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
SMILES
OC1=C2N=CC=CC2=CC=C1.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)
| Molecular Formula | C9H7NO |
| Molecular Weight | 145.158 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| Molecular Formula | C6H8O7 |
| Molecular Weight | 192.1235 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
DescriptionSources: http://drugcentral.org/drugcard/3290/viewCurator'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
Sources: http://drugcentral.org/drugcard/3290/view
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
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: GO:0030026 Sources: https://www.ncbi.nlm.nih.gov/pubmed/13960592 |
|||
Target ID: GO:0010960 Sources: https://www.ncbi.nlm.nih.gov/pubmed/13960592 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | TRIMOSAN Approved UseIncreasing and maintaining vaginal acidity in combination with other medicines. |
|||
| Primary | Unknown Approved UseUnknown |
|||
| Curative | Unknown Approved Use8-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. |
Overview
| CYP3A4 | CYP2C9 | CYP2D6 | hERG |
|---|---|---|---|
OverviewOther
| Other Inhibitor | Other Substrate | Other Inducer |
|---|---|---|
Drug as perpetrator​
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
Page: 46.0 |
no | |||
Page: 46.0 |
no | |||
Page: 47.0 |
no | |||
Page: 15.0 |
yes [IC50 10.1206 uM] | |||
Page: 19.0 |
yes [IC50 25.4219 uM] | |||
Page: 9.0 |
yes [IC50 3.4703 uM] |
Drug as victim
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
| weak [Km 301 uM] | ||||
| weak [Km 494 uM] | ||||
| weak | ||||
| yes [Km 0.48 uM] | ||||
| yes [Km 6.5 uM] | ||||
| yes [Km 96 uM] | ||||
| yes |
Tox targets
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
Page: 47.0 |
PubMed
| Title | Date | PubMed |
|---|---|---|
| The effect of hydroxyquinoline-based gel on pessary-associated bacterial vaginosis: a multicenter randomized controlled trial. | 2015-11 |
|
| 8-hydroxyquinoline inhibition of DNA synthesis and intragenic recombination during yeast meiosis. | 1978-06-14 |
|
| 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. | 1963-01 |
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/353531
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
Edited
Mon Mar 31 22:32:36 GMT 2025
by
admin
on
Mon Mar 31 22:32:36 GMT 2025
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| Record UNII |
K522O2O40B
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| Record Status |
Validated (UNII)
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EPA PESTICIDE CODE |
59802
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102928-43-8
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NON-SPECIFIC STOICHIOMETRY | |||
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K522O2O40B
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DBSALT002680
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205-136-6
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DTXSID1040326
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61080
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134-30-5
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52216-56-5
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ALTERNATIVE |
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PARENT -> SALT/SOLVATE | |||
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PARENT -> SALT/SOLVATE |