Brand Name(s) in US
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Sulfamethazine

Brand Name(s) in US
Product Name
Sulfamethazine
CAS No.
57-68-1
Chemical Name
Sulfamethazine
Synonyms
SULFADIMIDINE;Sulphadimidine;SM2;Sulphamethazine;L-30;Sulfamidine;SULFADIMIDIN;sulfametazina;SULFAMETAZINE;Sulfadimidine[1]
CBNumber
CB8116727
Molecular Formula
C12H14N4O2S
Formula Weight
278.33
MOL File
57-68-1.mol
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Sulfamethazine Property

Melting point:
197 °C
Boiling point:
294°C (rough estimate)
Density 
1.2997 (rough estimate)
refractive index 
1.6440 (estimate)
storage temp. 
2-8°C
solubility 
acetone: soluble50mg/mL
form 
Crystalline Powder
pka
7.4, 2.65(at 25℃)
color 
white to off-white
Water Solubility 
150mg/100mL (29 ºC)
Merck 
14,8905
BRN 
261304
Stability:
Stable, but light sensitive. Incompatible with strong oxidizing agents.
CAS DataBase Reference
57-68-1(CAS DataBase Reference)
NIST Chemistry Reference
Sulfamethazine(57-68-1)
IARC
3 (Vol. 79) 2001
EPA Substance Registry System
Sulfamethazine (57-68-1)
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Safety

Hazard Codes 
Xi
Risk Statements 
36/37/38
Safety Statements 
23-24/25-36-26
WGK Germany 
2
RTECS 
WO9275000
10
TSCA 
Yes
HS Code 
29350090
Hazardous Substances Data
57-68-1(Hazardous Substances Data)
Toxicity
LD50 i.p. in mice: 1.06 g/kg (Bobranski)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H315Causes skin irritation

H317May cause an allergic skin reaction

H319Causes serious eye irritation

H334May cause allergy or asthma symptoms or breathing difficulties if inhaled

H362May cause harm to breast-fed children

Precautionary statements

P201Obtain special instructions before use.

P260Do not breathe dust/fume/gas/mist/vapours/spray.

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P263Avoid contact during pregnancy/while nursing.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P272Contaminated work clothing should not be allowed out of the workplace.

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

P285In case of inadequate ventilation wear respiratory protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P304+P341IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P308+P313IF exposed or concerned: Get medical advice/attention.

P321Specific treatment (see … on this label).

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P333+P313IF SKIN irritation or rash occurs: Get medical advice/attention.

P342+P311IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.

P362Take off contaminated clothing and wash before reuse.

P363Wash contaminated clothing before reuse.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
PHR3136
Product name
Sulfamethazine
Purity
pharmaceutical secondary standard, certified reference material
Packaging
1G
Price
$173
Updated
2024/03/01
Sigma-Aldrich
Product number
46802
Product name
Sulfamethazine
Purity
VETRANAL , analytical standard
Packaging
250mg
Price
$68.7
Updated
2024/03/01
Sigma-Aldrich
Product number
1629000
Product name
Sulfamethazine
Purity
United States Pharmacopeia (USP) Reference Standard
Packaging
1g
Price
$436
Updated
2024/03/01
TCI Chemical
Product number
S0586
Product name
Sulfamethazine
Purity
>98.0%(HPLC)(T)
Packaging
25g
Price
$48
Updated
2024/03/01
TCI Chemical
Product number
S0586
Product name
Sulfamethazine
Purity
>98.0%(HPLC)(T)
Packaging
250g
Price
$356
Updated
2024/03/01
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Sulfamethazine Chemical Properties,Usage,Production

Brand Name(s) in US

Brand Name(s) in US

Description

Sulfamethazine is an antibacterial sulfonamide. Like other sulfonamides, sulfamethazine is bacteriostatic, competitively inhibiting dihydropteroate synthase to block folate synthesis and inhibit growth and multiplication. Sulfamethazine is metabolized by cytochrome P450 isoforms and arylamine N-acetyltransferase 2 in a sex-dependent manner.

Chemical Properties

White to Off-Solid

Originator

Cremomethazine,MSD,US,1947

Uses

Sulfamethazine is an antibacterial.This compound is a contaminant of emerging concern (CECs).

Definition

ChEBI: A sulfonamide consisting of pyrimidine with methyl substituents at the 4- and 6-positions and a 4-aminobenzenesulfonamido group at the 2-position.

Manufacturing Process

A flask heated in an oil bath is filled with 600 ml water and 60 g (1 mol) glacial acetic acid (or an equivalent quantity of diluted acetic acid). While stirring 235 g (1.1 mols) anhydrous p-aminobenzenesulfonamidoguanidine (or an equivalent quantity of a nonanhydrous product) and 122 g (1 mol) sodium acetylacetonate 100% purity (or an equivalent quantity of product of a lower purity) are introduced into the flask while stirring.
The temperature of the reaction mixture is brought to 102°C to 103°C, the mixture is further stirred at this temperature during 24 hours. The pH value of the mixture, which should range between 5 and 6 is checked during the reaction.
On expiry of the reaction period heating is cut off, the mass being cooled or allowed to cool down to 60°C.
Filtering under suction is effected, the solids on the filter being washed with 100 ml water at 80°C.
After drying of the product on the filter 256 g of 2-paminobenzenesulfonamido- 4,6-dimethylpyrimidine, melting point 196°C to 197°C, purity 99.5% are obtained. The output is 92% of the theory calculated with respect to the sodium acetylacetonate employed.

brand name

Calfspan Tablets [Veterinary] (Fort Dodge Animal Health); Sulka S Boluses [Veterinary] (Fort Dodge Animal Health); SulfaSURE SR Bolus [Veterinary] (Boehringer Ingelheim Animal Health);Crermomethazine;Deladine;Dimezathine;Hava-span;Intradin;Neotrizine;Rigesol;Rivodin;S-dimidine;Spanbolet;Sulka-s;Sulphamezathine;Sulphfmezatine;Superseptyl;Sustain iii;Tersulpha;Trisulfaminic;Trisulfaminie.

Therapeutic Function

Antimicrobial

World Health Organization (WHO)

Sulfadimidine, a sulfonamide anti-infective agent, was introduced in 1942 for the treatment of bacterial infections. The importance of sulfonamides has subsequently decreased as a result of increasing resistance and their replacement by antibiotics which are generally more active and less toxic. The sulfonamides are known to cause serious adverse effects such as renal toxicity, sometimes fatal exfoliative dermatitis and erythema multiforma and dangerous adverse reactions affecting blood formation such as agranulocytosis and haemolytic or aplastic anaemia. Sulfadimidine is still used in some countries as a injectable or oral antimicrobial for susceptible infections.

Antimicrobial activity

This drug is used for pneumococcal, staphylococcal, and streptococcal infections as well as for sepsis, gonorrhea, and other infectious diseases. Synonyms of this drug are sulfadiamezin and sulfadimidin.

General Description

Sulfamethazine’splasma half-life is 7 hours. This compound is similar inchemical properties to sulfamerazine and sulfadiazine butdoes have greater water solubility than either. Its pKa is 7.2.Because it is more soluble in acid urine than sulfamerazineis, the possibility of kidney damage from use of the drug isdecreased. The human body appears to handle the drugunpredictably; hence, there is some disfavor to its use in thiscountry except in combination sulfa therapy (in trisulfapyrimidines,USP) and in veterinary medicine.

General Description

Odorless sticky, white or creamy-white crystalline powder. Slightly bitter taste. An antibacterial.

Air & Water Reactions

Water solubility increases rapidly with increasing pH [Merck]. Insoluble in water.

Reactivity Profile

Sulfamethazine is sensitive to light and may also be sensitive to heat. The presence of oxygen and moisture may accelerate the effects of heat and light .

Fire Hazard

Flash point data for Sulfamethazine are not available; however, Sulfamethazine is probably combustible.

Pharmaceutical Applications

2-Sulfanilamido-4,6-methylpyrimidine (syn: sulphamethazine, sulfamezathine). A water-soluble compound, unstable on exposure to light. It is usually administered by mouth and is a component of some triple sulfonamide combinations.
The spectrum is typical of the group, but sulfadimidine exhibits relatively low potency. It is well absorbed after oral administration. It is extensively metabolized, predominantly by acetylation. The mean plasma half-life (1.5–5 h) varies with acetylator status.
In addition to side effects common to the group, a serious interaction between ciclosporin (cyclosporin A) and sulfadimidine, leading to reduced ciclosporin levels, has been reported.

Biochem/physiol Actions

Sulfamethazine is an antimicrobial sulfur drug that blocks the synthesis of dihydrofolic acid by inhibiting the enzyme dihydropteroate synthase. Sulfamethazine is a competitive inhibitor of bacterial para-aminobenzoic acid (PABA), which is required for bacterial synthesis of folic acid. It induces CYP3A4 expression and is acetylated by N-acetyltransferase. It exhibits sex dependent pharmacokinetics, metabolized by the male specific isoform CYP2C11. Sulfamethazine is bacteriostatic.

Safety Profile

Moderately toxic by intravenous and intraperitoneal routes. Experimental teratogenic and reproductive effects. Questionable carcinogen with experimental tumorigenic data. When heated to decomposition it emits very toxic fumes of SOx and NOx.

Synthesis

Sulfamethazine, N1 -(4,6-dimethyl-2-pyrimidinyl)sulfanilamide (33.1.13), is also synthesized in the aforementioned manner by reacting 4-acetylaminobenzenesulfonyl chloride with 2-amino-4,6-dimethylpyrimidine, which is in turn synthesized by condensing acetylacetone with guanidine followed by hydrolysis of the acetylamino group using a base.

Purification Methods

Crystallise it from dioxane or aqueous dioxane. [Caldwell et al. J Am Chem Soc 63 2188 1941, Roblin et al. J Am Chem Soc 64 567 1942, Beilstein 25 III/IV 2215.]

Sulfamethazine Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from Sulfamethazine manufacturers

Shaanxi TNJONE Pharmaceutical Co., Ltd
Product
Sulphadimidine 57-68-1
Price
US $0.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
1000kg
Release date
2024-03-25
Hebei Duling International Trade Co. LTD
Product
Sulfamethazine 57-68-1
Price
US $3.60/kg
Min. Order
1kg
Purity
99.5%HPLC
Supply Ability
20tons
Release date
2023-03-14
Wuhan Biocar Pharmacy Co., Ltd.
Product
Sulfamethazine 57-68-1
Price
US $9.90-9.90/kg
Min. Order
1kg
Purity
99.99%HPLC.USP42——Powder、Oil、Pills、Capsules、Tablets,Customiz
Supply Ability
10,000kg
Release date
2022-09-26

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