Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C20H26N2O2 |
Molecular Weight | 326.4326 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 5 / 5 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC[C@H]1C[N@@]2CC[C@H]1C[C@@H]2[C@@H](O)C3=C4C=C(OC)C=CC4=NC=C3
InChI
InChIKey=LJOQGZACKSYWCH-LHHVKLHASA-N
InChI=1S/C20H26N2O2/c1-3-13-12-22-9-7-14(13)10-19(22)20(23)16-6-8-21-18-5-4-15(24-2)11-17(16)18/h4-6,8,11,13-14,19-20,23H,3,7,9-10,12H2,1-2H3/t13-,14-,19+,20-/m0/s1
Molecular Formula | C20H26N2O2 |
Molecular Weight | 326.4326 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 4 / 4 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
DescriptionCurator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/24068450
http://www.ajtmh.org/content/s1-12/6/473.full.pdf
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/24068450
http://www.ajtmh.org/content/s1-12/6/473.full.pdf
Hydroquinidine is a pharmaceutical agent that acts as a class I antiarrhythmic agent (Ia) in the heart. Hydroquinidine is a d-rotatory alkaloid derived from cinchiona bark. It is closely related to quinidine, differing from the latter alkaloid only in containing two more atoms of hydrogen in the molecule. The drug causes increased action potential duration, as well as a prolonged QT interval. It is not approved by FDA, but marketed in Spain, France, Italy and Pakistan under the brand names Lentoquine, Sérécor LP, Idrochinidina Lirca and Austacute, respectively. Like all other class I antiarrhythmic agents, Hydroquinidine primarily works by blocking the fast inward sodium current (INa). Hydroquinidine is also used for the treatment of Malaria.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL364 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22869567 |
32.0 nM [IC50] | ||
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Lentoquine Approved UseIndications: arrhythmias |
|||
Curative | Unknown Approved UseUnknown |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
0.74 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7095920/ |
300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered: |
HYDROQUINIDINE unknown | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
0.55 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7095920/ |
500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered: |
HYDROQUINIDINE unknown | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
10.8 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7095920/ |
300 mg single, intravenous dose: 300 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
HYDROQUINIDINE unknown | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
150 mg 3 times / day multiple, oral Studied dose Dose: 150 mg, 3 times / day Route: oral Route: multiple Dose: 150 mg, 3 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
Disc. AE: Nausea, Epigastric pain... AEs leading to discontinuation/dose reduction: Nausea (25%) Sources: Epigastric pain (25%) |
738 mg 1 times / day multiple, oral Studied dose Dose: 738 mg, 1 times / day Route: oral Route: multiple Dose: 738 mg, 1 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
Disc. AE: Gastrointestinal disorder, Photophobia... AEs leading to discontinuation/dose reduction: Gastrointestinal disorder (20%) Sources: Photophobia (4%) Photosensitivity (2%) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Epigastric pain | 25% Disc. AE |
150 mg 3 times / day multiple, oral Studied dose Dose: 150 mg, 3 times / day Route: oral Route: multiple Dose: 150 mg, 3 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
Nausea | 25% Disc. AE |
150 mg 3 times / day multiple, oral Studied dose Dose: 150 mg, 3 times / day Route: oral Route: multiple Dose: 150 mg, 3 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
Photosensitivity | 2% Disc. AE |
738 mg 1 times / day multiple, oral Studied dose Dose: 738 mg, 1 times / day Route: oral Route: multiple Dose: 738 mg, 1 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
Gastrointestinal disorder | 20% Disc. AE |
738 mg 1 times / day multiple, oral Studied dose Dose: 738 mg, 1 times / day Route: oral Route: multiple Dose: 738 mg, 1 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
Photophobia | 4% Disc. AE |
738 mg 1 times / day multiple, oral Studied dose Dose: 738 mg, 1 times / day Route: oral Route: multiple Dose: 738 mg, 1 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
yes [Inhibition 10 uM] | ||||
yes [Inhibition 10 uM] | ||||
yes [Ki 0.013 uM] | ||||
yes [Km 100 uM] |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 8 | 12 |
no |
PubMed
Title | Date | PubMed |
---|---|---|
[Hepatitis caused by quinidine. Study of a case and review of the literature]. | 1986 Mar |
|
Safety and effectiveness of oral quinidine in cardioversion of persistent atrial fibrillation. | 2001 Dec |
|
[Adverse drug reactions in three older patients, even without changes in medication]. | 2003 Mar 29 |
|
The relationship of physico-chemical properties and structure to the differential antiplasmodial activity of the cinchona alkaloids. | 2003 Sep 1 |
|
The molecular phenotype of endocapillary proliferation: novel therapeutic targets for IgA nephropathy. | 2014 |
Patents
Sample Use Guides
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/1933143
Curator's Comment: Recordings were made from acutely dissociated melanotrophs, obtained following the enzymatic treatment and
mechanical disruption of the neuro-intermediate lobe of the
pituitary gland of the adult male rat
Halfmaximal inhibition of IK(f) at o mV occurred with 23 + 7.8uM
hydroquinidine
Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 18:47:52 GMT 2025
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Mon Mar 31 18:47:52 GMT 2025
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Record UNII |
8P68XPY4HG
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Record Status |
Validated (UNII)
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C01BA13
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m6113
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27220
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215-862-5
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Related Record | Type | Details | ||
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SALT/SOLVATE -> PARENT |
Related Record | Type | Details | ||
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PARENT -> METABOLITE |
URINE
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Related Record | Type | Details | ||
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ACTIVE MOIETY |