DEBRISOQUIN

Details

Stereochemistry	ACHIRAL
Molecular Formula	C10H13N3
Molecular Weight	175.2303
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

NC(=N)N1CCC2=CC=CC=C2C1

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	175.2303
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2601584 | https://www.ncbi.nlm.nih.gov/pubmed/8471132 | https://www.ncbi.nlm.nih.gov/pubmed/19102711

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.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Cytochrome P450 2D6 62 Target ID: CHEMBL289 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8911874 \| https://www.ncbi.nlm.nih.gov/pubmed/17273835 \| https://www.ncbi.nlm.nih.gov/pubmed/19102711	Substrate 661
Monoamine oxidase A 52 Target ID: CHEMBL1951 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2601584	Inhibitor 8504	0.5 µM [IC50]
Monoamine oxidase B 75 Target ID: CHEMBL2039 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2601584	Inhibitor 8504	8.8 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Hypertension 575 Sources: https://www.ncbi.nlm.nih.gov/pubmed/5296799 http://dtb.bmj.com/content/5/11/44 https://www.ncbi.nlm.nih.gov/pubmed/14286208 https://jamanetwork.com/journals/jamainternalmedicine/article-abstract/575083?redirect=true	Primary		Approved 8583	DECLINAX Approved Use Hypertension

F_unbound

Value	Dose	Co-administered	Analyte	Population
75% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7378259/			DEBRISOQUIN plasma	Homo sapiens

Doses

Dose	Population	Adverse events
10 mg single, oral Studied dose Dose: 10 mg Route: oral Route: single Dose: 10 mg Sources: https://pubmed.ncbi.nlm.nih.gov/3168394/	healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/3168394/	Sources: https://pubmed.ncbi.nlm.nih.gov/3168394/
69 mg single, oral Studied dose Dose: 69 mg Route: oral Route: single Dose: 69 mg Sources: https://jamanetwork.com/journals/jamainternalmedicine/article-abstract/576442	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: unknown Food Status: UNKNOWN Sources: https://jamanetwork.com/journals/jamainternalmedicine/article-abstract/576442	Sources: https://jamanetwork.com/journals/jamainternalmedicine/article-abstract/576442

PubMed

Title	Date	PubMed
Influence of chronic renal failure on stereoselective metoprolol metabolism in hypertensive patients.	2005-12	16291718
Metabolism of N-hydroxyguanidines (N-hydroxydebrisoquine) in human and porcine hepatocytes: reduction and formation of glucuronides.	2005-10	16033947
Cytochrome P450 mRNA expression in peripheral blood lymphocytes as a predictor of enzyme induction.	2005-09	16041547
Effect of age and postoperative time on cytochrome p450 enzyme activity following liver transplantation.	2005-06	15901748
Functional analysis of CYP2D6.31 variant: homology modeling suggests possible disruption of redox partner interaction by Arg440His substitution.	2005-05-01	15726636
In vivo effects of goldenseal, kava kava, black cohosh, and valerian on human cytochrome P450 1A2, 2D6, 2E1, and 3A4/5 phenotypes.	2005-05	15900287
[Assessment of CYP2D6 activity as a form of optimizing antidepressant therapy].	2005-03-23	15779673
[CYP 2D6 activity profile among patients with depression].	2005-03-23	15779672
Determination of cytochrome P450 2D6 (CYP2D6) gene copy number by real-time quantitative PCR.	2005	16192683
The AGNP-TDM Expert Group Consensus Guidelines: focus on therapeutic monitoring of antidepressants.	2005	16156382
Clinical assessment of effects of botanical supplementation on cytochrome P450 phenotypes in the elderly: St John's wort, garlic oil, Panax ginseng and Ginkgo biloba.	2005	15974642
Determination of debrisoquine and 4-hydroxydebrisoquine by high-performance liquid chromatography: application to the evaluation of CYP2D6 genotype and debrisoquine metabolic ratio relationship.	2005	15843230
Influence of phenylalanine 120 on cytochrome P450 2D6 catalytic selectivity and regiospecificity: crucial role in 7-methoxy-4-(aminomethyl)-coumarin metabolism.	2004-12-01	15498516
Genetics in melanoma.	2004-12	15609895
Bioequivalence revisited: influence of age and sex on CYP enzymes.	2004-12	15592333
Assessment of in vivo CYP2D6 activity: differential sensitivity of commonly used probes to urine pH.	2004-12	15545311
The roles of amino acid residues at positions 43 and 45 in microsomal contents and enzymatic functions of rat CYP2D1 and CYP2D2.	2004-11-12	15474473
In vivo assessment of botanical supplementation on human cytochrome P450 phenotypes: Citrus aurantium, Echinacea purpurea, milk thistle, and saw palmetto.	2004-11	15536458
A case report of a poor metabolizer of CYP2D6 presented with unusual responses to nortriptyline medication.	2004-10	15483356
Fatal intoxication cases: cytochrome P450 2D6 and 2C19 genotype distributions.	2004-10	15349706
Genetic polymorphisms of hormone-related genes and prostate cancer risk in the Japanese population.	2004-08-28	15330195
The role of cytochrome P450 enzymes in the metabolism of risperidone and its clinical relevance for drug interactions.	2004-08	15270204
Assessment of drug-drug interaction potential of enfuvirtide in human immunodeficiency virus type 1-infected patients.	2004-06	15179410
Relationship between Type A and B personality and debrisoquine hydroxylation capacity.	2004-06	15151524
Polymorphic cytochrome P450 2D6: humanized mouse model and endogenous substrates.	2004-05	15237854
Ethnic differences in genetic polymorphisms of CYP2D6, CYP2C19, CYP3As and MDR1/ABCB1.	2004-04	15499174
Relationship between haloperidol plasma concentration, debrisoquine metabolic ratio, CYP2D6 and CYP2C9 genotypes in psychiatric patients.	2004-03	15048614
Pharmacokinetic and pharmacodynamic assessment of a five-probe metabolic cocktail for CYPs 1A2, 3A4, 2C9, 2D6 and 2E1.	2004-02	14748815
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	15529418
Altered distribution of the debrisoquine oxidative phenotypes in children with type 1 diabetes mellitus.	2004	14726620
CYP1A1 and CYP2D6 polymorphism and risk of lung cancer in a North Indian population.	2003-11-07	14602525
Polymorphisms in the CYP1B1 gene are associated with increased risk of prostate cancer.	2003-10-20	14562027
The hepatic and intestinal metabolic activities of P450 in rats with surgery- and drug-induced renal dysfunction.	2003-10	14620512
Metabolism of citalopram enantiomers in CYP2C19/CYP2D6 phenotyped panels of healthy Swedes.	2003-10	12968986
CSF taurine level is influenced by plasma cholesterol and the CYP2D6 phenotype.	2003-10	12957331
Interferon-beta treatment in patients with multiple sclerosis does not alter CYP2C19 or CYP2D6 activity.	2003-09	12919185
Effect of ketoconazole on venlafaxine plasma concentrations in extensive and poor metabolisers of debrisoquine.	2003-09	12898080
Disposition of debrisoquine and nortriptyline in Korean subjects in relation to CYP2D6 genotypes, and comparison with Caucasians.	2003-06	12814461
The Karolinska cocktail for phenotyping of five human cytochrome P450 enzymes.	2003-06	12811361
Stereoselective metabolism of metoprolol: enantioselectivity of alpha-hydroxymetoprolol in plasma and urine.	2003-06	12774293
Cytochrome P450 expression and testosterone metabolism in the liver of deer.	2003-05-01	12679052
Quinine 3-hydroxylation as a biomarker reaction for the activity of CYP3A4 in man.	2003-05	12743670
Coordinated intrahepatic and extrahepatic regulation of cytochrome p4502D6 in healthy subjects and in patients after liver transplantation.	2003-05	12732845
Thioridazine steady-state plasma concentrations are influenced by tobacco smoking and CYP2D6, but not by the CYP2C9 genotype.	2003-05	12682803
Cytochrome P450 in vitro reaction phenotyping: a re-evaluation of approaches used for P450 isoform identification.	2003-04	12642457
Role of the smoking-induced cytochrome P450 (CYP)1A2 and polymorphic CYP2D6 in steady-state concentration of olanzapine.	2003-04	12640212
Interaction of serum proteins with CYP isoforms in human liver microsomes: inhibitory effects of human and bovine albumin, alpha-globulins, alpha-1-acid glycoproteins and gamma-globulins on CYP2C19 and CYP2D6.	2003-03-14	12597994
Effect of hepatic impairment on the pharmacokinetics of atomoxetine and its metabolites.	2003-03	12621383
Alteration in catalytic properties of human CYP2D6 caused by substitution of glycine-42 with arginine, lysine and glutamic acid.	2003	15618721
Factors predisposing to postural hypotensive symptoms in the treatment of high blood pressure.	1975-10	127594

Patents

Sample Use Guides

In Vivo Use Guide

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 `Wed Apr 02 06:51:50 GMT 2025` Edited by `admin` on `Wed Apr 02 06:51:50 GMT 2025`
Record UNII	X31CDK040E
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

DEBRISOQUIN

Common Name

English

DEBRISOQUINE

Preferred Name

English

Debrisoquine [WHO-DD]

Common Name

English

2(1H)-ISOQUINOLINECARBOXIMIDAMIDE, 3,4-DIHYDRO-

Systematic Name

English

DEBRISOQUIN [MI]

Common Name

English

debrisoquine [INN]

Common Name

English

3,4-DIHYDRO-2(1H)-ISOQUINOLINECARBOXAMIDINE

Systematic Name

English

Classification Tree Code System Code

WHO-VATC

QC02CC04