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Sulfamethoxazole

 
Dental Dictionary: sulfamethoxazole
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n

trade names: Gamazole, Gantanol, Urabak; drug class: sulfonamide; action: interferes with bacterial biosynthesis of proteins by competitive antagonism of paraaminobenzoic acid (PABA); uses: treatment of urinary tract infections, lymphogranuloma venereum, and systemic infections.

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Drug Info: Sulfamethoxazole
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Chemical formula:



Sulfamethoxazole tablets

What are sulfamethoxazole tablets?

SULFAMETHOXAZOLE (Gantanol®) is a sulfonamide antibiotic. Sulfamethoxazole stops the growth of certain bacteria. It treats urinary tract infections and some other infections. Generic sulfamethoxazole tablets are available.

What should I tell my health care provider before I take this medicine?

They need to know if you have any of these conditions:
• asthma
• blood disorders
• dental disease
• glucose-6-phosphate dehydrogenase deficiency (G6PD deficiency)
• kidney disease
• liver disease
• porphyria
• vitamin deficiency
• other chronic illness
• an unusual or allergic reaction to 'sulfa drugs,' sulfite preservatives, furosemide or thiazide diuretics (water pills), oral diabetes medicines, or other medicines, foods, dyes, or preservatives
• pregnant or trying to get pregnant
• breast-feeding

How should I take this medicine?

Take sulfamethoxazole tablets by mouth. Follow the directions on the prescription label. Swallow tablets whole with a full glass of water. Take your doses at regular intervals. Do not take your medicine more often than directed. Finish the full course prescribed by your prescriber or health care professional even if you think your condition is better. Do not stop taking except on your prescriber's advice.

Contact your pediatrician or health care professional regarding the use of this medicine in children. Special care may be needed.

What if I miss a dose?

If you miss a dose, take it as soon as you can. If it is almost time for your next dose, take only that dose. Do not take double or extra doses. There should be an interval of at least 6 to 8 hours between doses.

What drug(s) may interact with sulfamethoxazole?

• cyclosporine
• doxercalciferol
• medicines for diabetes that are taken by mouth
• methenamine
• methotrexate
• phenylbutazone
• phenytoin
• ramelteon
• sulfinpyrazone
• voriconazole
• warfarin
• water pills

Tell your prescriber or health care professional about all other medicines you are taking, including non-prescription medicines, nutritional supplements, or herbal products. Also tell your prescriber or health care professional if you are a frequent user of drinks with caffeine or alcohol, if you smoke, or if you use illegal drugs. These may affect the way your medicine works. Check with your health care professional before stopping or starting any of your medicines.

What should I watch for while taking sulfamethoxazole?

Tell your prescriber or health care professional if your symptoms do not improve in 2 or 3 days, or if you develop a skin rash.

If you are taking this medicine for a long time you must visit your prescriber or health care professional for regular blood checks.

Sulfamethoxazole can cause blood problems. This can mean slow healing and a risk of infection. Problems can arise if you need dental work, and in the day to day care of your teeth. Try to avoid damage to your teeth and gums when you brush or floss your teeth.

If you are a diabetic using insulin or oral hypoglycemics (like glyburide) monitor your blood glucose carefully. If you get an unusual reaction stop using sulfamethoxazole at once and call your prescriber or health care professional for advice.

Drink several glasses of water a day. This will help to reduce possible kidney problems.

Keep out of the sun, or wear protective clothing outdoors and use a sunscreen. Do not use sun lamps or sun tanning beds or booths.

You may get drowsy or dizzy. Do not drive, use machinery, or do anything that needs mental alertness until you know how sulfamethoxazole affects you. To reduce the risk of dizzy or fainting spells, do not sit or stand up quickly, especially if you are an older patient.

If you are going to have surgery, tell your prescriber or health care professional that you are using sulfamethoxazole.

What side effects may I notice from taking sulfamethoxazole?

Elderly patients are more likely to get side effects.
Side effects that you should report to your prescriber or health care professional as soon as possible:
• blood in urine
• bluish fingernails or lips
• dark yellow or brown urine
• cough
• difficulty breathing
• increased sensitivity to the sun or ultraviolet light
• joint aches or pains
• less urine passed
• muscle aches or pains
• pain or difficulty passing urine
• redness, blistering, peeling or loosening of the skin, including inside the mouth
• skin rash, hives, or itching
• sore mouth
• sore throat, fever
• swelling of the neck
• unusual bruising or bleeding
• unusual tiredness or weakness
• yellowing of the eyes or skin

Side effects that usually do not require medical attention (report to your prescriber or health care professional if they continue or are bothersome):
• diarrhea
• drowsiness, dizziness
• headache
• loss of appetite
• nausea, vomiting
• stomach pain

Where can I keep my medicine?

Keep out of the reach of children in a container that small children cannot open.

Store at room temperature between 15 and 30 degrees C (59 and 86 degrees F). Protect from light. Keep container tightly closed. Throw away any unused medicine after the expiration date.


Last updated: 7/1/2002

Important Disclaimer: The drug information provided here is for educational purposes only. It is intended to supplement, not substitute for, the diagnosis, treatment and advice of a medical professional. This drug information does not cover all possible uses, precautions, side effects and interactions. It should not be construed to indicate that this or any drug is safe for you. Consult your medical professional for guidance before using any prescription or over the counter drugs.

Veterinary Dictionary: sulfamethoxazole
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An antibacterial sulfonamide, especially useful in acute urinary tract infections and in infections of wounds and soft tissues. Commonly combined with trimethoprim.

Wikipedia: Sulfamethoxazole
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Sulfamethoxazole
Systematic (IUPAC) name
4-amino-N-(5-methylisoxazol-3-yl)-benzenesulfonamide
Identifiers
CAS number 723-46-6
ATC code J01EC01 QJ01EQ11
PubChem 5329
DrugBank APRD00076
ChemSpider 5138
Chemical data
Formula C10H11N3O3S 
Mol. mass 253.279 g/mol
SMILES eMolecules & PubChem
Physical data
Melt. point 3 °C (37 °F)
Pharmacokinetic data
Bioavailability  ?
Protein binding 70%
Metabolism Hepatic acetylation and glucuronidation
Half life 10 hours
Excretion Renal
Therapeutic considerations
Pregnancy cat.

C (Au, U.S.)
Legal status

Prescription Only (S4)(AU) ℞-only
Routes Oral
 Yes check.svgY(what is this?)  (verify)

Sulfamethoxazole (abbreviated SMX[1][2] and less reliably[3] SMZ[4][5][6]) 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 SXT, SMX-TMP and SMZ-TMP,[7] or TMP-SMX and TMP-SMZ), also known under trade names such as Bactrim, Septrin, or Septra. Its primary activity is against susceptible forms of Streptococcus, Staphylococcus aureus, Escherichia coli, Haemophilus influenzae, and oral anaerobes. It is commonly used to treat urinary tract infections. In addition can be used as an alternative to amoxicillin-based antibiotics to treat sinusitis. It can also be used to treat toxoplasmosis.

Other names include: sulfamethylisoxazol, sulfisomezole, MS 53, RO 4 2130,[8][1][2] and sulfamethazole.[9]

Contents

Mechanism of action

Sulfonamides are structural analogs and competitive antagonists of para-aminobenzoic acid (PABA). They inhibit normal bacterial utilization of PABA for the synthesis of folic acid, an important metabolite in DNA synthesis.[10] The effects seen are usually bacteriostatic in nature. Folic acid is not synthesized in humans, but is instead a dietary requirement. This allows for the selective toxicity to bacterial cells (or any cell dependent on synthesizing folic acid) over human cells. Bacterial resistance to sulfamethoxazole are caused by mutations in the folic acid enzyme that inhibit PABA from binding and block folic acid synthesis.

Tetrahydrofolate synthesis pathway

Side effects

The most common side effect of sulfamethoxazole/trimethoprim is gastrointestinal upset. 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.

Gardnerella

A TM-SXT (or simply SXT) disk impregnated with trimethoprim and sulfamethoxazole may be used to help identify an organism as Gardnerella vaginalis; it is sensitive to the TM-SXT disk. Sulfamethoxazole can also cause nausea, severe stomach or abdomen pains. Headaches commonly occur when taking sulfamethoxazole. Muscle pains sometimes occur when taking this medicine. If symptoms persist or you have trouble breathing or you have swelling of the face, mouth or tongue discontinue medicine or get emergency medical help for swelling of the face, mouth or tongue these are often symptoms of a severe allergic reaction.

See also

Notes

  1. ^ a b PubChem, "Sulfamethoxazole - Substance Summary"
  2. ^ a b ChemDB, "Sulfamethoxazole"
  3. ^ "SMZ" is not found in databases, but often seen in the published literature; it could however be confused with sulfamethazine, also seen abbreviated SMZ.
  4. ^ 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. 
  5. ^ 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. 
  6. ^ 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
  7. ^ SMZ-TMP in Abstract of "Cutaneous hypersensitivity to sulfamethoxazole-trimethoprim (SMZ TMP) in HIV infected patients" at nlm.nih.gov
  8. ^ BIAM, "Sulfamethoxazole"
  9. ^ Sulfamethazole in "Clinical Diabetes: Case Study: A 90-Year-Old Man With Confusion and Night Sweats", and "Chronic Granulomatous Disease"
  10. ^ Martindale, The extra pharmacopoeia, 30th ed, p. 208

References

External links

v • d • e
Antibacterials: nucleic acid inhibitors (J01E, J01M)
Antifolates
(inhibits
purine metabolism,
thereby inhibiting
DNA and RNA synthesis)
Sulfamethoxazole · Sulfadiazine# · Sulfamoxole
Other/ungrouped
Combinations
Topoisomerase
inhibitors/
quinolones/
(inhibits
DNA replication)
Related agents (DG)
Anaerobic DNA
inhibitors
Nitro- imidazole derivatives
Nitrofuran derivatives
RNA synthesis
#WHO-EM. ‡Withdrawn from market. CLINICAL TRIALS: †Phase III. §Never to phase III

This entry is from Wikipedia, the leading user-contributed encyclopedia. It may not have been reviewed by professional editors (see full disclaimer)

 
 

 

Copyrights:

Dental Dictionary. Mosby's Dental Dictionary. Copyright © 2004 by Elsevier, Inc. All rights reserved.  Read more
Drug Info. Gold Standard. Copyright © 2008 by Gold Standard. All rights reserved.  Read more
Veterinary Dictionary. Saunders Comprehensive Veterinary Dictionary 3rd Edition. Copyright © 2007 by D.C. Blood, V.P. Studdert and C.C. Gay, Elsevier. All rights reserved.  Read more
Wikipedia. This article is licensed under the Creative Commons Attribution/Share-Alike License. It uses material from the Wikipedia article "Sulfamethoxazole".  Read more