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Mechanism of Action
Sulfamethoxazole¿¡ ´ëÇÑ Mechanism_Of_Action Á¤º¸ Sulfonamides inhibit bacterial dihydrofolate synthetase, causing interference in the conversion of p -aminobenzoic acid (PABA) into folic acid. As folic acid is a coenzyme responsible for the transport of one-carbon fragments from one molecule to another, it is an essential component of bacterial development. Pyrimethamine and trimethoprim inhibit dihydrofolate reductase, the immediate next step, and therefore act synergistically with the sulfonamides.Trimethoprim¿¡ ´ëÇÑ Mechanism_Of_Action Á¤º¸ Trimethoprim binds to bacterial dihydrofolate reductase, subsequently interfering with the uptake of p -aminobenzoic acid (PABA) into folic acid. As folic acid is a coenzyme responsible for the transport of one-carbon fragments from one molecule to another, it is an essential component of bacterial development. Sulfonamides inhibit bacterial dihydrofolate synthetase, the enzyme immediately preceding dihydrofolate reductase, and therefore act synergistically with trimethoprim.
Pharmacology
Sulfamethoxazole¿¡ ´ëÇÑ Pharmacology Á¤º¸ Sulfamethoxazole is a sulfonamide drug that inhibits bacterial synthesis of dihydrofolic acid by competing with para-aminobenzoic acid (PABA). Sulfamethoxazole is normally given in combination with Trimethoprim (a dihydrofolate reductase inhibitor). Studies have shown that bacterial resistance develops more slowly with the combination of the two drugs than with either Trimethoprim or Sulfamethoxazole alone.Trimethoprim¿¡ ´ëÇÑ Pharmacology Á¤º¸ Trimethoprim, a synthetic antiinfective agent, is used to treat and prevent urinary tract infections, diarrhea, and, when combined with either sulfamethoxazole or dapsone, Pneumocystis carinii infections.
Metabolism
Sulfamethoxazole¿¡ ´ëÇÑ Metabolism Á¤º¸ # Phase_1_Metabolizing_Enzyme:Cytochrome P450 2C9 (CYP2C9)
Protein Binding
Sulfamethoxazole¿¡ ´ëÇÑ ´Ü¹é°áÇÕ Á¤º¸ 70%Trimethoprim¿¡ ´ëÇÑ ´Ü¹é°áÇÕ Á¤º¸ Approximately 45%
Half-life
Sulfamethoxazole¿¡ ´ëÇÑ ¹Ý°¨±â Á¤º¸ 10 hoursTrimethoprim¿¡ ´ëÇÑ ¹Ý°¨±â Á¤º¸ 8-10 hours
Absorption
Sulfamethoxazole¿¡ ´ëÇÑ Absorption Á¤º¸ Rapidly absorbed following oral administration.Trimethoprim¿¡ ´ëÇÑ Absorption Á¤º¸ Not Available
Pharmacokinetics
SulfamethoxazoleÀÇ ¾à¹°µ¿·ÂÇÐÀÚ·á
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¼Ò½Ç : 60-80%°¡ ¹Ìº¯Èü·Î ½Å¹è¼³
Biotransformation
Sulfamethoxazole¿¡ ´ëÇÑ Biotransformation Á¤º¸ Hepatic. The metabolism of sulfamethoxazole occurs predominately by N4-acetylation, although the glucuronide conjugate has been identified.Trimethoprim¿¡ ´ëÇÑ Biotransformation Á¤º¸ Not Available
Toxicity
Sulfamethoxazole¿¡ ´ëÇÑ Toxicity Á¤º¸ Not AvailableTrimethoprim¿¡ ´ëÇÑ Toxicity Á¤º¸ LD50 =4850 (orally in mice)
Drug Interactions
Sulfamethoxazole¿¡ ´ëÇÑ Drug_Interactions Á¤º¸ Not AvailableTrimethoprim¿¡ ´ëÇÑ Drug_Interactions Á¤º¸ Not Available
CYP450 Drug Interaction
[CYP450 TableÁ÷Á¢Á¶È¸] Sulfamethoxazole¿¡ ´ëÇÑ P450 table SUBSTRATES
CYP 2C9
NSAIDs:
diclofenac
ibuprofen
piroxicam
Oral Hypoglycemic Agents:
tolbutamide
glipizide
Angiotensin II Blockers:
NOT candesartan
irbesartan
losartan
NOT valsartan
celecoxib
fluvastatin naproxen
phenytoin
**sulfamethoxazole**
tamoxifen
tolbutamide
torsemide
warfarin
INHIBITORS
CYP 2C9
amiodarone
fluconazole
isoniazid
INDUCERS
CYP 2C9
rifampin
secobarbital
Food Interaction
Sulfamethoxazole¿¡ ´ëÇÑ Food Interaction Á¤º¸ Take on empty stomach: 1 hour before or 2 hours after meals.Take with a full glass of water.Do not take calcium, aluminium, magnesium or iron supplements within 2 hours of taking this medication.Trimethoprim¿¡ ´ëÇÑ Food Interaction Á¤º¸ Take on empty stomach: 1 hour before or 2 hours after meals.Take with a full glass of water.Do not take calcium, aluminium, magnesium or iron supplements within 2 hours of taking this medication.
Drug Target
[Drug Target]
Description
Sulfamethoxazole¿¡ ´ëÇÑ Description Á¤º¸ A bacteriostatic antibacterial agent that interferes with folic acid synthesis in susceptible bacteria. Its broad spectrum of activity has been limited by the development of resistance. (From Martindale, The Extra Pharmacopoeia, 30th ed, p208)Trimethoprim¿¡ ´ëÇÑ Description Á¤º¸ A pyrimidine inhibitor of dihydrofolate reductase, it is an antibacterial related to pyrimethamine. The interference with folic acid metabolism may cause a depression of hematopoiesis. It is potentiated by sulfonamides and the trimethoprim-sulfamethoxazole combination is the form most often used. It is sometimes used alone as an antimalarial. trimethoprim resistance has been reported. [PubChem]
Drug Category
Sulfamethoxazole¿¡ ´ëÇÑ Drug_Category Á¤º¸ Anti-Infective AgentsAnti-InfectivesSulfonamidesTrimethoprim¿¡ ´ëÇÑ Drug_Category Á¤º¸ Anti-Infective Agents, UrinaryAnti-InfectivesAntimalarialsFolic Acid Antagonists
Smiles String Canonical
Sulfamethoxazole¿¡ ´ëÇÑ Smiles_String_canonical Á¤º¸ CC1=CC(NS(=O)(=O)C2=CC=C(N)C=C2)=NO1Trimethoprim¿¡ ´ëÇÑ Smiles_String_canonical Á¤º¸ COC1=CC(CC2=CN=C(N)N=C2N)=CC(OC)=C1OC
Smiles String Isomeric
Sulfamethoxazole¿¡ ´ëÇÑ Smiles_String_isomeric Á¤º¸ CC1=CC(NS(=O)(=O)C2=CC=C(N)C=C2)=NO1Trimethoprim¿¡ ´ëÇÑ Smiles_String_isomeric Á¤º¸ COC1=CC(CC2=CN=C(N)N=C2N)=CC(OC)=C1OC
InChI Identifier
Sulfamethoxazole¿¡ ´ëÇÑ InChI_Identifier Á¤º¸ InChI=1/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)/f/h13HTrimethoprim¿¡ ´ëÇÑ InChI_Identifier Á¤º¸ InChI=1/C14H18N4O3/c1-19-10-5-8(6-11(20-2)12(10)21-3)4-9-7-17-14(16)18-13(9)15/h5-7H,4H2,1-3H3,(H4,15,16,17,18)/f/h15-16H2
Chemical IUPAC Name
Sulfamethoxazole¿¡ ´ëÇÑ Chemical_IUPAC_Name Á¤º¸ 4-amino-N-(5-methyl-1,2-oxazol-3-yl)benzenesulfonamideTrimethoprim¿¡ ´ëÇÑ Chemical_IUPAC_Name Á¤º¸ 5-[(3,4,5-trimethoxyphenyl)methyl]pyrimidine-2,4-diamine
Drug-Induced Toxicity Related Proteins
SULFAMETHOXAZOLE ÀÇ Drug-Induced Toxicity Related ProteinÁ¤º¸Replated Protein :Myeloperoxidase Drug :sulfamethoxazole Toxicity :agranulocytosis. [¹Ù·Î°¡±â] Replated Protein :Myeloperoxidase Drug :sulfamethoxazole Toxicity :lupus. [¹Ù·Î°¡±â]
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