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phenprocoumon

Trade name: liquamar

Small moleculeapproved

Approved

Dec 30, 1957

Phenprocoumon is the dominant anticoagulant in clinical use in several continental European countries. It used for the prevention and treatment of thromboembolic disease including venous thrombosis, thromboembolism, and pulmonary embolism as well as for the prevention of ischemic stroke in patients with atrial fibrillation. Phenprocoumon inhibits vitamin K reductase, resulting in depletion of the reduced form of vitamin K (vitamin KH2). Bleedings are the most important side -effects of oral anticoagulants. The gastrointestinal and the urinary tract are often affected; the most dangerous are intracerebral hemorrhages. A great number of drugs increase the risk of bleeding of oral anticoagulants. Enzyme inhibitors (e.g. allopurinol, androgens, cimetidine, ciprofloxacin, co-trimoxazole, certain anti-inflammatory agents, fibrates, imidazoles, macrolide antibiotics, etc.) reinforce, and enzyme inducers (e.g. barbiturates, rifampicin) and oral contraceptives reduce, the anticoagulant action. — NCATS

Clinical trial activity

19 trials · 31 clinical orgs · 1 marketing orgs

Phase 1
1
Phase 2
8
Phase 3
6
Phase 4
10

Earliest trial started May 1, 2003 (NCT00067093)

Timeline

1950s

  1. Dec 30, 1957

    Organon — Earliest FDA Approval

  2. Dec 30, 1957

    Organon — NDA Organization

2000s

  1. Jan 1, 2003

    Earliest Phase 3 Sponsor(trial)

2010s

  1. Jan 1, 2013

    Earliest Phase 1 Sponsor(trial)

  2. Jan 1, 2013

    Earliest Phase 2 Sponsor(trial)

Indications

Approved for

Studied for

Mechanism of action

Approval history

  • approvedDec 30, 1957

Chemistry & pharmacology

Loading structure…

SMILES

CCC(c1ccccc1)c1c(O)c2ccccc2oc1=O
Mol. weight
280.32 g/mol
Lipinski Ro5
Pass
Rule of 3
No
Chirality
Racemic Mixture
Inorganic
No
Polymer
No
Delivery
Oral
Availability
Discontinued

Oral

Yes

Parenteral

No

Topical

No

Sources

Also known as

  • 3-(1-phenylpropyl)-4-hydroxycoumarin
  • 3-(1-phenylpropyl)-4-hydroxycoumarin
  • 3-(1'-phenyl-propyl)-4-oxycoumarin
  • 3-(1'-phenyl-propyl)-4-oxycoumarin
  • 3-(alpha-ethylbenzyl)-4-hydroxycoumarin
  • 3-(alpha-ethylbenzyl)-4-hydroxycoumarin
  • 3-(alpha-phenylpropyl)-4-hydroxycoumarin
  • 3-(alpha-phenylpropyl)-4-hydroxycoumarin
  • 4-hydroxy-3-(1-phenylpropyl)-2h-1-benzopyran-2-one
  • 4-hydroxy-3-(1-phenylpropyl)-2h-1-benzopyran-2-one
  • 4-hydroxy-3-(1-phenylpropyl)-2h-chromen-2-one
  • 4-hydroxy-3-(1-phenylpropyl)-2h-chromen-2-one
  • fencumar
  • fenprocumon
  • fenprocumon
  • fenprocumone
  • fenprocumone
  • liquamar
  • liquamar
  • liquamar
  • liquamar
  • marcoumar
  • marcoumar
  • marcoumar
  • marcoumar
  • marcumar
  • marcumar
  • phenprocoumarol
  • phenprocoumarol
  • phenprocoumarol
  • phenprocoumarole
  • phenprocoumarole
  • phenprocoumarole
  • phenprocoumon
  • phenprocoumon
  • phenprocoumon
  • phenprocoumon
  • phenprocoumon
  • phenprocoumon
  • phenprocoumon
  • phenprocoumon
  • phenprocoumon
  • phenprocoumon
  • phenprocoumon
  • phenprocoumon
  • phenprocoumone
  • phenprocoumone
  • phenprocoumonum
  • phenprocoumonum
  • phenprocumone
  • phenprocumone
  • phenprocumone

Clinical trials

NCT IDPhaseStart dateSponsor(s)
NCT03463317Phase 4Feb 28, 2018Atrial Fibrillation Network, German Center for Cardiovascular Research e. V. (DZHK), Humboldt University, Stiftung Institut fuer Herzinfarktforschung
NCT02933697Phase 3Apr 1, 2017Bristol-Myers Squibb, German Atrial Fibrillation Network, Pfizer
NCT02981472Phase 2Jan 4, 2017Bristol-Myers Squibb, Pfizer
NCT02591225Phase 4Oct 1, 2015Boehringer Ingelheim, University of Ulm
NCT02256683Phase 4Jul 1, 2014Boehringer Ingelheim, German Atrial Fibrillation Network, Johannes Gutenburg University
NCT02046460Phase 4Sep 1, 2013University of Basel, University of Bern, University of Lausanne
NCT01849666Phase 1Sep 1, 2013Roche
NCT02066662Phase 4Jul 1, 2013Bayer, RWTH Aachen University
NCT01830543Phase 3May 1, 2013Bayer, Janssen Pharmaceutica NV, Johnson and Johnson
NCT02872649Phase 2Jan 1, 2013Medical University of Vienna, University of Vienna
NCT01812200Phase 4Oct 1, 2012University of Vienna
NCT01674647Phase 3Oct 1, 2012Bayer, Johnson and Johnson
NCT01352702Phase 4May 1, 2011Technical University of Munich
NCT01339819Phase 4Apr 1, 2011Technical University of Munich
NCT01164046Phase 3Aug 1, 2010University of Amsterdam, University of Groningen
NCT00895505Phase 3Feb 1, 2008German Federal Ministry of Education and Research, German Research Foundation, University of Bonn
NCT00586287Phase 4Jan 1, 2007Cantonal Hospital of St. Gallen
NCT00528671Phase 4Jan 1, 2006Ruhr University Bochum, University of Heidelberg, University of Kiel
NCT00067093Phase 3May 1, 2003Sanofi
Showing 19 of 19 trials
Page 1 / 1

Organizations

Research & Development (31)

OrganizationOrg typeTrialsAs lead sponsorPhasesEarliest year
BayerFor profit3122012
Boehringer IngelheimFor profit2012014
Bristol-Myers SquibbFor profit2122017
German Atrial Fibrillation NetworkAcademic/Hospital2122014
Johnson and JohnsonFor profit2112012
PfizerFor profit2022017
Technical University of MunichAcademic/Hospital2212011
University of ViennaAcademic/Hospital2122012
Atrial Fibrillation NetworkAcademic/Hospital1012018
Cantonal Hospital of St. GallenAcademic/Hospital1112007
German Center for Cardiovascular Research e. V. (DZHK)Government1012018
German Federal Ministry of Education and ResearchGovernment1012008
German Research FoundationAcademic/Hospital1012008
Humboldt UniversityAcademic/Hospital1112018
Janssen Pharmaceutica NVFor profit1012013
Johannes Gutenburg UniversityAcademic/Hospital1112014
Medical University of ViennaAcademic/Hospital1112013
RocheFor profit1112013
Ruhr University BochumAcademic/Hospital1112006
RWTH Aachen UniversityAcademic/Hospital1112013
31 organizations
Page 1 / 2

Marketing (1)

OrganizationOrg typeRelationshipDate
OrganonFor profitNDADec 30, 1957