2438-72-4 Usage
Description
Bufexamac is a hydroxamic acid derived from phenylacetamide, with the benzene moiety substituted at C-4 by a butoxy group. It is a non-steroidal anti-inflammatory drug (NSAID) known for its anti-inflammatory, analgesic, and antipyretic properties. Bufexamac is used both topically and rectally, and is particularly effective as a specific inhibitor of class IIB histone deacetylases (HDAC6 and HDAC10). It is available under various brand names, such as Anderm, Paraderm, Parfenac, Bufemac, and Bufexine ratiopharm.
Uses
Used in Pharmaceutical Industry:
Bufexamac is used as an anti-inflammatory agent for the treatment of various skin conditions characterized by inflammation, such as insect bites, burns, plant stings, psoriasis, hemorrhoidal symptoms, eczema, and inflammation of the skin following radiotherapy. It can also be used before radiotherapy to help prevent inflammation caused by radiation therapy.
Used as an Analgesic:
Bufexamac serves as an analgesic, providing pain relief for patients suffering from various conditions that cause inflammation and discomfort.
Used as an Antipyretic:
Bufexamac is utilized as an antipyretic to help reduce fever and alleviate the discomfort associated with elevated body temperatures.
Used as an Alternative to Topical Corticosteroids:
Many patients with eczematous disorders prefer using Bufexamac as an alternative to topical corticosteroids due to its effectiveness in managing inflammation and related symptoms.
Used in Research and Development:
Bufexamac's role as a specific inhibitor of class IIB histone deacetylases (HDAC6 and HDAC10) makes it a valuable compound in the field of research and development, particularly in the study of epigenetics and the development of novel therapeutic strategies for various diseases.
Originator
Parfenac,Lederle,UK,1973
Manufacturing Process
(1) 136 g of p-hydroxyacetophenone, 140 g of butyl bromide, 152 g of
potassium carbonate, 17 g of potassium iodide and 275 cc of ethanol are
mixed and then refluxed for 48 hours. The reaction mixture is cooled, diluted
with water, then extracted with ether. The ethereal phase is washed with a 10% sodium hydroxide solution, then with water, followed by drying, ether is
evaporated and the product distilled under reduced pressure. 168 g of pbutyloxyacetophenone
are obtained with yield of 87% (160°-162°C at 11 mm
Hg).
(2) 192 g of p-butyloxyacetophenone, 42 g of sulfur and 130 g of morpholine
are mixed and then refluxed for 14 hours. The resulting solution is poured into
water and stirred until crystallization of the sulfurated complex. The latter is
filtered, washed with water and dried, Production: 270 g (88% yield).
(3) 200 g of sodium hydroxide are dissolved in 1,500 cc of ethanol and then
293 g of the thus-obtained sulfurated complex are added. The mixture is
refluxed overnight, The mixture is distilled to separate the maximum of the
alcohol and then diluted with water. The resulting solution is acidified with
hydrochloric acid, and extracted with ether. The ethereal phase is washed with
water, followed by extraction with a 10% sodium carbonate solution. The
carbonated solution is acidified with 10% hydrochloric acid, and the resulting
precipitate of p-n-butyloxyphenylacetic acid is filtered and dried. 100 g of this
product are obtained (70% yield).
(4) 208 g of p-n-butyloxyphenylacetic acid, 368 g of ethanol and 18 cc of
sulfuric acid are refluxed for 5 hours. The mixture is diluted with water, after
which it is extracted with ether. The ethereal phase is successively washed
with water, then with carbonate, and again with water, following which it is
dried and distilled to remove solvent. The ester is then distilled at a reduced
pressure. 200 g of ethyl p-butyloxyphenylecetate are thus obtained with yield
of 61% (186°C at 8 mm Hg).
(5) 7 g of hydroxylamine hydrochloride are dissolved in 100 cc of methanol. A
solution of 5 g of sodium in 150 cc of methanol is added and the salt
precipitate is separated by filtration. 22 g of ethyl p-n-butyloxyphenylacetate
are added to the filtrate and the mixture is refluxed for 1 hour. The mixture is
cooled and acidified with 20% hydrochloric acid. 14.7 g of p-nbutyloxyphenylacetohydroxamic
acid are thus obtained with yield of 71%
(melting point: 153°-155°C).
World Health Organization (WHO)
Bufexamac, an analgesic and anti-inflammatory agent, was
introduced in 1974 for the topical treatment of a wide range of dermatoses. The
drug is widely marketed and the World Health Organization is not aware of
restrictive action having been taken elsewhere.
Contact allergens
Bufexamac is an arylacetic nonsteroidal anti-inflammatory
drug. It induces allergic contact dermatitis,
eczematous or erythema multiforme like type, and
even generalized eruptions like acute generalized
exanthematous pustulosis.
Check Digit Verification of cas no
The CAS Registry Mumber 2438-72-4 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 2,4,3 and 8 respectively; the second part has 2 digits, 7 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 2438-72:
(6*2)+(5*4)+(4*3)+(3*8)+(2*7)+(1*2)=84
84 % 10 = 4
So 2438-72-4 is a valid CAS Registry Number.
InChI:InChI=1/C12H17NO3/c1-2-3-8-16-11-6-4-10(5-7-11)9-12(14)13-15/h4-7,15H,2-3,8-9H2,1H3,(H,13,14)
2438-72-4Relevant articles and documents
Hydroxamic acid inhibitors of 5-lipoxygenase: Quantitative structure-activity relationships
Summers,Kim,Mazdiyasni,Holms,Ratajczyk,Stewart,Dyer,Carter
, p. 992 - 998 (2007/10/02)
An evaluation of the quantitative structure-activity relationships (QSAR) for more than 100 hydroxamic acids revealed that the primary physicochemical feature influencing the in vitro 5-lipoxygenase inhibitory potencies of these compounds is the hydrophobicity of the molecule. A significant correlation was observed between the octanol-water partition coefficient of the substituent attached to the carbonyl of the hydroxamate and in vitro inhibitory activity. This correlation held for hydroxamic acids of diverse structure and with potencies spanning 4 orders of magnitude. Although the hydrophobicity may be packaged in a variety of structural ways and still correlate with potency, the QSAR study revealed two major exceptions. Specifically, the hydrophobicity of portions of compounds in the immediate vicinity of the hydroxamic acid functionally does not appear to contribute to increased inhibition and the hydrophobicity of fragments beyond approximately 12 A from the hydroxamate do not influence potency. The QSAR study also demonstrated that inhibitory activity was enhanced when there was an alkyl group on the hydroxamate nitrogen, when electron-withdrawing substituents were present and when the hydroxamate was conjugated to an aromatic system. These observations provide a simple description of the lipoxygenase-hydroxamic acid binding site.
