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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 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 mixturesNot Available
Salts
Name/CASStructureProperties
Sulfadimethoxine sodium
ThumbNot applicableDBSALT000956
Categories
UNII30CPC5LDEX
CAS number122-11-2
WeightAverage: 310.329
Monoisotopic: 310.073575646
Chemical FormulaC12H14N4O4S
InChI KeyInChIKey=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
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
  • Aminopyrimidine
  • Alkyl aryl ether
  • Imidolactam
  • Pyrimidine
  • Primary aromatic amine
  • Heteroaromatic compound
  • Aminosulfonyl compound
  • Sulfonyl
  • Sulfonic acid derivative
  • Sulfonamide
  • Azacycle
  • Organoheterocyclic compound
  • Ether
  • Hydrocarbon derivative
  • Primary amine
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Pharmacology
IndicationFor use in the treatment of infections.
PharmacodynamicsSulfadimethoxine 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
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point203.5 °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 RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesJ01ED01
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

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
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 ]
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Drug created on December 10, 2007 05:36 / Updated on December 10, 2013 20:45