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Merck
CN

UC208

6-Hydroxywarfarin

Synonym(s):

3-(α-Acetonylbenzyl)-4,6-dihydrocoumarin, 4-6-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:
17834-02-5
Molecular Weight:
324.33
UNSPSC Code:
12161501
PubChem Substance ID:
329827657
MDL number:
MFCD00272665

Key Documents

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InChI

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

SMILES string

CC(=O)CC(c1ccccc1)C2=C(O)c3cc(O)ccc3OC2=O

InChI key

IQWPEJBUOJQPDE-UHFFFAOYSA-N

color

white

mp

119-120 °C

solubility

DMSO: soluble

storage temp.

2-8°C

Biochem/physiol Actions

CYP1A2/2C9 metabolite of (R)-warfarin

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Preparation Note

6-Hydroxywarfarin is soluble in 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

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
BGBC2178V
1385501V
1385501
017K3258
085K1338

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A E Rettie et al.
Chemical research in toxicology, 5(1), 54-59 (1992-01-01)
Previous kinetic studies have identified a high-affinity (S)-warfarin 7-hydroxylase present in human liver microsomes which appears to be responsible for the termination of warfarin's biological activity. Inhibition of the formation of (S)-7-hydroxywarfarin, the inactive, major metabolite of racemic warfarin in
Abdul Naveed Shaik et al.
Journal of pharmaceutical sciences, 105(6), 1976-1986 (2016-04-23)
The anticoagulant drug warfarin and the lipid-lowering statin drugs are commonly co-administered to patients with cardiovascular diseases. Clinically significant drug-drug interactions (DDIs) between these drugs have been recognized through case studies for many years, but the biochemical mechanisms causing these
Development of a method for the analysis of warfarin and metabolites in plasma and urine.
J X de Vries et al.
American clinical laboratory, 14(7), 20-21 (1995-06-07)
Steven Lane et al.
British journal of clinical pharmacology, 73(1), 66-76 (2011-06-23)
Warfarin is a drug with a narrow therapeutic index and large interindividual variability in daily dosing requirements. Patients commencing warfarin treatment are at risk of bleeding due to excessive anticoagulation caused by overdosing. The interindividual variability in dose requirements is
Stacie M Bratton et al.
The Journal of pharmacology and experimental therapeutics, 340(1), 46-55 (2011-10-06)
Coumadin (R-, S-warfarin) is a challenging drug to accurately dose, both initially and for maintenance, because of its narrow therapeutic range and wide interpatient variability and is typically administered as a racemic (Rac) mixture, which complicates the biotransformation pathways. The
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