スルファメチゾール
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出典(authority):フリー百科事典『ウィキペディア(Wikipedia)』「2014/09/01 16:22:31」(JST)
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Sulfamethizole
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Systematic (IUPAC) name |
4-amino-N-(5-methyl-1,3,4-thiadiazol-2-yl)- benzenesulfonamide |
Clinical data |
AHFS/Drugs.com |
Micromedex Detailed Consumer Information |
MedlinePlus |
a682231 |
Legal status |
? |
Pharmacokinetic data |
Protein binding |
98–99% |
Half-life |
3–8 hours |
Identifiers |
CAS number |
144-82-1 Y |
ATC code |
B05CA04 D06BA04 J01EB02 S01AB01 QJ01EQ02 |
PubChem |
CID 5328 |
DrugBank |
DB00576 |
ChemSpider |
5137 Y |
UNII |
25W8454H16 Y |
KEGG |
D00870 Y |
ChEBI |
CHEBI:9331 Y |
ChEMBL |
CHEMBL1191 Y |
Chemical data |
Formula |
C9H10N4O2S2 |
Mol. mass |
270.333 g/mol |
SMILES
- O=S(=O)(Nc1nnc(s1)C)c2ccc(N)cc2
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InChI
-
InChI=1S/C9H10N4O2S2/c1-6-11-12-9(16-6)13-17(14,15)8-4-2-7(10)3-5-8/h2-5H,10H2,1H3,(H,12,13) Y
Key:VACCAVUAMIDAGB-UHFFFAOYSA-N Y
|
Y (what is this?) (verify) |
Sulfamethizole is a sulfonamide antibiotic.
References
- Ratanajamit C, Skriver M, Nørgaard M, Jepsen P, Schønheyder H, Sørensen H (2003). "Adverse pregnancy outcome in users of sulfamethizole during pregnancy: a population-based observational study.". J Antimicrob Chemother 52 (5): 837–41. doi:10.1093/jac/dkg438. PMID 14519675.
- Kerrn M, Frimodt-Møller N, Espersen F (2003). "Effects of Sulfamethizole and Amdinocillin against Escherichia coli Strains (with Various Susceptibilities) in an Ascending Urinary Tract Infection Mouse Model". Antimicrob Agents Chemother 47 (3): 1002–9. doi:10.1128/AAC.47.3.1002-1009.2003. PMC 149286. PMID 12604534.
- Watanabe H, Hastings J (1990). "Inhibition of bioluminescence in Photobacterium phosphoreum by sulfamethizole and its stimulation by thymine". Biochim Biophys Acta 1017 (3): 229–34. doi:10.1016/0005-2728(90)90189-B. PMID 2372557.
Antibiotics and chemotherapeutics for dermatological use (D06)
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Antibiotics |
Tetracycline and derivatives
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- Demeclocycline
- Chlortetracycline
- Oxytetracycline
- Tetracycline
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Others
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- Amphenicol: Chloramphenicol
- Aminoglycosides: Neomycin
- Gentamicin
- Amikacin
- Streptogramin: Virginiamycin
- other: Fusidic acid
- Bacitracin
- Tyrothricin
- Mupirocin
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Chemotherapeutics |
Sulfonamides
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- Silver sulfadiazine
- Sulfathiazole
- Mafenide
- Sulfamethizole
- Sulfanilamide
- Sulfamerazine
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Antivirals
|
- Aciclovir
- Penciclovir
- Idoxuridine
- Edoxudine
- Imiquimod
- Resiquimod
- Podophyllotoxin
- Docosanol
- Tromantadine
- Inosine
- Lysozyme
- Ibacitabine
- Lysine
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Other
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- Ingenol mebutate
- Metronidazole
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|
|
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noco (i/b/d/q/u/r/p/m/k/v/f)/cong/tumr (n/e/d), sysi/epon
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proc, drug (D2/3/4/5/8/11)
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Antibacterials: nucleic acid inhibitors (J01E, J01M)
|
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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
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Intermediate-
acting |
- Sulfamethoxazole
- Sulfadiazine#
- Sulfamoxole
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Long-
acting |
- Sulfadimethoxine
- Sulfadoxine
- Sulfalene
- Sulfametomidine
- Sulfametoxydiazine
- Sulfamethoxypyridazine
- Sulfaperin
- Sulfamerazine
- Sulfaphenazole
- Sulfamazone
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Other/ungrouped |
- Sulfacetamide
- Sulfadicramide
- Sulfametrole
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Combinations |
- Trimethoprim/sulfamethoxazole#
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Topoisomerase
inhibitors/
quinolones/
(inhibits
DNA replication) |
1st g. |
- Cinoxacin‡
- Flumequine
- Nalidixic acid
- Oxolinic acid
- Pipemidic acid
- Piromidic acid
- Rosoxacin
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Fluoro-
quinolones |
2nd g. |
- Ciprofloxacin#
- Enoxacin‡
- Fleroxacin‡
- Lomefloxacin
- Nadifloxacin
- Ofloxacin
- Norfloxacin
- Pefloxacin
- Rufloxacin
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3rd g. |
- Balofloxacin
- Grepafloxacin‡
- Levofloxacin
- Pazufloxacin
- Sparfloxacin‡
- Temafloxacin‡
- Tosufloxacin
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4th g. |
- Besifloxacin
- Clinafloxacin†
- Garenoxacin
- Gemifloxacin
- Moxifloxacin
- Gatifloxacin‡
- Sitafloxacin
- Trovafloxacin‡/Alatrofloxacin‡
- Prulifloxacin
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Vet. |
- Danofloxacin
- Difloxacin
- Enrofloxacin
- Ibafloxacin
- Marbofloxacin
- Orbifloxacin
- Pradofloxacin
- Sarafloxacin
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Related (DG) |
- Aminocoumarins: Novobiocin
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Anaerobic DNA
inhibitors |
Nitro- imidazole derivatives |
- Metronidazole#
- Tinidazole
- Ornidazole
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Nitrofuran derivatives |
- Nitrofurantoin#
- Furazolidone‡
- Nifurtoinol
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RNA synthesis |
Rifamycins/
RNA polymerase |
- Rifampicin#
- Rifabutin
- Rifapentine
- Rifaximin
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- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
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gr+f/gr+a (t)/gr-p (c)/gr-o
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drug (J1p, w, n, m, vacc)
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UpToDate Contents
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English Journal
- Ipso-hydroxylation and subsequent fragmentation: a novel microbial strategy to eliminate sulfonamide antibiotics.
- Ricken B, Corvini PF, Cichocka D, Parisi M, Lenz M, Wyss D, Martínez-Lavanchy PM, Müller JA, Shahgaldian P, Tulli LG, Kohler HP, Kolvenbach BA.Author information Institute for Ecopreneurship, School of Life Sciences, University of Applied Sciences and Arts Northwestern Switzerland, Muttenz, Switzerland.AbstractSulfonamide antibiotics have a wide application range in human and veterinary medicine. Because they tend to persist in the environment, they pose potential problems with regard to the propagation of antibiotic resistance. Here, we identified metabolites formed during the degradation of sulfamethoxazole and other sulfonamides in Microbacterium sp. strain BR1. Our experiments showed that the degradation proceeded along an unusual pathway initiated by ipso-hydroxylation with subsequent fragmentation of the parent compound. The NADH-dependent hydroxylation of the carbon atom attached to the sulfonyl group resulted in the release of sulfite, 3-amino-5-methylisoxazole, and benzoquinone-imine. The latter was concomitantly transformed to 4-aminophenol. Sulfadiazine, sulfamethizole, sulfamethazine, sulfadimethoxine, 4-amino-N-phenylbenzenesulfonamide, and N-(4-aminophenyl)sulfonylcarbamic acid methyl ester (asulam) were transformed accordingly. Therefore, ipso-hydroxylation with subsequent fragmentation must be considered the underlying mechanism; this could also occur in the same or in a similar way in other studies, where biotransformation of sulfonamides bearing an amino group in the para-position to the sulfonyl substituent was observed to yield products corresponding to the stable metabolites observed by us.
- Applied and environmental microbiology.Appl Environ Microbiol.2013 Sep;79(18):5550-8. doi: 10.1128/AEM.00911-13. Epub 2013 Jul 8.
- Sulfonamide antibiotics have a wide application range in human and veterinary medicine. Because they tend to persist in the environment, they pose potential problems with regard to the propagation of antibiotic resistance. Here, we identified metabolites formed during the degradation of sulfamethoxa
- PMID 23835177
- Short-acting sulfonamides near term and neonatal jaundice.
- Klarskov P, Andersen JT, Jimenez-Solem E, Torp-Pedersen C, Poulsen HE.Author information Laboratory of Clinical Pharmacology Q7642, Rigshospitalet, Copenhagen, Denmark. pia.klarskov@mail.dkAbstractOBJECTIVE: To investigate the association between maternal use of sulfamethizole near term and the risk of neonatal jaundice.
- Obstetrics and gynecology.Obstet Gynecol.2013 Jul;122(1):105-10. doi: 10.1097/AOG.0b013e318298314f.
- OBJECTIVE: To investigate the association between maternal use of sulfamethizole near term and the risk of neonatal jaundice.METHODS: We conducted a nationwide population-based retrospective cohort study using Danish registers. All Danish women giving birth between 1995 and 2007 were included from t
- PMID 23743470
- Pharmacophore modeling, homology modeling, and in silico screening reveal mammalian target of rapamycin inhibitory activities for sotalol, glyburide, metipranolol, sulfamethizole, glipizide, and pioglitazone.
- Khanfar MA, AbuKhader MM, Alqtaishat S, Taha MO.Author information Drug Discovery Unit, Department of Pharmaceutical Sciences, Faculty of Pharmacy, University of Jordan, Amman 11942, Jordan.AbstractMammalian target of rapamycin (mTOR) is a serine/threonine kinase and member of the PI3K-related kinase (PIKK) family. It plays a central role in integrating signals from metabolism, energy homeostasis, cell cycle, and stress response. Aberrant PI3K/mTOR activation is commonly observed in diseases such as cancer, diabetes and Alzheimer's disease. Accordingly, we developed common feature binding hypotheses for a set of 6 potent mTOR antagonists. The generated models were validated using receiver operating characteristic (ROC) curve analyses. To gain better insight into ligand-mTOR interactions, a homology model for the kinase domain of mTOR was built using the crystallographic structure of PI3Kγ as template. The optimal pharmacophore model was further improved based on detailed docking studies of potent training compound in the homology model. The modified binding model was employed as 3D search query to screen our in-house-built database of established drugs. Subsequent in vitro screening of captured hits showed that six of them have submicromolar to low micromolar bioactivities, namely, glyburide, metipranolol, sulfamethizole, glipizide, pioglitazone, and sotalol.
- Journal of molecular graphics & modelling.J Mol Graph Model.2013 May;42:39-49. doi: 10.1016/j.jmgm.2013.02.009. Epub 2013 Mar 13.
- Mammalian target of rapamycin (mTOR) is a serine/threonine kinase and member of the PI3K-related kinase (PIKK) family. It plays a central role in integrating signals from metabolism, energy homeostasis, cell cycle, and stress response. Aberrant PI3K/mTOR activation is commonly observed in diseases s
- PMID 23545333
Japanese Journal
- Serotypes, Antimicrobial Resistance, and Genomic Analysis of Salmonella Isolates from Slaughtered Swine in Gunma Prefecture, Japan
- 高田 勇人,井上 伸子,天田 貴昌,信澤 敏夫,中嶋 隆,石岡 大成,藤田 雅弘,森田 幸雄
- 日本獣医師会雑誌 61(1), 65-69, 2008
- … Typhimurium isolates showed resistanceto ampicillin, chloramphenicol, streptomycin, tetracycline, florfenicol and sulfamethizole. …
- NAID 130003848642
- Sulfamethizole capsules containing contrast medium for assessment of gastric emptying in functional dyspepsia patients
- cisapride長期投与による糖尿病性胃排出遅延の改善が血糖コントロールに与える影響
- 石井 圭太,田辺 聡,三橋 利温,西元寺 克禮
- 日本消化器病學會雜誌 = The Japanese journal of gastro-enterology 92(10), 1724-1733, 1995-10-05
- … Liquid gastric emptying, evaluated using a sulfamethizole technique, also improved but not significantly. …
- NAID 10005242981
Related Links
- sulfamethizole /sul·fa·meth·i·zole/ (-meth?ĭ-zōl) a sulfonamide used in urinary tract infections. sulfamethizole [sul″fah-meth´ĭ-zōl] a sulfonamide used in urinary tract infections. sulfamethizole (sul´fəmeth´izōl), n brand name: Thiosulfil ...
- Read more about the pharmacogenomics of sulfamethizole on PharmGKB. ... PharmGKB contains no dosing guidelines for this drug/small molecule. To report known genotype-based dosing guidelines, or if you are interested in ...
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