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Details

Stereochemistry ACHIRAL
Molecular Formula C9H7NO.C6H8O7
Molecular Weight 337.2821
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 8-HYDROXYQUINOLINE CITRATE

SMILES

c1cc2cccnc2c(c1)O.C(C(=O)O)C(CC(=O)O)(C(=O)O)O

InChI

InChIKey=GTOQWWQKBBZILU-UHFFFAOYSA-N
InChI=1S/C9H7NO.C6H8O7/c11-8-5-1-3-7-4-2-6-10-9(7)8;7-3(8)1-6(13,5(11)12)2-4(9)10/h1-6,11H;13H,1-2H2,(H,7,8)(H,9,10)(H,11,12)

HIDE SMILES / InChI

Molecular Formula C6H8O7
Molecular Weight 192.1238
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C9H7NO
Molecular Weight 145.1583
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 https://www.ncbi.nlm.nih.gov/pubmed/25935783 | https://www.ams.usda.gov/sites/default/files/media/Hydroxyquinoline%20Sulfate%20TR.pdf | https://www.ncbi.nlm.nih.gov/pubmed/13960592

8-Hydroxyquinoline is is a heterocyclic phenol, exhibiting antiseptic, disinfectant and pesticide properties. It is used to prevent and treat vaginal bacterial infections, but the efficacy was not proven in clinical trial. 8-Hydroxyquinoline is used in over-the-counter remedies for diaper rash and oral health care. Its use for veterinary treatment of bacterial an skin infections is not approved by FDA. 8-Hydroxyquinoline acts by inhibition of RNA synthesis and DNA replication by chelating the dissociable cations Mn2+ and Mg2+.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
TRIMOSAN

Approved Use

Increasing and maintaining vaginal acidity in combination with other medicines.
Primary
Unknown

Approved Use

Unknown
Curative
Unknown

Approved Use

8-Hydroxyquinoline was used in veterinary for treatment of poultry diseases, for treatment of intestinal infections caused by bacteria or protozoa, for bacterial and fungal skin infections.
PubMed

PubMed

TitleDatePubMed
Antimicrobial activity of 8-quinolinol, its salts with salicylic acid and 3-hydroxy-2-naphthoic acid, and the respective copper (II) chelates in liquid culture.
1963 Jan
8-hydroxyquinoline inhibition of DNA synthesis and intragenic recombination during yeast meiosis.
1978 Jun 14
The effect of hydroxyquinoline-based gel on pessary-associated bacterial vaginosis: a multicenter randomized controlled trial.
2015 Nov
Patents

Sample Use Guides

Relagard vaginal gel: attach the enclosed applicator to the tube of Relagard by screwing it on clockwise. Squeeze the tube to force the contents into the barrel until the applicator is filled. Detach the applicator from the tube and gently insert it into the vagina as far as it will comfortably go. Press the plunger and deposit the medication until the barrel of the applicator is emptied. For treatment of bacterial and protozoal infections is administered to cattle topically or orally.
Route of Administration: Other
In Vitro Use Guide
Complete inhibition of sporulation was observed in two strains of Saccharomyces cerevisiae to which 8-hydroxyquinoline was added at a final concentration of 5 microgram/ml during the initial 4 to 6 h of sporulation. The cells were most sensitive to the inhibitor during 4 to 6 interval beginning at approximately 2 h (T2). Its addition during that interval resulted in 70 to 80% lethality in strain 4579 and about 40% in API at T24. When present from T0 onward, 5 microgram/ml of 8-hydroxyquinoline severely inhibited premeiotic DNA replication and reduced the frequency of intragenic recombination at the ade 2 and leu 2 loci by 70 and 100%, respectively, relative to control cultures which did not have the inhibitor present.
Substance Class Chemical
Created
by admin
on Sat Jun 26 12:27:36 UTC 2021
Edited
by admin
on Sat Jun 26 12:27:36 UTC 2021
Record UNII
K522O2O40B
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
8-HYDROXYQUINOLINE CITRATE
Systematic Name English
8-QUINOLINOL, 2-HYDROXY-1,2,3-PROPANETRICARBOXYLATE (1:1)
Systematic Name English
EPA PESTICIDE CHEMICAL CODE 059802
Code English
8-QUINOLINOL, 2-HYDROXY-1,2,3-PROPANETRICARBOXYLATE (1:1) (SALT)
Systematic Name English
8-HQC
Common Name English
8-QUINOLINOL, CITRATE
Systematic Name English
8-HYDROXYQUINOLINIUM CITRATE
Common Name English
2-HYDROXYPROPANE-1,2,3-TRICARBOXYLIC ACID, QUINOLIN-8-OL
Common Name English
CITROXIN
Brand Name English
J422.611I
Code English
8-QUINOLINOL, CITRATE (1:1) (SALT)
Common Name English
Classification Tree Code System Code
EPA PESTICIDE CODE 59802
Created by admin on Sat Jun 26 12:27:37 UTC 2021 , Edited by admin on Sat Jun 26 12:27:37 UTC 2021
Code System Code Type Description
CAS
102928-43-8
Created by admin on Sat Jun 26 12:27:37 UTC 2021 , Edited by admin on Sat Jun 26 12:27:37 UTC 2021
NON-SPECIFIC STOICHIOMETRY
FDA UNII
K522O2O40B
Created by admin on Sat Jun 26 12:27:37 UTC 2021 , Edited by admin on Sat Jun 26 12:27:37 UTC 2021
PRIMARY
DRUG BANK
DBSALT002680
Created by admin on Sat Jun 26 12:27:37 UTC 2021 , Edited by admin on Sat Jun 26 12:27:37 UTC 2021
PRIMARY
ECHA (EC/EINECS)
205-136-6
Created by admin on Sat Jun 26 12:27:37 UTC 2021 , Edited by admin on Sat Jun 26 12:27:37 UTC 2021
PRIMARY
EPA CompTox
134-30-5
Created by admin on Sat Jun 26 12:27:37 UTC 2021 , Edited by admin on Sat Jun 26 12:27:37 UTC 2021
PRIMARY
PUBCHEM
61080
Created by admin on Sat Jun 26 12:27:37 UTC 2021 , Edited by admin on Sat Jun 26 12:27:37 UTC 2021
PRIMARY
CAS
134-30-5
Created by admin on Sat Jun 26 12:27:37 UTC 2021 , Edited by admin on Sat Jun 26 12:27:37 UTC 2021
PRIMARY
CAS
52216-56-5
Created by admin on Sat Jun 26 12:27:37 UTC 2021 , Edited by admin on Sat Jun 26 12:27:37 UTC 2021
ALTERNATIVE
Related Record Type Details
PARENT -> SALT/SOLVATE
PARENT -> SALT/SOLVATE