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Substance Name: Nalidixic acid [USAN:USP:INN:BAN:JAN]
RN: 389-08-2
UNII: 3B91HWA56M
InChIKey: MHWLWQUZZRMNGJ-UHFFFAOYSA-N
Note
- A synthetic 1,8-naphthyridine antimicrobial agent with a limited bacteriocidal spectrum. It is an inhibitor of the A subunit of bacterial DNA GYRASE.
Molecular Formula
- C12-H12-N2-O3
Molecular Weight
- 232.238
- All
- Classifications
- Links to Resources
- Names & Synonyms
- Registry Numbers
- Structure Descriptors
- Toxicity
- Physical Properties
Classification Codes
- Anti-Bacterial Agents
- Anti-Infective Agents
- Antibacterial
- Antineoplastic Agents
- Drug / Therapeutic Agent
- Enzyme Inhibitors
- Human Data
- Mutation Data
- Nucleic Acid Synthesis Inhibitors
- Reproductive Effect
- Topoisomerase II Inhibitors
- Tumor Data
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Other Resources (Internet Locators)
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Names and Synonyms
Name of Substance
- Nalidixic acid
- Nalidixic acid [USAN:USP:INN:BAN:JAN]
MeSH Heading
- Nalidixic acid
Synonyms
- 1,4-Dihydro-1-ethyl-7-methyl-4-oxo-1,8-naphthyridine-3-carboxylic acid
- 1-Aethyl-7-methyl-1,8-naphthyridin-4-on-3-karbonsaeure
- 1-Aethyl-7-methyl-1,8-naphthyridin-4-on-3-karbonsaeure [German]
- 1-Ethyl-1,4-dihydro-7-methyl-4-oxo-1,8-naphthyridine-3-carboxylic acid
- 1-Ethyl-7-methyl-1,4-dihydro-1,8-naphthyridin-4-one-3-carboxylic acid
- 1-Ethyl-7-methyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid
- 3-Carboxy-1-ethyl-7-methyl-1,8-naphthidin-4-one
- 3-Carboxy-1-ethyl-7-methyl-1,8-naphthyridin-4-one
- 5-25-07-00384 (Beilstein Handbook Reference)
- Acide 1-etil-7-metil-1,8-naftiridin-4-one-3-carbossilico
- Acide 1-etil-7-metil-1,8-naftiridin-4-one-3-carbossilico [Italian]
- Acide nalidixico
- Acide nalidixico [Italian]
- Acide nalidixique
- Acide nalidixique [French]
- Acide nalidixique [INN-French]
- Acido nalidissico
- Acido nalidissico [DCIT]
- Acido nalidixico
- Acido nalidixico [INN-Spanish]
- Acidum nalidixicum
- Acidum nalidixicum [INN-Latin]
- Betaxina
- BRN 0750515
- CCRIS 2365
- Cybis
- Dixiben
- Dixinal
- EINECS 206-864-7
- HSDB 3241
- Innoxalon
- Jicsron
- Kusnarin
- Naldixic acid
- Nalidic acid
- Nalidicron
- Nalidixan
- Nalidixate
- Nalidixic acid
- Nalidixin
- Nalidixinic acid
- Nalitucsan
- Nalix
- Nalurin
- Narigix
- Naxuril
- NCI-C56199
- NegGram
- Nevigramon
- Nicelate
- Nogram
- NSC-82174
- Poleon
- Sicmylon
- Specifen
- Specifin
- Unaserus
- UNII-3B91HWA56M
- Uralgin
- Uriben
- Uriclar
- Urisal
- Urodixin
- Uroman
- Uroneg
- Uronidix
- Uropan
- WIN 18,320
- Wintomylon
Systematic Names
- 1,8-Naphthyridine-3-carboxylic acid, 1-ethyl-1,4-dihydro-7-methyl-4-oxo-
- Nalidixic acid
Superlist Name
- Nalidixic acid
Registry Numbers
CAS Registry Number
- 389-08-2
FDA UNII
- 3B91HWA56M
Related Registry Number
- 3374-05-8 (hydrochloride salt, anhydrous)
System Generated Number
- 0000389082
Structure Descriptors
InChI
InChI=1S/C12H12N2O3/c1-3-14-6-9(12(16)17)10(15)8-5-4-7(2)13-11(8)14/h4-6H,3H2,1-2H3,(H,16,17)InChIKey
MHWLWQUZZRMNGJ-UHFFFAOYSA-NSmiles
CCN1C=C(C(=O)Toxicity
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
child | TDLo | unreported | 1200mg/kg/20D (1200mg/kg) | BLOOD: OTHER CHANGES | "Toxicology of Drugs and Chemicals," Deichmann, W.B., New York, Academic Press, Inc., 1969Vol. -, Pg. 414, 1969. |
mouse | LD50 | intraperitoneal | 600mg/kg (600mg/kg) | United States Patent Document. Vol. #4552882, | |
mouse | LD50 | intravenous | 101mg/kg (101mg/kg) | Antimicrobial Agents and Chemotherapy Vol. -, Pg. 117, 1970. | |
mouse | LD50 | oral | 572mg/kg (572mg/kg) | Toxicology and Applied Pharmacology. Vol. 18, Pg. 185, 1971. | |
mouse | LD50 | subcutaneous | 500mg/kg (500mg/kg) | Toxicology and Applied Pharmacology. Vol. 18, Pg. 185, 1971. | |
rat | LD50 | intraperitoneal | 319mg/kg (319mg/kg) | Antimicrobial Agents and Chemotherapy Vol. -, Pg. 117, 1970. | |
rat | LD50 | intravenous | 1160mg/kg (1160mg/kg) | Drugs in Japan Vol. -, Pg. 908, 1995. | |
rat | LD50 | oral | 2040mg/kg (2040mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) SKIN AND APPENDAGES (SKIN): HAIR: OTHER BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD | Chemotherapy Vol. 28(Suppl, |
rat | LD50 | subcutaneous | 1584mg/kg (1584mg/kg) | Antimicrobial Agents and Chemotherapy Vol. -, Pg. 117, 1970. | |
women | TDLo | oral | 40mg/kg (40mg/kg) | BRAIN AND COVERINGS: INCREASED INTRACRANIAL PRESSURE BEHAVIORAL: COMA | Acta Medica Scandinavica. Vol. 216, Pg. 237, 1984. |
women | TDLo | oral | 160mg/kg/2D (160mg/kg) | SKIN AND APPENDAGES (SKIN): SWEATING: OTHER ENDOCRINE: HYPERGLYCEMIA BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD | British Medical Journal. Vol. 2, Pg. 1518, 1977. |
women | TDLo | oral | 560mg/kg (560mg/kg) | BEHAVIORAL: COMA CARDIAC: EKG CHANGES NOT DIAGNOSTIC OF ABOVE | Intensive Care Medicine. Vol. 5, Pg. 141, 1979. |
Physical Properties
Physical Property | Value | Units | Temp (deg C) | Source |
---|---|---|---|---|
Melting Point | 229.5 | deg C | EXP | |
pKa Dissociation Constant | 8.6 | (none) | EXP | |
log P (octanol-water) | 1.59 | (none) | EXP | |
Water Solubility | 100 | mg/L | 23 | EXP |
Vapor Pressure | 3.56E-07 | mm Hg | 25 | EST |
Henry's Law Constant | 5.12E-16 | atm-m3/mole | 25 | EST |
Atmospheric OH Rate Constant | 2.15E-11 | cm3/molecule-sec | 25 | EST |
Physical property data is provided to ChemIDplus by SRC, Inc.