SULFAMETHIZOLE Chemical 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)

EPA Substance Registry System

Sulfamethizole (144-82-1)

Safety Information

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

MSDS

• Language:English Provider:SigmaAldrich

SULFAMETHIZOLE Usage And Synthesis

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(144-82-1)Related Product Information

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• 3-[4-(5-ETHYL-[1,3,4]THIADIAZOL-2-YLSULFAMOYL)-PHENYLCARBAMOYL]-ACRYLIC ACID
• SULFAETHIDOLE SODIUM