Sulfamethazine

Identification

Summary

Sulfamethazine is an antibacterial agent used in the treatment of various bacterial infections, such as bronchitis, prostatitis, and urinary tract infections.

Generic Name
Sulfamethazine
DrugBank Accession Number
DB01582
Background

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

Type
Small Molecule
Groups
Approved, Investigational, Vet approved
Structure
Thumb
Weight
Average: 278.33
Monoisotopic: 278.083746402
Chemical Formula
C12H14N4O2S
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
  • Sulfamethazine
  • Sulfamezathine
  • Sulphadimethylpyrimidine
  • Sulphamethazine
External IDs
  • BN-2409
  • NSC-67457
  • NSC-683529

Pharmacology

Indication

For the treatment bacterial infections causing bronchitis, prostatitis and urinary tract infections.

Pharmacology
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Associated Conditions
Contraindications & Blackbox Warnings
Contraindications
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Pharmacodynamics

Sulfamethazine 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 action

Sulfonamides 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.

TargetActionsOrganism
ADihydropteroate synthase
inhibitor
Escherichia coli (strain K12)
Absorption

Rapidly absorbed following oral administration.

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
Medicalerrors
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Toxicity

Sulfamethazine 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.

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AcarboseThe therapeutic efficacy of Acarbose can be increased when used in combination with Sulfamethazine.
AcetohexamideThe therapeutic efficacy of Acetohexamide can be increased when used in combination with Sulfamethazine.
AlbiglutideThe therapeutic efficacy of Albiglutide can be increased when used in combination with Sulfamethazine.
AlogliptinThe therapeutic efficacy of Alogliptin can be increased when used in combination with Sulfamethazine.
BenzylpenicillinSulfamethazine may decrease the excretion rate of Benzylpenicillin which could result in a higher serum level.
BromocriptineThe therapeutic efficacy of Bromocriptine can be increased when used in combination with Sulfamethazine.
CanagliflozinThe therapeutic efficacy of Canagliflozin can be increased when used in combination with Sulfamethazine.
ChlorpropamideThe therapeutic efficacy of Chlorpropamide can be increased when used in combination with Sulfamethazine.
CholestyramineCholestyramine can cause a decrease in the absorption of Sulfamethazine resulting in a reduced serum concentration and potentially a decrease in efficacy.
ColesevelamColesevelam can cause a decrease in the absorption of Sulfamethazine resulting in a reduced serum concentration and potentially a decrease in efficacy.
Interactions
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Food Interactions
No interactions found.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Sulfamethazine sodium7Z13P9Q95C1981-58-4NGIVTUVVBWOTNT-UHFFFAOYSA-N
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Trisulfaminic SusSulfamethazine (167 mg / 5 mL) + Mepyramine maleate (6.25 mg / 5 mL) + Pheniramine maleate (6.25 mg / 5 mL) + Phenylpropanolamine hydrochloride (12.5 mg / 5 mL) + Sulfadiazine (167 mg / 5 mL) + Sulfamerazine (167 mg / 5 mL)SuspensionOralShepherd Pharmaceuticals Inc.1959-12-312001-04-11Canada flag
Trisulfaminic TabSulfamethazine (167 mg) + Mepyramine maleate (6.25 mg) + Pheniramine maleate (6.25 mg) + Phenylpropanolamine hydrochloride (12.5 mg) + Sulfadiazine (167 mg) + Sulfamerazine (167 mg)TabletOralShepherd Pharmaceuticals Inc.1959-12-312001-04-11Canada flag
ซัลฟาโคSulfamethazine (167 MG/5ML) + Sulfadiazine (167 MG/5ML) + Sulfamerazine (167 MG/5ML)Suspensionบริษัท โรงงานเภสัชกรรมแหลมทองการแพทย์ จำกัด จำกัด1987-05-15Not applicableThailand flag
ไตรซัลฟาไพริมิดีนSulfamethazine (167 MG) + Sulfadiazine (167 MG) + Sulfamerazine (167 MG)Tabletบริษัท อินแพคฟาร์มา จำกัด1987-09-222020-09-29Thailand flag
ไตรซัลฟาไพริมิดีนSulfamethazine (167 MG) + Sulfadiazine (167 MG) + Sulfamerazine (167 MG)Tabletบริษัท อินแพคฟาร์มา จำกัด1987-06-192020-09-29Thailand flag

Categories

ATC Codes
J01EB03 — SulfadimidineG01AE10 — Combinations of sulfonamidesJ01EE05 — Sulfadimidine and trimethoprim
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This 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.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Benzenesulfonamides
Direct Parent
Aminobenzenesulfonamides
Alternative Parents
Benzenesulfonyl compounds / Aniline and substituted anilines / Pyrimidines and pyrimidine derivatives / Organosulfonamides / Heteroaromatic compounds / Aminosulfonyl compounds / Azacyclic compounds / Primary amines / Organopnictogen compounds / Organic oxides
show 1 more
Substituents
Amine / Aminobenzenesulfonamide / Aminosulfonyl compound / Aniline or substituted anilines / Aromatic heteromonocyclic compound / Azacycle / Benzenesulfonyl group / Heteroaromatic compound / Hydrocarbon derivative / Organic nitrogen compound
show 12 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
sulfonamide, pyrimidines, sulfonamide antibiotic (CHEBI:102265)
Affected organisms
Not Available

Chemical Identifiers

UNII
48U51W007F
CAS number
57-68-1
InChI Key
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

References

General References
Not Available
Human Metabolome Database
HMDB0015522
KEGG Compound
C19530
PubChem Compound
5327
PubChem Substance
46507146
ChemSpider
5136
BindingDB
50238670
RxNav
10178
ChEBI
102265
ChEMBL
CHEMBL446
ZINC
ZINC000000057494
Therapeutic Targets Database
DAP001241
PharmGKB
PA451542
Wikipedia
Sulfadimidine
MSDS
Download (73 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • C.O. Truxton Inc.
  • Spectrum Pharmaceuticals
Dosage Forms
FormRouteStrength
Powder
SuspensionOral
TabletOral
Suspension
Tablet500 mg
Tablet
Prices
Unit descriptionCostUnit
Sulfamethazine powder1.74USD g
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)198.5 °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 RuleNoChemAxon
MDDR-like RuleNoChemAxon
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)

Spectra

Mass Spec (NIST)
Download (8.13 KB)
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0pk9-2970000000-abb9e31dc053c1d21884
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0zi0-0590000000-2e8e1e943731aa842e16
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0kmi-0950000000-9e91e580b580594989a0
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-00di-0920000000-216c25f077b257c6979d
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-00di-0900000000-127b8b6e862f77ce8c13
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-004i-0090000000-4841dadd912e95b736ce
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-000i-0910000000-fbf298bf77be3c0c7d4a
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-004i-0090000000-92cfb9d3f1565228cb1b
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-004i-0690000000-6900746badf188ab1500
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0abi-1910000000-5d3d9cc74470d1da9673
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0abc-3900000000-10a72542fb3fce7c8e67
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-05fu-5900000000-0ad8b99c3c478536a01e
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0avl-8900000000-d30171fd393f511058d6
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-004i-0090000000-bf48a8bbb6d06696db15
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-004i-0690000000-4789a5291d234b5d0375
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0abi-1910000000-2364d173d7cd8dae0c76
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0abc-3900000000-330131b76908d2b6ec6d
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-05fu-6900000000-0437ddca2816d4b382ad
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0603-7900000000-71014d7adacf773403b4
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-000i-0910000000-ddb50106bf908846aa9b
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0abc-2910000000-f56221aae64496f78e4b
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-05fu-4900000000-95b487899628a8694b93
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-000i-0920000000-e0e94f67285e005d0e3d
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-000i-0910000000-6ba4c4c069a0eec7ba03
MS/MS Spectrum - , positiveLC-MS/MSsplash10-004i-0590000000-97c8e7a982f4f8f5c92e
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0kdi-2690000000-d311ca6b0cea5c0bc915
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a4j-0590000000-47a21930039c345e0211
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a4j-0590000000-18c2d26e19ce37b1ec6d

Targets

Drugtargets
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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
Uniprot Name
Dihydropteroate synthase
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. [Article]
  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. [Article]
  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. [Article]

Enzymes

Kind
Protein
Organism
Mycobacterium tuberculosis
Pharmacological action
Unknown
Actions
Substrate
General Function
Catalyzes the transfer of the acetyl group from acetyl coenzyme A to the free amino group of arylamines and hydrazines (PubMed:18795795). Is able to utilize not only acetyl-CoA, but also n-propionyl-CoA and acetoacetyl-CoA as acyl donors, although at a lower rate (PubMed:19014350). As acetyl-CoA and propionyl-CoA are products of cholesterol catabolism and the nat gene is likely present in the same operon than genes involved in cholesterol degradation, this enzyme could have a role in the utilization and regulation of these CoA species (PubMed:19014350).
Specific Function
Arylamine n-acetyltransferase activity
Gene Name
nat
Uniprot ID
P9WJI5
Uniprot Name
Arylamine N-acetyltransferase
Molecular Weight
31028.88 Da
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. [Article]

Carriers

Kind
Protein
Organism
Humans
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 colloid...
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
Serum albumin
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. doi: 10.1159/000136629. [Article]
  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. [Article]

Drug created on August 29, 2007 14:54 / Updated on April 30, 2021 13:05