CLONIXIN LYSINE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C13H11ClN2O2.C6H14N2O2
Molecular Weight	408.879
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

NCCCC[C@H](N)C(O)=O.CC1=C(Cl)C=CC=C1NC2=NC=CC=C2C(O)=O

InChI

InChIKey=CVNFYQCHAWFYQI-ZSCHJXSPSA-N

InChI=1S/C13H11ClN2O2.C6H14N2O2/c1-8-10(14)5-2-6-11(8)16-12-9(13(17)18)4-3-7-15-12;7-4-2-1-3-5(8)6(9)10/h2-7H,1H3,(H,15,16)(H,17,18);5H,1-4,7-8H2,(H,9,10)/t;5-/m.0/s1

HIDE SMILES / InChI

Molecular Formula	C13H11ClN2O2
Molecular Weight	262.692
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	C6H14N2O2
Molecular Weight	146.1876
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/4935715 | https://www.ncbi.nlm.nih.gov/pubmed/10189073 | https://www.epharmapedia.com/medicine/profile/182894 | https://www.roemmers.com.ar/sites/default/files/DorixinaComprimidos_1.pdf

Clonixin is a nonsteroidal agent. It is an anilino-nicotinic acid derivative. It is a drug of anti-inflammatory antipyretic and analgesic activity that produces minor digestive side-effects. At high concentrations, clonixin inhibited PGE2 formed by COX-2 and partly by COX-1 activity. The drug is indicated for the relief of headaches, muscle aches, joint, dental, ear, dysmenorrhea, post-traumatic, post-surgical, gynecological. Adverse effects are occasionally nausea, dizziness, and somnolence, were mild and transient. On rare occasions, and administering high doses, it is possible the appearance of dry mouth or constipation. Concomitant use of anticholinergic drugs to be avoided by the possibility that they enhance their effects atropine.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Cyclooxygenase-1 131 Target ID: CHEMBL221 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11721323 \| https://www.ncbi.nlm.nih.gov/pubmed/10189073 \| https://www.roemmers.com.ar/sites/default/files/DorixinaComprimidos_1.pdf	Inhibitor 8504
Cyclooxygenase-2 201 Target ID: CHEMBL230 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11721323 \| https://www.ncbi.nlm.nih.gov/pubmed/10189073 \| https://www.roemmers.com.ar/sites/default/files/DorixinaComprimidos_1.pdf	Inhibitor 8504

Conditions

Condition	Modality	Highest Phase	Product
Migraine 107 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10667284 https://www.ncbi.nlm.nih.gov/pubmed/11299430 https://www.ncbi.nlm.nih.gov/pubmed/16614691	Primary	Approved 8583	Dorixina Approved Use Indicated for relief of headaches, muscle aches, joint, dental, ear, dysmenorrhea, post-traumatic, post-surgical, gynecological.
Rheumatoid arthritis 320 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1092517 https://www.ncbi.nlm.nih.gov/pubmed/4576980	Palliative	Approved 8583	Dorixina Approved Use Indicated for relief of headaches, muscle aches, joint, dental, ear, dysmenorrhea, post-traumatic, post-surgical, gynecological.
Pain 619 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9504193 https://www.ncbi.nlm.nih.gov/pubmed/4197784	Primary	Approved 8583	Dorixina Approved Use Indicated for relief of headaches, muscle aches, joint, dental, ear, dysmenorrhea, post-traumatic, post-surgical, gynecological.

C_max

Value	Dose	Co-administered	Analyte	Population
29.4 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/20420792/	250 mg single, oral dose: 250 mg route of administration: Oral experiment type: SINGLE co-administered:		CLONIXIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED

AUC

Value	Dose	Co-administered	Analyte	Population
49.88 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/20420792/	250 mg single, oral dose: 250 mg route of administration: Oral experiment type: SINGLE co-administered:		CLONIXIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
1.3 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/20420792/	250 mg single, oral dose: 250 mg route of administration: Oral experiment type: SINGLE co-administered:		CLONIXIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED

F_unbound

Value	Dose	Co-administered	Analyte	Population
3% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/16614691/	unknown		CLONIXIN LYSINE plasma	Homo sapiens

Doses

Dose	Population	Adverse events
200 mg single, intravenous Studied dose Dose: 200 mg Route: intravenous Route: single Dose: 200 mg Sources: https://pubmed.ncbi.nlm.nih.gov/18545786/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/18545786/	Other AEs: Injection site pain, Heartburn... Other AEs: Injection site pain (87%) Heartburn (13%) Sources: https://pubmed.ncbi.nlm.nih.gov/18545786/

AEs

AE	Significance	Dose	Population
Heartburn	13%	200 mg single, intravenous Studied dose Dose: 200 mg Route: intravenous Route: single Dose: 200 mg Sources: https://pubmed.ncbi.nlm.nih.gov/18545786/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/18545786/
Injection site pain	87%	200 mg single, intravenous Studied dose Dose: 200 mg Route: intravenous Route: single Dose: 200 mg Sources: https://pubmed.ncbi.nlm.nih.gov/18545786/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/18545786/

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inducer 1087			inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP19A1 429	UGT1A4 399 UGT1A1 479 UGT1A3 470 UGT1A10 331 P-gp 2052 UGT1A8 323 UGT2B7 456 UGT1A6 343 UGT1A7 249 UGT1A9 423

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
CYP19A1 430	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/28718#section=Biological-Test-Results Page: 6.0	no
CYP3A4 2633	inducer 1966 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/28718#section=Biological-Test-Results Page: 164.0	no

Drug as victim

Target	Modality	Activity
P-gp 2052	substrate 4014 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/28718#section=Biological-Test-Results Page: 162 \| 164	no
UGT1A1 479	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/15047194/	no
UGT1A4 399	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/15047194/	no
UGT1A6 343	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/15047194/	no
UGT1A10 331	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/15047194/	weak
UGT1A7 249	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/15047194/	weak
UGT1A8 323	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/15047194/	weak
UGT1A9 423	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/15047194/	weak
UGT1A3 470	substrate 4014 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzNTQyNDM1IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDEzMzI5NzEifX0=	yes [Km 624 uM]
UGT2B7 456	substrate 4014 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkw0MzcwIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDEzMzI5NzEifX0=	yes [Km 64 uM]

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/28718#section=Biological-Test-Results Page: 126.0

PubMed

Title	Date	PubMed
Pharmacokinetics of enrofloxacin and flunixin meglumine and interactions between both drugs after intravenous co-administration in healthy and endotoxaemic rabbits.	2008-09	17644374
Attenuation of ischaemic injury in the equine jejunum by administration of systemic lidocaine.	2008-06	18321812
Extralabel use of nonsteroidal anti-inflammatory drugs in cattle.	2008-03-01	18312175
Flunixin horse pill use in human associated with peptic ulcer disease.	2008-03	18303143
Escherichia coli mastitis in cattle being treated for Staphylococcus aureus intramammary infection.	2008-02-02	18245748
Effect of preoperative administration of erythromycin or flunixin meglumine on postoperative abomasal emptying rate in dairy cows undergoing surgical correction of left displacement of the abomasum.	2008-02-01	18241110
Effectiveness of administration of phenylbutazone alone or concurrent administration of phenylbutazone and flunixin meglumine to alleviate lameness in horses.	2008-02	18241011
Outcome of medical and surgical treatment of cecal impaction in horses: 114 cases (1994-2004).	2007-11-01	17975999
Effect of flunixin meglumine on cytokine levels in experimental endotoxemia in mice.	2007-09	17718807
Assessment of post-laparotomy pain in laboratory mice by telemetric recording of heart rate and heart rate variability.	2007-08-02	17683523
Suspected panosteitis in a camel.	2007-08-01	17669048
Treatment of acute puerperal metritis with flunixin meglumine in addition to antibiotic treatment.	2007-08	17638987
FDA issues reminder on correct use of flunixin meglumine.	2007-07-01	17671994
Evaluation of the renal effects of flunixin meglumine, ketoprofen and meloxicam in budgerigars (Melopsittacus undulatus).	2007-06-16	17575249
Effects of the cyclooxygenase inhibitor meloxicam on recovery of ischemia-injured equine jejunum.	2007-06	17542694
Effects of flunixin meglumine and transportation on establishment of pregnancy in beef cows.	2007-06	17371785
Pharmacokinetic interactions of flunixin meglumine and enrofloxacin in ICR mice.	2007-04	17460352
Effect of the administration of flunixin meglumine on pregnancy rates in Holstein heifers.	2007-03-24	17384292
Rapid method for the determination of non-steroidal anti-inflammatory drugs in animal tissue by liquid chromatography-mass spectrometry with ion-trap detector.	2007-03-14	17386745
Outbreak of neurologic disease caused by equine herpesvirus-1 at a university equestrian center.	2007-03-07	17338164
The effect of a topical anaesthetic formulation, systemic flunixin and carprofen, singly or in combination, on cortisol and behavioural responses of Merino lambs to mulesing.	2007-03	17359309
In vitro effects of reactive oxygen metabolites, with and without flunixin meglumine, on equine colonic mucosa.	2007-03	17331021
Evaluation of adverse effects of long-term oral administration of carprofen, etodolac, flunixin meglumine, ketoprofen, and meloxicam in dogs.	2007-03	17331014
Effects of cyclooxygenase inhibition on the gastrointestinal tract.	2006-11	16859903
Pharmacokinetics of flunixin meglumine in swine after intravenous dosing.	2006-10	16958790
Effects of flunixin meglumine on selected clinicopathologic variables, and serum testosterone concentration in stallions after endotoxin administration.	2006-09	16922834
Questions dosage used in equine study.	2006-05	16649904
Equine herpes myeloencephalopathy in a 12-year-old American quarter horse.	2006-04	16627115
Malabsorptive maldigestive disorder with concurrent Salmonella in a 3-year-old quarter horse.	2006-04	16627107
Acute diarrhea in the adult horse: case example and review.	2006-04	16627106
Postpartum hemoperitoneum and septic peritonitis in a Thoroughbred mare.	2006-04	16627105
Actinobacillus peritonitis in a Warmblood gelding.	2006-04	16627098
Efficacy of ceftiofur and flunixin in the early treatment of bronchopneumonia in weaners.	2006-03-04	16517821
Effects of phenylbutazone alone or in combination with flunixin meglumine on blood protein concentrations in horses.	2006-03	16506899
Pharmacokinetics of flunixin after intravenous administration in healthy and endotoxaemic rabbits.	2006-01	16362612
Lysine clonixinate vs naproxen sodium for the acute treatment of migraine: a double-blind, randomized, crossover study.	2005-12-14	16614691
COX-1 and COX-2 inhibition in horse blood by phenylbutazone, flunixin, carprofen and meloxicam: an in vitro analysis.	2005-10	15939622
Effect of a CIDR insert and flunixin meglumine, administered at the time of embryo transfer, on pregnancy rate and resynchronization of estrus in beef cattle.	2005-09-01	16054492
Pharmacokinetic interactions of flunixin meglumine and enrofloxacin in dogs.	2005-07	16111160
Technical Note: Improved technique for fitting pigs with steered ileocecal valve cannulas.	2005-07	15956465
Interaction of clonixin with EPC liposomes used as membrane models.	2005-06	15858845
Effect of anti-inflammatory drugs on splenocyte membrane fluidity.	2005-04-01	15766721
Investigation of the effect of black walnut extract on in vitro ion transport and structure of equine colonic mucosa.	2005-03	15822589
Evaluating postoperative analgesics in mice using telemetry.	2005-02	15766208
Use of force plate analysis to compare the analgesic effects of intravenous administration of phenylbutazone and flunixin meglumine in horses with navicular syndrome.	2005-02	15757129
Effects of non-steroidal anti-inflammatory drugs on pain-related behaviour in a model of articular pain in the domestic fowl.	2005-02	15500842
Effects of cyclooxygenase inhibitors flunixin and deracoxib on permeability of ischaemic-injured equine jejunum.	2005-01	15651739
[Slaughter emergency].	2004-11-01	15559393
Effects of ischemia and the cyclooxygenase inhibitor flunixin on in vitro passage of lipopolysaccharide across equine jejunum.	2004-10	15524324
Field evaluation of flunixin meglumine in the supportive treatment of caprine mastitis.	2004-10	15500577

Patents

Sample Use Guides

In Vivo Use Guide

200 mg single dose

Route of Administration: Intravenous

In Vitro Use Guide

clonixin (Clx) between 1 x 10(-6) M and 3 x 10(-4) M, decreases the overshoot (OS), action potential amplitude (APA), Vmax and frequency of primary and subsidiary cells, however pacemaker cells differ in their sensitivity to Clx. At 2 x 10(-6) M, Clx completely blocked the spontaneous beating of primary cells.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:49:27 GMT 2025` Edited by `admin` on `Mon Mar 31 18:49:27 GMT 2025`
Record UNII	06PW4M190R
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CLONIXIN LYSINATE

Preferred Name

English

CLONIXIN LYSINE

Common Name

English

2-(3-CHLORO-O-TOLUIDINO)NICOTINIC ACID, LYSINE SALT

Common Name

English

CLONIXIN LYSINE SALT [MI]

Common Name

English

R-173

Code

English

L-104

Code

English

LYSINE CLONIXINATE

Common Name

English

CLONIXIN LYSINE [MART.]

Common Name

English

Clonixin lysinate [WHO-DD]

Common Name

English

L-LYSINE, 2-((3-CHLORO-2-METHYLPHENYL)AMINO)-3-PYRIDINECARBOXYLATE (1:1)

Common Name

English

CLONIXIN LYSINE SALT

Common Name

English

Code System Code Type Description

PUBCHEM

3080836