Peringatan Keamanan

The oral LD50 of sulfamethoxazole in mice and rats is 2300 mg/kg and 6200 mg/kg, respectively.L11866

Signs or symptoms of sulfonamide overdose include anorexia, colic, nausea, vomiting, dizziness, headache, drowsiness, and unconsciousness. Less common symptoms may include pyrexia, hematuria, and crystalluria. Later manifestations of overdose may include blood dyscrasias and jaundice.L11830 Treatment should be symptomatic and supportive, and may include gastric lavage or forced emesis if applicable. Monitor patient lab work for evidence of blood dyscrasias or electrolyte imbalances.L11830

Sulfamethoxazole

DB01015

small molecule approved

Deskripsi

Sulfamethoxazole is a bacteriostatic sulfonamide antibiotic that interferes with folic acid synthesis in susceptible bacteria.L11830 It is generally given in combination with trimethoprim, which inhibits a sequential step in bacterial folic acid synthesis - these agents work synergistically to block two consecutive steps in the biosynthesis of nucleic acids and proteins which are necessary for bacterial growth and division, and using them in conjunction helps to slow the development of bacterial resistance.L11830 In this combination, sulfamethoxazole is useful for the treatment of a variety of bacterial infections, including those of the urinary, respiratory, and gastrointestinal tracts.

Struktur Molekul 2D

Berat 253.278
Wujud solid

Peta Jejaring Molekuler
Legenda: Obat • Target • Gen • Enzim • (Panah → menunjukkan arah efek / relasi) • Transporter • Carrier

Profil Farmakokinetik

Waktu Paruh (Half-Life) The average serum half-life of sulfamethoxazole is 10 hours and may be increased in patients with severely impaired renal function.[L11830]
Volume Distribusi The volume of distribution sulfamethoxazole following a single oral dose was found to be 13 L.[A179830] Sulfamethoxazole distributes into sputum, vaginal fluid, middle ear fluid, breast milk, and the placenta.[L11830]
Klirens (Clearance) The oral and renal clearance of sulfamethoxazole have been estimated as 1.2 ± 0.2 and 0.22 ± 0.05 L/h, respectively.[A191122]

Absorpsi

Sulfamethoxazole is rapidly absorbed following oral administration and has a bioavailability of 85-90%.A179830 The Tmax is approximately 1-4 hours following oral administration, and the Cmax at steady-state is 57.4 - 68.0 ?g/mL.L11830

Metabolisme

Sulfamethoxazole metabolism is mediated primarily by arylamine N-acetyltransferase (NAT) enzymes, which are responsible for acetylation of sulfamethoxazole at its N4 position.A415,L11830 Sulfamethoxazole may also undergo oxidation at its C5 and N4 atoms, the latter of which is catalyzed by CYP2C9.L11830 Glucuronidation of the N4 atom, likely mediated by unspecified UGT enzymes, is an additional minor route of metabolism.A415 None of the identified metabolites of sulfamethoxazole appear to carry antimicrobial activity.L11830 The hydroxylamine metabolite of sulfamethoxazole, generated via oxidation by CYP2C9, may be further converted to a more reactive nitroso- metabolite.A415

Rute Eliminasi

Elimination occurs primarily via glomerular filtration and tubular secretion in the kidneys, with urine concentrations generally considerably higher than plasma concentrations.L11830 Approximately 84.5% of a single oral dose of sulfamethoxazole is recovered in the urine within 72 hours, of which ~30% is free sulfamethoxazole and the remainder is the N4-acetylated metabolite.L11830

Interaksi Obat

1882 Data
Pegvisomant The risk or severity of hypoglycemia can be increased when Pegvisomant is combined with Sulfamethoxazole.
Cimetidine Cimetidine may decrease the excretion rate of Sulfamethoxazole which could result in a higher serum level.
Troglitazone Troglitazone may decrease the excretion rate of Sulfamethoxazole which could result in a higher serum level.
Reserpine Reserpine may decrease the excretion rate of Sulfamethoxazole which could result in a higher serum level.
Progesterone Progesterone may decrease the excretion rate of Sulfamethoxazole which could result in a higher serum level.
Chlorpromazine Chlorpromazine may decrease the excretion rate of Sulfamethoxazole which could result in a higher serum level.
Bosentan Bosentan may decrease the excretion rate of Sulfamethoxazole which could result in a higher serum level.
Ethinylestradiol Ethinylestradiol may decrease the excretion rate of Sulfamethoxazole which could result in a higher serum level.
Glyburide Glyburide may decrease the excretion rate of Sulfamethoxazole which could result in a higher serum level.
Ketoconazole Ketoconazole may decrease the excretion rate of Sulfamethoxazole which could result in a higher serum level.
Ursodeoxycholic acid Ursodeoxycholic acid may decrease the excretion rate of Sulfamethoxazole which could result in a higher serum level.
Cholic Acid Cholic Acid may decrease the excretion rate of Sulfamethoxazole which could result in a higher serum level.
Fusidic acid Fusidic acid may decrease the excretion rate of Sulfamethoxazole which could result in a higher serum level.
Simeprevir Simeprevir may decrease the excretion rate of Sulfamethoxazole which could result in a higher serum level.
Lenvatinib Lenvatinib may decrease the excretion rate of Sulfamethoxazole which could result in a higher serum level.
Valinomycin Valinomycin may decrease the excretion rate of Sulfamethoxazole which could result in a higher serum level.
Rifampin The serum concentration of Rifampin can be increased when it is combined with Sulfamethoxazole.
Olmesartan Olmesartan may decrease the excretion rate of Sulfamethoxazole which could result in a higher serum level.
Tipranavir Tipranavir may decrease the excretion rate of Sulfamethoxazole which could result in a higher serum level.
Pralsetinib Pralsetinib may decrease the excretion rate of Sulfamethoxazole which could result in a higher serum level.
Eliglustat The metabolism of Eliglustat can be decreased when combined with Sulfamethoxazole.
Nicotine The risk or severity of adverse effects can be increased when Sulfamethoxazole is combined with Nicotine.
Mecamylamine The risk or severity of adverse effects can be increased when Sulfamethoxazole is combined with Mecamylamine.
Pentolinium The risk or severity of adverse effects can be increased when Sulfamethoxazole is combined with Pentolinium.
Trimethaphan The risk or severity of adverse effects can be increased when Sulfamethoxazole is combined with Trimethaphan.
Hexamethonium The risk or severity of adverse effects can be increased when Sulfamethoxazole is combined with Hexamethonium.
Cyclopentamine The risk or severity of adverse effects can be increased when Sulfamethoxazole is combined with Cyclopentamine.
Cilostazol The metabolism of Cilostazol can be decreased when combined with Sulfamethoxazole.
Colchicine The metabolism of Colchicine can be decreased when combined with Sulfamethoxazole.
Fentanyl Fentanyl may decrease the excretion rate of Sulfamethoxazole which could result in a higher serum level.
Iloperidone The metabolism of Iloperidone can be decreased when combined with Sulfamethoxazole.
Retapamulin The metabolism of Retapamulin can be decreased when combined with Sulfamethoxazole.
Vardenafil The metabolism of Vardenafil can be decreased when combined with Sulfamethoxazole.
Eszopiclone The metabolism of Eszopiclone can be decreased when combined with Sulfamethoxazole.
Zopiclone The metabolism of Zopiclone can be decreased when combined with Sulfamethoxazole.
Lovastatin The metabolism of Lovastatin can be decreased when combined with Sulfamethoxazole.
Prilocaine The risk or severity of methemoglobinemia can be increased when Sulfamethoxazole is combined with Prilocaine.
Phenytoin The serum concentration of Phenytoin can be increased when it is combined with Sulfamethoxazole.
Fosphenytoin The serum concentration of Fosphenytoin can be increased when it is combined with Sulfamethoxazole.
Alfuzosin The metabolism of Alfuzosin can be decreased when combined with Sulfamethoxazole.
Methotrexate The risk or severity of adverse effects can be increased when Sulfamethoxazole is combined with Methotrexate.
Alprazolam The metabolism of Alprazolam can be decreased when combined with Sulfamethoxazole.
Warfarin The serum concentration of Warfarin can be increased when it is combined with Sulfamethoxazole.
Acenocoumarol The serum concentration of Acenocoumarol can be increased when it is combined with Sulfamethoxazole.
(R)-warfarin The serum concentration of (R)-warfarin can be increased when it is combined with Sulfamethoxazole.
R,S-Warfarin alcohol The serum concentration of R,S-Warfarin alcohol can be increased when it is combined with Sulfamethoxazole.
S,R-Warfarin alcohol The serum concentration of S,R-Warfarin alcohol can be increased when it is combined with Sulfamethoxazole.
(S)-Warfarin The serum concentration of (S)-Warfarin can be increased when it is combined with Sulfamethoxazole.
Midazolam The serum concentration of Midazolam can be increased when it is combined with Sulfamethoxazole.
Etanercept The risk or severity of myelosuppression can be increased when Sulfamethoxazole is combined with Etanercept.
Peginterferon alfa-2a The risk or severity of myelosuppression can be increased when Sulfamethoxazole is combined with Peginterferon alfa-2a.
Interferon alfa-n1 The risk or severity of myelosuppression can be increased when Sulfamethoxazole is combined with Interferon alfa-n1.
Interferon alfa-n3 The risk or severity of myelosuppression can be increased when Sulfamethoxazole is combined with Interferon alfa-n3.
Peginterferon alfa-2b The risk or severity of myelosuppression can be increased when Sulfamethoxazole is combined with Peginterferon alfa-2b.
Anakinra The risk or severity of myelosuppression can be increased when Sulfamethoxazole is combined with Anakinra.
Interferon gamma-1b The risk or severity of myelosuppression can be increased when Sulfamethoxazole is combined with Interferon gamma-1b.
Interferon alfa-2a The risk or severity of myelosuppression can be increased when Sulfamethoxazole is combined with Interferon alfa-2a.
Aldesleukin The risk or severity of myelosuppression can be increased when Sulfamethoxazole is combined with Aldesleukin.
Adalimumab The risk or severity of myelosuppression can be increased when Sulfamethoxazole is combined with Adalimumab.
Gemtuzumab ozogamicin The risk or severity of myelosuppression can be increased when Sulfamethoxazole is combined with Gemtuzumab ozogamicin.
Pegaspargase The risk or severity of myelosuppression can be increased when Sulfamethoxazole is combined with Pegaspargase.
Infliximab The risk or severity of myelosuppression can be increased when Sulfamethoxazole is combined with Infliximab.
Interferon beta-1b The risk or severity of myelosuppression can be increased when Sulfamethoxazole is combined with Interferon beta-1b.
Interferon alfacon-1 The risk or severity of myelosuppression can be increased when Sulfamethoxazole is combined with Interferon alfacon-1.
Trastuzumab The risk or severity of myelosuppression can be increased when Sulfamethoxazole is combined with Trastuzumab.
Rituximab The risk or severity of myelosuppression can be increased when Sulfamethoxazole is combined with Rituximab.
Basiliximab The risk or severity of myelosuppression can be increased when Sulfamethoxazole is combined with Basiliximab.
Muromonab The risk or severity of myelosuppression can be increased when Sulfamethoxazole is combined with Muromonab.
Ibritumomab tiuxetan The risk or severity of myelosuppression can be increased when Sulfamethoxazole is combined with Ibritumomab tiuxetan.
Tositumomab The risk or severity of myelosuppression can be increased when Sulfamethoxazole is combined with Tositumomab.
Alemtuzumab The risk or severity of myelosuppression can be increased when Sulfamethoxazole is combined with Alemtuzumab.
Cyclosporine The risk or severity of myelosuppression can be increased when Sulfamethoxazole is combined with Cyclosporine.
Alefacept The risk or severity of myelosuppression can be increased when Sulfamethoxazole is combined with Alefacept.
Efalizumab The risk or severity of myelosuppression can be increased when Sulfamethoxazole is combined with Efalizumab.
Antithymocyte immunoglobulin (rabbit) The risk or severity of myelosuppression can be increased when Sulfamethoxazole is combined with Antithymocyte immunoglobulin (rabbit).
Interferon alfa-2b The risk or severity of myelosuppression can be increased when Sulfamethoxazole is combined with Interferon alfa-2b.
Natalizumab The risk or severity of myelosuppression can be increased when Sulfamethoxazole is combined with Natalizumab.
Daclizumab The risk or severity of myelosuppression can be increased when Sulfamethoxazole is combined with Daclizumab.
Phenylalanine The risk or severity of myelosuppression can be increased when Sulfamethoxazole is combined with Phenylalanine.
Flunisolide The risk or severity of myelosuppression can be increased when Sulfamethoxazole is combined with Flunisolide.
Bortezomib The risk or severity of myelosuppression can be increased when Sulfamethoxazole is combined with Bortezomib.
Cladribine The risk or severity of myelosuppression can be increased when Sulfamethoxazole is combined with Cladribine.
Carmustine The risk or severity of myelosuppression can be increased when Sulfamethoxazole is combined with Carmustine.
Amsacrine The risk or severity of myelosuppression can be increased when Sulfamethoxazole is combined with Amsacrine.
Bleomycin The risk or severity of myelosuppression can be increased when Sulfamethoxazole is combined with Bleomycin.
Chlorambucil The risk or severity of myelosuppression can be increased when Sulfamethoxazole is combined with Chlorambucil.
Raltitrexed The risk or severity of myelosuppression can be increased when Sulfamethoxazole is combined with Raltitrexed.
Mitomycin The risk or severity of myelosuppression can be increased when Sulfamethoxazole is combined with Mitomycin.
Bexarotene The risk or severity of myelosuppression can be increased when Sulfamethoxazole is combined with Bexarotene.
Vindesine The risk or severity of myelosuppression can be increased when Sulfamethoxazole is combined with Vindesine.
Floxuridine The risk or severity of myelosuppression can be increased when Sulfamethoxazole is combined with Floxuridine.
Indomethacin The risk or severity of myelosuppression can be increased when Sulfamethoxazole is combined with Indomethacin.
Tioguanine The risk or severity of myelosuppression can be increased when Sulfamethoxazole is combined with Tioguanine.
Vinorelbine The risk or severity of myelosuppression can be increased when Sulfamethoxazole is combined with Vinorelbine.
Dexrazoxane The risk or severity of myelosuppression can be increased when Sulfamethoxazole is combined with Dexrazoxane.
Beclomethasone dipropionate The risk or severity of myelosuppression can be increased when Sulfamethoxazole is combined with Beclomethasone dipropionate.
Sorafenib The risk or severity of myelosuppression can be increased when Sulfamethoxazole is combined with Sorafenib.
Streptozocin The risk or severity of myelosuppression can be increased when Sulfamethoxazole is combined with Streptozocin.
Trifluridine The risk or severity of myelosuppression can be increased when Sulfamethoxazole is combined with Trifluridine.
Gemcitabine The risk or severity of myelosuppression can be increased when Sulfamethoxazole is combined with Gemcitabine.

Target Protein

Dihydropteroate synthase folP

Referensi & Sumber

Synthesis reference: Yasushi Takagishi, Kiichiro Ohsuga, Sadao Ohama, "Suppository containing sulfamethoxazole/trimethoprim complex and process for preparing the same." U.S. Patent US4461765, issued December, 1975.
Artikel (PubMed)
  • PMID: 9631140
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  • PMID: 12812351
    Khalil I, Ronn AM, Alifrangis M, Gabar HA, Satti GM, Bygbjerg IC: Dihydrofolate reductase and dihydropteroate synthase genotypes associated with in vitro resistance of Plasmodium falciparum to pyrimethamine, trimethoprim, sulfadoxine, and sulfamethoxazole. Am J Trop Med Hyg. 2003 May;68(5):586-9. doi: 10.4269/ajtmh.2003.68.586.
  • PMID: 22383850
    Yun MK, Wu Y, Li Z, Zhao Y, Waddell MB, Ferreira AM, Lee RE, Bashford D, White SW: Catalysis and sulfa drug resistance in dihydropteroate synthase. Science. 2012 Mar 2;335(6072):1110-4. doi: 10.1126/science.1214641.
  • PMID: 30020604
    Kemnic TR, Coleman M: Trimethoprim Sulfamethoxazole .
  • PMID: 29271734
    Novelli A, Rosi E: Pharmacological properties of oral antibiotics for the treatment of uncomplicated urinary tract infections. J Chemother. 2017 Dec;29(sup1):10-18. doi: 10.1080/1120009X.2017.1380357.
  • PMID: 1093654
    Bushby SR: Synergy of trimethoprim-sulfamethoxazole. Can Med Assoc J. 1975 Jun 14;112(13 Spec No):63-6.
  • PMID: 19515014
    Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1.
  • PMID: 7981016
    van der Ven AJ, Mantel MA, Vree TB, Koopmans PP, van der Meer JW: Formation and elimination of sulphamethoxazole hydroxylamine after oral administration of sulphamethoxazole. Br J Clin Pharmacol. 1994 Aug;38(2):147-50. doi: 10.1111/j.1365-2125.1994.tb04339.x.

Contoh Produk & Brand

Produk: 336 • International brands: 3
Produk
  • Apo Sulfamethoxazole Tab 500mg
    Tablet • 500 mg • Oral • Canada • Generic • Approved
  • Apo-sulfatrim Oral Suspension
    Suspension • - • Oral • Canada • Generic • Approved
  • Bactrim
    Tablet • - • Oral • US • Approved
  • Bactrim
    Tablet • - • Oral • US • Approved
  • Bactrim DS
    Tablet • - • Oral • US • Approved
  • Bactrim DS
    Tablet • - • Oral • US • Approved
  • Bactrim DS
    Tablet • - • Oral • US • Approved
  • Bactrim DS
    Tablet • - • Oral • US • Approved
Menampilkan 8 dari 336 produk.
International Brands
  • Gantanol
  • Sinomin
  • Urobak

Sekuens Gen/Protein (FASTA)

Sekuens dimuat saat dibutuhkan agar halaman tetap ringan.
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