DEBRISOQUIN SULFATE

Details

Stereochemistry	ACHIRAL
Molecular Formula	2C10H13N3.H2O4S
Molecular Weight	448.539
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OS(O)(=O)=O.NC(=N)N1CCC2=CC=CC=C2C1.NC(=N)N3CCC4=CC=CC=C4C3

InChI

InChIKey=CAYGYVYWRIHZCQ-UHFFFAOYSA-N

InChI=1S/2C10H13N3.H2O4S/c2*11-10(12)13-6-5-8-3-1-2-4-9(8)7-13;1-5(2,3)4/h2*1-4H,5-7H2,(H3,11,12);(H2,1,2,3,4)

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

Molecular Formula	H2O4S
Molecular Weight	98.078
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 61 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 49 Target ID: CHEMBL1951 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2601584	Inhibitor 8297	0.5 µM [IC50]
Monoamine oxidase B 72 Target ID: CHEMBL2039 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2601584	Inhibitor 8297	8.8 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Hypertension 567 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 8429	DECLINAX Approved Use Hypertension

PubMed

Title	Date	PubMed
Letter: Dementia associated with clonidine therapy.	1975 Mar 15	1125640
Moving toward genetic profiling in patient care: the scope and rationale of pharmacogenetic/ecogenetic investigation.	2001 Apr	11259356
The CYP2D6 humanized mouse: effect of the human CYP2D6 transgene and HNF4alpha on the disposition of debrisoquine in the mouse.	2001 Dec	11723233
Food increases the bioavailability of tolterodine but not effective exposure.	2001 Mar	11269570
Interaction of plasma proteins with cytochromes P450 mediated metabolic reactions: inhibition by human serum albumin and alpha-globulins of the debrisoquine 4-hydroxylation (CYP2D) in liver microsomes of human, hamster and rat.	2001 Mar 8	11246175
An interaction between the cytochrome P450 probe substrates chlorzoxazone (CYP2E1) and midazolam (CYP3A).	2001 Nov	11736864
The Paton Prize Award. The discovery of the debrisoquine hydroxylation polymorphism: scientific and clinical impact and consequences.	2001 Nov 1	11713734
Debrisoquine 4-hydroxylase (CYP2D6) genetic polymorphisms and susceptibility to schizophrenia in Chinese patients from Taiwan.	2001 Sep	11702057
A study of the expression of the xenobiotic-metabolising cytochrome P450 proteins and of testosterone metabolism in bovine liver.	2001 Sep 1	11585060
QTc interval lengthening is related to CYP2D6 hydroxylation capacity and plasma concentration of thioridazine in patients.	2002 Dec	12503836
Effect of chronic disulfiram administration on the activities of CYP1A2, CYP2C19, CYP2D6, CYP2E1, and N-acetyltransferase in healthy human subjects.	2002 Feb	11851639
4-Hydroxylation of debrisoquine by human CYP1A1 and its inhibition by quinidine and quinine.	2002 Jun	12023534
Relationship between risperidone and 9-hydroxy-risperidone plasma concentrations and CYP2D6 enzyme activity in psychiatric patients.	2002 Nov	12518271
New allelic arrangement CYP2D6*36 x 2 found in a Japanese poor metabolizer of debrisoquine.	2002 Nov	12439227
Is cytochrome P450 CYP2D activity present in pig liver?	2002 Oct	12530471
Diversity in the oxidation of substrates by cytochrome P450 2D6: lack of an obligatory role of aspartate 301-substrate electrostatic bonding.	2002 Sep 10	12206675
Role of the smoking-induced cytochrome P450 (CYP)1A2 and polymorphic CYP2D6 in steady-state concentration of olanzapine.	2003 Apr	12640212
Essential requirements for substrate binding affinity and selectivity toward human CYP2 family enzymes.	2003 Jan 1	12464242
Disposition of debrisoquine and nortriptyline in Korean subjects in relation to CYP2D6 genotypes, and comparison with Caucasians.	2003 Jun	12814461
Coordinated intrahepatic and extrahepatic regulation of cytochrome p4502D6 in healthy subjects and in patients after liver transplantation.	2003 May	12732845
Metabolism of citalopram enantiomers in CYP2C19/CYP2D6 phenotyped panels of healthy Swedes.	2003 Oct	12968986
Polymorphisms in the CYP1B1 gene are associated with increased risk of prostate cancer.	2003 Oct 20	14562027
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
Genetics in melanoma.	2004 Dec	15609895
Pharmacokinetic and pharmacodynamic assessment of a five-probe metabolic cocktail for CYPs 1A2, 3A4, 2C9, 2D6 and 2E1.	2004 Feb	14748815
Relationship between Type A and B personality and debrisoquine hydroxylation capacity.	2004 Jun	15151524
Fatal intoxication cases: cytochrome P450 2D6 and 2C19 genotype distributions.	2004 Oct	15349706
The AGNP-TDM Expert Group Consensus Guidelines: focus on therapeutic monitoring of antidepressants.	2005	16156382
Effect of age and postoperative time on cytochrome p450 enzyme activity following liver transplantation.	2005 Jun	15901748
In vivo effects of goldenseal, kava kava, black cohosh, and valerian on human cytochrome P450 1A2, 2D6, 2E1, and 3A4/5 phenotypes.	2005 May	15900287
Functional analysis of CYP2D6.31 variant: homology modeling suggests possible disruption of redox partner interaction by Arg440His substitution.	2005 May 1	15726636

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 `Fri Dec 15 15:01:23 UTC 2023` Edited by `admin` on `Fri Dec 15 15:01:23 UTC 2023`
Record UNII	Q94064N9NW
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

DEBRISOQUIN SULFATE

Official Name

English

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

Systematic Name

English

3,4-Dihydro-2(1H)-isoquinolinecarboxamidine sulfate (2:1)

Systematic Name

English

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

Systematic Name

English

DEBRISOQUINE SULFATE [MART.]

Common Name

English

DEBRISOQUIN SULPHATE

Common Name

English

DEBRISOQUIN SULFATE [USAN]

Common Name

English

NSC-139330

Code

English

Debrisoquine sulfate [WHO-DD]

Common Name

English

RO 5-3307/1

Code

English

DEBRISOQUINE SULFATE

Common Name

English

RO-5-3307/1

Code

English

DEBRISOQUIN SULFATE [MI]

Common Name

English

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

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C29713