144-82-1 Usage
Chemical Description
Sulfamethizole is a sulfonamide antibiotic used to treat bacterial infections.
Description
Sulfamethizole is a broad spectrum sulfonamide antibiotic (MIC90s = 1.25-5,000 μg/ml against clinical isolates of E. coli and K. pneumoniae). It inhibits dihydropteroate synthase, an enzyme involved in folate biosynthesis. Formulations containing sulfamethizole have previously been used to treat urinary tract infections.
Originator
Thiosulfil,Ayerst,US,1953
Uses
Different sources of media describe the Uses of 144-82-1 differently. You can refer to the following data:
1. This drug has antibacterial activity with respect to streptococci, pneumococci, staphylococci, meningococci, gonococci, colon bacillus, pathogenic dysentery, and others. It is not
very toxic. It is generally used for acute, uncomplicated infections of the urinary tract that are caused by sensitive organisms. Because it is removed quickly from the organism by the
kidneys, the level of drug in the plasma remains low, and therefore it is not used for treating infections that are localized in the urinary tract. Sulfisoxazole is the more preferred
drug. Synonyms of this drug are urosol, rufol, thiosulfil, and others.
2. Sulfonamide antibacterial.
3. Sulfamethizole is a sulfonamide based antibiotic that exhibit bactericidal activities towards gram-negative bacteria. Sulfamehizole was shown to be effective in treating gram-negative Bacillus AmpC en
zyme in elderly patients with lower respiratory tract infection and as well as against microbs responsible for tuberculosis.
Definition
ChEBI: A sulfonamide consisting of a 1,3,4-thiadiazole nucleus with a methyl substituent at C-5 and a 4-aminobenzenesulfonamido group at C-2.
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.
Brand name
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;Urotrex.
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.
General Description
Different sources of media describe the General Description of 144-82-1 differently. You can refer to the following data:
1. Sulfamethizole’splasma half-life is 2.5 hours. This compound is a white crystallinepowder soluble 1:2,000 in water.
2. White powder.
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
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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
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, (2009/12/02)
Pleckstrin homology domain binding compounds, pharmaceutical compositions including such compounds, and methods for their use are described herein.