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Identification
NameSulfamethazine
Accession NumberDB01582
TypeSmall Molecule
GroupsApproved, Vet Approved
Description

A sulfanilamide anti-infective agent. It has a spectrum of antimicrobial action similar to other sulfonamides. [PubChem]

Structure
Thumb
Synonyms
(P-Aminobenzolsulfonyl)-2-amino-4,6-dimethylpyrimidin
2-(4-Aminobenzenesulfonamido)-4,6-dimethylpyrimidine
2-(P-Aminobenzenesulfonamido)-4,6-dimethylpyrimidine
2-Sulfanilamido-4,6-dimethylpyrimidine
4-Amino-N-(2,6-dimethyl-4-pyrimidinyl)benzenesulfonamide
4-Amino-N-(4,6-dimethyl-pyrimidin-2-yl)-benzenesulfonamide
4-amino-N-(4,6-Dimethylpyrimidin-2-yl)benzenesulfonamide
4,6-Dimethyl-2-sulfanilamidopyrimidine
6-(4'-Aminobenzol-sulfonamido)-2,4-dimethylpyrimidin
N-(4,6-Dimethyl-2-pyrimidyl)sulfanilamide
N(1)-(4,6-Dimethyl-2-pyrimidinyl)sulfanilamide
N(1)-(4,6-Dimethyl-2-pyrimidyl)sulfanilamide
SMZ
Sulfadimethyldiazine
Sulfadimethylpyrimidine
Sulfadimidina
Sulfadimidine
Sulfadimidinum
Sulfametazina
Sulfametazyny
Sulfamezathine
Sulphadimethylpyrimidine
Sulphamethazine
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixtures
NameLabellerIngredients
Trisulfaminic SusShepherd Pharmaceuticals Inc.
Trisulfaminic TabShepherd Pharmaceuticals Inc.
SaltsNot Available
Categories
UNII48U51W007F
CAS number57-68-1
WeightAverage: 278.33
Monoisotopic: 278.083746402
Chemical FormulaC12H14N4O2S
InChI KeyInChIKey=ASWVTGNCAZCNNR-UHFFFAOYSA-N
InChI
InChI=1S/C12H14N4O2S/c1-8-7-9(2)15-12(14-8)16-19(17,18)11-5-3-10(13)4-6-11/h3-7H,13H2,1-2H3,(H,14,15,16)
IUPAC Name
4-amino-N-(4,6-dimethylpyrimidin-2-yl)benzene-1-sulfonamide
SMILES
CC1=CC(C)=NC(NS(=O)(=O)C2=CC=C(N)C=C2)=N1
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as aminobenzenesulfonamides. These are organic compounds containing a benzenesulfonamide moiety with an amine group attached to the benzene ring.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzenesulfonamides
Direct ParentAminobenzenesulfonamides
Alternative Parents
Substituents
  • Aminobenzenesulfonamide
  • Sulfonylaniline
  • Substituted aniline
  • Aniline
  • Pyrimidine
  • Primary aromatic amine
  • Heteroaromatic compound
  • Aminosulfonyl compound
  • Sulfonyl
  • Sulfonic acid derivative
  • Sulfonamide
  • Azacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Primary amine
  • Organosulfur compound
  • Organonitrogen compound
  • Amine
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Pharmacology
IndicationFor the treatment bacterial infections causing bronchitis, prostatitis and urinary tract infections.
PharmacodynamicsSulfamethazine is a sulfonamide drug that inhibits bacterial synthesis of dihydrofolic acid by competing with para-aminobenzoic acid (PABA) for binding to dihydropteroate synthetase (dihydrofolate synthetase). Sulfamethazine is bacteriostatic in nature. Inhibition of dihydrofolic acid synthesis decreases the synthesis of bacterial nucleotides and DNA.
Mechanism of actionSulfonamides inhibit the enzymatic conversion of pteridine and p-aminobenzoic acid (PABA) to dihydropteroic acid by competing with PABA for binding to dihydrofolate synthetase, an intermediate of tetrahydrofolic acid (THF) synthesis. THF is required for the synthesis of purines and dTMP and inhibition of its synthesis inhibits bacterial growth. Pyrimethamine and trimethoprim inhibit dihydrofolate reductase, another step in THF synthesis, and therefore act synergistically with the sulfonamides.
Related Articles
AbsorptionRapidly absorbed following oral administration.
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicitySulfamethazine may cause nausea, vomiting, diarrhea and hypersensitivity reactions. Hematologic effects such as anemia, agranulocytosis, thrombocytopenia and hemolytic anemia in patients with glucose-6-phosphate dehydrogenase deficiency may also occur. Sulfamethoxazole may displace bilirubin from albumin binding sites causing jaundice or kernicterus in newborns.
Affected organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9908
Blood Brain Barrier+0.9275
Caco-2 permeable+0.6203
P-glycoprotein substrateNon-substrate0.8692
P-glycoprotein inhibitor INon-inhibitor0.888
P-glycoprotein inhibitor IINon-inhibitor0.9281
Renal organic cation transporterNon-inhibitor0.8643
CYP450 2C9 substrateNon-substrate0.7791
CYP450 2D6 substrateNon-substrate0.909
CYP450 3A4 substrateNon-substrate0.7382
CYP450 1A2 substrateNon-inhibitor0.9368
CYP450 2C9 inhibitorNon-inhibitor0.8639
CYP450 2D6 inhibitorNon-inhibitor0.9661
CYP450 2C19 inhibitorNon-inhibitor0.9481
CYP450 3A4 inhibitorNon-inhibitor0.8309
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8112
Ames testNon AMES toxic0.9132
CarcinogenicityNon-carcinogens0.9182
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.1354 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9434
hERG inhibition (predictor II)Non-inhibitor0.8515
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
Suspensionoral
Tabletoral
Prices
Unit descriptionCostUnit
Sulfamethazine powder1.74USD g
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point198.5 °CPhysProp
water solubility1500 mg/L (at 29 °C)MERCK INDEX (1983); at pH 7
logP0.89BIOBYTE (1995)
pKa7.59SANGSTER (1994)
Predicted Properties
PropertyValueSource
Water Solubility0.23 mg/mLALOGPS
logP0.43ALOGPS
logP0.65ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)6.99ChemAxon
pKa (Strongest Basic)2.04ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area97.97 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity73.38 m3·mol-1ChemAxon
Polarizability28.8 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Download (8.13 KB)
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesJ01EB03J01EE05
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (73 KB)
Interactions
Drug Interactions
Drug
MecamylamineThe risk or severity of adverse effects can be increased when Sulfamethazine is combined with Mecamylamine.
Food Interactions
  • Do not take calcium, aluminium, magnesium or iron supplements within 2 hours of taking this medication.

Targets

Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
yes
Actions
inhibitor
General Function:
Metal ion binding
Specific Function:
Catalyzes the condensation of para-aminobenzoate (pABA) with 6-hydroxymethyl-7,8-dihydropterin diphosphate (DHPt-PP) to form 7,8-dihydropteroate (H2Pte), the immediate precursor of folate derivatives.
Gene Name:
folP
Uniprot ID:
P0AC13
Molecular Weight:
30614.855 Da
References
  1. Hong YL, Hossler PA, Calhoun DH, Meshnick SR: Inhibition of recombinant Pneumocystis carinii dihydropteroate synthetase by sulfa drugs. Antimicrob Agents Chemother. 1995 Aug;39(8):1756-63. [PubMed:7486915 ]
  2. Friaza V, Morilla R, Respaldiza N, de la Horra C, Calderon EJ: Pneumocystis jiroveci dihydropteroate synthase gene mutations among colonized individuals and Pneumocystis pneumonia patients from Spain. Postgrad Med. 2010 Nov;122(6):24-8. doi: 10.3810/pgm.2010.11.2219. [PubMed:21084778 ]
  3. Thijssen HH: A simplified radioassay method of dihydropteroate synthetase activity in Escherichia coli and its application for an inhibition study of p-aminobenzoi acid derivatives. Anal Biochem. 1973 Jun;53(2):579-85. [PubMed:4577373 ]

Enzymes

Kind
Protein
Organism
Mycobacterium tuberculosis
Pharmacological action
unknown
Actions
substrate
General Function:
Not Available
Specific Function:
Not Available
Gene Name:
nat
Uniprot ID:
P0A5L8
Molecular Weight:
Not Available
References
  1. Derewlany LO, Knie B, Koren G: Arylamine N-acetyltransferase activity of the human placenta. J Pharmacol Exp Ther. 1994 May;269(2):756-60. [PubMed:8182542 ]

Carriers

Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Toxic substance binding
Specific Function:
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloidal osmotic pressure of blood. Major zinc transporter in plasma, typically binds about 80% of all plasma zinc.
Gene Name:
ALB
Uniprot ID:
P02768
Molecular Weight:
69365.94 Da
References
  1. Bratlid D, Bergan T: Displacement of albumin-bound antimicrobial agents by bilirubin. Pharmacology. 1976;14(5):464-72. [PubMed:1031216 ]
  2. Angelakou A, Valsami G, Koupparis M, Macheras P: Use of 1-anilino-8-napthalenesulphonate as an ion probe for the potentiometric study of the binding of sulphonamides to bovine serum albumin and plasma. J Pharm Pharmacol. 1993 May;45(5):434-8. [PubMed:8099962 ]
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Drug created on August 29, 2007 08:54 / Updated on August 17, 2016 12:23