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| | Betamethasone 17-valerate Basic information |
| Product Name: | Betamethasone 17-valerate | | Synonyms: | pregna-1,4-diene-3,20-dione,9-fluoro-11,21-dihydroxy-16-methyl-17-((1-oxopenty;9-fluoro-11beta,17,21-trihydroxy-16beta-methylpregna-1,4-diene-3,20-dione 17-valerate;9ALPHA-FLUORO-16BETA-METHYLPREDNISOLONE 17-VALERATE;9ALPHA-FLUORO-16BETA-METHYL-11BETA,17ALPHA,21-TRIHYDROXY-1,4-PREGNADIENE-3,20-DIONE 17-VALERATE;1,4-PREGNADIENE-11BETA,17ALPHA,21-TRIOL-9ALPHA-FLUORO-16BETA-METHYL-3,20-DIONE 17-VALERATE;1,4-pregnadiene-11b,17a,21-triol-9a-fluoro-16b-methyl-3,20-dione 17-valerate;9α-Fluoro-16β-methylprednisolone 17-valerate, Betnovate, 9α-Fluoro-16β-methyl-11β,17α,21-trihydroxy-1,4-pregnadiene-3,20-dione 17-valerate, 1,4-Pregnadiene-11β,17α,21-triol-9α-fluoro-16β-methyl-3,20-dione 17-valerate;BetaMethasone valerate (Betnovate) | | CAS: | 2152-44-5 | | MF: | C27H37FO6 | | MW: | 476.58 | | EINECS: | 218-439-3 | | Product Categories: | API;BETA-VAL;2152-44-5 | | Mol File: | 2152-44-5.mol |  |
| | Betamethasone 17-valerate Chemical Properties |
| Melting point | 183-184° | | alpha | D +77° (dioxane) | | Boiling point | 598.9±50.0 °C(Predicted) | | density | 1.1174 (estimate) | | storage temp. | 2-8°C | | solubility | Practically insoluble in water, freely soluble in acetone and in methylene chloride, soluble in ethanol (96 per cent). | | pka | 12.90±0.70(Predicted) | | color | White | | Merck | 13,1183 | | BRN | 4240001 | | InChIKey | SNHRLVCMMWUAJD-SUYDQAKGSA-N | | SMILES | [C@]12(C)C[C@@H]([C@]3(F)[C@@]4(C)C=CC(=O)C=C4CC[C@@]3([H])[C@]1([H])C[C@H](C)[C@@]2(C(=O)CO)OC(=O)CCCC)O |&1:0,3,4,6,16,18,21,23,r| | | CAS DataBase Reference | 2152-44-5(CAS DataBase Reference) | | EPA Substance Registry System | .beta.-Methasone 17-valerate (2152-44-5) |
| Hazard Codes | Xn | | Risk Statements | 48 | | Safety Statements | 22-24/25 | | RTECS | TU3835000 | | HS Code | 2937229000 | | Toxicity | mouse,LD50,intraperitoneal,632mg/kg (632mg/kg),Shikoku Igaku Zasshi. Shikoku Medical Journal. Vol. 29, Pg. 153, 1973. |
| | Betamethasone 17-valerate Usage And Synthesis |
| Description | Betamethasone 17-valerate is a synthetic glucocorticoid ester. It is the 17-valerate ester of betamethasone. Betamethasone 17-valerate is often used to treat mild eczema with good efficacy and lower incidence of steroid induced adverse effects due to its lower potency compared to other glucocorticoids. It is available in cream, ointment, lotion, and foam preparations for topical use. | | Chemical Properties | White Solid | | Originator | Valisone,Schering,US,1967 | | Uses | Betamethasone 17-Valerate is a glucocorticoid with anti-inflammatory properties and immunosuppressive activity. It is an antiepileptic non-selective phosphodiesterase inhibitor. Topical application of Betamethasone 17-Valerate has been shown to inhibit heat-induced vasodilatation in man. As a medium-strength corticosteroid, this medication is used to treat a variety of skin conditions (such as eczema, dermatitis, allergies, rash). Betamethasone reduces the swelling, itching, and redness that can occur in these types of conditions. | | Indications | Betamethasone valerate (Psorion, Beta-Val, Luxiq) is a synthetic fluorinated corticosteroid. | | Definition | ChEBI: Betamethasone valerate is a steroid ester that is betamethasone in which the hydroxy group at the 17alpha position has been converted to the corresponding pentanoate ester. It has a role as an anti-inflammatory drug. It is a steroid ester, a 20-oxo steroid, a 21-hydroxy steroid, an 11beta-hydroxy steroid, a fluorinated steroid, a 3-oxo-Delta(1),Delta(4)-steroid and a primary alpha-hydroxy ketone. It is functionally related to a betamethasone. | | Manufacturing Process | The valerate is made from betamethasone as a starting material as follows: A
suspension of 9α-fluoro-11β,17α,21-trihydroxy-16β-methylpregna-1,4-diene-
3,20-dione(betamethasone) (2 grams) in sodium dried benzene (500 ml) was
distilled vigorously for a few minutes, toluene-p-sulfonic acid monohydrate (30
mg) and methyl orthovalerate (5 ml) were added and distillation was
continued for 10 minutes. The mixture was then boiled under reflux for 1.5
hours after which time unreacted betamethasone alcohol (400 mg) was
removed by filtration. The benzene solution was treated with solid sodium
.bicarbonate and a few drops of pyridine, filtered and evaporated to dryness
at about 50°C. The residue, in ether, was filtered through grade III basic
alumina (20grams) to remove traces of unreacted betamethasone alcohol, the
ether removed in vacuo and the residue of crude betamethasone 17,21-
methyl orthovalerate was treated with acetic acid (20ml) and a few drops of
water and left overnight at room temperature.
The acetic acid solution was poured into water (100 ml) and extracted with
chloroform. The chloroform extracts were washed in turn with water, saturated
sodium bicarbonate solution and water, dried and evaporated in vacuo. The
residual gum was triturated with ether and a white crystalline solid (1.16
grams) isolated by filtration. Recrystallization from ether (containing a small
amount of acetone)-petroleum ether gave 9α-fluoro-11β,21-dihydroxy-16β-
methyl-17α-valeryloxypregna-1,4-diene-3,20-dione (871 mg) as fine needles. | | Brand name | Betatrex (Savage); Luxiq (Connetics); Valisone (Schering). | | Therapeutic Function | Corticosteroid | | Biochem/physiol Actions | Betamethasone 17-valerate is a synthetic glucocorticoid. It exhibitstherapeutic effects against various allergic and inflammatory skin diseases. Betamethasone 17-valerate also possesses anti-inflammatory properties. |
| | Betamethasone 17-valerate Preparation Products And Raw materials |
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