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.
In the US, sulfadimethoxine is one of the products that have been withdrawn or removed from the market after being found to be unsafe or not effective.1
- Type
- Small Molecule
- Groups
- Approved, Vet approved, Withdrawn
- 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.
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Avoid life-threatening adverse drug eventsImprove clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events & improve clinical decision support.- 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
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.Improve decision support & research outcomes with our structured adverse effects data.- 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAcarbose The therapeutic efficacy of Acarbose can be increased when used in combination with Sulfadimethoxine. Acetohexamide The therapeutic efficacy of Acetohexamide can be increased when used in combination 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. Benzylpenicillin Sulfadimethoxine may decrease the excretion rate of Benzylpenicillin which could result in a higher serum level. Bromocriptine The therapeutic efficacy of Bromocriptine can be increased when used in combination with Sulfadimethoxine. Canagliflozin The therapeutic efficacy of Canagliflozin can be increased when used in combination with Sulfadimethoxine. Chloroprocaine The therapeutic efficacy of Sulfadimethoxine can be decreased when used in combination with Chloroprocaine. Chlorpropamide The therapeutic efficacy of Chlorpropamide can be increased when used in combination with Sulfadimethoxine. Cholestyramine Cholestyramine 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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- Not Available
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- 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 Antibacterial 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)
- 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
- Code of Federal Regulations 216.24: Drug products withdrawn or removed from the market for reasons of safety or effectiveness. [Link]
- 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 Injection, solution Tablet Powder Solution - 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) 1.99 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. [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
- 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 November 19, 2022 17:55