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Sulfamethoxazole

Brand Name(s) in US Sulfonamide drugs Mechanism of action Chemical Properties Uses Production method
Sulfamethoxazole
Sulfamethoxazole structure
CAS No.
723-46-6
Chemical Name:
Sulfamethoxazole
Synonyms
SMZ;SMX;A047;ms53;Trib;MS 53;Septra;Bactrim;Radonil;Septran
CBNumber:
CB6473303
Molecular Formula:
C10H11N3O3S
Formula Weight:
253.28
MOL File:
723-46-6.mol

Sulfamethoxazole Properties

Melting point:
166 °C
Boiling point:
482℃
Density 
1.3915 (rough estimate)
refractive index 
1.6630 (estimate)
Flash point:
>110°(230°F)
storage temp. 
0-6°C
solubility 
Practically insoluble in water, freely soluble in acetone, sparingly soluble in ethanol (96 per cent). It dissolves in dilute solutions of sodium hydroxide and in dilute acids.
form 
neat
pka
pKa 5.60±0.05 (Uncertain)
Water Solubility 
Soluble in ethanol or acetone. Very slightly soluble in water
Sensitive 
Light Sensitive
Merck 
14,8918
BRN 
6732984
Stability:
Stable, but light sensitive. Incompatible with strong oxidizing agents.
CAS DataBase Reference
723-46-6(CAS DataBase Reference)
NIST Chemistry Reference
Sulfanilamide, n1-(5-methyl-3-isoxazolyl)-(723-46-6)
EPA Substance Registry System
Benzenesulfonamide, 4-amino-N-(5-methyl-3-isoxazolyl)- (723-46-6)
SAFETY
  • Risk and Safety Statements
Symbol(GHS) 
GHS07
Signal word  Warning
Hazard statements  H315-H317-H319-H335
Precautionary statements  P280g-P302+P352a-P321-P501a-P264-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313-P280-P305+P351+P338-P261-P333+P313-P337+P313-P280a-P304+P340-P405
Hazard Codes  Xi,Xn
Risk Statements  36/37/38-43-22
Safety Statements  26-36-36/37/39-22
WGK Germany  2
RTECS  WP0700000
Hazard Note  Irritant
TSCA  Yes
HazardClass  IRRITANT
HS Code  29350090
Toxicity LD50 orally in mice: 3662 mg/kg (Yamamoto)

Sulfamethoxazole price More Price(14)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 31737 Sulfamethoxazole VETRANAL 723-46-6 250mg $46.6 2018-11-22 Buy
Sigma-Aldrich 1631001 Sulfamethoxazole United States Pharmacopeia (USP) Reference Standard 723-46-6 200mg $352.8 2018-11-20 Buy
TCI Chemical S0361 Sulfamethoxazole >98.0%(HPLC)(T) 723-46-6 25g $30 2018-11-22 Buy
Alfa Aesar J67346 Sulfamethoxazole, 50 mg/ml in distilled water sterile-filtered 723-46-6 25ml $37.1 2018-11-20 Buy
Alfa Aesar J66565 Sulfamethoxazole 98% 723-46-6 100g $122 2018-11-20 Buy

Sulfamethoxazole Chemical Properties,Uses,Production

Brand Name(s) in US

Gantanol

Sulfonamide drugs

Sulfa drugs have a relative broad antimicrobial spectrum and have certain inhibitory effect against most Gram-positive bacteria and gram-negative bacteria. However, different sulfonamide drugs have different extent of antibacterial efficacy. With the wide application of sulfonamide drugs, it will also be easy to lead to resistant strains; in particular the opportunity of resistant Staphylococcus aureus will be even higher than other kinds of resistant strains.
According to the absorption situations after oral administration, the sulfonamide drugs can be classified into two categories, the first category is easily absorbed sulfonamide drugs, which is characterized by rapid absorption. Generally, their plasma concentrations can reach peak at 2-4 hours after the administration (5 hour for long-acting drugs). This kind of sulfonamide drugs are mainly used for systemic infections. Another kind of drugs is hardly or poorly absorbed after oral administration with most of them being excreted through the intestinal tract and is mainly used for treating intestinal infections.
Sulfamethoxazole is a broad-spectrum antibiotic with particularly strong efficacy on Staphylococcus aureus and Escherichia coli and can be used for the treatment of urinary tract infections and fowl cholera. Sulfamethoxazole belongs to a systemic, moderate sulfonamide drug. It can compete with PABA through taking effect on the bacterial in vivo dihydrofolate synthase, preventing the bacterial synthesis of dihydrofolate and thereby inhibiting the bacterial growth and reproduction. It, together with other three kinds of sulfonamide drugs: sulfadiazine, sulfisoxazole and trisulfapyrimidine are currently excellent drugs for the treatment of nocardiosis. It has a half-life of 10 to 12 hours and can be partially acetylated. This product, although has the number of required medication be less than sulfisoxazole (2 times per day instead of four times), but its acetylated metabolites has a low solubility in the urine so the likelihood of large crystals formation in urine is bit higher. Patients should maintain enough hydrated conditions (the daily adult urine output should be not less than 1,500ml). When being used in combination with the synergist trimethoprim, its antibacterial activity can get significantly enhanced. Sulfamethoxazole compound (sulfamethoxazole/trimethoprim namely SMZ/TMP) can often give better efficacy than monotherapy (see dihydrofolate reductase inhibitors). Clinically it is commonly used for the treatment of urinary tract infections, respiratory tract infections, typhoid, and salmonella infections, Pneumocystis carinii echinococcosis and nocardiosis. It can also be used for preventing meningococcal meningitis. Some clinicians advocate use minocycline, erythromycin or ampicillin in combination with sulfamethoxazole to treat such infections. However, there has been no clinical data for proving that combination therapy is superior to single administration of sulfonamide. Sulfamethoxazole compound (TMP/SMZ), minocycline (Minocin) and amikacin can also be used for the treatment of nocardia infection.

Mechanism of action

It is known that bacterial can synthesize thymidine, purine and finally synthesize DNA and need folic acid derivatives, tetrahydrofolate as cofactors. Most bacterial cells can’t allow the penetration of folic acid and instead needs the synthesis through aminobenzoic acid (PABA). Sulfonamide has a similar structure to PABA and thus can competitively inhibit the synthesis of the direct precursor of dihydrofolate, dihy-dropteroic acid through the reaction between PABA and pteridine. Mammalian cells, instead, is not inhibited since they require preformed folate and is not capable of synthesizing this product.
Treatment concentration of sulfonamide drug sulfamethoxazole is primarily bacteriostatic agents. However, when the bacteria is grown in the medium containing purine, amino aicd but very low concentration of thymine, the sulfonamide drugs can produce a bactericidal effect, that is, "thymine lethal defect". This bactericidal effect has been demonstrated in human blood and urine (Then and Angehrn, 1973 A and B; see also Pratt and Fekety, 1986).
The effect of sulfonamide drug-induced inhibition of bacterial cell growth can be reversed upon supplement in vitro of some substances (such as thymidine, purines, methionine and serine) to the growth medium. This may have important clinical significance. Because the pus generated by cells destruction may contain a large amount of these substances. It is therefore, upon purulent infection, the effect of the drug may be inhibited probably due to the presence of such substances. Furthermore, for the in vitro susceptibility testing, the medium can’t contain PABA for which even in trace amount, the test results can be disturbed.
The above information is edited by the chemicalbook of Dai Xiongfeng.

Chemical Properties

It is white crystalline powder and is odorless with slightly bitter taste. It has a melting point of 168 ℃. It is very slightly soluble in water, soluble in dilute acid, dilute alkali or ammonia.

Uses

As an antimicrobial agent, it is particularly effective in treating Staphylococcus aureus and E. coli. It is mainly used for the treatment of fowl cholera.
It can be used as anti-infective drug and can be used for the treatment and prevention of acute and chronic urinary tract infections, respiratory infections, intestinal infections, Salmonella infections, children acute otitis media, and meningitis.

Production method

It can be produced from 5-methyl-isobutyl-3-carboxamide via degradation, condensation and hydrolysis successively.
Use 5-methyl-isobutyl-3-carboxamide as raw materials, it is degraded into 5-methyl-isoxazol-3 amine under the action of sodium hypochlorite solution, then condense with para-acetamidophenoxymethyl chloride to generate 3-(p-acetamide benzenesulfonamido)-5-methylisoxazole with further hydrolysis under alkaline conditions to give 3-(p-amino benzenesulfonamido)-5-methylisoxazole.

Chemical Properties

solid

Uses

An antibacterial drug. Sulfonamide antibiotic that blocks the synthesis of dihydrofolic acid by inhibiting the enzyme dihydropteroate synthase.

Uses

antibacterial, antipneumocystis

Definition

ChEBI: An isoxazole (1,2-oxazole) compound having a methyl substituent at the 5-position and a 4-aminobenzenesulfonamido group at the 3-position.

brand name

Gantanol (Roche); Urobak (Shionogi).

Antimicrobial activity

The intrinsic activity is similar to that of sulfadiazine.

General Description

Crystals or white powder.

General Description

Sulfamethoxazole’s plasma half-life is 11 hours. Sulfamethoxazole is a sulfonamide drug closely relatedto sulfisoxazole in chemical structure and antimicrobial activity.It occurs as a tasteless, odorless, almost white crystallinepowder. The solubility of sulfamethoxazole in the pHrange of 5.5 to 7.4 is slightly lower than that of sulfisoxazole but higher than that of sulfadiazine, sulfamerazine, or sulfamethazine.Following oral administration, sulfamethoxazole is notabsorbed as completely or as rapidly as sulfisoxazole, andits peak blood level is only about 50% as high.

Air & Water Reactions

Insoluble in water.

Fire Hazard

Flash point data for Sulfamethoxazole are not available but Sulfamethoxazole is probably non-flammable.

Pharmaceutical Applications

This is the sulfonamide component of co-trimoxazole. It is slightly soluble in water.

Pharmacokinetics

Oral absorption: 85%
Cmax 800 mg oral: c.50 mg/L after 3–6 h
Plasma half-life: 6–20 h
Volume of distribution: 12–18 L
Plasma protein binding: 65%
Penetration of extravascular sites, including the CSF, is good. It crosses the placenta and achieves levels in breast milk of about 10% of the simultaneous plasma concentration. It is extensively metabolized, but about 30% of the dose is excreted unchanged in urine so that high concentrations are achieved.

Clinical Use

Sulfamethoxazole is used only in combination with the diaminopyrimidine trimethoprim.

Side effects

Unwanted effects are those common to sulfonamides. In addition, benign intracranial hypertension has been reported in children. Most side effects of co-trimoxazole are thought to be attributable to the sulfonamide component.

Safety Profile

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

Sulfamethoxazole Preparation Products And Raw materials

Raw materials

Preparation Products


Sulfamethoxazole Suppliers

Global( 285)Suppliers
Supplier Tel Fax Email Country ProdList Advantage
Shenzhen Sendi Biotechnology Co.Ltd.
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Henan DaKen Chemical CO.,LTD.
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Mainchem Co., Ltd.
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career henan chemical co
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Xiamen AmoyChem Co., Ltd
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View Lastest Price from Sulfamethoxazole manufacturers

Image Release date Product Price Min. Order Purity Supply Ability Manufacturer
2018-12-19 Sulfamethoxazole
723-46-6
US $8.00 / kg 1kg 99% 10MT career henan chemical co
2018-03-15 Sulfamethoxazole
723-46-6
US $10.00 / KG 10KG 99% 10MT Hubei XinRunde Chemical Co., Ltd.

Sulfamethoxazole Spectrum


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