Clobetasol propionate
From DrugPedia: A Wikipedia for Drug discovery
(Difference between revisions)
| Line 9: | Line 9: | ||
</jmol> | </jmol> | ||
</td></tr></table> | </td></tr></table> | ||
| - | + | ||
| - | [http:// | + | [http://crdd.osdd.net/raghava/hmrbase/test_extract.php?db=arun&table=nphormonet&id=1029&show=SHOW-3D Show 3-D Structure] |
| + | |||
| + | {{Drugbox | ||
| + | | IUPAC_name = [(8S,9R,10S,11S,13S,14S,16S,17R)-17-(2-chloroacetyl)-9-fluoro-11-hydroxy-10,13,16-trimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl] propanoate | ||
| + | | CAS_number = 25122-46-7 | ||
| + | | CAS_supplemental = | ||
| + | | ATC_suffix = AD01 | ||
| + | | ATC_supplemental = | ||
| + | | PubChem = 123917 | ||
| + | | ChemSpiderID = 30399 | ||
| + | | DrugBank = APRD00876 | ||
| + | | chemical_formula =C<sub>2</sub><sub>5</sub>H<sub>3</sub><sub>2</sub>ClFO<sub>5</sub> | ||
| + | | molecular_weight = 466.97 | ||
| + | | smiles = CCC(=O)OC1(C(CC2C1(CC(C3(C2CCC4=CC(=O)C=CC43C)F)O)C)C)C(=O)CCl | ||
| + | | synonyms = Enterolactone | ||
| + | | density = | ||
| + | | melting_point = 195.5-197(EXP) | ||
| + | | boiling_point = | ||
| + | | solubility = 3.86(EST) at 25<sup>o</sup>C | ||
| + | | specific_rotation = | ||
| + | | sec_combustion = | ||
| + | | bioavailability = | ||
| + | | protein_bound = | ||
| + | | metabolism = | ||
| + | | elimination_half-life = | ||
| + | | excretion = | ||
| + | | pregnancy_category= | ||
| + | | dependency_liability = | ||
| + | | routes_of_administration =[[Topical]] | ||
| + | }} | ||
A derivative of PREDNISOLONE with high glucocorticoid activity and low mineralocorticoid activity. Absorbed through the skin faster than FLUOCINONIDE, it is used topically in treatment of PSORIASIS but may cause marked adrenocortical suppression. | A derivative of PREDNISOLONE with high glucocorticoid activity and low mineralocorticoid activity. Absorbed through the skin faster than FLUOCINONIDE, it is used topically in treatment of PSORIASIS but may cause marked adrenocortical suppression. | ||
| + | |||
| + | '''Clobetasol propionate''' is a [[corticosteroid]] used to treat various skin disorders including [[eczema]] and [[psoriasis]]. It comes in ointment and [[emollient]] cream presentations. It has very high potency and typically should not be used with [[occlusive dressings]], or for extended continous use (beyond two weeks). It is also used to treat several [[auto-immune]] diseases including [[alopecia areata]] and [[lichen planus]] (auto immune skin nodules). | ||
| + | |||
| + | Clobetasol propionate is marketed and sold worldwide under numerous names including '''Clobex''', '''Temovate''' (US), '''Tenovate''', '''Dermovate''', '''Dermatovate''', '''Butavate''' and, '''Movate'''. | ||
==General Properties== | ==General Properties== | ||
| Line 49: | Line 82: | ||
3.86(EST) at 25C | 3.86(EST) at 25C | ||
| + | == Forms == | ||
| + | *Clobetasol propionate ointment USP 0.05%, supplied in Olux 15 g, 30 g, 45 g, and 60 g tubes. | ||
| + | *Temovate & emollient 0.05%, supplied in 15 g (NDC 0173-0454-01), 30 g (NDC 0173-0454-02) and 60 g (NDC 0173-0454-03) tubes. | ||
| + | *Clobetasol propionate foam 0.05% | ||
| + | *Clobetasol propionate cream 0.05% | ||
| + | *Clobetasol propionate gel 0.05% | ||
| + | *Clobestasol propianate spray 0.05% | ||
| + | == Possible side effects == | ||
| + | *[[Acneform eruptions]] | ||
| + | *Allergic contact [[dermatitis]] | ||
| + | *[[Burning sensation]] | ||
| + | *[[Cracking]] and [[fissuring]] | ||
| + | *[[Cushing's syndrome]] | ||
| + | *[[Dryness]] | ||
| + | *[[Erythema]] | ||
| + | *[[Glaucoma]] | ||
| + | *[[Folliculitis]] | ||
| + | *[[Hypertrichosis]] | ||
| + | *[[Hypopigmentation]] | ||
| + | *[[Itching]] | ||
| + | *[[Irritation]] | ||
| + | *[[Miliaria]] | ||
| + | *[[Numbness]] of fingers | ||
| + | *[[Perioral dermatitis]] | ||
| + | *[[Pruritus]] | ||
| + | *[[Secondary infection]] | ||
| + | *[[Skin atrophy]] | ||
| + | *[[Skin maceration]] | ||
| + | *[[Stinging]] | ||
| + | *[[Striae]] | ||
| + | *[[Telangiectasia]] | ||
| + | |||
| + | ==Risk to pregnant women== | ||
| + | According to the California Environmental Protection Agency, clobetasol propionate should not be used by pregnant women, or women expecting to become pregnant soon, as studies with rats shows a risk of birth defects (http://www.oehha.ca.gov/prop65/CRNR_notices/admin_listing/requests_info/referenced_docs/frpkg5r.html): | ||
| + | |||
| + | <blockquote>"Studies in the rat following oral administration at dosage levels up to 50 mg/kg per day revealed that the females exhibited an increase in the number of resorbed embryos and a decrease in the number of living fetuses at the highest dose. Pregnancy: [[Teratogenic]] Effects (i.e., possibility of causing abnormailities in fetuses): Pregnancy Category C: Clobetasol propionate has not been tested for teratogenicity when applied topically; however, it is absorbed percutaneously, and when administered subcutaneously it was a significant teratogen in both the rabbit and mouse. Clobetasol propionate has greater teratogenic potential than steroids that are less potent.There are no adequate and well-controlled studies of the teratogenic effects of clobetasol propionate in pregnant women. Temovate Cream and Ointment should be used during pregnancy only if the potential benefit justifies the potential risk to the fetus."</blockquote> | ||
==External Links== | ==External Links== | ||
| Line 55: | Line 124: | ||
*[http://www.drugbank.ca/drugs/DB01013]Drugbank | *[http://www.drugbank.ca/drugs/DB01013]Drugbank | ||
| - | [[ | + | [[Category:Hormones]] |
| + | [[Category:Propionates]] | ||
Current revision
|
|
| Clobetasol propionate
| |
| Systematic (IUPAC) name | |
| [(8S,9R,10S,11S,13S,14S,16S,17R)-17-(2-chloroacetyl)-9-fluoro-11-hydroxy-10,13,16-trimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl] propanoate | |
| Identifiers | |
| CAS number | |
| ATC code | ? |
| PubChem | |
| DrugBank | |
| ChemSpider | |
| Chemical data | |
| Formula | C25H32ClFO5 |
| Mol. mass | 466.97 |
| SMILES | & |
| Synonyms | Enterolactone |
| Physical data | |
| Melt. point | 195.5-197(EXP) °C |
| Solubility in water | 3.86(EST) at 25oC mg/mL |
| Pharmacokinetic data | |
| Bioavailability | ? |
| Metabolism | ? |
| Half life | ? |
| Excretion | ? |
| Therapeutic considerations | |
| Pregnancy cat. |
? |
| Legal status | |
| Routes | Topical |
A derivative of PREDNISOLONE with high glucocorticoid activity and low mineralocorticoid activity. Absorbed through the skin faster than FLUOCINONIDE, it is used topically in treatment of PSORIASIS but may cause marked adrenocortical suppression.
Clobetasol propionate is a corticosteroid used to treat various skin disorders including eczema and psoriasis. It comes in ointment and emollient cream presentations. It has very high potency and typically should not be used with occlusive dressings, or for extended continous use (beyond two weeks). It is also used to treat several auto-immune diseases including alopecia areata and lichen planus (auto immune skin nodules).
Clobetasol propionate is marketed and sold worldwide under numerous names including Clobex, Temovate (US), Tenovate, Dermovate, Dermatovate, Butavate and, Movate.
Contents |
[edit] General Properties
*Molecular Weight
466.97
*Molecular Formula
C25H32ClFO5
*IUPAC NAME
[(8S,9R,10S,11S,13S,14S,16S,17R)-17-(2-chloroacetyl)-9-fluoro-11-hydroxy-10,13,16-trimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl] propanoate
*Canonical Smiles
CCC(=O)OC1(C(CC2C1(CC(C3(C2CCC4=CC(=O)C=CC43C)F)O)C)C)C(=O)CCl
*Isomeric Smiles
CCC(=O)O[C@@]1([C@H](C[C@@H]2[C@@]1(C[C@@H]([C@]3([C@H]2CCC4=CC(=O)C=C[C@@]43C)F)O)C)C)C(=O)CCl
[edit] PhysioChemical Properties
*Melting Point
195.5-197(EXP)
*LogP
3.5(EXP)
*Water Solubility
3.86(EST) at 25C
[edit] Forms
- Clobetasol propionate ointment USP 0.05%, supplied in Olux 15 g, 30 g, 45 g, and 60 g tubes.
- Temovate & emollient 0.05%, supplied in 15 g (NDC 0173-0454-01), 30 g (NDC 0173-0454-02) and 60 g (NDC 0173-0454-03) tubes.
- Clobetasol propionate foam 0.05%
- Clobetasol propionate cream 0.05%
- Clobetasol propionate gel 0.05%
- Clobestasol propianate spray 0.05%
[edit] Possible side effects
- Acneform eruptions
- Allergic contact dermatitis
- Burning sensation
- Cracking and fissuring
- Cushing's syndrome
- Dryness
- Erythema
- Glaucoma
- Folliculitis
- Hypertrichosis
- Hypopigmentation
- Itching
- Irritation
- Miliaria
- Numbness of fingers
- Perioral dermatitis
- Pruritus
- Secondary infection
- Skin atrophy
- Skin maceration
- Stinging
- Striae
- Telangiectasia
[edit] Risk to pregnant women
According to the California Environmental Protection Agency, clobetasol propionate should not be used by pregnant women, or women expecting to become pregnant soon, as studies with rats shows a risk of birth defects (http://www.oehha.ca.gov/prop65/CRNR_notices/admin_listing/requests_info/referenced_docs/frpkg5r.html):
"Studies in the rat following oral administration at dosage levels up to 50 mg/kg per day revealed that the females exhibited an increase in the number of resorbed embryos and a decrease in the number of living fetuses at the highest dose. Pregnancy: Teratogenic Effects (i.e., possibility of causing abnormailities in fetuses): Pregnancy Category C: Clobetasol propionate has not been tested for teratogenicity when applied topically; however, it is absorbed percutaneously, and when administered subcutaneously it was a significant teratogen in both the rabbit and mouse. Clobetasol propionate has greater teratogenic potential than steroids that are less potent.There are no adequate and well-controlled studies of the teratogenic effects of clobetasol propionate in pregnant women. Temovate Cream and Ointment should be used during pregnancy only if the potential benefit justifies the potential risk to the fetus."
