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Merck

UC211

7-Hydroxywarfarin

Synonym(s):

3-(α-Acetonylbenzyl)-4,7-dihydrocoumarin, 4-7-Dihydroxy-3-(3-oxo-1-phenylbutyl)-2H-1-benzopyran-2-one

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About This Item

Empirical Formula (Hill Notation):
C19H16O5
CAS Number:
17834-03-6
Molecular Weight:
324.33
NACRES:
NA.77
PubChem Substance ID:
329827660
UNSPSC Code:
12161501
MDL number:
MFCD00272668

InChI

1S/C19H16O5/c1-11(20)9-15(12-5-3-2-4-6-12)17-18(22)14-8-7-13(21)10-16(14)24-19(17)23/h2-8,10,15,21-22H,9H2,1H3

SMILES string

CC(CC(C1=C(O)C(C=CC(O)=C2)=C2OC1=O)C3=CC=CC=C3)=O

InChI key

SKFYEJMLNMTTJA-UHFFFAOYSA-N

form

solid

color

white

mp

220 °C

solubility

DMSO: soluble

storage temp.

2-8°C

Quality Level

200

Related Categories

Biochem/physiol Actions

CYP2C9 metabolite of (S)-warfarin.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Preparation Note

7-Hydroxywarfarin is soluble in DMSO.

Application

7-Hydroxywarfarin can be used for the metabolic assays of (S)-warfarin.

pictograms

CorrosionExclamation mark
GHS05,GHS07

signalword

Danger

hcodes

H302,H318

Hazard Classifications

Acute Tox. 4 Oral - Eye Dam. 1

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000141460
0000141460
0000106199
0000039873
0000092238

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Tae Inoue et al.
Drug metabolism and disposition: the biological fate of chemicals, 36(12), 2429-2433 (2008-09-12)
Chimeric mice having humanized livers were constructed by transplantation of human hepatocytes. In this study, we investigated whether these mice have a capacity for drug metabolism similar to that of humans by examining hydroxylation of S-warfarin, which is predominantly metabolized
Masahiro Utoh et al.
Biochemical pharmacology, 95(2), 110-114 (2015-03-25)
Cynomolgus monkeys are widely used as non-human primate species in preclinical studies, due to their close evolutionary relationship to humans. Monkey cytochrome P450 2C19 (formerly known as P450 2C75), highly homologous to human P450 2C19, has been identified to be
D Lang et al.
Journal of chromatography. B, Biomedical applications, 672(2), 305-309 (1995-10-20)
The formation of 7-hydroxywarfarin in incubations of (S)-warfarin with human liver microsomes reflects their cytochrome P-4502C9 activity. This paper describes a rapid high-performance liquid chromatographic method for the determination of 7-hydroxywarfarin with high sensitivity, selectivity, and a simple sample clean-up
Xuemin Jiang et al.
British journal of clinical pharmacology, 57(5), 592-599 (2004-04-20)
M: The aim of this study was to investigate the effect of St John's wort and ginseng on the pharmacokinetics and pharmacodynamics of warfarin. This was an open-label, three-way crossover randomized study in 12 healthy male subjects, who received a
D J Black et al.
Drug metabolism and disposition: the biological fate of chemicals, 24(4), 422-428 (1996-04-01)
Consistent with expectations based on human in vitro microsomal experiments, administration of fluconazole (400 mg/day) for 6 days to six human volunteers significantly reduced the cytochrome P450 (P450)-dependent metabolic clearance of the warfarin enantiomers. In particular, P4502C9 catalyzed 6- and
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