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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

Signal Word

Danger

Hazard Statements

H302,H318

Hazard Classifications

Acute Tox. 4 Oral - Eye Dam. 1

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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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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