Sulfadimethoxine
Identification
- Name
- Sulfadimethoxine
- Accession Number
- DB06150
- 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.
- Type
- Small Molecule
- Groups
- Approved, Vet approved
- Structure
Structure for Sulfadimethoxine (DB06150)
- 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.
- Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
Learn More- 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
Learn about our commercial Adverse Effects data.
Learn More- Toxicity
- Not Available
- Affected organisms
- Humans and other mammals
- 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.
Drug Interaction Unlock Additional DataAcarbose The therapeutic efficacy of Acarbose can be increased when used in combination with Sulfadimethoxine. Acenocoumarol The metabolism of Acenocoumarol can be decreased when combined with Sulfadimethoxine. Acetohexamide The therapeutic efficacy of Acetohexamide can be increased when used in combination with Sulfadimethoxine. Acetylsalicylic acid The metabolism of Acetylsalicylic acid can be decreased when combined with Sulfadimethoxine. Albiglutide The therapeutic efficacy of Albiglutide can be increased when used in combination with Sulfadimethoxine. Alogliptin The therapeutic efficacy of Alogliptin can be increased when used in combination with Sulfadimethoxine. Alosetron The metabolism of Alosetron can be decreased when combined with Sulfadimethoxine. Aminophenazone The metabolism of Aminophenazone can be decreased when combined with Sulfadimethoxine. Amitriptyline The metabolism of Amitriptyline can be decreased when combined with Sulfadimethoxine. Amprenavir The metabolism of Amprenavir can be decreased when combined with Sulfadimethoxine. Additional Data Available- Extended DescriptionExtended DescriptionAvailable for Purchase
Extended description of the mechanism of action and particular properties of each drug interaction.
Learn more - SeveritySeverityAvailable for Purchase
A severity rating for each drug interaction, from minor to major.
Learn more - Evidence LevelEvidence LevelAvailable for Purchase
A rating for the strength of the evidence supporting each drug interaction.
Learn more - ActionActionAvailable for Purchase
An effect category for each drug interaction. Know how this interaction affects the subject drug.
Learn more
- Food Interactions
- Not Available
Products
- Product Ingredients
Ingredient UNII CAS InChI Key Sulfadimethoxine sodium 49DG2B481W 1037-50-9 DQDZQHMCPDUUPC-UHFFFAOYSA-N - International/Other Brands
- Abcid / Agribon
Categories
- ATC Codes
- J01ED01 — Sulfadimethoxine
- J01ED — Long-acting sulfonamides
- J01E — SULFONAMIDES AND TRIMETHOPRIM
- J01 — ANTIBACTERIALS FOR SYSTEMIC USE
- J — ANTIINFECTIVES FOR SYSTEMIC USE
- Drug Categories
- Amides
- Amines
- Aniline Compounds
- Anti-Infective Agents
- Antibacterials for Systemic Use
- Antiinfectives for Systemic Use
- Cytochrome P-450 CYP2C9 Inhibitors
- Cytochrome P-450 CYP2C9 Inhibitors (strength unknown)
- Cytochrome P-450 Enzyme Inhibitors
- Genito Urinary System and Sex Hormones
- Gynecological Antiinfectives and Antiseptics
- Long-Acting Sulfonamides
- Sulfanilamides
- Sulfonamides
- SULFONAMIDES AND TRIMETHOPRIM
- Sulfones
- Sulfur Compounds
- 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)
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
- External Links
- Human Metabolome Database
- HMDB0015621
- KEGG Drug
- D01142
- PubChem Compound
- 5323
- PubChem Substance
- 99443234
- ChemSpider
- 5132
- BindingDB
- 50238669
- 10172
- ChEBI
- 32161
- ChEMBL
- CHEMBL62193
- ZINC
- ZINC000013233295
- PharmGKB
- PA165958357
- Wikipedia
- Sulfadimethoxine
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Tablet 0.5 G Tablet 500 MG - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 203.5 °C PhysProp water solubility 343 mg/L YALKOWSKY,SH & DANNENFELSER,RM (1992) logP 1.63 HANSCH,C ET AL. (1995) - Predicted Properties
Property Value Source Water Solubility 0.278 mg/mL ALOGPS logP 1.08 ALOGPS logP 1.26 ChemAxon logS -3 ALOGPS pKa (Strongest Acidic) 6.91 ChemAxon pKa (Strongest Basic) 1.95 ChemAxon Physiological Charge -1 ChemAxon Hydrogen Acceptor Count 7 ChemAxon Hydrogen Donor Count 2 ChemAxon Polar Surface Area 116.43 Å2 ChemAxon Rotatable Bond Count 4 ChemAxon Refractivity 77.75 m3·mol-1 ChemAxon Polarizability 29.6 Å3 ChemAxon Number of Rings 2 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule No ChemAxon MDDR-like Rule No ChemAxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9555 Blood Brain Barrier + 0.8357 Caco-2 permeable - 0.5449 P-glycoprotein substrate Non-substrate 0.8399 P-glycoprotein inhibitor I Non-inhibitor 0.904 P-glycoprotein inhibitor II Non-inhibitor 0.9792 Renal organic cation transporter Non-inhibitor 0.9154 CYP450 2C9 substrate Non-substrate 0.6674 CYP450 2D6 substrate Non-substrate 0.9053 CYP450 3A4 substrate Non-substrate 0.7198 CYP450 1A2 substrate Non-inhibitor 0.9206 CYP450 2C9 inhibitor Non-inhibitor 0.9071 CYP450 2D6 inhibitor Non-inhibitor 0.9413 CYP450 2C19 inhibitor Non-inhibitor 0.9257 CYP450 3A4 inhibitor Non-inhibitor 0.8601 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.792 Ames test Non AMES toxic 0.76 Carcinogenicity Non-carcinogens 0.8237 Biodegradation Not ready biodegradable 0.997 Rat acute toxicity 1.7027 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9822 hERG inhibition (predictor II) Non-inhibitor 0.8789
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
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
- 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. [PubMed:10725317]
Drug created on December 10, 2007 05:36 / Updated on June 12, 2020 10:52