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SULFAMETHIZOLE

CAS No.
144-82-1
Chemical Name:
SULFAMETHIZOLE
Synonyms
SULFAMETHIZOL;thiosulfil;SULFAMETHIAZOLE;uroz;famet;rufol;VK 53;rp2145;Urifon;Urolin
CBNumber:
CB4266501
Molecular Formula:
C9H10N4O2S2
Molecular Weight:
270.33
MDL Number:
MFCD00053363
MOL File:
144-82-1.mol
MSDS File:
SDS
Last updated:2024-12-18 14:08:52

SULFAMETHIZOLE Properties

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)
FDA UNII 25W8454H16
ATC code B05CA04,D06BA04,J01EB02,S01AB01
EPA Substance Registry System Sulfamethizole (144-82-1)

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS07
Signal word  Warning
Hazard statements  H317
Precautionary statements  P280
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
NFPA 704
0
2 0

SULFAMETHIZOLE price More Price(30)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich Y0002168 Sulfamethizole for system suitability CRS, European Pharmacopoeia (EP) Reference Standard 144-82-1 Y0002168 $153 2024-03-01 Buy
Sigma-Aldrich PHR3242 Sulfamethizole pharmaceutical secondary standard, certified reference material 144-82-1 500MG $201 2024-03-01 Buy
Sigma-Aldrich 46842 Sulfamethizole VETRANAL?, analytical standard 144-82-1 250MG $40.62 2024-03-01 Buy
Sigma-Aldrich 1630009 Sulfamethizole United States Pharmacopeia (USP) Reference Standard 144-82-1 200mg $250 2024-03-01 Buy
TCI Chemical S0360 Sulfamethizole >98.0%(HPLC)(T) 144-82-1 25g $96 2024-03-01 Buy
Product number Packaging Price Buy
Y0002168 Y0002168 $153 Buy
PHR3242 500MG $201 Buy
46842 250MG $40.62 Buy
1630009 200mg $250 Buy
S0360 25g $96 Buy

SULFAMETHIZOLE Chemical Properties,Uses,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

Sulfonamide antibacterial.

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.

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.
CB4266501-1.jpg
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.
CB4266501-2.jpg

SULFAMETHIZOLE Preparation Products And Raw materials

Raw materials

Preparation Products

Global( 221)Suppliers
Supplier Tel Email Country ProdList Advantage
CONIER CHEM AND PHARMA LIMITED
+8618523575427 sales@conier.com China 49374 58
career henan chemical co
+86-0371-86658258 +8613203830695 factory@coreychem.com China 29811 58
TargetMol Chemicals Inc.
+1-781-999-5354 +1-00000000000 marketing@targetmol.com United States 32161 58
HANGZHOU CLAP TECHNOLOGY CO.,LTD
86-571-88216897,88216896 13588875226 sales@hzclap.com CHINA 6312 58
Dideu Industries Group Limited
+86-29-89586680 +86-15129568250 1026@dideu.com China 22785 58
AFINE CHEMICALS LIMITED
+86-0571-85134551 sales@afinechem.com China 15352 58
Dayang Chem (Hangzhou) Co.,Ltd.
571-88938639 +8617705817739 info@dycnchem.com China 52849 58
Labnetwork lnc.
+86-27-50766799 +8618062016861 contact@labnetwork.com China 19987 58
TargetMol Chemicals Inc.
support@targetmol.com United States 38631 58
PT CHEM GROUP LIMITED
+86-85511178; +86-85511178; peter68@ptchemgroup.com China 35425 58

View Lastest Price from SULFAMETHIZOLE manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Sulfamethizole pictures 2024-11-19 Sulfamethizole
144-82-1
US $29.00 / mL 99.37% 10g TargetMol Chemicals Inc.
Sulfamethizole pictures 2024-11-19 Sulfamethizole
144-82-1
US $29.00 / mL 99.37% 10g TargetMol Chemicals Inc.
SULFAMETHIZOLE USP/EP/BP pictures 2021-07-13 SULFAMETHIZOLE USP/EP/BP
144-82-1
US $1.10 / g 1g 99.9% 100 Tons Min Dideu Industries Group Limited
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 ultrasul urocydal urodiaton urolucosil urosulfin uroz utrasul N1-(5-methyl-1,3,4-thiadiazol-2-yl)sulphanilamide Sulamethizole SULFAMETHIZOLE VETRANAL, 250 MG 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 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 Sulfamethizole CRS Sulfamethizole> Benzenesulfonamide, 4-amino-N-(5-methyl-1,3,4-thiadiazol-2-yl)- SULFAMETHIZOLE USP/EP/BP Sulfamethizole (1630009) thiosulfil SULFAMETHIAZOLE SULFAMETHIZOL