Definition
Sulfamethoxazole is an antibiotic used to treat bacterial infections of the skin, urinary tract infections, bronchitis, Salmonella infections, children acute otitis media, and meningitis, and prostatitis. It is effective against gram-negative and gram-positive bacteria like E Coli and Listeria Monocytogenes. It is generally administered in combination with trimethoprim. This combination medicine is also used to treat middle ear infections, pneumonia, respiratory infections, chancroid, and prevention of toxoplasma encephalitis in AIDS patients. (1)
Chemical and Physical Features
CAS number: 723-46-6 (2)
Molecular Structure: (3)
Molecular Formula: C10H11N3O3S (4)
Weight: 253.28 g/mol (4)
Appearance:
Sulfamethoxazole is a white crystalline powder.
Sulfamethoxazole comes in powder, tablets, injection, and oral suspension forms. (5)
Other Physical Features:
Sulfamethoxazole is a yellow to white crystalline powder. It is odorless and bitter.
Sulfamethoxazole is insoluble in ethyl ether, slightly soluble in water and benzene, and soluble in ethanol and methanol.
Sulfamethoxazole is stable in air, but sensitive to light. It is incompatible with strong oxidizing agents. (5)(6)
Brand Names
Some of the brand names of Sulfamethoxazole are Gantanol, Azo Gantanol,
Combination brand names (containing Sulfamethoxazole and trimethoprim) are- Bactrim, Bactrim DS, Sulfatrim Pediatric, Septra DS, Alcorim F, Antrima, chemotrin Forte, Ciplin, Co-Trimoxazole, Colizole, Cotribid, Cotrimoxazole, Kombina, L-Trim, Larprim. (7)(8)(9)
Sulfamethoxazole forms and specifications
Sulfamethoxazole API Powder 99%
Sulfamethoxazole API Powder 99% is readily used as a raw material in veterinarian applications, in the categories of feed grade, food grade, and medicinal grade. (10)
Sulfamethoxazole Tablets
Tablets are generally available in the combination form containing Sulfamethoxazole and trimethoprim. They are to be administered orally along with a full glass of water to avoid certain effects such as crystals in urine.
Acetyl Sulfamethoxazole powder
Acetyl Sulfamethoxazole powder is a metabolite of the sulfonamide bacteriostatic sulfamethoxazole. It is a white powder or found as crystals, and needs to be protected from light and moisture. It can be used for waste determination and as a reference for sulfamethoxazole impurity determination. (11)
Sulfamethoxazole sodium powder
Sulfamethoxazole sodium powder is a sulphonamide bacteria-killing antibiotic. It is a white powder used to treat urinary tract infections. It is also used to treat toxoplasmosis. Sulfamethoxazole sodium powder is also used as pharmaceutical raw material. (10)
Sulfamethoxazole and trimethoprim
Sulfamethoxazole and trimethoprim are a combination medication given to reduce the ability of bacteria to utilize folic acid for growth. The dihydrofolic acid production is inhibited by sulfamethoxazole and the production of tetrahydrofolic acid is inhibited by trimethoprim. Together they are more effective than when administered alone. (12)
Mechanism of action of Sulfamethoxazole
Para-aminobenzoic acid (PABA) is a structural analog of sulfanilamide. Sulfamethoxazole competes with PABA to bind to dihydropteroate synthetase. This stops the conversion of PABA and dihydropteroate diphosphate to dihydrofolic acid. This interruption ceases the possibility of production of folic acid which is essential for bacterial growth and replication. Resultantly, sulfamethoxazole is called a bacteriostatic antibiotic. (1)
Sulfamethoxazole manufacturing process
The process of manufacturing sulfamethoxazole is carried out by degrading, condensing, and hydrolyzing 5-methyl-isobutyl-3-carboxamide. The degradation is done using the action of sodium hypochlorite solution. It is condensed with para-acetamidophenoxymethyl chloride. This generates 3-(p-acetamide benzenesulfonamide)-5-methylisoxazole on further hydrolysis under alkaline conditions. This is further cleaved to yield sulfamethoxazole. (13)
Sulfamethoxazole uses
Sulfamethoxazole for UTI- Sulfamethoxazole is administered along with trimethoprim under the brand names of Bactrim and Septra. It is used in severe and complicated conditions of urinary tract infections in adults and children above 2 months. It acts against bacteria like Klebsiella species, E Coli, Enterobacter species, Proteus mirabilis, Morganella morganii, and Proteus Vulgaris. (14)
Middle ear infections- Middle ear infections generally start after a sore throat, cold, or any other upper respiratory issues. Fluid starts to accumulate behind the eardrum due to this infection. This infection can be treated by administering the antibiotic sulfamethoxazole. (15)
Other uses- Sulfamethoxazole can be used to treat other infections like pneumonia, skin infection, bronchitis, Salmonella infections, children acute otitis media, and meningitis, prostatitis, respiratory infections, chancroid, and prevention of toxoplasma encephalitis in AIDS patients, gonorrhea, fowl cholera. (12)
Sulfamethoxazole dosage
For Pneumocystis Pneumonia Prophylaxis for adults- Sulfamethoxazole-trimethoprim 800 mg-160 mg orally once a day.
For Urinary Tract Infection for adults- Sulfamethoxazole-trimethoprim 800 mg-160 mg orally every 12 hours for 10 to 14 days.
For Shigellosis for adults- Sulfamethoxazole-trimethoprim 800 mg-160 mg orally every 12 hours for 5 days.
For Bronchitis for adults- Sulfamethoxazole-trimethoprim 800 mg-160 mg orally every 12 hours for 14 days.
For Traveler's Diarrhoea for adults- Sulfamethoxazole-trimethoprim 800 mg-160 mg orally every 12 hours for 5 days.
For Cystitis for adults- Sulfamethoxazole-trimethoprim 800 mg-160 mg orally twice a day.
For Pyelonephritis for adults- Sulfamethoxazole-trimethoprim 800 mg-160 mg orally twice a day.
For Granuloma Inguinale for adults- Sulfamethoxazole-trimethoprim 800 mg-160 mg orally twice a day.
For Toxoplasmosis – Prophylaxis for adults- Sulfamethoxazole-trimethoprim 800 mg-160 mg orally once a day or Sulfamethoxazole-trimethoprim 800 mg-160 mg orally 3 times a week OR sulfamethoxazole-trimethoprim 400 mg-80 mg orally once a day.
For Protozoan Infection for adults- Sulfamethoxazole-trimethoprim 800 mg-160 mg orally (or IV) 4 times a day for 10 days OR sulfamethoxazole-trimethoprim 800 mg-160 mg orally (or IV) twice a day for 7 to 10 days. (16)
Sulfamethoxazole side effects
The most common side effects of sulfamethoxazole are skin allergic reactions (urticaria, blistering of the skin, changes in skin color, and rashes) and gastrointestinal disturbances (vomiting, nausea, and anorexia), black tarry stools, chest pain, chills, dark urine, dizziness, fever, general tiredness, nausea, headache, sore throat, stomach pain, trouble breathing and swollen glands.
Some of the allergic reactions include the entire Gel-Coombs spectrum of hyperactivity reactions.
Type 1 reactions include immunoglobulin E-mediated reactions like anaphylaxis, urticaria, and angioedema.
The non-type 1 hypersensitivities include kidney and liver function abnormalities.
The other severe side effects include Stevens-Johnson syndrome, fulminant hepatic necrosis, toxic epidermal necrolysis, aplastic anemia, agranulocytosis, and other blood dyscrasias. (1)
Sulfamethoxazole API Price
The API price of sulfamethoxazole is around $320 per 250gms. (17)
Sulfamethoxazole API manufacturers in China
Below are some pharmaceutical api manufacturers in China.
Shouguang Fukang Pharmaceutical Co., Ltd.
Shouguang Fukang Pharmaceutical Co. Ltd. was founded in 1997. It focuses on developing, manufacturing and distributing pharmaceutical raw materials, intermediates, bromide compounds, and color former of thermal papers. Their main products include trimethoprim, sulfamethoxazole, omeprazole, metformin hydrogen chloride, hydrea, and other products. (18)(19)
Anhui Chengshi Pharmaceutical Co., Ltd
Anhui Chengshi Pharmaceutical Co., Ltd was established in 1970. They indulge in the establishment of SVP production, oral solid preparation, bottle injection production, syrups, eyes, and ear drops production, tablet, and capsule production, API production, powder for injection, and medical apparatus and instrument production. (20)
Shandong Ruiying Pharmaceutical Group Co., Ltd.
Shandong Ruiying Pharmaceutical Group Co., Ltd. was founded in 1990. They are involved in research and development, pilot production, production, and sales of APIs and intermediates of cephalosporins, penicillin, antibiotics, and antineoplastic drugs. (21)
Luohe Nanjiecun Pharmaceutical Group Pharmacy Co., Ltd
The Henan Luohe Pharmaceutical Factory, which is a predecessor of Luohe Nanjiecun Pharmaceutical Group Pharmacy Co., Ltd, was established in 1988. They are the nation’s main producers of Rifamycin series API. The product series include Rifampicin, Rifaximin, Rifabutin, Rifapentine, Rifamycin sodium, and Rifamycin S. (22)
You can also find details around more suppliers for sulfamethoxazole API in bulk at PharmaSources.com. PharmaSources.com is one of the leading and trustworthy vertical e-commerce online pharmaceutical marketplaces. It holds information on quality pharmaceutical products and suppliers for its esteemed global customers and delivers comprehensive services to 90,000+ active members. They provide services to about 211 countries and regions. PharmaSources.com has covered 30 major pharmaceutical categories across the supply chain and has notably been successful in selling over 1,600,000 products in these categories. (23)
Sources:
1) https://en.wikipedia.org/wiki/Sulfamethoxazole
2) https://go.drugbank.com/drugs/DB01015
3) https://commons.wikimedia.org/wiki/File:Sulfamethoxazole.png
4) https://pubchem.ncbi.nlm.nih.gov/compound/Sulfamethoxazole
5) https://pubchem.ncbi.nlm.nih.gov/compound/Sulfamethoxazole#section=Regulatory-Information
6) file:///C:/Users/admin/Downloads/mono79-15%20(1).pdf
7) https://go.drugbank.com/drugs/DB01015
8) https://www.drugs.com/ingredient/sulfamethoxazole.html
9) https://www.drugsupdate.com/brand/showavailablebrands/703
10) https://hongbaiyi.en.made-in-china.com/product/nZsGFIpcffkd/China-High-Quality-API-Sulfamethoxazole-99-Powder-CAS-723-46-6.html
11) https://www.chemodex.com/products/n4-acetylsulfamethoxazole/
12) https://www.medicinenet.com/sulfamethoxazole_and_trimethoprim/article.htm#what_else_should_i_know_about_sulfamethoxazole_and_trimethoprim
13) https://www.chemicalbook.com/ChemicalProductProperty_EN_CB6473303.htm
14) https://www.rxlist.com/bactrim-drug.htm#indications
15) https://www.nationwidechildrens.org/family-resources-education/family-resources-library/middle-ear-infection-otitis-media-in-adults
16) https://www.drugs.com/dosage/sulfamethoxazole-trimethoprim.html
17) https://www.chemicalbook.com/ChemicalProductProperty_EN_CB6473303.htm
18) https://www.bloomberg.com/profile/company/ABOYWZ:CH
19) https://www.chembuyersguide.com/partners/fukang.html
20) http://www.chengshipharm.com/index.php
21) http://en.ruiying.cn/
22) https://www.njcpharma.com/
23) www.Pharmasources.com
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