スルファメチアジン
- 関
- sulfadimidine
WordNet
- a sulfa drug used like sulfadiazine and also in veterinary medicine (同)sulfamezathine
Wikipedia preview
出典(authority):フリー百科事典『ウィキペディア(Wikipedia)』「2015/11/25 21:14:06」(JST)
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Sulfamethazine
|
Systematic (IUPAC) name |
4-amino-N-(4,6-dimethylpyrimidin-2-yl)
benzenesulfonamide
|
Clinical data |
AHFS/Drugs.com |
International Drug Names |
Identifiers |
CAS Number |
57-68-1 Y |
ATC code |
J01EB03 QJ01EQ03 QP51AG01 |
PubChem |
CID: 5327 |
DrugBank |
DB01582 Y |
ChemSpider |
5136 Y |
UNII |
48U51W007F Y |
KEGG |
D02436 Y |
ChEBI |
CHEBI:102265 Y |
ChEMBL |
CHEMBL446 Y |
NIAID ChemDB |
027749 |
Chemical data |
Formula |
C12H14N4O2S |
Molecular mass |
278.33 g/mol |
SMILES
-
O=S(=O)(Nc1nc(cc(n1)C)C)c2ccc(N)cc2
|
InChI
-
InChI=1S/C12H14N4O2S/c1-8-7-9(2)15-12(14-8)16-19(17,18)11-5-3-10(13)4-6-11/h3-7H,13H2,1-2H3,(H,14,15,16) Y
-
Key:ASWVTGNCAZCNNR-UHFFFAOYSA-N Y
|
Physical data |
Melting point |
176 °C (349 °F) |
Y (what is this?) (verify) |
Sulfadimidine or sulfamethazine is a sulfonamide antibacterial.
There are non-standardizeda abbreviations for it as "sulfadimidine" (abbreviated SDI[1][2] and more commonly but less reliablyb SDD[3][4]) and as "sulfamethazine" (abbreviated SMT[5][6] and more commonly but less reliablyc SMZ[7][8]). Other names include sulfadimerazine, sulfadimezine, and sulphadimethylpyrimidine.
Notes
- ^a Abbreviations are not found in the databases (such as ChemDB, ChemIDplus, PubChem), but often seen in the published literature.[citation needed]
- ^b "SDD" is not found in databases, but often seen in the published literature; it could however be confused with Tiferron/Sodium catechol sulfate (1,2-Dihydroxybenzene-3,5-disulfonic acid disodium Salt), uncommon but found officially abbreviated SDD in the ChemIDplus database.[9]
- ^c "SMZ" is not found in databases, but often seen in the published literature; it could however be confused with sulfamethoxazole, also seen abbreviated SMZ.[citation needed]
References
- ^ Romváry, A; Simon, F (1992). "Sulfonamide residues in eggs". Acta veterinaria Hungarica 40 (1–2): 99–106. ISSN 0236-6290. PMID 1476095.
- ^ Reddy; Jain, S. K.; Uppal, R. P. (1988). "Pharmacokinetic studies of sulphonamides in poultry". Indian Journal of Animal Sciences.
- ^ Kamakura, K; Hasegawa, M; Koiguchi, S; Miyata, M; Okamoto, K; Narita, M; Hirahara, Y; Yamana, T; et al. (1993). "Studies on the identification of sulfadimidine in pork by high performance liquid chromatography with photodiode array detector and gas chromatograph-mass spectrometry". Eisei Shikenjo hokoku. Bulletin of National Institute of Hygienic Sciences (111): 61–5. ISSN 0077-4715. PMID 7920569.
- ^ Garg, SK; Ghosh, SS; Mathur, VS (Jan 1986). "Comparative pharmacokinetic study of four different sulfonamides in combination with trimethoprim in human volunteers". International journal of clinical pharmacology, therapy, and toxicology 24 (1): 23–5. ISSN 0174-4879. PMID 3485584.
- ^ Peña, MS; Salinas, F; Mahedero, MC; Aaron, JJ (Feb 1994). "Solvent effect on the determination of sulfamethazine by room-temperature photochemically induced fluorescence". Talanta 41 (2): 233–6. doi:10.1016/0039-9140(94)80113-4. ISSN 0039-9140. PMID 18965913.
- ^ Kaniou, S; Pitarakis, K; Barlagianni, I; Poulios, I (Jul 2005). "Photocatalytic oxidation of sulfamethazine". Chemosphere 60 (3): 372–80. doi:10.1016/j.chemosphere.2004.11.069. ISSN 0045-6535. PMID 15924956.
- ^ Calvo, R; Sarabia, S; Carlos, R; Du Souich, P (Mar 1987). "Sulfamethazine absorption and disposition: effect of surgical procedures for gastroduodenal ulcers". Biopharmaceutics & drug disposition 8 (2): 115–24. doi:10.1002/bdd.2510080203. ISSN 0142-2782. PMID 3593892.
- ^ De Liguoro, M; Fioretto, B; Poltronieri, C; Gallina, G (Jun 2009). "The toxicity of sulfamethazine to Daphnia magna and its additivity to other veterinary sulfonamides and trimethoprim". Chemosphere 75 (11): 1519–24. doi:10.1016/j.chemosphere.2009.02.002. ISSN 0045-6535. PMID 19269673.
- ^ http://chem.sis.nlm.nih.gov/chemidplus/ProxyServlet?objectHandle=Search&actionHandle=getAll3DMViewFiles&nextPage=jsp%2Fcommon%2FChemFull.jsp%3FcalledFrom%3Dlite&chemid=000149451&formatType=_3D[dead link]
Further reading
- ChemDB. "Sulfamethazine", ChemDB, National Institute of Allergy and Infectious Diseases (NIAID), National Institutes of Health (NIH)
- Sulfadimidine in the ChemIDplus database
- PubChem. "Sulfamethazine - Substance Summary", PubChem, National Center for Biotechnology Information (NCBI), National Library of Medicine (NLM), National Institutes of Health (NIH)
Antibacterials: nucleic acid inhibitors (J01E, J01M)
|
|
Antifolates
(inhibits
purine metabolism,
thereby inhibiting
DNA and RNA synthesis) |
DHFR inhibitor |
- 2,4-Diaminopyrimidine
- Trimethoprim#
- Brodimoprim
- Tetroxoprim
- Iclaprim†
|
|
Sulfonamides
(DHPS inhibitor) |
Short-
acting |
- Sulfaisodimidine
- Sulfamethizole
- Sulfadimidine
- Sulfapyridine
- Sulfafurazole
- Sulfanilamide
- Sulfathiazole
- Sulfathiourea
|
|
Intermediate-
acting |
- Sulfamethoxazole
- Sulfadiazine#
- Sulfamoxole
|
|
Long-
acting |
- Sulfadimethoxine
- Sulfadoxine
- Sulfalene
- Sulfametomidine
- Sulfametoxydiazine
- Sulfamethoxypyridazine
- Sulfaperin
- Sulfamerazine
- Sulfaphenazole
- Sulfamazone
|
|
Other/ungrouped |
- Sulfacetamide
- Sulfadicramide
- Sulfametrole
|
|
|
Combinations |
- Trimethoprim/sulfamethoxazole#
|
|
|
Topoisomerase
inhibitors/
quinolones/
(inhibits
DNA replication) |
1st g. |
- Cinoxacin‡
- Flumequine‡
- Nalidixic acid‡
- Oxolinic acid‡
- Pipemidic acid‡
- Piromidic acid‡
- Rosoxacin‡
|
|
Fluoro-
quinolones |
2nd g. |
- Ciprofloxacin#
- Ofloxacin
- Enoxacin‡
- Fleroxacin‡
- Lomefloxacin‡
- Nadifloxacin‡
- Norfloxacin‡
- Pefloxacin‡
- Rufloxacin‡
|
|
3rd g. |
- Levofloxacin
- Balofloxacin‡
- Grepafloxacin‡
- Pazufloxacin‡
- Sparfloxacin‡
- Temafloxacin‡
- Tosufloxacin‡
|
|
4th g. |
- Besifloxacin
- Gatifloxacin
- Finafloxacin
- Gemifloxacin
- Moxifloxacin
- Clinafloxacin†
- Garenoxacin‡
- Prulifloxacin‡
- Sitafloxacin‡
- Trovafloxacin‡/Alatrofloxacin‡
|
|
Vet. |
- Danofloxacin
- Difloxacin
- Enrofloxacin
- Ibafloxacin
- Marbofloxacin
- Orbifloxacin
- Pradofloxacin
- Sarafloxacin
|
|
Related (DG) |
- Aminocoumarins: Novobiocin
|
|
|
|
Anaerobic DNA
inhibitors |
Nitro- imidazole derivatives |
- Metronidazole#
- Tinidazole
- Ornidazole
|
|
Nitrofuran derivatives |
- Nitrofurantoin#
- Furazolidone‡
- Nifurtoinol
|
|
|
RNA synthesis |
Rifamycins/
RNA polymerase |
- Rifampicin#
- Rifabutin
- Rifapentine
- Rifaximin
|
|
|
- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
Index of bacterial disease
|
|
Description |
|
|
Disease |
- Gram-positive firmicutes
- Gram-positive actinobacteria
- Gram-negative proteobacteria
- Gram-negative non-proteobacteria
- Cholera
- Tuberculosis
|
|
Treatment |
- Antibiotics
- cell wall
- nucleic acid
- mycobacteria
- protein synthesis
- other
- Antibodies
|
|
|
UpToDate Contents
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English Journal
- Sulfamethazine degradation in water by the VUV/UV process: Kinetics, mechanism and antibacterial activity determination based on a mini-fluidic VUV/UV photoreaction system.
- Li M1, Wang C1, Yau M1, Bolton JR2, Qiang Z3.
- Water research.Water Res.2017 Jan 1;108:348-355. doi: 10.1016/j.watres.2016.11.018. Epub 2016 Nov 4.
- A mini-fluidic VUV/UV photoreaction system (MVPS) was developed in our previous study, and it was demonstrated as a powerful tool for studies on pollutant degradation by the VUV/UV process. In this study, we investigated the VUV/UV photodegradation of sulfamethazine (SMN), one of the most frequently
- PMID 27847148
- The effect of structurally related impurities on crystallinity reduction of sulfamethazine by grinding.
- Hamada Y1, Ono M2, Ohara M2, Yonemochi E3.
- International journal of pharmaceutics.Int J Pharm.2016 Dec 30;515(1-2):416-421. doi: 10.1016/j.ijpharm.2016.09.069. Epub 2016 Oct 5.
- In this study, the effect of structurally related impurities on crystallinity reduction of sulfamethazine by grinding was evaluated. The crystallinity of sulfamethazine was not decreased when it was ground alone. However, when structurally related impurities with sulfonamide derivatives were blended
- PMID 27720875
- Bioconcentration, metabolism, and biomarker responses in marine medaka (Oryzias melastigma) exposed to sulfamethazine.
- Zhao S1, Wang X2, Li Y1, Lin J3.
- Aquatic toxicology (Amsterdam, Netherlands).Aquat Toxicol.2016 Dec;181:29-36. doi: 10.1016/j.aquatox.2016.10.026. Epub 2016 Oct 27.
- The antibiotic sulfamethazine (SM2) is commonly used in agriculture and livestock for its broad-spectrum antibacterial properties. Due to its widespread application, SM2 is frequently detected in surface water and sediments. The objective of this study was to investigate the bioconcentration, distri
- PMID 27810490
Japanese Journal
- Effects of Sulfamethazine on Induction of Precocious Puberty in Japanese Quails (Coturnix japonica) Assessed through Monitoring the Hormonal Changes and Gonadal Development
- SEDQYAR Manila,KANDIEL Mohamed M.M.,WENG Qiang [他],NAGAOKA Kentarou,WATANABE Gen,TAYA Kazuyoshi
- The Journal of reproduction and development 58(5), 563-568, 2012-10-01
- … To investigate the effect of dietary supplementation of sulfamethazine (SMZ) on growth performance, gonadal development and hormonal changes, male and female Japanese quails (Coturnix japonica) were fed a control diet with or without SMZ (0.2%) from one day post hatching until 6 weeks of age. …
- NAID 10031123301
- Studies on the Preparation and Properties of Sol-Gel Molecularly Imprinted Polymer Based on Tetramethoxysilane and Methyltrimethoxysilane for Recognized Sulfonamides
- Lee Sung-Chuan,Peng Chun-Li,Chen Hui
- Polymer journal 41(12), 1092-1097, 2009-12-15
- NAID 10026363091
- Use of the total error approach to evaluate the performance of a semi-quantitative immunological method (BIACORE method) for detecting sulfamethazine in bovine milk
- LAURENTIE Michel,GAUDIN Valerie
- Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 877(23), 2375-2379, 2009-08-01
- NAID 10028021534
Related Links
- sulfamethazine | C12H14N4O2S | CID 5327 - structure, chemical names, physical and chemical properties, classification, patents, literature, biological activities, safety/hazards/toxicity information, supplier lists, and more. ... ...
- Sigma-Aldrich offers Sigma-S6256, Sulfamethazine for your research needs. Find product specific information including CAS, MSDS, protocols and references. ... Biochem/physiol Actions An antimicrobial sulfur drug. Induces ...
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