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Merck
CN

UC209

4-Hydroxywarfarin

Synonym(s):

4-Hydroxy-3-[1´-(4´´-hydroxyphenyl)-3´-oxobutyl]-2H-1-benzopyran-2-one

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About This Item

Empirical Formula (Hill Notation):
C19H16O5
CAS Number:
24579-14-4
Molecular Weight:
324.33
NACRES:
NA.77
PubChem Substance ID:
329827658
UNSPSC Code:
12161501
MDL number:
MFCD00272666

Key Documents

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InChI

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

SMILES string

CC(=O)CC(c1ccc(O)cc1)C2=C(O)c3ccccc3OC2=O

InChI key

RRZWAMPDGRWRPF-UHFFFAOYSA-N

form

solid

color

off-white

solubility

DMSO: soluble, methanol: soluble

storage temp.

2-8°C

Application

4-Hydroxywarfarin has been used to study its effects on the inhibition of CYP2C9-mediated S-warfarin metabolism.

Biochem/physiol Actions

Minor CYP3A4 metabolite od (S)-warfarin.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Preparation Note

4-Hydroxywarfarin is soluble in methanol and DMSO.

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
561-041-1V
561-041-1
BCBB8321V
BCBB8321
085K1341

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J S Ngui et al.
Drug metabolism and disposition: the biological fate of chemicals, 29(6), 877-886 (2001-05-17)
It has been demonstrated that the activity of cytochrome P450 (CYP)3A4 in certain cases is stimulated by quinidine (positive heterotropic cooperativity). We report herein that the 4'- and 10-hydroxylation of S- and R-warfarin are enhanced in human liver microsomal incubations
J D Rizzo et al.
Journal of pharmaceutical sciences, 78(3), 183-189 (1989-03-01)
Warfarin, an anticoagulant and "metabolic probe" for cytochrome P-450 isozyme multiplicity, is metabolized to 4'-hydroxywarfarin, a principle mammalian metabolite, using the fungus Cunninghamella bainieri (UI-3065). The metabolite was isolated from cell suspension cultures and characterized by analytical (TLC, HPLC, GC-MS)
Aref Zayed et al.
Acta pharmaceutica (Zagreb, Croatia), 70(3), 343-357 (2020-02-20)
In this study, high-performance liquid chromatography with fluorescence detection (HPLC-FLD) has been used for the first time, for direct determination of warfarin and its major metabolite, 7-hydroxywarfarin, in rat plasma. The simple and sensitive method was developed using Fortis® reversed-phase
Heather Wang et al.
Journal of chromatography. A, 1622, 460895-460895 (2020-05-16)
Baseline separation and analysis of multicomponent mixtures of closely related pharmaceuticals using single column selectivity can often be challenging, requiring the combination of orthogonal stationary and mobile phase methods to monitor all the species and optimize reaction outcomes. In recent
So-Young Kim et al.
Drug metabolism letters, 6(3), 157-164 (2013-01-22)
Coumadin (R/S-warfarin) is a highly efficacious and widely used anticoagulant; however, its highly variable metabolism remains an important contributor to uncertainties in therapeutic responses. Pharmacogenetic studies report conflicting findings on the clinical relevance of CYP2C19. A resolution to this controversy
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