Drug Details

General Information of the Drug (ID: DR7498)
Name
Sulfamethoxazole
Synonyms
sulfamethoxazole; 723-46-6; Sulphamethoxazole; Gantanol; Sulfisomezole; Sulfamethoxazol; 4-Amino-N-(5-methyl-3-isoxazolyl)benzenesulfonamide; Metoxal; Sulfamethylisoxazole; Simsinomin; Radonil; Sinomin; Sulphamethoxazol; Sulpha-methoxizole; Bactrim; Sulfamethalazole; Azo-gantanol; 4-amino-N-(5-methylisoxazol-3-yl)benzenesulfonamide; Sulphamethylisoxazole; Urobak; Ro 4-2130; 3-Sulfanilamido-5-methylisoxazole; Gantanol-DS; Sulphisomezole; 4-amino-N-(5-methyl-1,2-oxazol-3-yl)benzenesulfonamide; 5-Methyl-3-sulfanilamidoisoxazole; MS 53; 3-Sulphanilamido-5-methylisoxazole; Benzenesulfonamide, 4-amino-N-(5-methyl-3-isoxazolyl)-; 5-Methyl-3-sulphanil-amidoisoxazole; 3-(p-Aminophenylsulfonamido)-5-methylisoxazole; 5-Methyl-3-sulfanylamidoisoxazole; N'-(5-Methyl-3-isoxazolyl)sulfanilamide; N1-(5-Methyl-3-isoxazolyl)sulfanilamide; N'-(5-Methylisoxazol-3-yl)sulphanilamide; 3-(para-Aminophenylsulphonamido)-5-methylisoxazole; Sulfamethoxazole-d4; Sulmeprim; Trimeth/Sulfa; A047; SMX; Sulfamethoxazole sodium; UNII-JE42381TNV; N(sup 1)-(5-Methyl-3-isoxazolyl)sulphanilamide; CHEBI:9332; N'-(5-Methyl-3-isoxazole)sulfanilamide; Sulfamethoxizole; Ro 6-2580/11; 4-Amino-N-(5-methyl-isoxazol-3-yl)-benzenesulfonamide; Sulfanilamide, N'-(5-methyl-3-isoxazolyl)-; Sulfanilamide, N1-(5-methyl-3-isoxazolyl)-; 4-AMINO-N-(5-METHYL-3-ISOXAZOYL)BENZENESULFONAMIDE; Sulfametoxazol; Bactrimel; Gamazole; MFCD00010546; CHEMBL443; N1-(5-Methylisoxazol-3-yl)sulfanilamide; MLS000069732; JE42381TNV; 4-amino-N-(5-methyl-1,2-oxazol-3-yl)benzene-1-sulfonamide; Solfametossazolo; N(sup1)-(5-Methyl-3-isoxazolyl)sulfanilamide; 5-Methyl-3-sulfonylamidoisoxazole; STX-608; Sulfamethoxazolum; NSC147832; 4-Amino-N-(5-methyl-3-isoxazolyl)-benzenesulfonamide; NSC-147832; NCGC00016533-05; NCGC00186654-01; CAS-723-46-6; SMR000058223; DSSTox_CID_6064; Solfametossazolo [DCIT]; 3-(p-Aminobenzenesulfonamido)-5-methylisoxazole; DSSTox_RID_78001; DSSTox_GSID_26064; [(4-aminophenyl)sulfonyl](5-methylisoxazol-3-yl)amine; Sulfametoxazol [INN-Spanish]; Sulfamethoxazolum [INN-Latin]; CCRIS 567; HSDB 3186; SR-01000000217; EINECS 211-963-3; NSC 147832; BRN 0226453; N(sup 1)-(5-Methyl-3-isoxazolyl)sulfanilamide; Sulfanilamide, N(1)-(5-methyl-3-isoxazolyl)-; 08D; Prestwick_453; ALBB-002089; Septran (Salt/Mix); Septrin (Salt/Mix); Sulfamethoxazole,(S); Eusaprim (Salt/Mix); Ro-4-2130; Spectrum_000994; Sulfamethoxazole(USAN); Sulfamethoxazole-13C6; Opera_ID_882; Maybridge1_007190; Prestwick0_000177; Prestwick1_000177; Prestwick2_000177; Prestwick3_000177; Spectrum2_000788; Spectrum3_000584; Spectrum4_000345; Spectrum5_000982; Sulfamethoxazole [USAN:USP:INN:BAN:JAN]; Epitope ID:114999; Co-trimoxazole (Salt/Mix); SCHEMBL3656; Oprea1_114486; Oprea1_285680; BSPBio_000073; BSPBio_002028; KBioGR_000749; KBioSS_001474; MLS001055354; MLS001074165; MLS006011871; BIDD:GT0731; DivK1c_000649; SPECTRUM1500550; SPBio_000896; SPBio_001994; ARONIS018156; BPBio1_000081; DTXSID8026064; component of Bactrim (Salt/Mix); GTPL10933; HMS502A11; HMS561O18; JLKIGFTWXXRPMT-UHFFFAOYSA-; KBio1_000649; KBio2_001474; KBio2_004042; KBio2_006610; KBio3_001528; ZINC89763; EBD3403; N1-(5-methylisoxazol-3-yl)-4-aminobenzene-1-sulfonamide; WLN: T5NOJ C1 EMSWR DZ; NINDS_000649; HMS1568D15; HMS1921A21; HMS2092K03; HMS2095D15; HMS2233L13; HMS3259E06; HMS3372M22; HMS3655O22; HMS3712D15; Pharmakon1600-01500550; BCP02881; HY-B0322; Sulfamethoxazole (JP17/USP/INN); Sulfamethoxazole, analytical standard; Tox21_110480; Tox21_200353; ANW-43073; BBL004554; BDBM50029770; CCG-40166; HTS001394; KM1475; NSC757328; Ro-42130; s1915; SBB057675; SBB071655; STK007988; AKOS000200952; component of Azo Gantanol (Salt/Mix); Tox21_110480_1; BS-3542; DB01015; MCULE-1450176600; NC00537; NSC-757328; RP-2145; IDI1_000649; NCGC00016533-01; NCGC00016533-02; NCGC00016533-03; NCGC00016533-04; NCGC00016533-06; NCGC00016533-07; NCGC00016533-08; NCGC00016533-09; NCGC00016533-10; NCGC00016533-11; NCGC00016533-12; NCGC00016533-14; NCGC00021995-03; NCGC00021995-04; NCGC00021995-05; NCGC00257907-01; AC-11118; AK-36221; H463; ST024740; SY018888; BCP0726000283; N'-(5-Methyl-3-isoxazolyl)-Sulfanilamide; N1-(5-methyl-3-isoxazolyl)-Sulfanilamide; N1-(5-Methyl-3-isoxazolyl)sulphanilamide; SBI-0051524.P003; DB-055629; AB00052099; BB 0242379; FT-0602616; N^1-(5-Methyl-3-isoxazolyl)-Sulfanilamide; ST51006798; SW196670-3; C07315; D00447; J10090; Sulfamethoxazole 100 microg/mL in Acetonitrile; AB00052099-14; AB00052099-16; AB00052099_17; AB00052099_18; Ndimethyl1-(5-methyl-3-isoxazolyl)-Sulfanilamide; Q415843; Q-201762; SR-01000000217-2; SR-01000000217-3; Sulfamethoxazole, VETRANAL(TM), analytical standard; Sulfanilamide, N1-(5-methyl-3-isoxazolyl)- (8CI); 4-Amino-N-(5-methylisoxazol-3-yl)benzenesulphonamide; BRD-K28494619-001-05-0; BRD-K28494619-001-15-9; BRD-K28494619-001-26-6; Z57198677; 4-Amino-N-(5-methyl-isoxazol-3-yl)-benzene sulfonamide; Sulfamethoxazole, British Pharmacopoeia (BP) Reference Standard; Sulfamethoxazole, certified reference material, TraceCERT(R); 4-amino-N-(5-methyl-1,2-oxazol-3-yl)benzenesulfonamide; SMX; SMZ; Sulfamethoxazole, European Pharmacopoeia (EP) Reference Standard; Sulfamethoxazole, United States Pharmacopeia (USP) Reference Standard; Sulfamethoxazole, Pharmaceutical Secondary Standard; Certified Reference Material; 129378-89-8
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Molecular Type
Small molecule
Disease Bacterial infection [ICD-11: 1A00-1C4Z] Approved [1]
Structure
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2D MOL

3D MOL

ADMET Property
Absorption Cmax
The maximum plasma concentration (Cmax) of drug is 57.4-68.0 mg/L
Absorption Tmax
The time to maximum plasma concentration (Tmax) is 1-4 h
BDDCS Class
Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 2: low solubility and high permeability
Bioavailability
The bioavailability of drug is 85-90%
Clearance
The renal clearance of drug is 0.22 +/- 0.05 L/h
Elimination
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
Half-life
The concentration or amount of drug in body reduced by one-half in 10 hours
Metabolism
The drug is metabolized via the arylamine N-acetyltransferase (NAT) enzymes, which are responsible for acetylation of sulfamethoxazole at its N4 position
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 394.82001 micromolar/kg/day
Unbound Fraction
The unbound fraction of drug in plasma is 0.23%
Vd
The volume of distribution (Vd) of drug is 13 L
Water Solubility
The ability of drug to dissolve in water is measured as 0.392 mg/mL
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    Click to Show/Hide the Molecular Information and External Link(s) of This Natural Product
Formula
C10H11N3O3S
PubChem CID
5329
Canonical SMILES
CC1=CC(=NO1)NS(=O)(=O)C2=CC=C(C=C2)N
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)
InChIKey
JLKIGFTWXXRPMT-UHFFFAOYSA-N
CAS Number
CAS 723-46-6
ChEBI ID
CHEBI:9332
TTD Drug ID
D0R9OH
DrugBank ID
DB01015
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Natural Product(s) Able to Enhance the Efficacy of This Drug
          Selenium      Soil     Click to Show/Hide the Molecular Data of This NP
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [2]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    In-vivo Model This experiment was carried out on 30 Wistar rats weighing 100-125 g, liver cancer was induced by a carcinogenic dose of 200 mg/kg body weight, I.P. DENA when associated with fasting/refeeding.
                    Experimental
                    Result(s)		 Selenium and sulfonamide (sulfamethoxazole) together can possess synergistic chemopreventive action.
Target and Pathway
Target(s) Bacterial Dihydropteroate synthetase (Bact folP)  Molecule Info  [3]
References
Reference 1 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015
Reference 2 Combination of sulfamethoxazole and selenium in anticancer therapy: a novel approach. Mol Cell Biochem. 2013 Dec;384(1-2):279-85.
Reference 3 In vitro activities of novel antifolate drug combinations against Plasmodium falciparum and human granulocyte CFUs. Antimicrob Agents Chemother. 1995 Apr;39(4):948-52.
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