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Oxolinic acid

Oxolinic acid Structure
CAS No.
14698-29-4
Chemical Name:
Oxolinic acid
Synonyms
oxolinic;5-ETHYL-8-OXO-5,8-DIHYDRO-[1,3]DIOXOLO[4,5-G]QUINOLINE-7-CARBOXYLIC ACID;w4565;utibid;ossian;oxoboi;pietil;s-0208;uroxol;starner
CBNumber:
CB8177186
Molecular Formula:
C13H11NO5
Molecular Weight:
261.23
MOL File:
14698-29-4.mol
Modify Date:
2024/5/27 15:57:40

Oxolinic acid Properties

Melting point 314-316°C (dec.)
Boiling point 473℃
Density 1.3038 (rough estimate)
refractive index 1.5500 (estimate)
Flash point >110°(230°F)
storage temp. 2-8°C
solubility Soluble in 0.5N NaOH with warming
form Crystalline Powder
pka 5.94±0.20(Predicted)
color White
Water Solubility 3.214mg/L(temperature not stated)
Sensitive Light Sensitive
Merck 13,7014
BRN 620635
Stability Stable. Combustible.
InChIKey KYGZCKSPAKDVKC-UHFFFAOYSA-N
CAS DataBase Reference 14698-29-4(CAS DataBase Reference)
EPA Substance Registry System Oxolinic acid (14698-29-4)

SAFETY

Risk and Safety Statements

Symbol(GHS) 
GHS07
Signal word  Warning
Hazard statements  H302
Precautionary statements  P264-P270-P301+P312-P501
Hazard Codes  Xn
Risk Statements  22
Safety Statements  22-24/25-60-36
WGK Germany  3
RTECS  JI5075000
10
HS Code  29349990
Toxicity LD50 in mice, rats (mg/kg): >6000, >2000 orally (Turner)
NFPA 704
0
1 0

Oxolinic acid price More Price(5)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich(India) O0877 Oxolinic acid quinolone antibiotic 14698-29-4 5G ₹11712.65 2022-06-14 Buy
Sigma-Aldrich(India) O0877 Oxolinic acid quinolone antibiotic 14698-29-4 25G ₹44404.15 2022-06-14 Buy
Sigma-Aldrich(India) 67126 Oxolinic acid analytical standard 14698-29-4 100MG ₹5910.45 2022-06-14 Buy
SRL 91088 Oxolinic Acid (OXO), 99% 14698-29-4 5Gms ₹8770 2022-05-26 Buy
SRL 91088 Oxolinic Acid (OXO), 99% 14698-29-4 25Gms ₹32890 2022-05-26 Buy
Product number Packaging Price Buy
O0877 5G ₹11712.65 Buy
O0877 25G ₹44404.15 Buy
67126 100MG ₹5910.45 Buy
91088 5Gms ₹8770 Buy
91088 25Gms ₹32890 Buy

Oxolinic acid Chemical Properties,Uses,Production

Description

Bacterial DNA gyrase is a heterodimeric type II topoisomerase that negatively supercoils circular double-stranded DNA. Oxolinic acid is a quinolone antibiotic that inhibits bacterial DNA gyrase, but not eukaryotic topoisomerases, reversibly binding gyrase subunit A in gyrase-DNA complexes, blocking supercoiling activity and inhibiting DNA synthesis at 0.5-5 μg/ml. Oxolinic acid also blocks neuronal uptake of dopamine in mammals (IC50 = 4.3 μM), leading to an increase in locomotor activity.

Chemical Properties

Crystalline Solid

Uses

Oxolinic acid is a quinolone antibiotic used for studies on DNA winding and coiling and for studies on dopaminergic neurotransmission processes. It is used to study new transmissible resistance mechanisms qnrA, qnrB, qnrS, and aac(6′)Ib-cr, in Escherichia

Definition

ChEBI: A quinolinemonocarboxylic acid having the carboxy group at position 7 as well as oxo and ethyl groups at positions 4 and 1 respectively and a dioxolo ring fused at the 5- and 6-positions. A synthetic antibiotic, it is used in veterinary medicine for the tr atment of bacterial infections in cattle, pigs and poultry.

Antimicrobial activity

Like nalidixic acid, this drug is effective with respect to Gram-negative microorganisms and is used for the same indications. Synonyms of this drug are nidantin, prodoxol, ocolin, uroxol, and others.

General Description

Chemical structure: quinolone

Pharmaceutical Applications

An oral 4-quinolone with a tricyclic structure. Its antibacterial spectrum is very similar to that of nalidixic acid, but it is more active againstEnterobacteriaceae (MIC 0.25–2 mg/L). Grampositive bacteria, Ps. aeruginosa and anaerobes are resistant.
After repeated doses of 750 mg twice daily, mean plasma concentrations are initially very low, but steady state is reached at the third day and Cmax is around 3.5 mg/L. Administration with food delays absorption. Binding to plasma protein is about 80%. It undergoes complex biotransformation, and an enterohepatic cycle may account for the increase in the apparent elimination half-life from 4 to 15 h over 7 days of treatment as well as for the 20% of dose which can be recovered from the feces. About 50% of the dose appears in the urine in the first 24 h, partly in the form of metabolites, some of which display antibacterial activity.
Side effects common to the quinolones occur frequently. About one-quarter of patients treated with 750 mg every 12 h suffer nausea and vomiting or restlessness and insomnia. Its only use is in the treatment of lower urinary tract infections.

Safety Profile

Moderately toxic by ingestion. Low toxicity by skin contact. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx.

Purification Methods

Purify the acid by recrystallisation from aqueous Me2CO, 95% EtOH or dimethylformamide. It has UV 220, (255.5sh), max 259.5, 268, (298sh, 311sh), 321 and 326nm [ 14.8, (36.8sh), 38.4, 38.4, (6.4sh, 9.2sh), 10.8 and 11.2 x 103]. [Kaminsky & Mettzer J Med Chem 11 160 1968, Beilstein 17 H 6, 17 I 3, 17 II 202, 17 III/IV 13, 17/1 V 11.]

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1-ethyl-1,4-dihydro-6,7-methylenedioxy-4-oxo-3-quinolinecarboxylicacid 1-ethyl-6,7-methylenedioxo-4-quinoline-3-carboxlicacid utibid w4565 OXOLINIC ACID 5,8-DIHYDRO-5-ETHYL-8-OXO-1,3-DIOXOLO[4,5-G]QUINOLINE-7-CARBOXYLIC ACID 5-ethyl-5,8-dihydro-8-oxo-1,3-dioxolo[4,5-g]quinoline-7-carboxylic acid AKOS 94417 Oxolinic acid solution OXOLINIC ACID STANDARD SOLUTION OXOLINIC ACID F&D VERSION OF O0877 OXOLINIC ACID 97+% 5-Ethyl-5,8-dihydro-8-oxo-1,3-dioxolo[4.5]quinole-7-carboxylicacid 1,3-Dioxolo4,5-gquinoline-7-carboxylic acid, 5-ethyl-5,8-dihydro-8-oxo- 5-Ethyl-5,8-dihydro-8-oxo-1,3-Dioxolo[4,5-γ],quinoline-7-carboxylic Acid 1-Ethyl-6,7-methylenedioxo-4-quinoline-3-carboxylic acid 1-ethyl-6,7-methylenedioxy-4-quinolone-3-carboxylicacid 5-g)quinoline-7-carboxylicacid,5-ethyl-5,8-dihydro-8-oxo-3-dioxolo(4 5-g]quinoline-7-carboxylicacid,5-ethyl-5,8-dihydro-8-oxo-3-dioxolo[4 dioxacin emyrenil gramurin nidantin nsc-110364 ossian oxoboi pietil prodoxal prodoxol s-0208 starner ultibid uritrate uro-alvar urotrate uroxol 5-ethyl-5,8-dihydro-8-oxo [1,3]-dioxolo [4,5-g] quinoline-7-arboxylic acid Oxlinic Acid 5-ethyl-8-keto-[1,3]dioxolo[4,5-g]quinoline-7-carboxylic acid 5-ethyl-8-oxo-[1,3]dioxolo[4,5-g]quinoline-7-carboxylic acid Oxolinic acid,5,8-Dihydro-5-ethyl-8-oxo-1,3-dioxolo[4,5-g]quinoline-7-carboxylic acid Oxolinic Acid, EP 5-Ethyl-5,8-dihydro-8-oxo- Oxilinic acid OXOLINIC ACID IMPURITY oxolinic acid:5-ethyl-5,8-dihydro-8-oxo-1,3-dioxolo(4,5-g)QUINOLINE-7-carboxylic acid OXOLINIC ACID, QUINOLONE ANTIBIOTIC 2,3-dihydrofuran-5-carboxylic acid Oxolinic acid CAS NO.: 14698-29-4 CAS NO.14698-29-4 Oxolinic acid Solution, 1000ppm Oxolinate Dioxacin(TM) oxolinic acid 20%wp Purity Oxolinic Acid Oxolinic acid@100 μg/mL in Acetonirtile Oxolinic Acid Standard Oxolinic acid CRS Oxolinic acid Solution in DMSO, 1000μg/mL