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Details

Stereochemistry ACHIRAL
Molecular Formula C16H10NO2.Na
Molecular Weight 271.2459
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CINCHOPHEN SODIUM

SMILES

[Na+].[O-]C(=O)C1=C2C=CC=CC2=NC(=C1)C3=CC=CC=C3

InChI

InChIKey=ZSOINCKGNIMAEG-UHFFFAOYSA-M
InChI=1S/C16H11NO2.Na/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 Na
Molecular Weight 22.9898
Charge 1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C16H10NO2
Molecular Weight 248.2561
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
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 Sat Dec 16 09:58:10 UTC 2023
Edited
by admin
on Sat Dec 16 09:58:10 UTC 2023
Record UNII
454ZOQ4L8N
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CINCHOPHEN SODIUM
Common Name English
CINCHOPHEN SODIUM SALT
Common Name English
SODIUM 2-PHENYLQUINOLINE-4-CARBOXYLATE
Systematic Name English
SODIUM CINCHOPHEN
Systematic Name English
SODIUM 2-PHENYLCINCHONINATE
Systematic Name English
4-QUINOLINECARBOXYLIC ACID, 2-PHENYL-, SODIUM SALT (1:1)
Systematic Name English
CINCHONINIC ACID, 2-PHENYL-, SODIUM SALT
Common Name English
4-QUINOLINECARBOXYLIC ACID, 2-PHENYL-, SODIUM SALT
Systematic Name English
2-PHENYLCINCHONINIC ACID SODIUM SALT
Common Name English
Code System Code Type Description
CAS
5949-18-8
Created by admin on Sat Dec 16 09:58:10 UTC 2023 , Edited by admin on Sat Dec 16 09:58:10 UTC 2023
PRIMARY
PUBCHEM
23691042
Created by admin on Sat Dec 16 09:58:10 UTC 2023 , Edited by admin on Sat Dec 16 09:58:10 UTC 2023
PRIMARY
ECHA (EC/EINECS)
227-710-5
Created by admin on Sat Dec 16 09:58:10 UTC 2023 , Edited by admin on Sat Dec 16 09:58:10 UTC 2023
PRIMARY
EPA CompTox
DTXSID20208187
Created by admin on Sat Dec 16 09:58:10 UTC 2023 , Edited by admin on Sat Dec 16 09:58:10 UTC 2023
PRIMARY
FDA UNII
454ZOQ4L8N
Created by admin on Sat Dec 16 09:58:10 UTC 2023 , Edited by admin on Sat Dec 16 09:58:10 UTC 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
SOLVATE->ANHYDROUS