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SML2365

Sigma-Aldrich

Phenprocoumon

≥97% (HPLC)

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Synonym(s):
2-Hydroxy-3-(1-phenylpropyl)-4H-1-benzopyran-4-one, 4-Hydroxy-3-(1-phenylpropyl)-2H-1-Benzopyran-2-one
Empirical Formula (Hill Notation):
C18H16O3
CAS Number:
435-97-2
Molecular Weight:
280.32
MDL number:
MFCD00865273
NACRES:
NA.77

Assay

≥97% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

2-8°C

InChI

1S/C18H16O3/c1-2-13(12-8-4-3-5-9-12)16-17(19)14-10-6-7-11-15(14)21-18(16)20/h3-11,13,20H,2H2,1H3

InChI key

QNDUUBVQYBBRBW-UHFFFAOYSA-N

Biochem/physiol Actions

Phenprocoumon is a coumarin derivative that inhibits vitamin K and acts as a long acting oral anticoagulant. It was recently found to act synergistically with flutamide to modulate the stability of the androgen receptor (AR) and resensitize AR-mutant prostate cancer cells to flutamide.

Pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

Signal Word

Danger

Hazard Classifications

Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation - Acute Tox. 3 Oral - Repr. 2 - STOT RE 2

Storage Class Code

6.1C - Combustible, acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

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Marco P Licciardello et al.
Nature chemical biology, 13(7), 771-778 (2017-05-23)
Approved drugs are invaluable tools to study biochemical pathways, and further characterization of these compounds may lead to repurposing of single drugs or combinations. Here we describe a collection of 308 small molecules representing the diversity of structures and molecular
Alexander Gombert et al.
Journal of vascular surgery. Venous and lymphatic disorders, 8(1), 89-94 (2019-10-28)
Surgical desobliteration or endophlebectomy of the common femoral vein during deep venous recanalization with complementary polytetrafluoroethylene (PTFE) arteriovenous fistula (AVF), may lead to higher rates of surgical site infection (SSI). It has been reported that closed incisional negative pressure wound
Eleanor Hüttel et al.
Thrombosis and haemostasis, 117(5), 870-879 (2017-02-24)
The aim of this observational cohort study was to specify the risk of the vitamin K antagonist (VKA) phenprocoumon during first trimester of pregnancy, in particular to estimate the risk of birth defects and spontaneous fetal loss. Four hundred eight
Stefan H Hohnloser et al.
Clinical research in cardiology : official journal of the German Cardiac Society, 106(8), 618-628 (2017-03-16)
Non-vitamin K antagonist oral anticoagulants (NOACs) are at least as effective and safe as vitamin K antagonists (VKAs) for stroke prevention in atrial fibrillation (AF). All pivotal trials have compared NOACs to warfarin. However, other VKAs are commonly used, for

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