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SULFAMETHIZOLE

CAS No.144-82-1
Chemical Name:SULFAMETHIZOLE
CBNumber:CB4266501
Molecular Formula:C9H10N4O2S2
Formula Weight:270.33
MOL File:144-82-1.mol

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)
FDA UNII 25W8454H16
ATC code B05CA04,D06BA04,J01EB02,S01AB01
EPA Substance Registry System Sulfamethizole (144-82-1)
UNSPSC Code 41116107
NACRES NA.24

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

NFPA 704:

	0
2		0

Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal wordWarning
Hazard statements H317
Precautionary statements P280

SULFAMETHIZOLE Price More Price(4)

Brand: Sigma-Aldrich(India)
Product number: S5632
Product name : Sulfamethizole
Purity: analytical standard, ≥99% (HPLC)
Packaging: 10G
Price: ₹7187.8
Updated: 2022/06/14
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Brand: Sigma-Aldrich(India)
Product number: S5632
Product name : Sulfamethizole
Purity: analytical standard, ≥99% (HPLC)
Packaging: 25G
Price: ₹11009.03
Updated: 2022/06/14
Buy: Buy

Brand: Sigma-Aldrich(India)
Product number: 46842
Product name : Sulfamethizole
Purity: VETRANAL?, analytical standard
Packaging: 250MG
Price: ₹5011.98
Updated: 2022/06/14
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Brand: TCI Chemicals (India)
Product number: S0360
Product name : Sulfamethizole
Purity:
Packaging: 25G
Price: ₹5900
Updated: 2022/05/26
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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 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.

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.