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Details

Stereochemistry ACHIRAL
Molecular Formula C9H7NO.C6H8O7
Molecular Weight 337.2815
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 8-HYDROXYQUINOLINE CITRATE

SMILES

OC1=CC=CC2=C1N=CC=C2.OC(=O)CC(O)(CC(O)=O)C(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

Description

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

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
TRIMOSAN
Primary
Unknown
Curative
Unknown

Drug as perpetrator​

Drug as victim

Tox targets

PubMed

Sample Use Guides

In Vivo Use Guide
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.