Phenprocoumon

Phenprocoumon
Clinical data
Trade namesMarcoumar, Marcumar, Falithrom
AHFS/Drugs.comInternational Drug Names
MedlinePlusa699003
Pregnancy
category
Routes of
administration		By mouth
ATC code
Legal status
Legal status
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability100%[1]
Protein binding99%
MetabolismLiver (CYP2C9, CYP3A4)
MetabolitesHydroxyl derivatives, glucuronides
Elimination half-life6–7 days
ExcretionKidney
Identifiers
  • (RS)-4-hydroxy-3-(1-phenylpropyl)-2H-chromen-2-one
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.006.464 Edit this at Wikidata
Chemical and physical data
FormulaC18H16O3
Molar mass280.323 g·mol−1
3D model (JSmol)
Melting point177–181 °C (351–358 °F)
  • OC=1c3ccccc3OC(=O)C=1C(CC)c2ccccc2
  • 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/h3-11,13,19H,2H2,1H3 checkY
  • Key:DQDAYGNAKTZFIW-UHFFFAOYSA-N checkY
  (verify)

Phenprocoumon (marketed under the brand names Marcoumar, Marcumar and Falithrom) is a long-acting anticoagulant to be taken by mouth, and a coumarin derivative.[2] It acts as a vitamin K antagonist and inhibits blood clotting (coagulation) by blocking synthesis of coagulation factors II, VII, IX and X. It is used for the prophylaxis and treatment of thromboembolic disorders such as heart attacks and pulmonary (lung) embolism. The most common adverse effect is bleeding. The drug interacts with a large number of other medications, including aspirin and St John's Wort. It is the standard coumarin used in Germany,[3] Austria,[4] and other European countries.[5]

  1. ^ Cite error: The named reference Arzneistoff-Profile was invoked but never defined (see the help page).
  2. ^ Haustein KO (1999). "Pharmacokinetic and pharmacodynamic properties of oral anticoagulants, especially phenprocoumon". Seminars in Thrombosis and Hemostasis. 25 (1): 5–11. doi:10.1055/s-2007-996417. PMID 10327214.
  3. ^ Geisslinger G, Menzel S (15 September 2017). Wenn Arzneimittel wechselwirken (in German). Stuttgart: Wissenschaftliche Verlagsgesellschaft. pp. 15–18. ISBN 978-3-8047-3747-1.
  4. ^ Cite error: The named reference AC was invoked but never defined (see the help page).
  5. ^ Phenprocoumon International Drug Names. Accessed 2021-08-25.