflammation, persistent application of large quantities may result in a more severe rebound inflammation when the medication is withdrawn, sometimes called "Betnovate face". thumb|A tube of 'Betnovate ointment' cream and it's box.
