Identification
NameSulfadimethoxine
Accession NumberDB06150
TypeSmall Molecule
GroupsApproved, Vet Approved
Description

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.

Structure
Thumb
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
Abcid (tn)
Agribon (tn)
N(1)-(2,6-Dimethoxy-4-pyrimidinyl)sulfanilamide
Sulfadimethoxine
Sulfadimethoxinum
Sulfadimethoxydiazine
Sulfadimetoxina
Sulphadimethoxine
External IDs Not Available
Product Ingredients
IngredientUNIICASInChI KeyDetails
Sulfadimethoxine sodium49DG2B481W 1037-50-9DQDZQHMCPDUUPC-UHFFFAOYSA-NDetails
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
Categories
UNII30CPC5LDEX
CAS number122-11-2
WeightAverage: 310.329
Monoisotopic: 310.073575646
Chemical FormulaC12H14N4O4S
InChI KeyZZORFUFYDOWNEF-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
Pharmacology
Indication

For use in the treatment of infections.

Structured Indications Not Available
Pharmacodynamics

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

Mechanism of actionNot Available
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
Pharmacogenomic Effects/ADRs Not Available
Interactions
Drug Interactions
DrugInteractionDrug group
DexketoprofenThe risk or severity of adverse effects can be increased when Dexketoprofen is combined with Sulfadimethoxine.Approved
MecamylamineThe risk or severity of adverse effects can be increased when Sulfadimethoxine is combined with Mecamylamine.Approved
Food InteractionsNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesG01AE10 — Combinations of sulfonamidesJ01ED01 — Sulfadimethoxine
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Clinical Trials
Clinical Trials Not Available
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
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)1.95ChemAxon
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
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-000t-0960000000-4c56988c713477efd105View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0a4i-0009000000-f2128f2fce62999cb716View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0a4i-0009000000-ccda245feefab7d2bd86View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0a4i-2429000000-29cebf2b6eb7f0d6fa3dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-014i-8910000000-8accee4b36ee278d892fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-014i-9700000000-4424c4504af2babbb3beView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-014i-9600000000-83e5ad4bc8bfce2e0713View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0a4i-0009000000-88d4fd97a1710d90ea0aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0a4i-0009000000-d5196629814cc9a54aa8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0a4i-2429000000-d8e5bcd5f851f3c92887View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-01b9-6900000000-64279bf9c022308e0a22View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-01b9-8900000000-3ace2e3886f14e2ea920View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-014i-9400000000-e2fed07103b2f17ab4ccView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-000t-0960000000-e0d34039fdec2c716285View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0bt9-0905000000-78aa6da956c32ba36241View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0a4i-0910000000-7b5873eb9276bcb413beView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0k96-0910000000-24de656de5a8714caacbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0udl-0900000000-cf83e971f45b0faf66d2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0a4j-0980000000-cfe01946ddd1b175abb5View in MoNA
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
Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as aminobenzenesulfonamides. These are organic compounds containing a benzenesulfonamide moiety with an amine group attached to the benzene ring.
KingdomChemical entities
Super ClassOrganic compounds
ClassBenzenoids
Sub ClassBenzene and substituted derivatives
Direct ParentAminobenzenesulfonamides
Alternative ParentsBenzenesulfonyl compounds / Aniline and substituted anilines / Alkyl aryl ethers / Pyrimidines and pyrimidine derivatives / Primary aromatic amines / Organosulfonamides / Imidolactams / Heteroaromatic compounds / Aminosulfonyl compounds / Azacyclic compounds
SubstituentsAminobenzenesulfonamide / Benzenesulfonyl group / Aniline or substituted anilines / Alkyl aryl ether / Primary aromatic amine / Pyrimidine / Organosulfonic acid amide / Imidolactam / Organic sulfonic acid or derivatives / Heteroaromatic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptorsaromatic ether, substituted aniline, sulfonamide, pyrimidines, sulfonamide antibiotic (CHEBI:32161 )

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
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 unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenyto...
Gene Name:
CYP2C9
Uniprot ID:
P11712
Uniprot Name:
Cytochrome P450 2C9
Molecular Weight:
55627.365 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Drug created on December 10, 2007 05:36 / Updated on June 11, 2017 16:42