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Oxolinic acid

Description References
Oxolinic acid
Oxolinic acid structure
CAS No.
14698-29-4
Chemical Name:
Oxolinic acid
Synonyms
w4565;utibid;ossian;oxoboi;pietil;s-0208;uroxol;starner;ultibid;dioxacin
CBNumber:
CB8177186
Molecular Formula:
C13H11NO5
Formula Weight:
261.23
MOL File:
14698-29-4.mol

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)
FDA UNII
L0A22B22FT
ATC code
J01MB05
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+P312a-P330-P501a-P301+P312+P330
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)

Oxolinic acid price More Price(11)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 67126 Oxolinic acid analytical standard 14698-29-4 100mg $58.6 2021-03-22 Buy
Sigma-Aldrich O0877 Oxolinic acid quinolone antibiotic 14698-29-4 5g $113 2021-03-22 Buy
Sigma-Aldrich O0240000 Oxolinic acid European Pharmacopoeia (EP) Reference Standard 14698-29-4 $190 2021-03-22 Buy
Alfa Aesar J66637 Oxolinic acid, 98% 14698-29-4 5g $150 2021-03-22 Buy
Alfa Aesar J66637 Oxolinic acid, 98% 14698-29-4 25g $582 2021-03-22 Buy

Oxolinic acid Chemical Properties,Uses,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

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

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.

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.

Chemical 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.

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.]

Oxolinic acid Preparation Products And Raw materials

Raw materials

Preparation Products


Oxolinic acid Suppliers

Global( 275)Suppliers
Supplier Tel Fax Email Country ProdList Advantage
Masteam Bio-tech Co., Ltd.
86-15897918789 86-15200345168
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Qingdao Trust Agri Chemical Co.,Ltd
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Henan Tianfu Chemical Co.,Ltd.
0371-55170693
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career henan chemical co
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sales@coreychem.com CHINA 29954 58
Wuhan Boyuan Import & Export Co., LTD
+8618033787409
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Hubei Jusheng Technology Co.,Ltd.
86-18871470254
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Hebei Guanlang Biotechnology Co., Ltd.
+8619930503282
sales3@crovellbio.com China 5882 58

View Lastest Price from Oxolinic acid manufacturers

Image Release date Product Price Min. Order Purity Supply Ability Manufacturer
2021-11-26 Oxolinic Acid
14698-29-4
US $10.00 / Kg/Bag 1Kg/Bag 99% 20 Tons Hebei Zhanyao Biotechnology Co. Ltd
2021-11-26 Oxolinic acid
14698-29-4
US $126.00 / Kg/Bag 1KG 98% 1T Baoji Guokang Bio-Technology Co., Ltd.
2021-11-25 Oxolinic acid
14698-29-4
US $10.00 / Kg/Drum 1KG 99% 5000tons per month Wuhan Mulei New Material Technology Co. Ltd

Oxolinic acid Spectrum


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