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UC209

Sigma-Aldrich

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
MDL number:
MFCD00272666
UNSPSC Code:
12161501
PubChem Substance ID:
329827658
NACRES:
NA.77

form

solid

color

off-white

solubility

DMSO: soluble
methanol: soluble

storage temp.

2-8°C

SMILES string

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

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

InChI key

RRZWAMPDGRWRPF-UHFFFAOYSA-N

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_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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

Certificates of Analysis (COA)

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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)
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
Drew R Jones et al.
Drug metabolism letters, 4(4), 213-219 (2010-07-10)
Effective coumadin (R/S-warfarin) therapy is complicated by inter-individual variability in metabolism. Recent studies have demonstrated that CYP3A isoforms likely contribute to patient responses and clinical outcomes. Despite a significant focus on CYP3A4, little is known about CYP3A5 and CYP3A7 metabolism
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
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
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