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D1306

Sigma-Aldrich

Debrisoquine sulfate

powder, ≥98% (TLC)

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:
Molecular Weight:
448.54
EC Number:
MDL number:
UNSPSC Code:
12352204
PubChem Substance ID:
NACRES:
NA.32

product name

Debrisoquine sulfate,

Assay

≥98% (TLC)

Quality Level

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

Signal Word

Warning

Hazard Statements

Precautionary Statements

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)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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
Ping-Ching Hsu et al.
Molecular carcinogenesis, 56(2), 594-606 (2016-06-25)
Smoking-related biomarkers for lung cancer and other diseases are needed to enhance early detection strategies and to provide a science base for tobacco product regulation. An untargeted metabolomics approach by ultra-performance liquid chromatography-quadrupole-time of flight mass spectrometry (UHPLC-Q-TOF MS) totaling

Articles

Phase I biotransformation reactions increase drug compound polarity, mainly occurring in hepatic circulation.

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