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Policy.4nita/sandbox
Clinical data
AHFS/Drugs.comMicromedex Detailed Consumer Information
Pregnancy
category
  • AU: C
Routes of
administration		Oral, IV
ATC code
Legal status
Legal status
Pharmacokinetic data
Protein binding70%
MetabolismHepatic acetylation and glucuronidation
Elimination half-life10 hours
ExcretionRenal
Identifiers
  • 4-Amino-N-(5-methylisoxazol-3-yl)-benzenesulfonamide
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
NIAID ChemDB
Chemical and physical data
FormulaC10H11N3O3S
Molar mass253.279 g/mol g·mol−1
3D model (JSmol)
Melting point169 °C (336 °F)
  • O=S(=O)(Nc1noc(c1)C)c2ccc(N)cc2
  • InChI=1S/C10H11N3O3S/c1-7-6-10(12-16-7)13-17(14,15)9-4-2-8(11)3-5-9/h2-6H,11H2,1H3,(H,12,13) checkY
  • Key:JLKIGFTWXXRPMT-UHFFFAOYSA-N checkY
  (verify)

[1]Sulfamethoxazole (also spelled sulphamethoxazole (BRIT)) (abbreviated SMZ or SMX)[2][3][4] is a sulfonamide bacteriostatic antibiotic.

It is most often used as part of a synergistic combination with trimethoprim in a 5:1 ratio in co-trimoxazole (abbreviated SMZ-TMP and SMX-TMP,[5] or TMP-SMZ and TMP-SMX), also known under trade names such as Bactrim, Septrin, or Septra; in Eastern Europe it is marketed as Biseptol. Its primary activity is against susceptible strains of Streptococcus, Staphylococcus aureus (including methicillin resistant strains), Escherichia coli, Haemophilus influenzae, and oral anaerobes. It is commonly used to treat urinary tract infections. In addition it can be used as an alternative to amoxicillin-based antibiotics to treat sinusitis. It can also be used to treat toxoplasmosis and it is the drug of choice for Pneumocystis pneumonia, which affects primarily patients with HIV.

Other names include: sulfamethylisoxazol, sulfisomezole, MS 53, RO 4 2130[6][7] and sulfamethazole.[8]

Side effects

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The most common side effect of sulfamethoxazole/trimethoprim is gastrointestinal upset (reference needed). Allergies to sulfa-based medications typically cause skin rashes, hives, or trouble breathing or swallowing and warrant immediate discontinuation of the medication and contact with doctor immediately. Sulfamethoxazole/trimethoprim is also known to increase blood concentrations of the drug warfarin (U.S. brand name: Coumadin) and can cause an unexpected increase in clotting time and uncontrolled bleeding. Neutropenia and thrombocytopenia also are rare adverse effects to be monitored if a patient is placed on long-term therapy. Sulfamethoxazole is also a Stevens–Johnson syndrome (SJS) inducing substance.[citation needed]

Sulfamethoxazole can also cause nausea or severe stomach or abdominal pain. Headaches commonly occur when taking sulfamethoxazole. Muscle pain sometimes occurs when taking this medication. If symptoms persist, one should contact his/her physician. If trouble breathing or swelling of the face, mouth, or tongue occurs, one should discontinue the medication and get emergency medical help. These are often symptoms of a severe allergic reaction (anaphylaxis).

Sulfamethoxazole/trimethoprim can lead to a megaloblastic anemia in some patients because it is a folate antagonist.[9]

Mechanism of action

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Sulfamethoxazole, a sulfonamide, is a structural analog of para-aminobenzoic acid (PABA). They compete with PABA to bind to dihydropteroate synthetase and inhibit conversion of PABA and dihydropteroate diphosphate to dihydrofolic acid, or dihydrofolate. [9] Inhibiting the production of dihydrofolate intermediate interferes with the normal bacterial synthesis of folic acid (folate). Folate is an essential metabolite for bacterial growth and replication because it is used in DNA synthesis, primarily at thymidylate and purine biosynthesis, and amino acids synthesis, including serine, glycine and methionine. [10] Hence, blockage of folate production inhibits the folate-dependent metabolic processes for bacterial growth and makes sulfamethoxazole a bacteriostatic antibiotic.[11]

Tetrahydrofolate synthesis pathway

Sulfonamides are selective against bacteria because it interferes with the synthesis of folate, a process which does not occur in humans. [12]

See also

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Notes

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  1. ^ "Sulfonamides and Sulfonamide Combinations".
  2. ^ Ma, M.; Cheng, Y.; Xu, Z.; Xu, P.; Qu, H.; Fang, Y.; Xu, T.; Wen, L. (2007). "Evaluation of polyamidoamine (PAMAM) dendrimers as drug carriers of anti-bacterial drugs using sulfamethoxazole (SMZ) as a model drug". European Journal of Medicinal Chemistry. 42 (1): 93–8. doi:10.1016/j.ejmech.2006.07.015. PMID 17095123.
  3. ^ Garg, S.K.; Ghosh, S.S.; Mathur, V.S. (1986). "Comparative pharmacokinetic study of four different sulfonamides in combination with trimethoprim in human volunteers". International Journal of Clinical Pharmacology, Therapy, and Toxicology. 24 (1): 23–5. PMID 3485584.
  4. ^ SMZ in Abstract of "Rat model of concurrent Pneumocystis carinii (Pc), Toxoplasma gondii (Tg), and Mycobacterium avium complex (MAC) infections for assessment of multiple prophylaxis" at ncbi.nlm.nih.gov
  5. ^ SMZ-TMP in Abstract of "Cutaneous hypersensitivity to sulfamethoxazole-trimethoprim (SMZ TMP) in HIV infected patients" at nlm.nih.gov
  6. ^ PubChem. "Sulfamethoxazole - Substance Summary", PubChem, National Center for Biotechnology Information (NCBI), National Library of Medicine (NLM), National Institutes of Health (NIH)
  7. ^ ChemDB. "Sulfamethoxazole", ChemDB, National Institute of Allergy and Infectious Diseases (NIAID), National Institutes of Health (NIH)
  8. ^ Sulfamethazole in "Clinical Diabetes: Case Study: A 90-Year-Old Man With Confusion and Night Sweats", and "Chronic Granulomatous Disease"
  9. ^ a b USMLE World Step1, Qbank Pharmacology, 2009, Q106
  10. ^ "Sulfonamides and Sulfonamide Combinations: Antibacterial Agents: Merck Veterinary Manual". www.merckvetmanual.com. Retrieved 2015-11-05.
  11. ^ "Sulfamethoxazole". {{cite journal}}: Cite journal requires |journal= (help)
  12. ^ "Sulfonamides - Infectious Diseases". Merck Manuals Professional Edition. Retrieved 2015-11-05.
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Category:Anilines Category:Aromatic amines Category:Isoxazoles Category:Sulfonamide antibiotics Category:Dihydropteroate synthetase inhibitors Category:Equine medications

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