Basic information
- CAS
14698-29-4- Standard SMILES
CCn1cc(C(=O)O)c(=O)c2cc3c(cc21)OCO3- InChIKey
KYGZCKSPAKDVKC-UHFFFAOYSA-N- Molecular formula
- C13H11NO5
- Average molar mass
- 261.23 g/mol
- Monoisotopic mass
- 261.06372245
Overview
Oxolinic acid is 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 treatment of bacterial infections in cattle, pigs and poultry. It has a role as an enzyme inhibitor, an antimicrobial agent, an antiinfective agent, an antifungal agent and an antibacterial drug. It is a quinolinemonocarboxylic acid, an organic heterotricyclic compound, an aromatic carboxylic acid, an oxacycle and a quinolone antibiotic. It is a conjugate acid of an oxolinate.
Names & identifiers
- Preferred name
- Oxolinic Acid
- IUPAC
- 5-ethyl-8-oxo-[1,3]dioxolo[4,5-g]quinoline-7-carboxylic acid
- English name
- Oxolinic acid
- Molecular formula
- C13H11NO5
- Molecular weight
- 261.23
Names & synonyms
oxolinic acid14698-29-4UtibidProdoxalOssianPietilAcido oxolinicoAcide oxoliniqueAcidum oxolinicumNSC-110364AqualinicW 4565
Show more names
oxolinic5-ETHYL-8-OXO-5,8-DIHYDRO-[1,3]DIOXOLO[4,5-G]QUINOLINE-7-CARBOXYLIC ACIDw4565oxobois-0208uroxolstarner
5-ethyl-8-oxo-[1,3]dioxolo[4,5-g]quinoline-7-carboxylic acid1-Ethyl-6,7-methylenedioxy-4-quinolone-3-carboxylic acid5-Ethyl-8-oxo-5,8-dihydro[1,3]dioxolo[4,5-g]quinoline-7-carboxylic acidDTXSID10210891-Ethyl-1,4-dihydro-6,7-methylenedioxy-4-oxo-3-quinolinecarboxylic acid5-Ethyl-5,8-dihydro-8-oxo-1,3-dioxolo(4,5-g)quinoline-7-carboxylic acidL0A22B22FTCHEBI:138856
Database identifiers
- CAS
14698-29-4- PubChem CID
- 4628
- DTXSID
DTXSID1021089- ChEMBL
CHEMBL416755- ChEBI
CHEBI:138856- UNII
- L0A22B22FT
- EC Number
Properties
Computed structural properties
- XLogP
- -0.2
- Topological polar surface area
- 76.1 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 2
- Heavy atoms
- 19
- Formal charge
- 0
- Complexity
- 446
Experimental & physicochemical properties
Drugs
Pharmaceuticals -> Antibiotics (Quinolones)
Pharmaceuticals -> Antibiotics
LogP1.01
Color/FormCRYSTALS FROM DIMETHYLFORMAMIDE
Melting Point314-316 °C
Collision Cross Section
152.6 Ų [M+H]+ [CCS Type: DT; Buffer gas: N2; Ionization: APCI+; Dataset: TOXCAST; Source Identifier: DTXSID1021089]
147.8 Ų [M+H]+ [CCS Type: TW]
167.2 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with Waters Major Mix]
149.1 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
150.35 Ų [M+H]+
Physicochemical properties
- Melting point
- 314 · 314-316°C (dec.)
- Boiling point
- 473 ℃ · 473℃
- Density
- 1.3038 · 1.3038 (rough estimate)
- refractive index
- 1.55 · 1.5500 (estimate)
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H302 (98.9%): Harmful if swallowed [Warning Acute toxicity, oral]
P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 93 reports by companies from 5 notifications to the ECHA C&L Inventory.
Warning
H332: Harmful if inhaled [Warning Acute toxicity, inhalation]
Hazard information
Regulatory InformationOxolinic acid: Does not have an individual approval but may be used under an appropriate group standard
Other Safety InformationIMAP assessments - 1,3-Dioxolo[4,5-g]quinoline-7-carboxylic acid, 5-ethyl-5,8-dihydro-8-oxo-: Environment tier I assessment
Hazard Classes and Categories
Acute Tox. 4 (98.9%)
Acute toxicity (Inhalation: Dusts and mists) - Category 4
Toxicology
InteractionsOXOLINIC ACID ANTAGONIZED HYPNOTIC ACTION OF SODIUM BARBITOL IN MICE & RATS. EFFECTS OF OXOLINIC ACID WERE ANTAGONIZED BY ALPHA-METHYLTYROSINE, PIMOZIDE, RESERPINE, & DIAZEPAM.
Human Toxicity Excerpts
CNS TOXICITY HAS INCL INSOMNIA (MOST FREQUENT), RESTLESSNESS, DIZZINESS, HEADACHE, DROWSINESS, & VISUAL DISTURBANCES. ... GI REACTIONS INCL NAUSEA (MOST FREQUENT), VOMITING, ABDOMINAL DISCOMFORT & DIARRHEA.
LESS FREQUENT...REACTIONS INCL FEVER, SKIN ERUPTIONS, PHOTOSENSITIVITY, PALPITATIONS, DYSPNEA & SENSE OF CHEST TIGHTNESS. TRANSIENT ELEVATIONS OF SERUM BILIRUBIN, SGOT & ALKALINE PHOSPHATASE, AS WELL AS LEUKOPENIA & HEMOLYTIC ANEMIA HAVE ALSO BEEN DESCRIBED.
Chemistry & industry
Pharmacology
ATC Code
J - Antiinfectives for systemic use
QJ - Antiinfectives for systemic use
Mechanism of Action
...INTERFERENCE WITH DEOXYRIBONUCLEIC ACID (DNA) SYNTH. OXOLINIC ACID, HOWEVER, HAS DEMONSTRATED 10-FOLD GREATER /THAN NALIDIXIC ACID/ ABILITY TO INHIBIT DNA REPLICATION, WHICH IS PARALLELED BY ITS GREATER IN VITRO ACTIVITY FOR ENTEROBACTERIACEAE.
Biological Half-Life
AFTER REPEATED DOSING, BIPHASIC EXCRETION PATTERN HAS BEEN OBSERVED. INITIAL PHASE IS RAPID WITH T/2 OF ABOUT 1.5 HR, & IS FOLLOWED BY SLOW PHASE WITH T/2 OF ABOUT 15 HR. URINARY CONCN OF UNCONJUGATED DRUG RANGE FROM 15-155 UG/ML IN PT WITH NORMAL RENAL FUNCTION.
Metabolism/Metabolites
YIELDS 1-ETHYL-1,4-DIHYDRO-7-HYDROXY-6-METHOXY-6-OXOQUINOLINE-3-CARBOXYLIC ACID IN RAT, RABBIT, DOG; YIELDS OXOLINOYL-BETA-D-GLUCURONIC ACID IN RAT, RABBIT, DOG; CREW, MC, MELGAR, MD, HAYNES, LJ, GALA, RL, & DICARLO, FJ, XENOBIOTICA, 1, 193 (1971). /FROM TABLE/
MAJOR URINARY METABOLITE WAS GLUCURONIDE OF OXOLINIC ACID...THIS COMPD WAS BIOLOGICALLY ACTIVE WHEREAS ALMOST ALL DRUG GLUCURONIDES ARE BIOLOGICALLY INERT...
MeSH Pharmacological Classification
Substances capable of killing agents causing urinary tract infections or of preventing them from spreading.
Substances that inhibit the growth or reproduction of BACTERIA.
Compounds that inhibit the activity of DNA TOPOISOMERASE II. Included in this category are a variety of ANTINEOPLASTIC AGENTS which target the eukaryotic form of topoisomerase II and ANTIBACTERIAL AGENTS which target the prokaryotic form of topoisomerase II.
Absorption, Distribution and Excretion
AFTER INGESTION OF OXOLINIC ACID, 5-ETHYL-5,8-DIHYDRO-8 -OXO-1,3-DIOXOLO-[4,5-G]QUINOLINE-7-CARBOXYLIC ACID, BY HUMAN SUBJECTS, URINE CONTAINED SMALL QUANTITY OF BIOLOGICALLY-INACTIVE & UNIDENTIFIED OXOLINIC ACID COMPLEX, BUT NO UNCHANGED OXOLINIC ACID.
Related reactions
4 records
Compound notes
Loading…