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Details

Stereochemistry ACHIRAL
Molecular Formula C16H10NO2.Li
Molecular Weight 255.1967
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CINCHOPHEN LITHIUM

SMILES

c1ccc(cc1)-c2cc(c3ccccc3n2)C(=O)[O-].[Li+]

InChI

InChIKey=YHIPORGBUOVHKG-UHFFFAOYSA-M
InChI=1S/C16H11NO2.Li/c18-16(19)13-10-15(11-6-2-1-3-7-11)17-14-9-5-4-8-12(13)14;/h1-10H,(H,18,19);/q;+1/p-1

HIDE SMILES / InChI

Molecular Formula Li
Molecular Weight 6.94
Charge 1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C16H10NO2
Molecular Weight 248.2567
Charge -1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment:: Description was created based on several sources, including http://www.un.org/esa/coordination/CL12.pdf

Cinchophen, phenylcinchoninic acid, seems to have been discovered in 1887 by Doebner and Gieseke and to have been introduced into medicine under the trade name of atophan in 1908 by Nicolaier and Dohrn. Since that time it has been used extensively for gout as well as for other forms of arthritis and for the relief of pain of all types. Use of Cinchophen in humans ceased in the 1930s due to the discovery that it can cause serious liver damage.

Originator

Curator's Comment:: Cinchophen, phenylcinchoninic acid, seems to have been discovered in 1887 by Doebner and Gieseke and to have been introduced into medicine under the trade name of atophan in 1908 by Nicolaier and Dohrn.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P12841
Gene ID: 314322.0
Gene Symbol: Fos
Target Organism: Rattus norvegicus (Rat)
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
Atophan

Approved Use

It has been used extensively for gout as well as for other forms of arthritis and for the relief of pain of all types.
Doses

Doses

DosePopulationAdverse events​
485.9 mg 3 times / day multiple, oral
Dose: 485.9 mg, 3 times / day
Route: oral
Route: multiple
Dose: 485.9 mg, 3 times / day
Sources:
unhealthy, 19 years
n = 1
Health Status: unhealthy
Age Group: 19 years
Sex: F
Population Size: 1
Sources:
Other AEs: Jaundice, Nausea...
Other AEs:
Jaundice
Nausea
Abdominal pain
Sources:
485.9 mg 1 times / day multiple, oral
Dose: 485.9 mg, 1 times / day
Route: oral
Route: multiple
Dose: 485.9 mg, 1 times / day
Sources:
unhealthy, 38 years
n = 1
Health Status: unhealthy
Condition: acute rheumatism
Age Group: 38 years
Sex: F
Population Size: 1
Sources:
Disc. AE: Jaundice...
AEs leading to
discontinuation/dose reduction:
Jaundice (grade 5)
Sources:
300 mg 1 times / day multiple, oral (mean)
Dose: 300 mg, 1 times / day
Route: oral
Route: multiple
Dose: 300 mg, 1 times / day
Sources:
unhealthy, 57 - 67 years
n = 3
Health Status: unhealthy
Condition: gout
Age Group: 57 - 67 years
Sex: F
Population Size: 3
Sources:
Disc. AE: Hepatitis...
Other AEs: Hepatic failure...
AEs leading to
discontinuation/dose reduction:
Hepatitis (acute, 2 patients)
Other AEs:
Hepatic failure (severe|grade 5, 1 patient)
Sources:
0.5 g 1 times / day multiple, oral
Dose: 0.5 g, 1 times / day
Route: oral
Route: multiple
Dose: 0.5 g, 1 times / day
Sources:
unhealthy, 59 years
n = 1
Health Status: unhealthy
Age Group: 59 years
Sex: F
Population Size: 1
Sources:
Disc. AE: Hepatitis, Agranulocytosis...
AEs leading to
discontinuation/dose reduction:
Hepatitis
Agranulocytosis
Sources:
AEs

AEs

AESignificanceDosePopulation
Abdominal pain
485.9 mg 3 times / day multiple, oral
Dose: 485.9 mg, 3 times / day
Route: oral
Route: multiple
Dose: 485.9 mg, 3 times / day
Sources:
unhealthy, 19 years
n = 1
Health Status: unhealthy
Age Group: 19 years
Sex: F
Population Size: 1
Sources:
Jaundice
485.9 mg 3 times / day multiple, oral
Dose: 485.9 mg, 3 times / day
Route: oral
Route: multiple
Dose: 485.9 mg, 3 times / day
Sources:
unhealthy, 19 years
n = 1
Health Status: unhealthy
Age Group: 19 years
Sex: F
Population Size: 1
Sources:
Nausea
485.9 mg 3 times / day multiple, oral
Dose: 485.9 mg, 3 times / day
Route: oral
Route: multiple
Dose: 485.9 mg, 3 times / day
Sources:
unhealthy, 19 years
n = 1
Health Status: unhealthy
Age Group: 19 years
Sex: F
Population Size: 1
Sources:
Jaundice grade 5
Disc. AE
485.9 mg 1 times / day multiple, oral
Dose: 485.9 mg, 1 times / day
Route: oral
Route: multiple
Dose: 485.9 mg, 1 times / day
Sources:
unhealthy, 38 years
n = 1
Health Status: unhealthy
Condition: acute rheumatism
Age Group: 38 years
Sex: F
Population Size: 1
Sources:
Hepatitis acute, 2 patients
Disc. AE
300 mg 1 times / day multiple, oral (mean)
Dose: 300 mg, 1 times / day
Route: oral
Route: multiple
Dose: 300 mg, 1 times / day
Sources:
unhealthy, 57 - 67 years
n = 3
Health Status: unhealthy
Condition: gout
Age Group: 57 - 67 years
Sex: F
Population Size: 3
Sources:
Hepatic failure severe|grade 5, 1 patient
300 mg 1 times / day multiple, oral (mean)
Dose: 300 mg, 1 times / day
Route: oral
Route: multiple
Dose: 300 mg, 1 times / day
Sources:
unhealthy, 57 - 67 years
n = 3
Health Status: unhealthy
Condition: gout
Age Group: 57 - 67 years
Sex: F
Population Size: 3
Sources:
Agranulocytosis Disc. AE
0.5 g 1 times / day multiple, oral
Dose: 0.5 g, 1 times / day
Route: oral
Route: multiple
Dose: 0.5 g, 1 times / day
Sources:
unhealthy, 59 years
n = 1
Health Status: unhealthy
Age Group: 59 years
Sex: F
Population Size: 1
Sources:
Hepatitis Disc. AE
0.5 g 1 times / day multiple, oral
Dose: 0.5 g, 1 times / day
Route: oral
Route: multiple
Dose: 0.5 g, 1 times / day
Sources:
unhealthy, 59 years
n = 1
Health Status: unhealthy
Age Group: 59 years
Sex: F
Population Size: 1
Sources:
PubMed

PubMed

TitleDatePubMed
A series of quinoline analogues as potent inhibitors of C. albicans prolyl tRNA synthetase.
2001 Feb 26
Synthesis of brequinar analogue inhibitors of malaria parasite dihydroorotate dehydrogenase.
2005 Mar 15
Comprehensive screening and quantification of veterinary drugs in milk using UPLC-ToF-MS.
2008 Jul
Poly[bis-(μ-hemihydrogen 2-phenyl-quinoline-4-carboxyl-ato-κN,O)silver(I)].
2009 Jan 23
Bis(μ-2-phenyl-quinoline-4-carboxyl-ato)-κO,O':O;κO:O,O'-bis-[(2,2'-bipyridine-κN,N')(2-phenyl-quinoline-4-carboxyl-ato-κO,O')cadmium(II)].
2010 Dec 4
A correlation between the in vitro drug toxicity of drugs to cell lines that express human P450s and their propensity to cause liver injury in humans.
2014 Jan
Patents

Patents

Sample Use Guides

The mean dose was 300 mg/day for a mean duration of 3-4 months
Route of Administration: Unknown
Cinchophen (200 ug /ml) reduced the response of the isolated guinea-pig ileum to bradykinin.
Substance Class Chemical
Created
by admin
on Fri Jun 25 23:32:19 UTC 2021
Edited
by admin
on Fri Jun 25 23:32:19 UTC 2021
Record UNII
17Z71O8Z3D
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CINCHOPHEN LITHIUM
WHO-DD  
Common Name English
CINCHOPHEN LITHIUM [WHO-DD]
Common Name English
4-QUINOLINECARBOXYLIC ACID, 2-PHENYL-, LITHIUM SALT (1:1)
Common Name English
Code System Code Type Description
EVMPD
SUB01307MIG
Created by admin on Fri Jun 25 23:32:19 UTC 2021 , Edited by admin on Fri Jun 25 23:32:19 UTC 2021
PRIMARY
CAS
59672-07-0
Created by admin on Fri Jun 25 23:32:19 UTC 2021 , Edited by admin on Fri Jun 25 23:32:19 UTC 2021
PRIMARY
PUBCHEM
71300649
Created by admin on Fri Jun 25 23:32:19 UTC 2021 , Edited by admin on Fri Jun 25 23:32:19 UTC 2021
PRIMARY
EPA CompTox
59672-07-0
Created by admin on Fri Jun 25 23:32:19 UTC 2021 , Edited by admin on Fri Jun 25 23:32:19 UTC 2021
PRIMARY
FDA UNII
17Z71O8Z3D
Created by admin on Fri Jun 25 23:32:19 UTC 2021 , Edited by admin on Fri Jun 25 23:32:19 UTC 2021
PRIMARY
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PARENT -> SALT/SOLVATE
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ACTIVE MOIETY