Sulfamethoxazole: Difference between revisions

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{{drugbox
__NOTOC__
| IUPAC_name = 4-amino-''N''-(5-methylisoxazol-3-yl)-benzenesulfonamide 
{{Sulfadiazine}}
| CAS_number = 723-46-6
'''''For patient information, click <u>[[Sulfadiazine (patient information)|here]]'''''</u>.
|ATC_prefix = J01
|ATC_suffix = EC01
|PubChem = 5329
| DrugBank = APRD00076
| C = 10 |H = 11 |N = 3 |O = 3 |S = 1
| molecular_weight = 253.279 [[Gram|g]]/[[Mole (unit)|mol]]  
| smiles = CC1=CC(=NO1)NS(=O)(=O)C2=CC=C(C=C2)N
| melting_point = 3
| protein_bound = 70%
| metabolism = [[Liver|Hepatic]] [[acetylation]] and [[glucuronidation]]
| elimination_half-life = 10 [[hour]]s
| excretion = [[Kidney|Renal]]
| pregnancy_category = C <small>([[Australia|Au]], [[United States|U.S.]])</small>
| legal_AU = s4
| legal_status = ℞-only
| routes_of_administration = Oral
}}


{{SI}}
{{CMG}}; {{AE}} {{MM}}
==Overview==
'''Sulfadiazine''' is a [[sulfonamide]] [[antibiotic]].  It eliminates [[bacteria]] that cause infections by stopping the production of [[folic acid|folate]] inside the bacterial cell, and is commonly used to treat [[urinary tract infection]]s (UTIs).


{{CMG}}
==Category==
[[Sulfonamide]]


==US Brand Names==
SULFADIAZINE<sup>®</sup>


==FDA Package Insert==
'''  [[Sulfadiazine description|Description]]'''
'''| [[Sulfadiazine clinical pharmacology|Clinical Pharmacology]]'''
'''| [[Sulfadiazine indications and usage|Indications and Usage]]'''
'''| [[Sulfadiazine contraindications|Contraindications]]'''
'''| [[Sulfadiazine warnings and precautions|Warnings and Precautions]]'''
'''| [[Sulfadiazine adverse reactions|Adverse Reactions]]'''
'''| [[Sulfadiazine dosage and administration|Dosage and Administration]]'''
'''| [[Sulfadiazine how supplied|How Supplied]]'''
'''| [[Sulfadiazine labels and packages|Labels and Packages]]'''
==Mechanism of Action==
The systemic sulfonamides are bacteriostatic agents having a similar spectrum of activity. Sulfonamides competitively inhibit bacterial synthesis of folic acid (pteroylglutamic acid) from aminobenzoic acid. Resistant strains are capable of utilizing folic acid precursors or preformed folic acid.<ref name="dailymed.nlm.nih.gov">{{Cite web  | last =  | first =  | title = SULFADIAZINE TABLET [EON LABS, INC.] | url = http://dailymed.nlm.nih.gov/dailymed/lookup.cfm?setid=10549cba-9c15-4d2e-a68c-5afbc178591d | publisher =  | date =  | accessdate}}</ref>
==References==
{{Reflist|2}}
[[Category:Antibiotics]]
[[Category:Wikinfect]]
----------------------


'''Sulfamethoxazole''' is a [[Sulfonamide (medicine)|sulfonamide]] [[bacteriostatic]] [[antibiotic]]. It is most often used as part of a synergistic combination with [[trimethoprim]] in a 5:1 ratio in [[co-trimoxazole]], which is also known as [[Bactrim]], [[Septrin]], or Septra (also abbreviated SMX/TMP). 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]].
'''Sulfamethoxazole''' is a [[Sulfonamide (medicine)|sulfonamide]] [[bacteriostatic]] [[antibiotic]]. It is most often used as part of a synergistic combination with [[trimethoprim]] in a 5:1 ratio in [[co-trimoxazole]], which is also known as [[Bactrim]], [[Septrin]], or Septra (also abbreviated SMX/TMP). 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]].

Revision as of 01:15, 10 January 2014

Sulfadiazine
SULFADIAZINE® FDA Package Insert
Description
Clinical Pharmacology
Indications and Usage
Contraindications
Warnings and Precautions
Adverse Reactions
Dosage and Administration
How Supplied
Labels and Packages

For patient information, click here.

Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]; Associate Editor(s)-in-Chief: Mohamed Moubarak, M.D. [2]

Overview

Sulfadiazine is a sulfonamide antibiotic. It eliminates bacteria that cause infections by stopping the production of folate inside the bacterial cell, and is commonly used to treat urinary tract infections (UTIs).

Category

Sulfonamide

US Brand Names

SULFADIAZINE®

FDA Package Insert

Description | Clinical Pharmacology | Indications and Usage | Contraindications | Warnings and Precautions | Adverse Reactions | Dosage and Administration | How Supplied | Labels and Packages

Mechanism of Action

The systemic sulfonamides are bacteriostatic agents having a similar spectrum of activity. Sulfonamides competitively inhibit bacterial synthesis of folic acid (pteroylglutamic acid) from aminobenzoic acid. Resistant strains are capable of utilizing folic acid precursors or preformed folic acid.[1]

References

  1. ↑ "SULFADIAZINE TABLET [EON LABS, INC.]". Text " accessdate" ignored (help)

Sulfamethoxazole 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, which is also known as Bactrim, Septrin, or Septra (also abbreviated SMX/TMP). 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.

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.[1] 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 prevents the drug from binding and blocking folic acid synthesis.


File:THFsynthesispathway.png

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.

References

  1. ↑ Martindale, The extra pharmacopoeia, 30th ed, p. 208

External links

See also

Template:SulfonamideAntiBiotics


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