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D1306

Sigma-Aldrich

Debrisoquine sulfate

Synonym(s):

3,4-Dihydro-2(1H)-isoquinolinecarboximidamide, Debrisoquin sulfate, Ro 5-33071

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About This Item

Linear Formula:
C20H26N6 · H2SO4
CAS Number:
581-88-4
Molecular Weight:
448.54
EC Number:
209-472-4
MDL number:
MFCD00153791
UNSPSC Code:
12352204
PubChem Substance ID:
24277710
NACRES:
NA.32

Assay

≥98% (TLC)

Quality Level

200

form

powder

mp

285 °C

solubility

H2O: 20 mg/mL (with heat)

storage temp.

room temp

SMILES string

OS(O)(=O)=O.NC(=N)N1CCc2ccccc2C1.NC(=N)N3CCc4ccccc4C3

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)

InChI key

CAYGYVYWRIHZCQ-UHFFFAOYSA-N

Gene Information

human ... SLC6A2(6530)

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Biochem/physiol Actions

Debrisoquine is an anti-hypertensive agent. It is metabolized by cytochrome P4502D6.

Substrates

A substrate for cytochrome P450 CYP2D6; an indicator for genetic polymorphism in cytochrome P450.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302

Precautionary Statements

P301 + P312 + P330

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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E Jacqz-Aigrain et al.
Biochemical pharmacology, 41(11), 1657-1663 (1991-06-01)
Interindividual variations of debrisoquine metabolism was recently identified in non-human primates tested in vivo. The catalytical and immunological characterization of cytochrome P450IID subfamily was undertaken in hepatic microsomes from extensive metabolizer primates. The NADPH/O2 mediated metabolism of debrisoquine, dextromethorphan and
N E Caporaso et al.
Environmental health perspectives, 98, 101-105 (1992-11-01)
Debrisoquine is an antihypertensive drug that is metabolized by cytochrome P4502D6. Deficient metabolism is inherited as an autosomal recessive condition. We previously reported in a case-control study that extensive metabolizers of debrisoquine were at greater risk of lung cancer compared
J W Ho et al.
Analytical biochemistry, 203(2), 348-351 (1992-06-01)
Debrisoquine and sparteine are prototype substrates of a genetic deficiency in cytochrome P450-dependent drug metabolism. Sensitive assays of in vitro oxidation of sparteine and debrisoquine are required for evaluation of this polymorphism. The activities were measured by quantitative analysis of
The debrisoquine metabolic phenotype and DNA-based assays: implications of misclassification for the association of lung cancer and the debrisoquine metabolic phenotype.
Caporaso N E, et al.
Environmental Health Perspectives, 98, 101-105 (1992)
B Clement et al.
Biochemical pharmacology, 46(12), 2249-2267 (1993-12-14)
The microsomal N-hydroxylation of the strongly basic guanidinium group (debrisoquine) to N-hydroxyguanidine (N-hydroxydebrisoquine) and the retroreduction of the N-hydroxyguanidine are demonstrated for the first time. The reduction of the N-hydroxyguanidine by liver homogenates and hepatocytes is catalysed by a microsomal
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Articles

Phase I Drug Metabolism

Phase I biotransformation reactions introduce or expose functional groups on the drug with the goal of increasing the polarity of the compound. Although Phase I drug metabolism occurs in most tissues, the primary and first pass site of metabolism occurs during hepatic circulation.

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