Phenprocoumon

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Phenprocoumon
Phenprocoumon.svg
Systematic (IUPAC) name
(RS)-4-hydroxy-3-(1-phenylpropyl)-2H-chromen-2-one
Clinical data
Trade names Marcoumar, Marcumar, Falithrom
AHFS/Drugs.com International Drug Names
MedlinePlus a699003
Legal status
  • (Prescription only)
Pharmacokinetic data
Protein binding 99%
Metabolism hepatic to inactive metabolites
Biological half-life 5 to 6 days
Identifiers
CAS Registry Number 435-97-2 YesY
ATC code B01AA04
PubChem CID: 9908
IUPHAR/BPS 6839
DrugBank DB00946 YesY
ChemSpider 10441592 YesY
UNII Q08SIO485D YesY
KEGG D05457 YesY
ChEBI CHEBI:50438 YesY
ChEMBL CHEMBL1465 YesY
Chemical data
Formula C18H16O3
Molecular mass 280.318 g/mol
 YesY (what is this?)  (verify)

Phenprocoumon (marketed under the brand names Marcoumar, Marcumar and Falithrom) is a long-acting oral anticoagulant drug, a derivative of coumarin. It is a vitamin K antagonist that inhibits coagulation by blocking synthesis of coagulation factors II, VII, IX and X. It is used for the prophylaxis and treatment of thromboembolic disorders (thrombosis/pulmonary embolism). It is the standard coumarin used in Germany.

Phenprocoumon is a 4-hydroxycoumarin and inhibits vitamin K epoxide reductase.[1]

Synthesis[edit]

Phenprocoumon synthesis:[2][3][4] Grüssner, Balthasar, U.S. Patent 2,723,276 (1955 to Hoffmann-La Roche). U.S. Patent 2,872,457 (1959 to WARF); GB 805748  (1958 to Geigy).

References[edit]

  1. ^ Phenprocoumon at PharmGKB
  2. ^ Junek, H.; Ziegler, E. (1956). "Zur Chemie des 4-Hydroxy-cumarins". Monatshefte f�r Chemie 87: 218. doi:10.1007/BF00903605.  edit
  3. ^ Schroeder, C. H.; Titus, E. D.; Link, K. P. (1957). "A New Synthetic Approach to Some 3-Aralkyl-4-Hydroxycoumarins1". Journal of the American Chemical Society 79 (12): 3291. doi:10.1021/ja01569a085.  edit
  4. ^ Pohl, L. R.; Haddock, R.; Garland, W. A.; Trager, W. F. (1975). "Synthesis and thin-layer chromatographic, ultraviolet, and mass spectral properties of the anticoagulant phenprocoumon and its monohydroxylated derivatives". Journal of Medicinal Chemistry 18 (5): 513. doi:10.1021/jm00239a016.  edit

External links[edit]