Phenprocoumon

Phenprocoumon
Clinical data
Trade names	Marcoumar, Marcumar, Falithrom
AHFS/Drugs.com	International Drug Names
MedlinePlus	a699003
Pregnancy; category	Contraindicated;
Routes of; administration	By mouth
ATC code	B01AA04 (WHO) ;
Legal status
Legal status	In general: ℞ (Prescription only);
Pharmacokinetic data
Bioavailability	100%
Protein binding	99%
Metabolism	Liver (CYP2C9, CYP3A4)
Metabolites	Hydroxyl derivatives, glucuronides
Elimination half-life	6–7 days
Excretion	Kidney
Identifiers
	IUPAC name (RS)-4-hydroxy-3-(1-phenylpropyl)-2H-chromen-2-one;
CAS Number	435-97-2 ;
PubChem CID	9908;
IUPHAR/BPS	6839;
DrugBank	DB00946 ;
ChemSpider	10441592 ;
UNII	Q08SIO485D;
KEGG	D05457 ;
ChEBI	CHEBI:50438 ;
ChEMBL	ChEMBL1465 ;
CompTox Dashboard (EPA)	DTXSID5023459 ;
ECHA InfoCard	100.006.464
Chemical and physical data
Formula	C18H16O3
Molar mass	280.323 g·mol−1
3D model (JSmol)	Interactive image;
Melting point	177–181 °C (351–358 °F)
	SMILES OC=1c3ccccc3OC(=O)C=1C(CC)c2ccccc2;
	InChI 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 ; Key:DQDAYGNAKTZFIW-UHFFFAOYSA-N ;
	(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]

^ Cite error: The named reference Arzneistoff-Profile was invoked but never defined (see the help page).
^ 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.
^ Geisslinger G, Menzel S (15 September 2017). Wenn Arzneimittel wechselwirken (in German). Stuttgart: Wissenschaftliche Verlagsgesellschaft. pp. 15–18. ISBN 978-3-8047-3747-1.
^ Cite error: The named reference AC was invoked but never defined (see the help page).
^ Phenprocoumon International Drug Names. Accessed 2021-08-25.

[Arzneistoff-Profile-1] Cite error: The named reference Arzneistoff-Profile was invoked but never defined (see the help page).

[Haustein_1999-2] 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.

[Geisslinger-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.

[AC-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.

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