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Details

Stereochemistry ACHIRAL
Molecular Formula C16H10NO2.Na.2H2O
Molecular Weight 307.2764
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CINCHOPHEN SODIUM DIHYDRATE

SMILES

O.O.[Na+].[O-]C(=O)C1=CC(=NC2=C1C=CC=C2)C3=CC=CC=C3

InChI

InChIKey=YEUIDGLEQUXMGP-UHFFFAOYSA-M
InChI=1S/C16H11NO2.Na.2H2O/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);;2*1H2/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
Molecular Formula H2O
Molecular Weight 18.0153
Charge 0
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.

CNS Activity

Originator

Doebner, O.|Gieseke, M.
8
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

1908
8
Targets

Targets

Primary TargetPharmacologyConditionPotency
Proto-oncogene c-Fos
8
Target ID: P12841
Gene ID: 314322.0
Gene Symbol: Fos
Target Organism: Rattus norvegicus (Rat)
Activator
1430
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
Approved
8429
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:
https://pubmed.ncbi.nlm.nih.gov/18741907
unhealthy, 19 years
n = 1
Health Status: unhealthy
Age Group: 19 years
Sex: F
Population Size: 1
Sources:
https://pubmed.ncbi.nlm.nih.gov/18741907
Other AEs: Jaundice, Nausea...
Other AEs:
Jaundice
Nausea
Abdominal pain
Sources:
https://pubmed.ncbi.nlm.nih.gov/18741907
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:
https://pubmed.ncbi.nlm.nih.gov/20778752
unhealthy, 38 years
n = 1
Health Status: unhealthy
Condition: acute rheumatism
Age Group: 38 years
Sex: F
Population Size: 1
Sources:
https://pubmed.ncbi.nlm.nih.gov/20778752
Disc. AE: Jaundice...
AEs leading to
discontinuation/dose reduction:
Jaundice (grade 5)
Sources:
https://pubmed.ncbi.nlm.nih.gov/20778752
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:
https://pubmed.ncbi.nlm.nih.gov/1679861
unhealthy, 57 - 67 years
n = 3
Health Status: unhealthy
Condition: gout
Age Group: 57 - 67 years
Sex: F
Population Size: 3
Sources:
https://pubmed.ncbi.nlm.nih.gov/1679861
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:
https://pubmed.ncbi.nlm.nih.gov/1679861
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:
https://pubmed.ncbi.nlm.nih.gov/13470708
unhealthy, 59 years
n = 1
Health Status: unhealthy
Age Group: 59 years
Sex: F
Population Size: 1
Sources:
https://pubmed.ncbi.nlm.nih.gov/13470708
Disc. AE: Hepatitis, Agranulocytosis...
AEs leading to
discontinuation/dose reduction:
Hepatitis
Agranulocytosis
Sources:
https://pubmed.ncbi.nlm.nih.gov/13470708
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:
https://pubmed.ncbi.nlm.nih.gov/18741907
unhealthy, 19 years
n = 1
Health Status: unhealthy
Age Group: 19 years
Sex: F
Population Size: 1
Sources:
https://pubmed.ncbi.nlm.nih.gov/18741907
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:
https://pubmed.ncbi.nlm.nih.gov/18741907
unhealthy, 19 years
n = 1
Health Status: unhealthy
Age Group: 19 years
Sex: F
Population Size: 1
Sources:
https://pubmed.ncbi.nlm.nih.gov/18741907
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:
https://pubmed.ncbi.nlm.nih.gov/18741907
unhealthy, 19 years
n = 1
Health Status: unhealthy
Age Group: 19 years
Sex: F
Population Size: 1
Sources:
https://pubmed.ncbi.nlm.nih.gov/18741907
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:
https://pubmed.ncbi.nlm.nih.gov/20778752
unhealthy, 38 years
n = 1
Health Status: unhealthy
Condition: acute rheumatism
Age Group: 38 years
Sex: F
Population Size: 1
Sources:
https://pubmed.ncbi.nlm.nih.gov/20778752
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:
https://pubmed.ncbi.nlm.nih.gov/1679861
unhealthy, 57 - 67 years
n = 3
Health Status: unhealthy
Condition: gout
Age Group: 57 - 67 years
Sex: F
Population Size: 3
Sources:
https://pubmed.ncbi.nlm.nih.gov/1679861
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:
https://pubmed.ncbi.nlm.nih.gov/1679861
unhealthy, 57 - 67 years
n = 3
Health Status: unhealthy
Condition: gout
Age Group: 57 - 67 years
Sex: F
Population Size: 3
Sources:
https://pubmed.ncbi.nlm.nih.gov/1679861
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:
https://pubmed.ncbi.nlm.nih.gov/13470708
unhealthy, 59 years
n = 1
Health Status: unhealthy
Age Group: 59 years
Sex: F
Population Size: 1
Sources:
https://pubmed.ncbi.nlm.nih.gov/13470708
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:
https://pubmed.ncbi.nlm.nih.gov/13470708
unhealthy, 59 years
n = 1
Health Status: unhealthy
Age Group: 59 years
Sex: F
Population Size: 1
Sources:
https://pubmed.ncbi.nlm.nih.gov/13470708
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer
UGT1A1
204

UGT1A3
84

MRP2
383

OATP1B1
788
UGT1A1
418

UGT1A3
422
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
MRP2
475
 no
OATP1B1
803
 no
UGT1A1
254
 weak [IC50 3000 uM]
UGT1A3
93
 weak [IC50 3100 uM]
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
UGT1A1
418
 yes
UGT1A3
422
 yes
Sourcing

Sourcing

Vendor/AggregatorIDURL
ChemIDplus
855165138
https://chem.nlm.nih.gov/chemidplus/id/0855165138
EPA DSSTox
DTXSID40234726
https://comptox.epa.gov/dashboard/DTXSID40234726
PubChem
71300650
https://pubchem.ncbi.nlm.nih.gov/compound/71300650
Wikidata
Q27285387
PubMed

PubMed

TitleDatePubMed
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

JPH01249745A
8

Sample Use Guides

In Vivo Use Guide
The mean dose was 300 mg/day for a mean duration of 3-4 months
Route of Administration: Unknown
In Vitro Use Guide
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 11:53:04 UTC 2023
Edited
by admin
on Sat Dec 16 11:53:04 UTC 2023
Record UNII
ZDW83QKF9H
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CINCHOPHEN SODIUM DIHYDRATE
Common Name English
4-QUINOLINECARBOXYLIC ACID, 2-PHENYL-, SODIUM SALT, HYDRATE (1:1:2)
Systematic Name English
4-QUINOLINECARBOXYLIC ACID, 2-PHENYL-, SODIUM SALT, DIHYDRATE
Systematic Name English
Code System Code Type Description
CAS
114813-65-9
Created by admin on Sat Dec 16 11:53:04 UTC 2023 , Edited by admin on Sat Dec 16 11:53:04 UTC 2023
PRIMARY
PUBCHEM
44725916
Created by admin on Sat Dec 16 11:53:04 UTC 2023 , Edited by admin on Sat Dec 16 11:53:04 UTC 2023
PRIMARY
FDA UNII
ZDW83QKF9H
Created by admin on Sat Dec 16 11:53:04 UTC 2023 , Edited by admin on Sat Dec 16 11:53:04 UTC 2023
PRIMARY
Related Record Type Details
Structure of CINCHOPHEN
PARENT -> SALT/SOLVATE
Structure of CINCHOPHEN SODIUM
ANHYDROUS->SOLVATE
NIH
NCATS
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