Description References
ChemicalBook > CAS DataBase List > Oxolinic acid

Oxolinic acid

Description References
Product Name
Oxolinic acid
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
Formula Weight
261.23
MOL File
14698-29-4.mol
More
Less

Oxolinic acid Property

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)
More
Less

Safety

Hazard Codes 
Xn
Risk Statements 
22
Safety Statements 
22-24/25-60-36
WGK Germany 
3
RTECS 
JI5075000
10
HS Code 
29349990
Hazardous Substances Data
14698-29-4(Hazardous Substances Data)
Toxicity
LD50 in mice, rats (mg/kg): >6000, >2000 orally (Turner)
More
Less

Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P501Dispose of contents/container to..…

More
Less

N-Bromosuccinimide Price

Sigma-Aldrich
Product number
O0877
Product name
Oxolinic acid
Purity
quinolone antibiotic
Packaging
5g
Price
$138
Updated
2024/03/01
Sigma-Aldrich
Product number
67126
Product name
Oxolinic acid
Purity
analytical standard
Packaging
100mg
Price
$73.4
Updated
2024/03/01
Alfa Aesar
Product number
J66637
Product name
Oxolinic acid, 98%
Packaging
5g
Price
$170
Updated
2024/03/01
Alfa Aesar
Product number
J66637
Product name
Oxolinic acid, 98%
Packaging
25g
Price
$722
Updated
2024/03/01
Cayman Chemical
Product number
16789
Product name
Oxolinic Acid
Purity
≥98%
Packaging
1g
Price
$32
Updated
2024/03/01
More
Less

Oxolinic acid Chemical Properties,Usage,Production

Description

Developed in Japan in the 1970s, oxolinic acid belongs to the family of quinolone antibiotic, which is a synthetic antimicrobial agent aiming at gram-negative bacteria, especially those responsible for urinary tract infections. It is also commonly used in clinical for microbiological antimicrobial susceptibility tests against gram negative microbial isolates, providing antibiotic treatment options for infected patients. It can serve as a selective agent in several types of isolation media, for example, to isolate Gardnerella vaginalis. Besides, oxolinic acid can be applied in agriculture, which has proved to be effective against the seed-borne pathogen, such as Burkholderia glumae, a bacteria inducing grain rot, sheath rot, seedling rot, and bacterial panicle blight.
Oxolinic acid works by targeting DNA gyrase or topoisomerase II, enzymes vital for DNA synthesis, which ultimately inhibits DNA synthesis and cell division.

References

https://en.wikipedia.org/wiki/Oxolinic_acid
http://www.toku-e.com/product/oxolinic_acid/
https://www.goldbio.com/product/3027/oxolinic-acid

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

Originator

Prodoxol,Warner,UK,1974

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

Uses

Oxolinic acid is used to study new transmissible resistance mechanisms qnrA, qnrB, qnrS, and aac(6′)Ib-cr, in Escherichia coli and Salmonella enterica. Oxolinic acid is added to culture medium for the isolation of Gardnerella vaginalis.

Uses

Quinolone antibacterial.

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.

Manufacturing Process

A mixture of 27 parts by weight of 3,4-methylenedioxyaniline and 43 parts by weight of diethyl ethoxymethylenemalonate is heated at 80° to 90°C for 3 hours. The mixture is then heated at 80° to 90°C for 1 hour under about 15 mm pressure to remove the byproduct ethyl alcohol formed. The residue is recrystallized from ligroin (BP 60° to 90°C) to give diethyl[(3,4methylenetlioxyanilino)methylene] malonate as a yellow solid melting at 100° to 102°C. The analytical sample from ligroin melts at 101° to 102°C.
A mixture of 48 parts by weight of diethyl[(3,4-methylenedioxyanilino) methylene] malonate and 500 parts by weight of diphenyl ether is refluxed for 1 hour. The mixture is allowed to cool to about 25°C with stirring and 500 parts by weight of petroleum ether are added. Filtration gives 3-carbethoxy6,7-methylenedioxy-4-hydroxy-quinoline as a brown solid, MP 276° to 281°C. Several recrystallizations from dimethylformamide gives almost colorless analytical material, MP 285° to 286°C, (decomposes).
A mixture of 26 parts of 3-carbethoxy-6,7-methylenedioxy-4-hydroxyquinoline,16 parts of sodium hydroxide and 50 parts of dimethylformamide is heated at 70° to 75°C for 2 hours, then 31 parts of ethyl iodide is added over 1 hour with continued heating and stirring. After an additional 3 to 4 hours of heating (at 70° to 75°C) and stirring, the mixture is diluted with 500 parts of water, refluxed for 3 to 4 hours, acidified with concentrated hydrochloric acid and filtered to yield 18 to 22 parts of 1-ethyl-1,4-dihydro-6,7-methylenedioxy-4-oxo-3-quinoline-carboxylic acid, MP 309° to 314°C (decomposes). The analytical sample from dimethylformamide melts at 314° to 316°C (decomposes).

brand name

Utibid (ParkeDavis).

Therapeutic Function

Antibacterial (urinary)

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.

Biochem/physiol Actions

Oxolinic acid is a quinolone antibiotic. It is a DNA-gyrase (topoisomerase II) inhibitor used for studies on DNA winding and coiling and acts as a dopamine reuptake inhibitor for studies on dopaminergic neurotransmission processes.

Safety Profile

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

Synthesis

Oxolinic acid, 5-ethyl-5,8-dihydro-8-oxo-1-dioxolo[4,5-g]-quinolin- 7-carboxylic acid (33.2.9), is basically synthesized by the same synthetic scheme as nalidixic acid, although it uses 3,4-methylendioxyanyline (33.2.6) as the starting aromatic amine component, and not the 2-amino-6-methylpyridine used to make nalidixic acid. This compound is obtained by hydrogenation to 3,4-methylendioxy-1-nitrobenzene (33.2.5), which is in turn synthesized by nitrating 1,2-methylendioxybenzene with nitric acid. The resulting 3,4-methylendioxyaniline (33.2.6) is then reacted with ethoxymethylenmalonic ester to make the substitution product (33.2.7), which when heated cyclizes to ethyl ester of 4-hydroxy-6,7-methylendioxyquinolin-3-carboxylic acid (33.2.8). Hydrolyzis of this with a base in dimethylformamide and direct treating of the obtained product with ethyl iodide gives the desired oxolinic acid.

in vitro

previous study found that both inhibitors of dna gyrase of oxolinic acid and coumermycin a1 could block the dna synthesis in e. coli. moreover, the rate of bacterial dna synthesis first rapidly declined but then increased gradually at low concentrations of oxolinic acid. in varoius dna mutants, oxolinic acid was able to cause a rapid decline, followed by a slow decrease in synthesis rate of dna [1].

in vivo

animal study showed that the i.p. injection of oxolinic acid in mice could induce a dose dependent increase in locomotor activity, and such stimulation culminated at the 32 mg/kg dose and was smaller for higher doses at 64-128 mg/kg. when compared with haloperidol (d2 dopamine receptor antagonist) at increasing doses (50-100-200 mg/kg), the stimulant locomotor effect of oxolinic acid at 32 mg/kg was not reversed significantly. in addition, oxolinic acid at 32 mg/kg did not reverse the reserpine caused akinesia and even opposed the reversion that was induced by dexamphetamine [2].

IC 50

4.3 μm for dopamine uptake

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.]

References

[1] e c engle,s h manes, and k drlica. differential effects of antibiotics inhibiting gyrase. j bacteriol. 1982 jan; 149(1): 92–98.
[2] garcia de mateos-verchere j,vaugeois jm,naudin b,costentin j. behavioural and neurochemical evidence that the antimicrobial agent oxolinic acid is a dopamine uptake inhibitor. eur neuropsychopharmacol. 1998 dec;8(4):255-9.

Oxolinic acid Preparation Products And Raw materials

Raw materials

Preparation Products

More
Less

Oxolinic acid Suppliers

Dr. Ehrenstorfer GmbH
Tel
--
Fax
--
Email
info@analytical-standards.com
Country
Germany
ProdList
5545
Advantage
66
Incopharm Gmbh
Tel
--
Fax
--
Email
incopharm.hamburg@gmail.com
Country
Germany
ProdList
96
Advantage
58
Safic-Alcan Deutschland Gmbh
Tel
--
Fax
--
Email
lukas.weingarten@safic-alcan.de
Country
Germany
ProdList
58
Advantage
58
Opteby Scientific GmbH
Tel
--
Fax
--
Email
anfragen@opteby.com
Country
Germany
ProdList
170
Advantage
58
Andenex-Chemie Engelhard + Partner GmbH
Tel
--
Fax
--
Email
info@andenex.de
Country
Germany
ProdList
124
Advantage
58
HPC Standards GmbH
Tel
--
Fax
--
Email
chulze@hpc-standards.com
Country
Germany
ProdList
2139
Advantage
58
Burmester Pharmatrade Gmbh
Tel
--
Fax
--
Email
info@burmester-pharma.de
Country
Germany
ProdList
1347
Advantage
58
Service Chemical Inc.
Tel
--
Fax
--
Email
sales@chemos-group.com
Country
Germany
ProdList
6350
Advantage
71
AKos Consulting & Solutions GmbH
Tel
--
Fax
--
Email
akos@akosgmbh.de
Country
Germany
ProdList
6717
Advantage
72
More
Less

View Lastest Price from Oxolinic acid manufacturers

Henan Suikang Pharmaceutical Co.,Ltd.
Product
Oxolinic acid 14698-29-4
Price
US $0.00/kg
Min. Order
25kg
Purity
99.0%
Supply Ability
10tons
Release date
2024-04-26
Hebei Zhuanglai Chemical Trading Co.,Ltd
Product
Oxolinic Acid 14698-29-4
Price
US $75.00-25.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
20ton
Release date
2024-05-27
WUHAN FORTUNA CHEMICAL CO., LTD
Product
Oxolinic acid 14698-29-4
Price
US $0.00-0.00/Kg/Drum
Min. Order
1KG
Purity
98%-102%
Supply Ability
20 tons
Release date
2021-05-28

14698-29-4, Oxolinic acidRelated Search:


  • 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
  • 5-ETHYL-8-OXO-5,8-DIHYDRO-[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
  • 2,3-dihydrofuran-5-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
  • oxolinic
  • 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 CAS NO.: 14698-29-4 CAS NO.14698-29-4
  • oxolinic acid:5-ethyl-5,8-dihydro-8-oxo-1,3-dioxolo(4,5-g)QUINOLINE-7-carboxylic acid
  • OXOLINIC ACID, QUINOLONE ANTIBIOTIC
  • Oxolinic acid Solution, 1000ppm
  • Oxolinate
  • Dioxacin(TM)
  • oxolinic acid 20%wp
  • Purity Oxolinic Acid
  • Oxolinic acid@100 μg/mL in Acetonirtile
  • Oxolinic Acid Standard