Identification

Generic Name
Sulfadimethoxine
DrugBank Accession Number
DB06150
Background

Sulfadimethoxine is a sulfonamide antibiotic. Sulfadimethoxine is used to treat many infections including treatment of respiratory, urinary tract, enteric, and soft tissue infections. It is most frequently used in veterinary medicine, although it is approved in some countries for use in humans. Sulfadimethoxine inhibits bacterial synthesis of folic acid (pteroylglutamic acid) from para-aminobenzoic acid. Sulfadimethoxine is approved in Russia for use in humans, including children, and has been successfully used there for more than 35 years. It is widely available in Russia as an over-the-counter drug manufactured by a number of Russian pharmaceutical companies.

Type
Small Molecule
Groups
Approved, Vet approved
Structure
Weight
Average: 310.329
Monoisotopic: 310.073575646
Chemical Formula
C12H14N4O4S
Synonyms
  • 2,4-dimethoxy-6-sulfanilamido-1,3-diazine
  • 2,6-dimethoxy-4-(p-aminobenzenesulfonamido)pyrimidine
  • 2,6-dimethoxy-4-sulfanilamidopyrimidine
  • 4-amino-N-(2,6-dimethoxy-4-pyrimidinyl)benzenesulfonamide
  • 6-sulfanilamido-2,4-dimethoxypyrimidine
  • N(1)-(2,6-Dimethoxy-4-pyrimidinyl)sulfanilamide
  • Sulfadimethoxine
  • Sulfadimethoxinum
  • Sulfadimethoxydiazine
  • Sulfadimetoxina
  • Sulphadimethoxine

Pharmacology

Indication

For use in the treatment of infections.

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Sulfadimethoxine has been shown to be effective against streptococci, klebsiella, proteus, shigella, staphylococci, escherichia, and salmonella.

Mechanism of action
Not Available
Absorption

Not Available

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
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Toxicity

Not Available

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 Sulfadimethoxine.
AcetohexamideThe therapeutic efficacy of Acetohexamide can be increased when used in combination with Sulfadimethoxine.
AlbiglutideThe therapeutic efficacy of Albiglutide can be increased when used in combination with Sulfadimethoxine.
AlogliptinThe therapeutic efficacy of Alogliptin can be increased when used in combination with Sulfadimethoxine.
BenzylpenicillinSulfadimethoxine 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 Sulfadimethoxine.
CanagliflozinThe therapeutic efficacy of Canagliflozin can be increased when used in combination with Sulfadimethoxine.
ChlorpropamideThe therapeutic efficacy of Chlorpropamide can be increased when used in combination with Sulfadimethoxine.
CholestyramineCholestyramine can cause a decrease in the absorption of Sulfadimethoxine resulting in a reduced serum concentration and potentially a decrease in efficacy.
ColesevelamColesevelam can cause a decrease in the absorption of Sulfadimethoxine resulting in a reduced serum concentration and potentially a decrease in efficacy.
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Food Interactions
Not Available

Products

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Product Ingredients
IngredientUNIICASInChI Key
Sulfadimethoxine sodium49DG2B481W1037-50-9DQDZQHMCPDUUPC-UHFFFAOYSA-N
International/Other Brands
Abcid / Agribon

Categories

ATC Codes
J01ED01 — SulfadimethoxineG01AE10 — Combinations of sulfonamides
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 / Alkyl aryl ethers / Pyrimidines and pyrimidine derivatives / Organosulfonamides / Imidolactams / Heteroaromatic compounds / Aminosulfonyl compounds / Azacyclic compounds / Primary amines
show 3 more
Substituents
Alkyl aryl ether / Amine / Aminobenzenesulfonamide / Aminosulfonyl compound / Aniline or substituted anilines / Aromatic heteromonocyclic compound / Azacycle / Benzenesulfonyl group / Ether / Heteroaromatic compound
show 16 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
aromatic ether, substituted aniline, sulfonamide, pyrimidines, sulfonamide antibiotic (CHEBI:32161)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
30CPC5LDEX
CAS number
122-11-2
InChI Key
ZZORFUFYDOWNEF-UHFFFAOYSA-N
InChI
InChI=1S/C12H14N4O4S/c1-19-11-7-10(14-12(15-11)20-2)16-21(17,18)9-5-3-8(13)4-6-9/h3-7H,13H2,1-2H3,(H,14,15,16)
IUPAC Name
4-amino-N-(2,6-dimethoxypyrimidin-4-yl)benzene-1-sulfonamide
SMILES
COC1=NC(OC)=NC(NS(=O)(=O)C2=CC=C(N)C=C2)=C1

References

General References
Not Available
Human Metabolome Database
HMDB0015621
KEGG Drug
D01142
PubChem Compound
5323
PubChem Substance
99443234
ChemSpider
5132
BindingDB
50238669
RxNav
10172
ChEBI
32161
ChEMBL
CHEMBL62193
ZINC
ZINC000013233295
PharmGKB
PA165958357
Wikipedia
Sulfadimethoxine

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
Injection, solution
Tablet
Powder
Solution
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)203.5 °CPhysProp
water solubility343 mg/LYALKOWSKY,SH & DANNENFELSER,RM (1992)
logP1.63HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility0.278 mg/mLALOGPS
logP1.08ALOGPS
logP1.26ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)6.91ChemAxon
pKa (Strongest Basic)1.99ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area116.43 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity77.75 m3·mol-1ChemAxon
Polarizability29.6 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9555
Blood Brain Barrier+0.8357
Caco-2 permeable-0.5449
P-glycoprotein substrateNon-substrate0.8399
P-glycoprotein inhibitor INon-inhibitor0.904
P-glycoprotein inhibitor IINon-inhibitor0.9792
Renal organic cation transporterNon-inhibitor0.9154
CYP450 2C9 substrateNon-substrate0.6674
CYP450 2D6 substrateNon-substrate0.9053
CYP450 3A4 substrateNon-substrate0.7198
CYP450 1A2 substrateNon-inhibitor0.9206
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorNon-inhibitor0.9413
CYP450 2C19 inhibitorNon-inhibitor0.9257
CYP450 3A4 inhibitorNon-inhibitor0.8601
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.792
Ames testNon AMES toxic0.76
CarcinogenicityNon-carcinogens0.8237
BiodegradationNot ready biodegradable0.997
Rat acute toxicity1.7027 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9822
hERG inhibition (predictor II)Non-inhibitor0.8789
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
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/MSNot Available
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-000t-0960000000-4c56988c713477efd105
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0a4i-0009000000-f2128f2fce62999cb716
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0a4i-0009000000-ccda245feefab7d2bd86
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0a4i-2429000000-29cebf2b6eb7f0d6fa3d
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-014i-8910000000-8accee4b36ee278d892f
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-014i-9700000000-4424c4504af2babbb3be
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-014i-9600000000-83e5ad4bc8bfce2e0713
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0a4i-0009000000-88d4fd97a1710d90ea0a
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0a4i-0009000000-d5196629814cc9a54aa8
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0a4i-2429000000-d8e5bcd5f851f3c92887
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-01b9-6900000000-64279bf9c022308e0a22
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-01b9-8900000000-3ace2e3886f14e2ea920
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-014i-9400000000-e2fed07103b2f17ab4cc
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-000t-0960000000-e0d34039fdec2c716285
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-0a4i-0009000000-6a816a27b2d84825241f
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0bt9-0905000000-78aa6da956c32ba36241
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0a4i-0910000000-7b5873eb9276bcb413be
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0k96-0910000000-24de656de5a8714caacb
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0udl-0900000000-cf83e971f45b0faf66d2
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a4j-0980000000-cfe01946ddd1b175abb5
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-03di-0009000000-f11380ace14f72faa13c
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-08fr-0519000000-36e919c3df0544059369
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a4i-1910000000-33f9ff6783fd590680d7
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a4i-2900000000-44b1baf0490549befce6
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a4l-5900000000-e7baf7f98c9ed2fd8aa8
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0aou-9800000000-e03cc67534f7365c49d9
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-03di-0009000000-6d1a8501157460316c42
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-03di-0519000000-9d0575ba9c7dcff9db9d
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a4i-1910000000-182349cada4bfcff93c3
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a4i-2900000000-ae8523c33544de1df0d2
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a4l-5900000000-ed9f847ae156da8f89b6
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0aou-9800000000-9ca379011b6d4661582a
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a4i-0970000000-32ce0e75c6497d0ed06b
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-03di-0009000000-78dbef9a42f60e1ea122
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0a4i-0924000000-b767fd1a2b28b26b9b18
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0a4i-3900000000-97bf4a2fe344e3fa6fb9
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-052f-7900000000-03ddf82329867450bd3e
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-066u-9500000000-ad56c2e4a887d1ecbe48
MS/MS Spectrum - , positiveLC-MS/MSsplash10-03di-1519000000-1f09f980736030a73e9e
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0a4i-3910000000-0ac9853510aee4214006
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0bt9-2917000000-c6e310b94c2dbece6ea3

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
Curator comments
Data based on findings of 1 in vitro study.
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C9
Uniprot ID
P11712
Uniprot Name
Cytochrome P450 2C9
Molecular Weight
55627.365 Da
References
  1. Komatsu K, Ito K, Nakajima Y, Kanamitsu Si, Imaoka S, Funae Y, Green CE, Tyson CA, Shimada N, Sugiyama Y: Prediction of in vivo drug-drug interactions between tolbutamide and various sulfonamides in humans based on in vitro experiments. Drug Metab Dispos. 2000 Apr;28(4):475-81. [Article]

Carriers

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
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. Aver'eva EV, Kivman GIa, Markovich MN, Shraiber NF, Pognoevskii OT: [Competition of antibacterial drugs for binding sites of human serum albumin]. Antibiot Khimioter. 1988 Jun;33(6):444-8. [Article]

Drug created at December 10, 2007 12:36 / Updated at January 02, 2022 11:57