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Latest revision as of 15:38, 4 July 2024 edit undoMichael D. Turnbull (talk | contribs)Extended confirmed users13,865 editsm Upright better than fixed pixel width |
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{{Short description|Chemical compound}} |
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{{drugbox |
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{{cs1 config|name-list-style=vanc|display-authors=6}} |
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{{Drugbox |
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| Watchedfields = changed |
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| verifiedrevid = 444404903 |
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| IUPAC_name = 5-Nitro-''N′''--2-thiophenecarbohydrazide |
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| image = Nifurzide.svg |
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| width = 300 |
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<!--Clinical data--> |
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| tradename = |
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| Drugs.com = {{drugs.com|international|nifurzide}} |
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| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> |
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| pregnancy_US = <!-- A / B / C / D / X --> |
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| pregnancy_category = |
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| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 --> |
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| legal_CA = <!-- / Schedule I, II, III, IV, V, VI, VII, VIII --> |
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| legal_UK = <!-- GSL / P / POM / CD / Class A, B, C --> |
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| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V --> |
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| legal_status = |
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| routes_of_administration = |
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<!--Pharmacokinetic data--> |
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| bioavailability = |
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| protein_bound = |
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| metabolism = |
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| elimination_half-life = |
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| excretion = |
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<!--Identifiers--> |
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| CAS_number_Ref = {{cascite|correct|CAS}} |
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| CAS_number = 39978-42-2 |
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| ATC_prefix = A07 |
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| ATC_suffix = AX04 |
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| PubChem = 9571044 |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank = |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = Z35R6K4C26 |
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| UNII = Z35R6K4C26 |
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| verifiedrevid = 443642389 |
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| IUPAC_name = 5-nitro-''N'''-thiophene-2-carbohydrazide |
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| image = Nifurzide.png |
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| CAS_number = |
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| ATC_prefix = A07 |
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| ATC_suffix = AX04 |
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| PubChem = 9571044 |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank = |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG = D07251 |
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| KEGG = D07251 |
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| ChemSpiderID = 7845510 |
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| C=12|H=8|N=4|O=6|S=1 |
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| molecular_weight = 336.28012 g/mol |
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<!--Chemical data--> |
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| bioavailability = |
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| protein_bound = |
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| C=12 | H=8 | N=4 | O=6 | S=1 |
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| smiles = (=O)c1ccc(o1)/C=C/C=N/NC(=O)c2ccc(s2)(=O) |
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| metabolism = |
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| StdInChI = 1S/C12H8N4O6S/c17-12(9-4-6-11(23-9)16(20)21)14-13-7-1-2-8-3-5-10(22-8)15(18)19/h1-7H,(H,14,17)/b2-1+,13-7+ |
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| elimination_half-life = |
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| StdInChIKey = IDUMOVRJNBNOTR-BIZLIJPVSA-N |
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| excretion = |
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| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> |
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| pregnancy_US = <!-- A / B / C / D / X --> |
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| pregnancy_category= |
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| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 --> |
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| legal_CA = <!-- / Schedule I, II, III, IV, V, VI, VII, VIII --> |
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| legal_UK = <!-- GSL / P / POM / CD / Class A, B, C --> |
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| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V --> |
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| legal_status = |
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| routes_of_administration = |
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}} |
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}} |
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'''Nifurzide''' is a ] derivative and intestinal anti-infectious agent active against '']''.<ref>{{cite journal | vauthors = Delsarte A, Faway M, Frère JM, Coyette J, Calberg-Bacq CM, Heinen E | title = Nifurzide, a nitrofuran antiinfectious agent: interaction with Escherichia coli cells | journal = Antimicrobial Agents and Chemotherapy | volume = 19 | issue = 3 | pages = 477–86 | date = March 1981 | pmid = 7018391 | pmc = 181457 | doi = 10.1128/aac.19.3.477 }}</ref> |
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==Synthesis== |
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'''Nifurzide''' is an anti-infective. |
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:] |
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Esterification of 5-nitrothiophene-2-carboxylic acid (1) with ethanol gives the ] (2). Treatment with ] forms its ] (3). Nifurzide is the ] formed between (3) and 5-nitrofuran-2-acrylaldehyde (4).<ref>{{cite patent |country=US |number=3847911 |status=patent |gdate=1974-11-12 |fdate=1972-01-05 |pridate=1973-07-13 |inventor= Szarvasi E, Fontaine L | title = Novel substituted(nitrofurylacrylidene)hydrazines with antibacterial properties | url = https://patents.google.com/patent/US3847911A }}</ref><ref>{{cite journal | vauthors = Szarvasi E, Fontaine L, Betbeder-Matibet A | title = Antimicrobials. New nitrofuran derivatives | journal = Journal of Medicinal Chemistry | volume = 16 | issue = 3 | pages = 281–287 | date = March 1973 | pmid = 4200221 | doi = 10.1021/jm00261a027 }}</ref><ref>{{cite web |url=https://pharmaceutical-substances.thieme.com/ps/search-results?docUri=KD-14-0065 |title=Nifurzide | work = Pharmaceutical Substances |publisher=Thieme |access-date=2024-07-02 }}</ref> |
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== References == |
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{{reflist}} |
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{{Antidiarrheals, intestinal anti-inflammatory/anti-infective agents}} |
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{{Antidiarrheals, intestinal anti-inflammatory/anti-infective agents}} |
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{{gastrointestinal-drug-stub}} |
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{{gastrointestinal-drug-stub}} |