Sulfadiazine
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Basic Info
| Common Name | Sulfadiazine(F06216) |
| 2D Structure | |
| FRCD ID | F06216 |
| CAS Number | 68-35-9 |
| PubChem CID | 5215 |
| Formula | C10H10N4O2S |
| IUPAC Name | 4-amino-N-pyrimidin-2-ylbenzenesulfonamide |
| InChI Key | SEEPANYCNGTZFQ-UHFFFAOYSA-N |
| InChI | InChI=1S/C10H10N4O2S/c11-8-2-4-9(5-3-8)17(15,16)14-10-12-6-1-7-13-10/h1-7H,11H2,(H,12,13,14) |
| Canonical SMILES | C1=CN=C(N=C1)NS(=O)(=O)C2=CC=C(C=C2)N |
| Isomeric SMILES | C1=CN=C(N=C1)NS(=O)(=O)C2=CC=C(C=C2)N |
| Synonyms |
Liquadiazine
sulfadiazine
Sulphadiazine
Sulfapyrimidine
68-35-9
Sulfadiazin
Sulfazine
Sulfadiazene
Sulfapyrimidin
Adiazin
|
| Classifies |
Predicted: Veterinary Drug
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Benzenoids |
| Class | Benzene and substituted derivatives |
| Subclass | Benzenesulfonamides |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Aminobenzenesulfonamides |
| Alternative Parents | |
| Molecular Framework | Aromatic heteromonocyclic compounds |
| Substituents | Aminobenzenesulfonamide - Benzenesulfonyl group - Aniline or substituted anilines - Pyrimidine - Organosulfonic acid amide - Organic sulfonic acid or derivatives - Organosulfonic acid or derivatives - Heteroaromatic compound - Aminosulfonyl compound - Sulfonyl - Azacycle - Organoheterocyclic compound - Amine - Hydrocarbon derivative - Organic oxide - Organopnictogen compound - Organic oxygen compound - Primary amine - Organosulfur compound - Organonitrogen compound - Organic nitrogen compound - Aromatic heteromonocyclic compound |
| 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. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 250.276 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 6 |
| Rotatable Bond Count | 3 |
| Complexity | 327 |
| Monoisotopic Mass | 250.052 |
| Exact Mass | 250.052 |
| XLogP | -0.1 |
| Formal Charge | 0 |
| Heavy Atom Count | 17 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
ADMET
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB+ | 0.9383 |
| Human Intestinal Absorption | HIA+ | 0.9877 |
| Caco-2 Permeability | Caco2+ | 0.6988 |
| P-glycoprotein Substrate | Non-substrate | 0.9012 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.9130 |
| Non-inhibitor | 0.9156 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.8437 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.5997 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8031 |
| CYP450 2D6 Substrate | Non-substrate | 0.9150 |
| CYP450 3A4 Substrate | Non-substrate | 0.7671 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.9574 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.9220 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9548 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.9693 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.9020 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.8569 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9383 |
| Non-inhibitor | 0.8673 | |
| AMES Toxicity | Non AMES toxic | 0.9206 |
| Carcinogens | Non-carcinogens | 0.9393 |
| Fish Toxicity | Low FHMT | 0.8168 |
| Tetrahymena Pyriformis Toxicity | Low TPT | 0.6305 |
| Honey Bee Toxicity | Low HBT | 0.8407 |
| Biodegradation | Not ready biodegradable | 0.9973 |
| Acute Oral Toxicity | III | 0.6777 |
| Carcinogenicity (Three-class) | Non-required | 0.5084 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -3.1155 | LogS |
| Caco-2 Permeability | 1.1422 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 1.8353 | LD50, mol/kg |
| Fish Toxicity | 2.0791 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.2674 | pIGC50, ug/L |
MRLs
| Food | Product Code | Country | MRLs | Application Date | Notes |
|---|---|---|---|---|---|
| Pig,Fat | Japan | 0.1ppm | |||
| Other Terrestrial Mammals,Muscle | Japan | 0.1ppm | |||
| Pig,Muscle | Japan | 0.1ppm | |||
| Cattle,Muscle | Japan | 0.1ppm | |||
| Salmoniformes | Japan | 0.1ppm | |||
| Other Poultry,Eggs | Japan | 0.02ppm | |||
| Chicken,Eggs | Japan | 0.02ppm | |||
| Other Poultry Animals,Edible Offal | Japan | 0.1ppm | |||
| Chicken,Edible Offal | Japan | 0.1ppm | |||
| Other Poultry Animals,Kidney | Japan | 0.1ppm | |||
| Chicken,Kidney | Japan | 0.1ppm | |||
| Other Poultry Animals,Liver | Japan | 0.1ppm | |||
| Chicken,Liver | Japan | 0.1ppm | |||
| Other Poultry Animals,Fat | Japan | 0.1ppm | |||
| Chicken,Fat | Japan | 0.1ppm | |||
| Other Poultry Animals,Muscle | Japan | 0.1ppm | |||
| Chicken,Muscle | Japan | 0.1ppm | |||
| Milk | Japan | 0.07ppm | |||
| Other Terrestrial Mammals,Edible Offal | Japan | 0.1ppm | |||
| Pig,Edible Offal | Japan | 0.1ppm |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Development and validation of an LC-MS/MS method for the quantification oftiamulin, trimethoprim, tylosin, sulfadiazine and sulfamethazine in medicatedfeed. | Food Addit Contam Part A Chem Anal Control Expo Risk Assess | 2018May | 29324179 |
| Development and validation of multi-residue and multi-class method forantibacterial substances analysis in non-target feed by liquid chromatography -tandem mass spectrometry. | Food Addit Contam Part A Chem Anal Control Expo Risk Assess | 2018Mar | 29219766 |
| Stability study of veterinary drugs in standard solutions for LC-MS/MS screening in food. | Food Addit Contam Part A Chem Anal Control Expo Risk Assess | 2018Apr | 29377759 |
| The study of formulated Zoush ointment against wound infection and gene expression of virulence factors Pseudomonas aeruginosa. | BMC Complement Altern Med | 2018 Jun 15 | 29903005 |
| Using the lentiviral vector system to stably express chicken P-gp and BCRP inMDCK cells for screening the substrates and studying the interplay of bothtransporters. | Arch Toxicol | 2018 Jun | 29725709 |
| Occurrence, distribution, ecological and resistance risks of antibiotics insurface water of finfish and shellfish aquaculture in Bangladesh. | Chemosphere | 2017 Dec | 28888121 |
| Risk-based approach to developing a national residue sampling plan for testingunder European Union regulation for veterinary medicinal products andcoccidiostat feed additives in domestic animal production. | Food Addit Contam Part A Chem Anal Control Expo Risk Assess | 2016Jul | 27189753 |
| Development and validation of rapid multiresidue and multi-class analysis forantibiotics and anthelmintics in feed by ultra-high-performance liquidchromatography coupled to tandem mass spectrometry. | Food Addit Contam Part A Chem Anal Control Expo Risk Assess | 2016Aug | 27376829 |
| Monitoring of twenty-two sulfonamides in edible tissues: Investigation of newmetabolites and their potential toxicity. | Food Chem | 2016 Feb 1 | 26304340 |
| Feasibility of lettuce cultivation in sophoroliplid-enhanced washed soiloriginally polluted with Cd, antibiotics, and antibiotic-resistant genes. | Ecotoxicol Environ Saf | 2016 Feb | 26590696 |
| Monitoring and determination of sulfonamide antibiotics (sulfamethoxydiazine,sulfamethazine, sulfamethoxazole and sulfadiazine) in imported Pangasius catfish products in Thailand using liquid chromatography coupled with tandem massspectrometry. | Food Chem | 2016 Dec 1 | 27374578 |
| Environmental and human health risks of antimicrobials used in Fenneropenaeuschinensis aquaculture production in China. | Environ Sci Pollut Res Int | 2016 Aug | 27137193 |
| Target analysis and retrospective screening of veterinary drugs, ergot alkaloids, plant toxins and other undesirable substances in feed using liquid chromatography-high resolution mass spectrometry. | Talanta | 2016 | 26717812 |
| Determination of selected veterinary antimicrobials in poultry excreta byUHPLC-MS/MS, for application in Salmonella control programs. | Anal Bioanal Chem | 2015 Jun | 25633214 |
| Analysis of veterinary drug and pesticide residues in animal feed by high-resolution mass spectrometry: comparison between time-of-flight and Orbitrap. | Food Addit Contam Part A Chem Anal Control Expo Risk Assess | 2015 | 25785350 |
| The sensitivity of Daphnia magna and Daphnia curvirostris to 10 veterinary antibacterials and to some of their binary mixtures. | Chemosphere | 2014 Nov | 24630458 |
| Possibilities to control Ichthyophthirius multifiliis infestation with medicated feed in rainbow trout (Oncorhynchus mykiss) and chub (Leuciscus cephalus). | Parasitol Res | 2014 Mar | 24419403 |
| Antibiotic resistance of Vibrio species isolated from Sparus aurata reared inItalian mariculture. | New Microbiol | 2014 Jul | 25180847 |
| Wide-scope analysis of pesticide and veterinary drug residues in meat matrices byhigh resolution MS: detection and identification using Exactive-Orbitrap. | J Mass Spectrom | 2014 Jan | 24446260 |
| Simultaneous determination of 14 sulfonamides and tetracyclines in biogas plants by liquid-liquid-extraction and liquid chromatography tandem mass spectrometry. | Anal Bioanal Chem | 2014 Apr | 24535685 |