Nalidixic acid
Names
[ CAS No. ]:
389-08-2
[ Name ]:
Nalidixic acid
[Synonym ]:
uriben
EINECS 206-864-7
1,8-Naphthyridine-3-carboxylic acid, 1-ethyl-1,4-dihydro-7-methyl-4-oxo-
uroman
uropan
NegGram
NOGRAM
WIN-18320
nalidixic acid
Urisal
nalix
1-Ethyl-7-methyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid
Ethyl-7-methyl-1,8-naphthyridin-4-one-3-carboxylic Acid
1-Ethyl-1,4-dihydro-7-methyl-4-oxo-1,8-naphthyridine-3-carboxylic Acid
T66 BV EN GNJ CVQ E2 H1
poleon
negram
WINTOMYLON
cybis
uroneg
MFCD00006884
Biological Activity
[Description]:
[Related Catalog]:
[References]
[Related Small Molecules]
Chemical & Physical Properties
[ Density]:
1.3±0.1 g/cm3
[ Boiling Point ]:
413.1±45.0 °C at 760 mmHg
[ Melting Point ]:
227-229 °C(lit.)
[ Molecular Formula ]:
C12H12N2O3
[ Molecular Weight ]:
232.235
[ Flash Point ]:
203.6±28.7 °C
[ Exact Mass ]:
232.084793
[ PSA ]:
72.19000
[ LogP ]:
1.19
[ Vapour Pressure ]:
0.0±1.0 mmHg at 25°C
[ Index of Refraction ]:
1.605
[ Storage condition ]:
0-6°C
[ Stability ]:
Stable. Incompatible with strong oxidizing agents.
[ Water Solubility ]:
0.1 G/L (23 ºC)
MSDS
Toxicological Information
CHEMICAL IDENTIFICATION
- RTECS NUMBER :
- QN2885000
- CHEMICAL NAME :
- 1,8-Naphthyridine-3-carboxylic acid, 1-ethyl-1,4-dihydro-7-methyl-4-oxo-
- CAS REGISTRY NUMBER :
- 389-08-2
- BEILSTEIN REFERENCE NO. :
- 0750515
- LAST UPDATED :
- 199806
- DATA ITEMS CITED :
- 65
- MOLECULAR FORMULA :
- C12-H12-N2-O3
- MOLECULAR WEIGHT :
- 232.26
- WISWESSER LINE NOTATION :
- T66 BN EV JNJ B2 DVQ I1
HEALTH HAZARD DATA
ACUTE TOXICITY DATA
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Human - woman
- DOSE/DURATION :
- 40 mg/kg
- TOXIC EFFECTS :
- Brain and Coverings - increased intracranial pressure Behavioral - coma
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Human - woman
- DOSE/DURATION :
- 160 mg/kg/2D
- TOXIC EFFECTS :
- Behavioral - convulsions or effect on seizure threshold Endocrine - hyperglycemia Skin and Appendages - sweating
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Human - woman
- DOSE/DURATION :
- 560 mg/kg
- TOXIC EFFECTS :
- Behavioral - coma Cardiac - EKG changes not diagnostic of specified effects Nutritional and Gross Metabolic - metabolic acidosis
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Unreported
- SPECIES OBSERVED :
- Human - child
- DOSE/DURATION :
- 1200 mg/kg/20D
- TOXIC EFFECTS :
- Blood - other changes
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- 2040 mg/kg
- TOXIC EFFECTS :
- Behavioral - somnolence (general depressed activity) Behavioral - convulsions or effect on seizure threshold Skin and Appendages - hair
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Intraperitoneal
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- 319 mg/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Subcutaneous
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- 1584 mg/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Intravenous
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- 1160 mg/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- 572 mg/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Intraperitoneal
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- 600 mg/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Subcutaneous
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- 500 mg/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Intravenous
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- 101 mg/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- 24 gm/kg/30D-C
- TOXIC EFFECTS :
- Liver - changes in liver weight Endocrine - other changes Related to Chronic Data - death
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- 21840 mg/kg/13W-C
- TOXIC EFFECTS :
- Liver - changes in liver weight Nutritional and Gross Metabolic - weight loss or decreased weight gain
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- 31200 mg/kg/26W-I
- TOXIC EFFECTS :
- Lungs, Thorax, or Respiration - other changes Blood - changes in serum composition (e.g. TP, bilirubin, cholesterol) Blood - changes in leukocyte (WBC) count
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- 1400 mg/kg/2W-I
- TOXIC EFFECTS :
- Sense Organs and Special Senses (Eye) - retinal changes (pigmentary depositions, retinitis, other)
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- 43680 mg/kg/13W-C
- TOXIC EFFECTS :
- Liver - changes in liver weight Nutritional and Gross Metabolic - weight loss or decreased weight gain
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- 173 gm/kg/2Y-C
- TOXIC EFFECTS :
- Tumorigenic - Carcinogenic by RTECS criteria Skin and Appendages - tumors Reproductive - Tumorigenic effects - other reproductive system tumors
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- 173 gm/kg/2Y-C
- TOXIC EFFECTS :
- Tumorigenic - equivocal tumorigenic agent by RTECS criteria Lungs, Thorax, or Respiration - tumors Skin and Appendages - tumors
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- DOSE :
- 1320 mg/kg
- SEX/DURATION :
- female 9-14 day(s) after conception
- TOXIC EFFECTS :
- Reproductive - Specific Developmental Abnormalities - musculoskeletal system
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- DOSE :
- 3300 mg/kg
- SEX/DURATION :
- female 7-17 day(s) after conception
- TOXIC EFFECTS :
- Reproductive - Fertility - litter size (e.g. # fetuses per litter; measured before birth) Reproductive - Effects on Embryo or Fetus - extra-embryonic structures (e.g., placenta, umbilical cord) Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- DOSE :
- 3300 mg/kg
- SEX/DURATION :
- female 7-17 day(s) after conception
- TOXIC EFFECTS :
- Reproductive - Effects on Embryo or Fetus - fetal death Reproductive - Specific Developmental Abnormalities - musculoskeletal system Reproductive - Effects on Newborn - stillbirth
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- DOSE :
- 3300 mg/kg
- SEX/DURATION :
- female 7-17 day(s) after conception
- TOXIC EFFECTS :
- Reproductive - Effects on Newborn - live birth index (measured after birth) Reproductive - Effects on Newborn - viability index (e.g., # alive at day 4 per # born alive) Reproductive - Effects on Newborn - growth statistics (e.g.%, reduced weight gain)
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- DOSE :
- 3960 mg/kg
- SEX/DURATION :
- female 7-12 day(s) after conception
- TOXIC EFFECTS :
- Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Specific Developmental Abnormalities - musculoskeletal system
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- DOSE :
- 10400 mg/kg
- SEX/DURATION :
- female 6-18 day(s) after conception
- TOXIC EFFECTS :
- Reproductive - Fertility - litter size (e.g. # fetuses per litter; measured before birth) Reproductive - Effects on Embryo or Fetus - fetal death
- TYPE OF TEST :
- Sex chromosome loss and nondisjunction
MUTATION DATA
- TYPE OF TEST :
- DNA inhibition
- TEST SYSTEM :
- Mammal - domestic Cells - not otherwise specified
- DOSE/DURATION :
- 27 mg/L
- REFERENCE :
- AMACCQ Antimicrobial Agents and Chemotherapy. (American Soc. for Microbiology, 1913 I St., NW, Washington, DC 20006) V.1- 1972- Volume(issue)/page/year: 34,1955,1990 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X3708 No. of Facilities: 348 (estimated) No. of Industries: 1 No. of Occupations: 7 No. of Employees: 6188 (estimated) No. of Female Employees: 4169 (estimated)
Safety Information
[ Symbol ]:
GHS07
[ Signal Word ]:
Warning
[ Hazard Statements ]:
H302
[ Precautionary Statements ]:
P301 + P312 + P330
[ Personal Protective Equipment ]:
Eyeshields;Faceshields;Gloves;type N95 (US);type P1 (EN143) respirator filter
[ Hazard Codes ]:
Xn:Harmful;
[ Risk Phrases ]:
R40;R42/43;R63
[ Safety Phrases ]:
S22-S36/37-S45-S24
[ RIDADR ]:
NONH for all modes of transport
[ WGK Germany ]:
2
[ RTECS ]:
QN2885000
[ HS Code ]:
2933990090
Synthetic Route
Precursor & DownStream
Precursor
DownStream
Customs
[ HS Code ]: 2933990090
[ Summary ]:
2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%
Articles
J. Bacteriol. 196(16) , 3045-57, (2014)
The brucellae are the etiological agents of brucellosis, a worldwide-distributed zoonosis. These bacteria are facultative intracellular parasites and thus are able to adjust their metabolism to the ex...
Recovery of Pseudomonas aeruginosa culturability following copper- and chlorine-induced stress.FEMS Microbiol. Lett. 356(2) , 226-34, (2014)
This study investigated how quickly cells of the opportunistic pathogen Pseudomonas aeruginosa recover culturability after exposure to two of the most common environmental stressors present in drinkin...
Intestinal Epithelial Cell Tyrosine Kinase 2 Transduces IL-22 Signals To Protect from Acute Colitis.J. Immunol. 195 , 5011-24, (2015)
In the intestinal tract, IL-22 activates STAT3 to promote intestinal epithelial cell (IEC) homeostasis and tissue healing. The mechanism has remained obscure, but we demonstrate that IL-22 acts via ty...