Phenprocoumon

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Phenprocoumon

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
Half-life	5 to 6 days
Identifiers
CAS number	435-97-2^Y
ATC code	B01AA04
PubChem	CID 9908
DrugBank	DB00946
ChemSpider	10441592^Y
UNII	Q08SIO485D^Y
KEGG	D05457^Y
ChEBI	CHEBI:50438^Y
ChEMBL	CHEMBL1465^Y
Chemical data
Formula	C₁₈H₁₆O₃
Mol. mass	280.318 g/mol
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^Y Key:DQDAYGNAKTZFIW-UHFFFAOYSA-N^Y
Y (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]

References

↑ Phenprocoumon at PharmGKB

External links

DDB 29943

Antithrombotics (thrombolytics, anticoagulants and antiplatelet drugs) (B01)

Antiplatelet drugs

Glycoprotein IIb/IIIa inhibitors	Abciximab Eptifibatide Tirofiban

ADP receptor/P2Y₁₂ inhibitors	thienopyridines Clopidogrel Prasugrel Ticlopidine nucleotide/nucleoside analogs Cangrelor Elinogrel Ticagrelor

Prostaglandin analogue (PGI2)	Beraprost Iloprost Prostacyclin Treprostinil

COX inhibitors	Acetylsalicylic acid/Aspirin^# Aloxiprin Carbasalate calcium Indobufen Triflusal

Thromboxane inhibitors	thromboxane synthase inhibitors Dipyridamole (+Aspirin) Picotamide receptor antagonist Terutroban^†

Phosphodiesterase inhibitors	Cilostazol Dipyridamole Triflusal

Other	Cloricromen Ditazole

Anticoagulants

Vitamin K antagonists
(inhibit II, VII, IX, X)

Factor Xa inhibitors
(with some II inhibition)

Heparin group/ glycosaminoglycans/ (bind antithrombin)	low molecular weight heparin Bemiparin Certoparin Dalteparin Enoxaparin Nadroparin Parnaparin Reviparin Tinzaparin oligosaccharides Fondaparinux Idraparinux heparinoid Danaparoid Dermatan sulfate Sulodexide

Direct Xa inhibitors	xabans Apixaban Betrixaban Darexaban Edoxaban Otamixaban Rivaroxaban

Direct thrombin (II) inhibitors

bivalent: Hirudin
- Bivalirudin
- Desirudin
- Lepirudin
univalent: Argatroban
Dabigatran
Melagatran^‡
Ximelagatran^‡

Other

Thrombolytic drugs/
fibrinolytics

Non-medicinal

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

M: MYL

cell/phys (coag, heme, immu, gran), csfs

rbmg/mogr/tumr/hist, sysi/epon, btst

drug (B1/2/3+5+6), btst, trns

Types of coumarins

Aglycones

O-Methylated	Fraxetin Herniarin (7-O-Methylumbelliferone) Osthol Scopoletin (6-Methoxyumbelliferone)

glycosides

Aesculin (Esculetin 6-O-glucoside)
Fraxin (Fraxetin glucoside)
Skimmin (Umbelliferone 7-O-glucoside)
Scopolin
Umbelliferone 7-apiosylglucoside

derivatives

Furanocoumarins

Aglycones

Angelicin
Marmesin
Psoralen
Vaginol
Xanthotoxol (8-Hydroxypsoralen)

O-Methylated	Bergapten (5-methoxypsoralen) Isopimpinellin (5,8-Dimethoxypsoralene) Methoxsalen (8-Methoxypsoralen) Trioxsalen (2,5,9-Trimethylpsoralen)

Furanocoumarin glycosides

Apterin (vaginol glucoside)

Meroterpene furanocoumarin ether

Oligomers

Dicoumarol

Synthetic

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