Skip to Content
MilliporeSigma
All Photos(1)

Key Documents

UC209

Sigma-Aldrich

4-Hydroxywarfarin

Synonym(s):

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

Sign Into View Organizational & Contract Pricing


About This Item

Empirical Formula (Hill Notation):
C19H16O5
CAS Number:
Molecular Weight:
324.33
MDL number:
UNSPSC Code:
12161501
PubChem Substance ID:
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[1].

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

signalword

Danger

hcodes

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


Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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
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
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

Questions

Reviews

No rating value

Active Filters

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service