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
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)
Safety
- Hazard Codes
- Xi
- Risk Statements
- 36/37/38
- Safety Statements
- 23-24/25-36-26
- WGK Germany
- 2
- RTECS
- WO9275000
- F
- 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)
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..…
N-Bromosuccinimide Price
- Product number
- PHR3136
- Product name
- Sulfamethazine
- Purity
- pharmaceutical secondary standard, certified reference material
- Packaging
- 1G
- Price
- $173
- Updated
- 2024/03/01
- Product number
- 46802
- Product name
- Sulfamethazine
- Purity
- VETRANAL , analytical standard
- Packaging
- 250mg
- Price
- $68.7
- Updated
- 2024/03/01
- Product number
- 1629000
- Product name
- Sulfamethazine
- Purity
- United States Pharmacopeia (USP) Reference Standard
- Packaging
- 1g
- Price
- $436
- Updated
- 2024/03/01
- Product number
- S0586
- Product name
- Sulfamethazine
- Purity
- >98.0%(HPLC)(T)
- Packaging
- 25g
- Price
- $48
- Updated
- 2024/03/01
- Product number
- S0586
- Product name
- Sulfamethazine
- Purity
- >98.0%(HPLC)(T)
- Packaging
- 250g
- Price
- $356
- Updated
- 2024/03/01
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
- Product
- Sulfamethazine 57-68-1
- Price
- US $0.00/kg
- Min. Order
- 25kg
- Purity
- ＞99%
- Supply Ability
- 10tons
- Release date
- 2024-04-25
- Product
- Sulfadimidine Powder 57-68-1
- Price
- US $180.00/kg
- Min. Order
- 1kg
- Purity
- 99%
- Supply Ability
- 20ton
- Release date
- 2024-04-23
- Product
- sulfamethazine 57-68-1
- Price
- US $0.00-0.00/kg
- Min. Order
- 1kg
- Purity
- 99.99%
- Supply Ability
- 20 tons
- Release date
- 2024-04-10