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SULFAMETHIZOLE

Product Name
SULFAMETHIZOLE
CAS No.
144-82-1
Chemical Name
SULFAMETHIZOLE
Synonyms
SULFAMETHIZOL;thiosulfil;SULFAMETHIAZOLE;uroz;VK 53;famet;rufol;Urolin;Urifon;rp2145
CBNumber
CB4266501
Molecular Formula
C9H10N4O2S2
Formula Weight
270.33
MOL File
144-82-1.mol
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SULFAMETHIZOLE Property

Melting point:
210 °C
Boiling point:
176°C (rough estimate)
Density 
1.4704 (rough estimate)
refractive index 
1.6440 (estimate)
storage temp. 
2-8°C
solubility 
Acetonitrile (Slightly), DMSO (Slightly), Methanol (Slightly)
form 
Solid
pka
5.45(at 25℃)
color 
White to Off-White
Water Solubility 
529mg/L(20 ºC)
Merck 
14,8916
BRN 
255002
CAS DataBase Reference
144-82-1(CAS DataBase Reference)
EPA Substance Registry System
Sulfamethizole (144-82-1)
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Safety

Hazard Codes 
Xi
Risk Statements 
43
Safety Statements 
36/37
WGK Germany 
2
RTECS 
WP0875000
HS Code 
2935904000
Hazardous Substances Data
144-82-1(Hazardous Substances Data)
Toxicity
LD50 oral in rat: 3500mg/kg
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H317May cause an allergic skin reaction

Precautionary statements

P280Wear protective gloves/protective clothing/eye protection/face protection.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
Y0002168
Product name
Sulfamethizole for system suitability
Purity
CRS, European Pharmacopoeia (EP) Reference Standard
Packaging
Y0002168
Price
$153
Updated
2024/03/01
Sigma-Aldrich
Product number
PHR3242
Product name
Sulfamethizole
Purity
pharmaceutical secondary standard, certified reference material
Packaging
500MG
Price
$201
Updated
2024/03/01
Sigma-Aldrich
Product number
46842
Product name
Sulfamethizole
Purity
VETRANAL?, analytical standard
Packaging
250MG
Price
$40.62
Updated
2024/03/01
Sigma-Aldrich
Product number
1630009
Product name
Sulfamethizole
Purity
United States Pharmacopeia (USP) Reference Standard
Packaging
200mg
Price
$250
Updated
2024/03/01
TCI Chemical
Product number
S0360
Product name
Sulfamethizole
Purity
>98.0%(HPLC)(T)
Packaging
25g
Price
$96
Updated
2024/03/01
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SULFAMETHIZOLE Chemical Properties,Usage,Production

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

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.

Uses

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.

Uses

Sulfonamide antibacterial.

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

Sulfamethizole’splasma half-life is 2.5 hours. This compound is a white crystallinepowder soluble 1:2,000 in water.

General Description

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.

SULFAMETHIZOLE Preparation Products And Raw materials

Raw materials

Preparation Products

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SULFAMETHIZOLE Suppliers

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View Lastest Price from SULFAMETHIZOLE manufacturers

Dideu Industries Group Limited
Product
SULFAMETHIZOLE 144-82-1
Price
US $1.10/g
Min. Order
1g
Purity
99.9%
Supply Ability
100 Tons Min
Release date
2021-07-12
Career Henan Chemical Co
Product
SULFAMETHIZOLE 144-82-1
Price
US $3.00/KG
Min. Order
1KG
Purity
98%
Supply Ability
100KG
Release date
2020-01-29

144-82-1, SULFAMETHIZOLERelated Search:

TERT-BUTYL 4-(AMINOCARBONYL)TETRAHYDROPYRIDINE-1(2H)-CARBOXYLATE SULFAMETHIZOLE 4-AMINO-N-(5-ETHYL-[1,3,4]THIADIAZOL-2-YL)-BENZENESULFONAMIDE 1-Boc-4-(aminomethyl)piperidine tert-Butyl 4-(aminocarbothioyl)tetrahydropyridine-1(2H)-carboxylate Sulfanilamide BOC-3-CARBOXYMETHYL-1-PHENYL-1,3,8-TRIAZASPIRO[4 5]DECAN-4-ONE 4-(AMINO-METHOXYCARBONYL-METHYL)-PIPERIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER (S)-A-FMOC-D-BOC-4-PIPERIDYLGLYCINE 1-BOC-4-(AMINOCARBOXYMETHYL)PIPERIDINE glybuthiazol 1-T-BOC-PIPERIDINE-4-SPIRO-5'-[1',3'-BIS-T-BOC]-HYDANTOIN N-(TERT-BUTOXYCARBONYL)PIPERIDIN-4-YLMETHYLPIPERIDINE-4-CARBOXYLIC ACID (R)-N-ALPHA-(9-FLUORENYLMETHYLOXYCARBONYL)-N'-T-BUTYLOXYCARBONYL-4-PIPERIDYLGLYCINE Phthalylsulfamethizol (S)-4-(AMINO-METHOXYCARBONYL-METHYL)-PIPERIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER 3-[4-(5-ETHYL-[1,3,4]THIADIAZOL-2-YLSULFAMOYL)-PHENYLCARBAMOYL]-ACRYLIC ACID SULFAETHIDOLE SODIUM

  • 4-AMINO-N-[5-METHYL-1,3,4-THIADIAZOL-2-YL]-BENZENESULFONAMIDE
  • Sulfamethizole Solution, 100ppm
  • 4-Amino-N-(5-methyl-1,3,4-thiadiazol-2-yl)benzenesulfonamide, N1-(5-Methyl-1,3,4-thiadiazol-2-yl)sulfanilamide
  • Urifon
  • Urolin
  • VK 53
  • 4-Amino-N-(5-methyl-1,3,4-thiadiazol-2-yl)benzene-1-sulfonamide
  • 4-azanyl-N-(5-methyl-1,3,4-thiadiazol-2-yl)benzenesulfonamide
  • Sulfamethizole (200 mg)
  • LABOTEST-BB LT00772293
  • SULFAMETHYLTHIADIAZOLE
  • SULFAMETHIAZOLE
  • SULFAMETHIZOL
  • SULFAMETHIZOLE
  • SULPHAMETHIZOLE
  • N1-(5-METHYL-1,3,4-THIADIAZOL-2-YL)SULFANILAMIDE
  • Sulfamethizole solution,1000ppm
  • SULPHAMETHIAZOLE
  • 2-(p-aminobenzenesulfonamido)-5-methylthiadiazole
  • 2-methyl-5-sulfanilamido-1,3,4-thiadiazole
  • 2-sulfanilamido-5-methyl-1,3,4-thiadiazole
  • 4-amino-n-(5-methyl-1,3,4-thiadiazol-2-yl)-benzenesulfonamid
  • 5-methyl-2-sulfanilamido-1,3,4-thiadiazole
  • ayerlucil
  • famet
  • lucosil
  • methazol
  • microsul
  • n(1)-(5-methyl-1,3,4-thiadiazol-2-yl)-sulfanilamid
  • n(sup1)-(5-methyl-1,3,4-thiadiazol-2-yl)-sulfanilamid
  • n(sup1)-(5-methyl-1,3,4-thiadiazol-2-yl)-sulfanilamide
  • renasul
  • rp2145
  • rufol
  • salimol
  • sulfagram
  • sulfamethylizole
  • sulfapyelon
  • sulfstat
  • sulfurine
  • tetracid
  • thidicur
  • thiosulfil
  • ultrasul
  • urocydal
  • urodiaton
  • urolucosil
  • urosulfin
  • uroz
  • utrasul
  • N1-(5-methyl-1,3,4-thiadiazol-2-yl)sulphanilamide
  • Sulamethizole
  • SULFAMETHIZOLE VETRANAL, 250 MG
  • Sulfamethizole CRS
  • Sulfamethizole&gt
  • Benzenesulfonamide, 4-amino-N-(5-methyl-1,3,4-thiadiazol-2-yl)-
  • SULFAMETHIZOLE USP/EP/BP
  • Sulfamethizole (1630009)