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QuickView for nitrofurantoin (compound)
PubChem
| Name: | Nitrofurantoin |
|---|---|
| PubChem Compound ID: | 4509 |
| Description: | A urinary anti-infective agent effective against most gram-positive and gram-negative organisms. Although sulfonamides and antibiotics are usually the agents of choice for urinary tract infections, nitrofurantoin is widely used for prophylaxis and long-term suppression. |
| Molecular formula: | C8H6N4O5 |
| Molecular weight: | 238.157 g/mol |
| Synonyms: |
Furina; Prestwick1_000168; Furadontin; KBioGR_000629; Furobactina; Urolong; Spectrum3_000517; 67-20-9; KBio2_006619; Novofuran.
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DrugBank
Identification
| Name: | Nitrofurantoin |
|---|---|
| Name (isomeric): | DB00698 |
| Drug Type: | small molecule |
| Description: | A urinary anti-infective agent effective against most gram-positive and gram-negative organisms. Although sulfonamides and antibiotics are usually the agents of choice for urinary tract infections, nitrofurantoin is widely used for prophylaxis and long-term suppression. |
| Brand: | Furadoin, Macrodantin, Uro-Selz, Novofuran, N-Toin, Furadontin, Ivadantin, Furadonine, Upiol, Furabid, Macrofurin, Nierofu, Furatoin, Ituran, Macrobid, Nitrofur-C, Nitoin, Furalan, Zoofurin, Furaloid, Phenurin, Furadantine Mc, Urolisa, Ro-Antoin, Furadonin, Cistofuran, Trantoin, Furadantin, Furantoin, It-Uran, Urantoin, Fua Med, Uro-Tablinen, Furadantine, Furadantina MC, Furina, Furachel, Nitrofan, Welfurin, Uerineks, Furobactina, Furadantin Retard, USAF EA-2, Benkfuran, Furophen T, Cystit, Apo-Nitrofurantoin, Siraliden, Urofurin, Ceduran, Furadoine, Furanite, Parfuran, Nitrofuradantin, Urofuran, Cyantin, Furantoina, Macrodantina, Furophen T-Caps, Gerofuran, Macpac, Fur-Ren, Orafuran, Urolong, Furadantine-Mc, Berkfurin, Chemiofuran, Novo-Furantoin, Nitrex, Nifurantin, Furedan, Dantafur, Alfuran, Furan, Uvaleral, Macrofuran, Furadantoin, Urodin, Urizept, Fuamed |
| Category: | Anti-Infective Agents, Urinary, Anti-Infectives |
| CAS number: | 67-20-9 |
Pharmacology
| Indication: | May be used as an alternative in the treatment of urinary tract infections. May be used by females pericoitally for prophylaxis against recurrent cystitis related to coitus. |
|---|---|
| Pharmacology: | Nitrofurantoin exhibits bacteriostatic or bactericidal effects by inhibiting the synthesis of DNA, RNA, protein and cell wall synthesis. |
| Mechanism of Action: |
Nitrofurantoin is activated by bacterial flavoproteins (nitrofuran reductase) to active reduced reactive intermediates that are thought to modulate and damage ribosomal proteins or other macromolecules, especially DNA, causing inhibition of DNA, RNA, protein, and cell wall synthesis. The overall effect is inhibition of bacterial growth or cell deat...
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| Absorption: | Readily absorbed in GI tract primarily in small intestine. Enhanced by food or delayed gastric emptying via enhanced dissolution rate of the drug. |
| Protein binding: | 20-60% bound to plasma proteins |
| Biotransformation: | Partially metabolized in liver to aminofurantoin. |
| Half Life: | 0.3-1 hour |
| Toxicity: | Acute toxicity may cause vomiting. Adverse effects include nausea and urine discolouration. Rare hepatotoxic and hypersensitivity reactions have occurred. Hemolytic anemia is a risk in patients with G6PD deficiency. Ascending polyneuropathy may occur with prolonged therapy or in patients with low creatinine clearance. |
| Affected organisms: | Gram negative and gram positive bacteria |
Interactions
| Food interaction: |
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Targets
Enzymes
Transporters
