Oxolinic acid

Oxolinic acid
Systematic (IUPAC) name

5-Ethyl-8-oxo-5,8-dihydro[1,3]dioxolo[4,5-g]quinoline- 7-carboxylic acid
Clinical data
AHFS/Drugs.com	International Drug Names
Identifiers
CAS Number	14698-29-4^Y
ATC code	J01MB05 (WHO)
PubChem	CID 4628
ChemSpider	4467^N
UNII	L0A22B22FT^N
KEGG	D02301^N
ChEBI	CHEBI:138856^N
ChEMBL	CHEMBL416755^N
Chemical data
Formula	C₁₃H₁₁NO₅
Molar mass	261.23 g/mol
SMILES CCN1C=C(C(=O)C2=CC3=C(C=C21)OCO3)C(=O)O
InChI InChI=1S/C13H11NO5/c1-2-14-5-8(13(16)17)12(15)7-3-10-11(4-9(7)14)19-6-18-10/h3-5H,2,6H2,1H3,(H,16,17)^N Key:KYGZCKSPAKDVKC-UHFFFAOYSA-N^N
^NY (what is this?) (verify)

Oxolinic acid is a quinolone antibiotic developed in Japan in the 1970s.^[1]^[2] Dosages 12–20 mg/kg orally administered for five to ten days. The antibiotic works by inhibiting the enzyme DNA gyrase. It also acts as a dopamine reuptake inhibitor and has stimulant effects in mice.^[3]

References

↑ JP Patent 49138244
↑ Gleckman R, Alvarez S, Joubert DW, Matthews SJ (August 1979). "Drug therapy reviews: oxolinic acid". American Journal of Hospital Pharmacy 36 (8): 1077–9. PMID 384788.
↑ Garcia de Mateos-Verchere J, Vaugeois JM, Naudin B, Costentin J (December 1998). "Behavioural and neurochemical evidence that the antimicrobial agent oxolinic acid is a dopamine uptake inhibitor". European Neuropsychopharmacology : the Journal of the European College of Neuropsychopharmacology 8 (4): 255–9. doi:10.1016/S0924-977X(97)00083-7. PMID 9928913.

Antibacterials: nucleic acid inhibitors (J01E, J01M)

Antifolates
(inhibits
purine metabolism,
thereby inhibiting
DNA and RNA synthesis)

DHFR inhibitor

2,4-Diaminopyrimidine
- Trimethoprim^#
- Brodimoprim
- Tetroxoprim
- Iclaprim^†

Sulfonamides
(DHPS inhibitor)

Short- acting	Sulfaisodimidine Sulfamethizole Sulfadimidine Sulfapyridine Sulfafurazole Sulfanilamide Prontosil Sulfathiazole Sulfathiourea

Intermediate- acting	Sulfamethoxazole Sulfadiazine^# Sulfamoxole

Long- acting	Sulfadimethoxine Sulfadoxine Sulfalene Sulfametomidine Sulfametoxydiazine Sulfamethoxypyridazine Sulfaperin Sulfamerazine Sulfaphenazole Sulfamazone

Other/ungrouped	Sulfacetamide Sulfadicramide Sulfametrole

Combinations

Trimethoprim/sulfamethoxazole^#

Topoisomerase
inhibitors/
quinolones/
(inhibits
DNA replication)

1st g.

Fluoro-
quinolones

2nd g.	Ciprofloxacin^# Ofloxacin Enoxacin^‡ Fleroxacin^‡ Lomefloxacin^‡ Nadifloxacin^‡ Norfloxacin^‡ Pefloxacin^‡ Rufloxacin^‡

3rd g.	Levofloxacin Balofloxacin^‡ Grepafloxacin^‡ Pazufloxacin^‡ Sparfloxacin^‡ Temafloxacin^‡ Tosufloxacin^‡

4th g.	Besifloxacin Gatifloxacin Finafloxacin Gemifloxacin Moxifloxacin Clinafloxacin^† Garenoxacin^‡ Prulifloxacin^‡ Sitafloxacin^‡ Trovafloxacin^‡/Alatrofloxacin^‡

Vet.	Danofloxacin Difloxacin Enrofloxacin Ibafloxacin Marbofloxacin Orbifloxacin Pradofloxacin Sarafloxacin

Newer non-fluorinated

Nemonoxacin

Related (DG)

Aminocoumarins: Novobiocin

Anaerobic DNA
inhibitors

Nitro- imidazole derivatives	Metronidazole^# Tinidazole Ornidazole

Nitrofuran derivatives	Nitrofurantoin^# Furazolidone^‡ Nifurtoinol

RNA synthesis

Rifamycins/ RNA polymerase	Rifampicin^# Rifabutin Rifapentine Rifaximin Rifalazil^§

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

Dopaminergics

Receptor ligands

Agonists

Adamantanes Amantadine Memantine Rimantadine

Aminotetralins 7-OH-DPAT 8-OH-PBZI Rotigotine UH-232

Benzazepines 6-Br-APB Fenoldopam SKF-38,393 SKF-77,434 SKF-81,297 SKF-82,958 SKF-83,959

Ergolines Bromocriptine Cabergoline Dihydroergocryptine Epicriptine Lisuride LSD Pergolide

Dihydrexidine derivatives 2-OH-NPA A-86929 Adrogolide (ABT-431, DAS-431) Ciladopa Dihydrexidine Dinapsoline Dinoxyline Doxanthrine

Others A-68930 A-77636 A-412,997 ABT-670 ABT-724 Aplindore Apomorphine Aripiprazole Arketamine Bifeprunox BP-897 Captodiame CY-208,243 Dizocilpine Esketamine Etilevodopa Flibanserin Ketamine Melevodopa Modafinil Pardoprunox Phencyclidine PD-128,907 PD-168,077 PF-219,061 Piribedil Pramipexole Propylnorapomorphine Pukateine Quinagolide Quinelorane Quinpirole RDS-127 Ro10-5824 Ropinirole Rotigotine Roxindole Salvinorin A SKF-89,145 Sumanirole Terguride Umespirone WAY-100,635

Antagonists

Typical antipsychotics Acepromazine Azaperone Benperidol Bromperidol Clopenthixol Chlorpromazine Chlorprothixene Droperidol Flupentixol Fluphenazine Fluspirilene Haloperidol Levomepromazine Levosulpiride Loxapine Mesoridazine Nemonapride Penfluridol Perazine Periciazine Perphenazine Pimozide Prochlorperazine Promazine Sulforidazine Sulpiride Sultopride Thioridazine Thiothixene Trifluoperazine Triflupromazine Trifluperidol Zuclopenthixol

Atypical antipsychotics Amisulpride Asenapine Blonanserin Cariprazine Carpipramine Clocapramine Clorotepine Clozapine Gevotroline Iloperidone Lurasidone Melperone Molindone Mosapramine Olanzapine Paliperidone Perospirone Piquindone Quetiapine Remoxipride Risperidone Sertindole Tiospirone Zicronapine Ziprasidone Zotepine

Antiemetics AS-8112 Alizapride Bromopride Clebopride Domperidone Metoclopramide Thiethylperazine

Others Amoxapine Buspirone Butaclamol Ecopipam EEDQ Eticlopride Fananserin Hydroxyzine L-745,870 Nafadotride Nuciferine PNU-99,194 Raclopride Sarizotan SB-277,011-A SCH 23390 SKF-83,959 Sonepiprazole Spiperone Spiroxatrine Stepholidine Tetrahydropalmatine Tiapride UH-232 Yohimbine

Reuptake modulators

DAT

Inhibitors

Piperazines DBL-583 GBR-12783 GBR-12935 GBR-13069 GBR-13098 Nefazodone Vanoxerine

Piperidines 4-Fluoropethidine Benocyclidine (BTCP) Desoxypipradrol Dexmethylphenidate Difemetorex Ethylphenidate HDMP-28 Methylphenidate Pethidine (meperidine) Phencyclidine Pipradrol

Pyrrolidines Diphenylprolinol MDPV Naphyrone Prolintane Pyrovalerone

Tropanes Altropane Benzatropine (benztropine) Brasofensine CFT Cocaine Dichloropane Difluoropine Etybenzatropine (ethybenztropine) FE-β-CPPIT FP-β-CPPIT Ioflupane (¹²³I) RTI-55 RTI-112 RTI-113 RTI-121 RTI-126 RTI-150 RTI-177 RTI-229 RTI-336 Tenocyclidine Tesofensine Troparil Tropoxane WF-11 WF-23 WF-31 WF-33

Others Adrafinil Amifitadine Armodafinil Amfonelic acid Amineptine Ansofaxine BTQ BTS 74,398 Bupropion Chaenomeles speciosa Ciclazindol Dasotraline Desmethylsertraline Diclofensine Dimethocaine Diphenylpyraline Dizocilpine (MK-801) DOV-102,677 DOV-216,303 Efavirenz Esketamine EXP-561 Fencamfamine Fezolamine Fluorenol GYKI-52895 Indatraline Ketamine Lefetamine Levophacetoperane Liafensine LR-5182 Manifaxine Mazindol Medifoxamine Mesocarb Metaphit MIN-117 (WF-516) Modafinil Nefopam Nomifensine NS-2359 O-2172 Oroxylin A Perafensine Pridefine Radafaxine Rimcazole Sertraline Sibutramine Tametraline Tedatioxetine Tripelennamine Venlafaxine

Enhancers

Luteolin

Modulators

Agonist-like SoRI-9804

Antagonist-like SoRI-20041

VMATs

Inhibitors: Amiodarone; Amphetamines (e.g., amphetamine, methamphetamine, MDMA); Bietaserpine; Deserpidine; Efavirenz; GBR-12935; Ibogaine; Ketanserin; Lobeline; Reserpine; Rose bengal; Tetrabenazine; Vanoxerine (GBR-12909)

Releasing agents

Morpholines Fenbutrazate Fenmetramide Morazone Morforex Phendimetrazine Phenmetrazine Pseudophenmetrazine

Oxazolines 4-MAR Aminorex Clominorex Cyclazodone Fenozolone Fluminorex Pemoline Thozalinone

Phenethylamines (also amphetamines, cathinones, etc) 2-OH-PEA 4-CAB 4-FA 4-FMA 4-MA 4-MMA Alfetamine Amfecloral Amfepentorex Amfepramone Amphetamine (Dextroamphetamine Levoamphetamine) Amphetaminil β-Me-PEA BDB BOH Benzphetamine Buphedrone Bupropion Butylone Cathine Cathinone Clobenzorex Clortermine D-Deprenyl DMA DMMA Dimethylamphetamine Ephedrine Ethcathinone EBDB Ethylone Etilamfetamine Famprofazone Fenethylline Fenproporex Flephedrone Fludorex Furfenorex Hordenine 4-Hydroxyamphetamine Iofetamine (123I) Lophophine Mefenorex Mephedrone Metamfepramone Methamphetamine Dextromethamphetamine Levomethamphetamine Methcathinone Methedrone MMDA MMDMA MBDB MDA MDEA MDMA MDMPEA MDOH MDPEA Methylone Morforex Ortetamine pBA pCA pIA Pholedrine Phenethylamine Pholedrine Phenpromethamine Prenylamine Propylamphetamine Pseudoephedrine Tiflorex Tyramine Xylopropamine Zylofuramine

Piperazines 2C-B-BZP BZP MBZP MDBZP MeOPP

Others 2-ADN 2-AI 2-AT 4-BP 5-APDI 5-IAI Clofenciclan Cyclopentamine Cypenamine Cyprodenate Feprosidnine Gilutensin Heptaminol Hexacyclonate Indanorex Isometheptene Methylhexanamine Naphthylaminopropane Octodrine Phthalimidopropiophenone Phenylbiguanide Propylhexedrine Levopropylhexedrine Tuaminoheptane

Enzyme inhibitors

PAH

3,4-Dihydroxystyrene

AAAD

MAO

Nonselective Benmoxin Caroxazone Echinopsidine Furazolidone Hydralazine Indantadol Iproclozide Iproniazid Isocarboxazid Isoniazid Linezolid Mebanazine Metfendrazine Nialamide Octamoxin Paraxazone Phenelzine Pheniprazine Phenoxypropazine Pivhydrazine Procarbazine Safrazine Tranylcypromine

MAO-A selective Amiflamine Bazinaprine Befloxatone Brofaromine Cimoxatone Clorgiline CX157 (Tyrima) Eprobemide Esuprone Harmala alkaloids Methylene Blue Metralindole Minaprine Moclobemide Pirlindole Sercloremine Tetrindole Toloxatone

MAO-B selective Almoxatone D-Deprenyl Ethanol Ladostigil Lazabemide Milacemide Nicotine Pargyline^‡ Rasagiline Safinamide Selegiline (L-Deprenyl)

COMT

DBH

Others

Precursors

L-Phenylalanine → L-Tyrosine → L-DOPA (levodopa)

Cofactors

Ferrous iron (Fe²⁺)
Tetrahydrobiopterin
Vitamin B₃ (Niacin
Nicotinamide → NADPH)
Vitamin B₆ (Pyridoxine
Pyridoxamine
Pyridoxal → Pyridoxal phosphate)
Vitamin B₉ (Folic acid → Tetrahydrofolic acid)
Vitamin C (Ascorbic acid)
Zinc (Zn²⁺)

Neurotoxins

Others

Activity enhancers BPAP PPAP

Levodopa prodrugs XP21279

Others Bromantane (dopamine synthesis enhancer)

See also:: Adrenergics; Melatonergics; Serotonergics; List of dopaminergic drugs

Authority control	LCCN: sh95000379 GND: 4288852-9

This article is issued from Wikipedia - version of the Saturday, April 02, 2016. The text is available under the Creative Commons Attribution/Share Alike but additional terms may apply for the media files.

Oxolinic acid

See also

References