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Details

Stereochemistry ACHIRAL
Molecular Formula C10H13N3
Molecular Weight 175.2307
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DEBRISOQUIN

SMILES

c1ccc2CN(CCc2c1)C(=N)N

InChI

InChIKey=JWPGJSVJDAJRLW-UHFFFAOYSA-N
InChI=1S/C10H13N3/c11-10(12)13-6-5-8-3-1-2-4-9(8)7-13/h1-4H,5-7H2,(H3,11,12)

HIDE SMILES / InChI

Molecular Formula C10H13N3
Molecular Weight 175.2307
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Debrisoquin is an antihypertensive drug having guanethidine-like properties, which inhibits monoamine oxidase (MAO) and does not enter the brain. Debrisoquine was used for the treatment of hypertension. Debrisoquine hydroxylation phenotype has been the most used test in humans to evaluate CYP2D6 activity. Two debrisoquine hydroxylation phenotypes have been described: poor and extensive metabolizers. A group with a very low debrisoquine metabolic ratio within the extensive metabolizers, named ultrarapid metabolizers, has also been distinguished. This CYP2D6 variability can be for a large part alternatively determined by genotyping, which appears to be of clinical importance given CYP2D6 involvement in the metabolism of a large number of commonly prescribed drugs.

Originator

Curator's Comment:: # Hoffmann La Roche

Approval Year

PubMed

PubMed

TitleDatePubMed
Factors predisposing to postural hypotensive symptoms in the treatment of high blood pressure.
1975 Oct
Interindividual variations in levels and activities of cytochrome P-450 in liver microsomes of Chinese subjects.
2001 Mar
Gateways to Clinical Trials.
2002 Apr
Evaluation of approach to predict the contribution of multiple cytochrome P450s in drug metabolism using relative activity factor: effects of the differences in expression levels of NADPH-cytochrome P450 reductase and cytochrome b(5) in the expression system and the differences in the marker activities.
2002 Apr
QTc interval lengthening is related to CYP2D6 hydroxylation capacity and plasma concentration of thioridazine in patients.
2002 Dec
The pharmacokinetics of ketobemidone are not affected by CYP2D6 or CYP2C19 phenotype.
2002 Feb
Effect of chronic disulfiram administration on the activities of CYP1A2, CYP2C19, CYP2D6, CYP2E1, and N-acetyltransferase in healthy human subjects.
2002 Feb
Diclofenac does not interact with codeine metabolism in vivo: a study in healthy volunteers.
2002 Feb 27
The African-specific CYP2D617 allele encodes an enzyme with changed substrate specificity.
2002 Jan
Characterization of cytochrome P450 2D6 alleles using the Invader system.
2002 Jun
The effect of fluoxetine on the pharmacokinetics and safety of risperidone in psychotic patients.
2002 Mar
Low daily 10-mg and 20-mg doses of fluvoxamine inhibit the metabolism of both caffeine (cytochrome P4501A2) and omeprazole (cytochrome P4502C19).
2002 Mar
Characterization of cytochrome P450 2D6.1 (CYP2D6.1), CYP2D6.2, and CYP2D6.17 activities toward model CYP2D6 substrates dextromethorphan, bufuralol, and debrisoquine.
2002 May
Relationship between risperidone and 9-hydroxy-risperidone plasma concentrations and CYP2D6 enzyme activity in psychiatric patients.
2002 Nov
New allelic arrangement CYP2D6*36 x 2 found in a Japanese poor metabolizer of debrisoquine.
2002 Nov
The molecular and enzyme kinetic basis for the diminished activity of the cytochrome P450 2D6.17 (CYP2D6.17) variant. Potential implications for CYP2D6 phenotyping studies and the clinical use of CYP2D6 substrate drugs in some African populations.
2002 Nov 1
Is cytochrome P450 CYP2D activity present in pig liver?
2002 Oct
Effect of nortriptyline and paroxetine on CYP2D6 activity in depressed elderly patients.
2002 Oct
Cytochrome P450 phenotypic ratios for predicting herb-drug interactions in humans.
2002 Sep
Catalytic specificity of CYP2D isoforms in rat and human.
2002 Sep
Diversity in the oxidation of substrates by cytochrome P450 2D6: lack of an obligatory role of aspartate 301-substrate electrostatic bonding.
2002 Sep 10
Role of the smoking-induced cytochrome P450 (CYP)1A2 and polymorphic CYP2D6 in steady-state concentration of olanzapine.
2003 Apr
The relative contribution of monoamine oxidase and cytochrome p450 isozymes to the metabolic deamination of the trace amine tryptamine.
2003 Feb
Debrisoquine hydroxylase gene polymorphism (CYP2D6*4) in dementia with Lewy bodies.
2003 Jan
Essential requirements for substrate binding affinity and selectivity toward human CYP2 family enzymes.
2003 Jan 1
Enantioselective determination of metoprolol acidic metabolite in plasma and urine using liquid chromatography chiral columns: applications to pharmacokinetics.
2003 Jan 15
The Karolinska cocktail for phenotyping of five human cytochrome P450 enzymes.
2003 Jun
Effect of hepatic impairment on the pharmacokinetics of atomoxetine and its metabolites.
2003 Mar
Quinine 3-hydroxylation as a biomarker reaction for the activity of CYP3A4 in man.
2003 May
Coordinated intrahepatic and extrahepatic regulation of cytochrome p4502D6 in healthy subjects and in patients after liver transplantation.
2003 May
Thioridazine steady-state plasma concentrations are influenced by tobacco smoking and CYP2D6, but not by the CYP2C9 genotype.
2003 May
The hepatic and intestinal metabolic activities of P450 in rats with surgery- and drug-induced renal dysfunction.
2003 Oct
Metabolism of citalopram enantiomers in CYP2C19/CYP2D6 phenotyped panels of healthy Swedes.
2003 Oct
CSF taurine level is influenced by plasma cholesterol and the CYP2D6 phenotype.
2003 Oct
Polymorphisms in the CYP1B1 gene are associated with increased risk of prostate cancer.
2003 Oct 20
Interferon-beta treatment in patients with multiple sclerosis does not alter CYP2C19 or CYP2D6 activity.
2003 Sep
Effect of ketoconazole on venlafaxine plasma concentrations in extensive and poor metabolisers of debrisoquine.
2003 Sep
CYP1A1 and CYP2D6 polymorphism and risk of lung cancer in a North Indian population.
2003 Sep-Oct
Rapid determination of five probe drugs and their metabolites in human plasma and urine by liquid chromatography/tandem mass spectrometry: application to cytochrome P450 phenotyping studies.
2004
Altered distribution of the debrisoquine oxidative phenotypes in children with type 1 diabetes mellitus.
2004
Ethnic differences in genetic polymorphisms of CYP2D6, CYP2C19, CYP3As and MDR1/ABCB1.
2004 Apr
Pharmacokinetic and pharmacodynamic assessment of a five-probe metabolic cocktail for CYPs 1A2, 3A4, 2C9, 2D6 and 2E1.
2004 Feb
Relationship between Type A and B personality and debrisoquine hydroxylation capacity.
2004 Jun
Relationship between haloperidol plasma concentration, debrisoquine metabolic ratio, CYP2D6 and CYP2C9 genotypes in psychiatric patients.
2004 Mar
The roles of amino acid residues at positions 43 and 45 in microsomal contents and enzymatic functions of rat CYP2D1 and CYP2D2.
2004 Nov 12
The AGNP-TDM Expert Group Consensus Guidelines: focus on therapeutic monitoring of antidepressants.
2005
Determination of debrisoquine and 4-hydroxydebrisoquine by high-performance liquid chromatography: application to the evaluation of CYP2D6 genotype and debrisoquine metabolic ratio relationship.
2005
Influence of chronic renal failure on stereoselective metoprolol metabolism in hypertensive patients.
2005 Dec
Effect of age and postoperative time on cytochrome p450 enzyme activity following liver transplantation.
2005 Jun
Functional analysis of CYP2D6.31 variant: homology modeling suggests possible disruption of redox partner interaction by Arg440His substitution.
2005 May 1
Patents

Patents

Sample Use Guides

Adult: 10-20 mg once-bid, increased by 10-20 mg every 3 or 4 days according to severity of condition. Maintenance: 20-120 mg daily. Max Dosage: ≥300 mg daily. More: https://www.ndrugs.com/?s=declinax
Route of Administration: Oral
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Sat Jun 26 10:01:36 UTC 2021
Edited
by admin
on Sat Jun 26 10:01:36 UTC 2021
Record UNII
X31CDK040E
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DEBRISOQUIN
MI  
Common Name English
2(1H)-ISOQUINOLINECARBOXIMIDAMIDE, 3,4-DIHYDRO-
Systematic Name English
DEBRISOQUIN [MI]
Common Name English
DEBRISOQUINE [WHO-DD]
Common Name English
DEBRISOQUINE [INN]
Common Name English
3,4-DIHYDRO-2(1H)-ISOQUINOLINECARBOXAMIDINE
Systematic Name English
DEBRISOQUINE
INN   WHO-DD  
INN  
Official Name English
Classification Tree Code System Code
WHO-VATC QC02CC04
Created by admin on Sat Jun 26 10:01:36 UTC 2021 , Edited by admin on Sat Jun 26 10:01:36 UTC 2021
NCI_THESAURUS C29713
Created by admin on Sat Jun 26 10:01:36 UTC 2021 , Edited by admin on Sat Jun 26 10:01:36 UTC 2021
WHO-ATC C02CC04
Created by admin on Sat Jun 26 10:01:36 UTC 2021 , Edited by admin on Sat Jun 26 10:01:36 UTC 2021
Code System Code Type Description
RXCUI
3118
Created by admin on Sat Jun 26 10:01:36 UTC 2021 , Edited by admin on Sat Jun 26 10:01:36 UTC 2021
PRIMARY RxNorm
DRUG CENTRAL
788
Created by admin on Sat Jun 26 10:01:36 UTC 2021 , Edited by admin on Sat Jun 26 10:01:36 UTC 2021
PRIMARY
MERCK INDEX
M4116
Created by admin on Sat Jun 26 10:01:36 UTC 2021 , Edited by admin on Sat Jun 26 10:01:36 UTC 2021
PRIMARY Merck Index
PUBCHEM
2966
Created by admin on Sat Jun 26 10:01:36 UTC 2021 , Edited by admin on Sat Jun 26 10:01:36 UTC 2021
PRIMARY
DRUG BANK
DB04840
Created by admin on Sat Jun 26 10:01:36 UTC 2021 , Edited by admin on Sat Jun 26 10:01:36 UTC 2021
PRIMARY
CAS
1131-64-2
Created by admin on Sat Jun 26 10:01:36 UTC 2021 , Edited by admin on Sat Jun 26 10:01:36 UTC 2021
PRIMARY
NCI_THESAURUS
C75053
Created by admin on Sat Jun 26 10:01:36 UTC 2021 , Edited by admin on Sat Jun 26 10:01:36 UTC 2021
PRIMARY
INN
1968
Created by admin on Sat Jun 26 10:01:36 UTC 2021 , Edited by admin on Sat Jun 26 10:01:36 UTC 2021
PRIMARY
ECHA (EC/EINECS)
214-470-1
Created by admin on Sat Jun 26 10:01:36 UTC 2021 , Edited by admin on Sat Jun 26 10:01:36 UTC 2021
PRIMARY
EVMPD
SUB06928MIG
Created by admin on Sat Jun 26 10:01:36 UTC 2021 , Edited by admin on Sat Jun 26 10:01:36 UTC 2021
PRIMARY
FDA UNII
X31CDK040E
Created by admin on Sat Jun 26 10:01:36 UTC 2021 , Edited by admin on Sat Jun 26 10:01:36 UTC 2021
PRIMARY
EPA CompTox
1131-64-2
Created by admin on Sat Jun 26 10:01:36 UTC 2021 , Edited by admin on Sat Jun 26 10:01:36 UTC 2021
PRIMARY
WIKIPEDIA
DEBRISOQUINE
Created by admin on Sat Jun 26 10:01:36 UTC 2021 , Edited by admin on Sat Jun 26 10:01:36 UTC 2021
PRIMARY
ChEMBL
CHEMBL169901
Created by admin on Sat Jun 26 10:01:36 UTC 2021 , Edited by admin on Sat Jun 26 10:01:36 UTC 2021
PRIMARY
MESH
D003647
Created by admin on Sat Jun 26 10:01:36 UTC 2021 , Edited by admin on Sat Jun 26 10:01:36 UTC 2021
PRIMARY
Related Record Type Details
METABOLIC ENZYME -> SUBSTRATE
SALT/SOLVATE -> PARENT
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ACTIVE MOIETY