サルファ剤
WordNet
- a white odorless crystalline sulfa drug; the parent compound of most of the sulfa drugs
Wikipedia preview
出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2015/07/06 01:26:40」(JST)
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Sulfanilamide
|
| Systematic (IUPAC) name |
|
4-aminobenzenesulfonamide
|
| Clinical data |
| AHFS/Drugs.com |
Consumer Drug Information |
| Identifiers |
| CAS Registry Number |
63-74-1 Y |
| ATC code |
J01EB06 D06BA05 QJ01EQ06 |
| PubChem |
CID: 5333 |
| DrugBank |
DB00259 Y |
| ChemSpider |
5142 Y |
| UNII |
21240MF57M Y |
| KEGG |
D08543 Y |
| ChEBI |
CHEBI:45373 Y |
| ChEMBL |
CHEMBL21 Y |
| NIAID ChemDB |
019103 |
| Chemical data |
| Formula |
C6H8N2O2S |
| Molecular mass |
172.20 g/mol |
|
|
InChI
-
InChI=1S/C6H8N2O2S/c7-5-1-3-6(4-2-5)11(8,9)10/h1-4H,7H2,(H2,8,9,10) Y
-
Key:FDDDEECHVMSUSB-UHFFFAOYSA-N Y
|
| Physical data |
| Density |
1.08 g/cm3 |
| Melting point |
165 °C (329 °F) |
| Y (what is this?) (verify) |
Sulfanilamide (also spelled sulphanilamide) is a sulfonamide antibacterial. Chemically, it is an organic compound consisting of an aniline derivitized with a sulfonamide group.[1] Powdered sulfanilamide was used by the Allies in WWII to reduce infection rates and contributed to a dramatic reduction in mortality rates compared to previous wars.[2][3] Modern antibiotics have supplanted sulfanilamide on the battlefield; however, sulfanilamide remains in use for treatment of vaginal yeast infections.[4]
The term "sulfanilamides" is also used to describe a family of molecules containing these functional groups. Examples include:
- Furosemide, a loop diuretic
- Sulfadiazine, an antibiotic
- Sulfamethoxazole, an antibiotic
Contents
- 1 Mechanism of action
- 2 History
- 3 See also
- 4 External links
- 5 References
Mechanism of action
As a sulfonamide antibiotic, sulfanilamide functions by competitively inhibiting (i.e., by acting as a substrate analogue) enzymatic reactions involving para-aminobenzoic acid (PABA).[5] PABA is needed in enzymatic reactions that produce folic acid, which acts as a coenzyme in the synthesis of purines and pyrimidines. Mammals do not synthesize their own folic acid so are unaffected by PABA inhibitors, which selectively kill bacteria.
History
Sulfanilamide was first prepared in 1908 by Paul Gelmo as part of his dissertation for a doctoral degree from the Technische Hochsschule of Vienna, Austria.[6] It was patented in 1909.[7]
Gerhard Domagk, who directed the testing of the prodrug Prontosil in 1935,[8] and Jacques and Thérèse Tréfouël, who along with Federico Nitti and Daniel Bovet in the laboratory of Ernest Fourneau at the Pasteur Institute, determined sulfanilamide as the active form,[9] are generally credited with the discovery of sulfanilamide as a chemotherapeutic agent. Domagk was awarded the Nobel Prize for his work.[10]
See also
- Sulfonamide (medicine)
- Nazi human experimentation -- Sulfonamide experiments
- Elixir sulfanilamide
External links
- Sulfanilamides at the US National Library of Medicine Medical Subject Headings (MeSH)
References
- ^ Actor, P.; Chow, A. W.; Dutko, F. J.; McKinlay, M. A. (2005), "Chemotherapeutics", Ullmann's Encyclopedia of Industrial Chemistry, Weinheim: Wiley-VCH, doi:10.1002/14356007.a06_173
- ^ http://www.mtaofnj.org/content/WWII%20Combat%20Medic%20-%20Dave%20Steinert/wwii.htm#The%20Use%20of%20Sulfanilamide%20in%20World%20War%20II
- ^ http://www.med-dept.com/sulfa.php
- ^ http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=5333
- ^ Michael Kent, Advanced Biology, Oxford University Press, 2000, p. 46 ISBN 978-0-19-914195-1
- ^ Paul Gelmo (May 14, 1908) "Über Sulfamide der p-Amidobenzolsulfonsäure," Journal für Praktische Chemie, 77 : 369-382.
- ^ On May 18, 1909, Deutsches Reich Patentschrift number 226,239 for sulfanilamide was awarded to Heinrich Hörlein of the Bayer corporation.
- ^ G. Domagk, "Ein Beitrag zur Chemotherapie der bakteriellen Infektionen", Deutsche Medizinische Wochenschrift, 61, feb. 15, 1935, p. 250.
- ^ J. et T. Tréfouël, F. Nitti and D. Bovet, "Activité du p-aminophénylsulfamide sur l’infection streptococcique expérimentale de la souris et du lapin", C. R. Soc. Biol., 120, nov. 23, 1935, p. 756.
- ^ (French) Daniel Bovet, "Les étapes de la découverte de la sulfamidochrysoïdine dans les laboratoires de recherche de la firme Bayer à Wuppertal-Elberfeld (1927-1932)", in Une chimie qui guérit : Histoire de la découverte des sulfamides, Coll. "Médecine et Société", Payot, Paris, 1988, p. 307.
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Antibiotics and chemotherapeutics for dermatological use (D06)
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|
| Antibiotics |
|
Tetracycline and derivatives
|
- Demeclocycline
- Chlortetracycline
- Oxytetracycline
- Tetracycline
|
|
|
Others
|
- Amphenicol: Chloramphenicol
- Aminoglycosides: Neomycin
- Gentamicin
- Amikacin
- Streptogramin: Virginiamycin
- other: Fusidic acid
- Bacitracin
- Tyrothricin
- Mupirocin
|
|
|
| Chemotherapeutics |
|
Sulfonamides
|
- Silver sulfadiazine
- Sulfathiazole
- Mafenide
- Sulfamethizole
- Sulfanilamide
- Sulfamerazine
|
|
|
Antivirals
|
- Aciclovir
- Penciclovir
- Idoxuridine
- Edoxudine
- Imiquimod
- Resiquimod
- Podophyllotoxin
- Docosanol
- Tromantadine
- Inosine
- Lysozyme
- Ibacitabine
- Lysine
|
|
|
Other
|
- Ingenol mebutate
- Metronidazole
|
|
|
|
Index of skin
|
|
| Description |
- Anatomy
- Physiology
- Development
|
|
| Disease |
- Infections
- Vesiculobullous
- Dermatitis and eczema
- Papulosquamous
- Urticaria and erythema
- Radiation-related
- Pigmentation
- Mucinoses
- Keratosis, ulcer, atrophy, and necrobiosis
- Vasculitis
- Fat
- Neutrophilic and eosinophilic
- Congenital
- Neoplasms and cancer
- nevi and melanomas
- epidermis
- dermis
- Symptoms and signs
- Terminology
|
|
| Treatment |
- Procedures
- Drugs
- antibiotics
- disinfectants
- emollients and protectives
- itch
- psoriasis
- other
- Wound and ulcer
|
|
|
|
Antibacterials: nucleic acid inhibitors (J01E, J01M)
|
|
Antifolates
(inhibits
purine metabolism,
thereby inhibiting
DNA and RNA synthesis) |
| DHFR inhibitor |
- 2,4-Diaminopyrimidine
- Brodimoprim
- Diaveridine
- Iclaprim†
- Ormetoprim
- Trimethoprim#
- Tetroxoprim
|
|
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#
- Enoxacin‡
- Fleroxacin‡
- Lomefloxacin
- Nadifloxacin
- Ofloxacin
- Norfloxacin
- Pefloxacin
- Rufloxacin
|
|
| 3rd g. |
- Balofloxacin
- Grepafloxacin‡
- Levofloxacin
- Pazufloxacin
- Sparfloxacin‡
- Temafloxacin‡
- Tosufloxacin
|
|
| 4th g. |
- Besifloxacin
- Clinafloxacin†
- Garenoxacin
- Gemifloxacin
- Moxifloxacin
- Gatifloxacin‡
- Sitafloxacin
- Trovafloxacin‡/Alatrofloxacin‡
- Prulifloxacin
|
|
| 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
- Flow injection analysis of nitrate and nitrite in commercial baby foods.
- Chetty AA1, Prasad S2.
- Food chemistry.Food Chem.2016 Apr 15;197(Pt A):503-8. doi: 10.1016/j.foodchem.2015.10.079. Epub 2015 Oct 19.
- Commercial baby foods are an easy alternative to home-made meals especially for working parents in a nuclear family therefore it is imperative to determine the nitrate and nitrite content in commercially available baby foods varieties marketed in Fiji. A total of 108 baby food samples were analyzed
- PMID 26616981
- Antibiotic sulfanilamide biodegradation by acclimated microbial populations.
- Liao X1, Li B2, Zou R1, Xie S3, Yuan B4.
- Applied microbiology and biotechnology.Appl Microbiol Biotechnol.2016 Mar;100(5):2439-47. doi: 10.1007/s00253-015-7133-9. Epub 2015 Nov 13.
- Sulfonamide antibiotics are commonly detected in the environment. Microbial degradation can play an important role in the dissipation of sulfonamide antibiotics. However, many aspects regarding the influential factor and biodegradation pathway remain essentially unclear. Moreover, phylogenetic infor
- PMID 26563551
- Sulfonamide inhibition studies of the β-carbonic anhydrase from the pathogenic bacterium Vibrio cholerae.
- Del Prete S1, Vullo D2, De Luca V3, Carginale V3, Ferraroni M2, Osman SM4, AlOthman Z4, Supuran CT5, Capasso C6.
- Bioorganic & medicinal chemistry.Bioorg Med Chem.2016 Mar 1;24(5):1115-20. doi: 10.1016/j.bmc.2016.01.037. Epub 2016 Jan 22.
- The genome of the pathogenic bacterium Vibrio cholerae encodes for three carbonic anhydrases (CAs, EC 4.2.1.1) belonging to the α-, β- and γ-classes. VchCA, the α-CA from this species was investigated earlier, whereas the β-class enzyme, VchCAβ was recently cloned, characterized kinetically an
- PMID 26850377
Japanese Journal
- 亜硝酸イオンのザルツマン法による比色分析における試薬濃度と反応速度の影響
- 井上 友昭
- 分析化学 = Japan analyst 59(1), 35-41, 2010-01-05
- アゾ色素へ誘導する亜硝酸イオンの比色分析において，スルファニル酸又はスルファニルアミドとN-（1-ナフチル）エチレンジアミンの混合割合の本分析への影響及び本分析で起きているジアゾ化とカップリング反応を速度論的に検討し，これらを基に本分析への影響について考察した．本分析に広く用いられているザルツマン試薬〔スルファニル酸とN-（1-ナフチル）エチレンジアミンのリン酸酸性溶液〕を用いるよりもこれらの成分 …
- NAID 10025980916
- Deacylation of N-Formylanilines and N-Acetylanilines by Rat Liver Formamidase
- Kitamura Shigeyuki,Ueda Osamu,Sugihara Kazumi,Ohta Shigeru
- Journal of health science 49(6), 501-508, 2003-12-01
- … When N^4-formylsulfanilamide or N^4-acetylsulfanilamide was incubated with rat liver cytosol, the deacylated metabolite, sulfanilamide, was formed. …
- NAID 110003609111
Related Links
- Sulfanilamide (also spelled sulphanilamide) is a sulfonamide antibacterial. Chemically, it is a molecule containing the sulfonamide functional group attached to an aniline. As a sulfonamide antibiotic, it functions by competitively inhibiting ( i.e., ...
Related Pictures
★リンクテーブル★
[★]
- 英
- sulfonamides
- 関
- 抗菌薬
概念
- 葉酸合成系において代謝を拮抗阻害することで静菌作用を呈する薬物。
- 単剤で使うことはない？、という印象がある。
スルホンアミド系抗菌薬
[★]
- 英
- sulfa drugs, sulfa drug
- 同
- スルファニルアミド剤 sulfanilamide
- ラ
- sulfaminum
- 関
- ST合剤
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