144-82-1 Usage
Chemical Description
Sulfamethizole is a sulfonamide antibiotic used to treat bacterial infections.
Description
Sulfamethizole is a broad-spectrum sulfonamide antibiotic, characterized by its white crystalline powder form and solubility at a ratio of 1:2,000 in water. It is known for its antibacterial activity against various strains, including streptococci, pneumococci, staphylococci, meningococci, gonococci, colon bacillus, and pathogenic dysentery. Sulfamethizole inhibits dihydropteroate synthase, an enzyme involved in folate biosynthesis, and has a plasma half-life of 2.5 hours.
Uses
Used in Pharmaceutical Industry:
Sulfamethizole is used as a sulfonamide antibacterial agent for treating acute, uncomplicated infections of the urinary tract caused by sensitive organisms. Its quick removal from the organism by the kidneys makes it suitable for this application, although Sulfisoxazole is often the more preferred drug.
Used in Elderly Care:
Sulfamethizole is used as an antibiotic for treating gram-negative Bacillus AmpC enzyme in elderly patients with lower respiratory tract infections, as well as against microbes responsible for tuberculosis.
Used in Veterinary Medicine:
Sulfamethizole is also used in formulations to treat urinary tract infections in animals, due to its effectiveness against a wide range of bacterial strains.
Synonyms and Brand Names:
Sulfamethizole is known by various synonyms such as urosol, rufol, thiosulfil, and others. Some of its brand names include Thiosulfil (Wyeth), 3p methazol, Amer-azo, Azocline, Azotrex, Dorsec, Lucatyl, Methisul, Micturol ampicilina seda, Nicene, Orozl, Procijec, Proklar-m, Rp 2145, S-methizole, Spasmo-harnosal, Starisil, Suladyne, Sulfa gram, Thiosulfil a, Tiosulfan, Uratrac, Urolex, Uroluxcosil, Uro-nebactin, Uropeutic, and Urotrex.
Originator
Thiosulfil,Ayerst,US,1953
Manufacturing Process
To 10 grams acetaldehyde-thiosemicarbazone in 80 grams pyridine gradually
20 grams p-acetaminobenzolsulfonyl chloride is added. The reaction mixture is
heated about 1 hour on a water bath and is then charged in 1 liter water, to
which some acetic acid is added. The bottom sediment is sucked off and
washed with water, after which it is crystallized by alcohol. 20 grams of the
condensation product thus obtained is cleared in 100 cc water at about 30°C,
after which 45 grams calcium ferricyanide dissolved in about 100 cc water is
added. The reaction mixture is made slightly alkaline and held at a
temperature of about 80°C for 2 to 3 hours. It is important that the reaction mixture during the whole period of 2 to 3 hours is steadily held alkaline.After the said 2 to 3 hours the liquid is cooled and the bottom sediment,
which has a greenish color, is filtered off. The liquid sucked off eventually is
treated with active carbon, filtered and made slightly acid by means of acetic
acid, at which 2-amino-benzolsulfonamido-5-methyl-1,3,4-thiodiazol (melting
point 204° to 206°C) is precipitated.
Therapeutic Function
Antibacterial
World Health Organization (WHO)
Sulfamethizole, a sulfonamide anti-infective agent, was
introduced in 1953 for the treatment of bacterial infections. The importance of
sulfonamides has subsequently decreased as a result of increasing bacterial
resistance and their replacement by antibiotics which are generally more active
and less toxic. However sulfamethizole, which is rapidly eliminated, retains a place
in the treatment of urinary infections in some countries whereas in others its use has been discontinued.
Air & Water Reactions
Insoluble in water.
Fire Hazard
Flammability data is lacking for SULFAMETHIZOLE. SULFAMETHIZOLE is probably non-flammable.
Pharmaceutical Applications
2-Sulfanilamido-5-methyl-1,3,4-thiodiazole. A short-acting
sulfonamide (plasma half-life 2.5 h). Protein binding is c. 85%.
About 60% is excreted in the urine within 5 h. It was formerly
widely used in the treatment of urinary tract infection.
Synthesis
Sulfamethizole, N1-(5-methyl-1,3,4-thiadiazole-2-yl)sulfanilamide
(33.1.15), is synthesized in two ways. According to the first, 5-amino-2-methyl-1,3,4-
thiadiazole is reacted with 4-nitrobenzenesulfonyl chloride to make a nitro derivative
(33.1.14), which is then reduced using iron filings in acetic acid to give the desired sulfamethizole.The second method of making sulfamethizole consists of reacting 4-acetylaminobenzene sulfonyl chloride with thiosemicarbazone of acetaldehyde, and subsequent oxidative
cyclization of the product (33.1.16) to the substituted 1,3,4-thiadiazole in the presence of
potassium ferricyanide in base, along with the simultaneous removal of the protective
acetyl group.
Check Digit Verification of cas no
The CAS Registry Mumber 144-82-1 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,4 and 4 respectively; the second part has 2 digits, 8 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 144-82:
(5*1)+(4*4)+(3*4)+(2*8)+(1*2)=51
51 % 10 = 1
So 144-82-1 is a valid CAS Registry Number.
InChI:InChI=1/C9H10N4O2S2/c1-6-11-12-9(16-6)13-17(14,15)8-4-2-7(10)3-5-8/h2-5H,10H2,1H3,(H,12,13)
144-82-1Relevant articles and documents
MODULATORS OF IMMUNOINHIBITORY RECEPTOR PD-1, AND METHODS OF USE THEREOF
-
Page/Page column 52, (2011/07/30)
Disclosed are an assay to identify modulators of the PD-1 :PD-L pathway and PD-1 :PD-L pathway modulators, e.g., compounds and pharmaceutical compositions thereof. Methods for treating diseases influenced by modulation of the PD-1 :PD-L pathway such as, for example, autoimmune diseases, inflammatory disorders, allergies, transplant rejection, cancer, immune deficiency, and other immune system-related disorders, are also disclosed.
SMALL MOLECULE INHIBITORS OF THE PLECKSTRIN HOMOLOGY DOMAIN AND METHODS FOR USING SAME
-
Page/Page column 90, (2009/12/02)
Pleckstrin homology domain binding compounds, pharmaceutical compositions including such compounds, and methods for their use are described herein.