sintrom
Small moleculeexperimental
Acenocoumarol is mono-coumarin derivative with racemic mixture of R (+) and S (-) enantiomers. Acenocoumarol is structurally similar to vitamin K and is competitively able to inhibit the enzyme vitamin K-epoxide reductase. It exerts anticoagulant action by preventing the regeneration of reduced vitamin K by interfering with action of vitamin K epoxide reductase. Acenocoumarol is prescribed as the anticoagulant in various thromboembolic disorders. — NCATS
Clinical trial activity
20 trials · 27 clinical orgs · 0 marketing orgs
Phase 1
1
Phase 2
9
Phase 3
9
Phase 4
6
Earliest trial started Jan 1, 2002 (NCT00689520)
Timeline
Indications
Studied for
- Anticoagulants · Phase 2/Phase 3
- Antiphospholipid Syndrome · Phase 3
- Atrial Fibrillation · Phase 4
- Atrial Flutter · Phase 3
- Blood Coagulation Disorders · Phase 4
- Cerebral Intraventricular Hemorrhage · Phase 3
- Cerebrovascular Disorders · Phase 3
- Diabetes Mellitus · Phase 4
- Heart Valve Diseases · Phase 4
- Hematoma, Subdural · Phase 3
- Hemorrhage · Phase 3
- Intracranial Hemorrhage, Hypertensive · Phase 3
- Intracranial Hemorrhages · Phase 3
- Melanoma · Phase 1
- Neoplasms · Phase 3
- Percutaneous Coronary Intervention · Phase 3
- Pulmonary Embolism · Phase 4
- Stroke · Phase 4
- Subarachnoid Hemorrhage · Phase 3
- Thrombosis · Phase 4
- Venous Thromboembolism · Phase 4
- Venous Thrombosis · Phase 3
Mechanism of action
VKORC1 inhibitor
Inhibits the reduction of vitamin K by vitamin K epoxide reductase. This prevents carboxylation of vitamin K-dependent clotting factors, II, VII, XI and X, and interferes with coagulation.
Chemistry & pharmacology
Loading structure…
SMILES
CC(=O)CC(C1=CC=C(C=C1)[N+]([O-])=O)C2=C(O)C3=C(OC2=O)C=CC=C3- Mol. weight
- 353.3255 g/mol
- Lipinski Ro5
- Pass
- Rule of 3
- No
- Chirality
- Racemic Mixture
- Inorganic
- No
- Polymer
- No
Oral
No
Parenteral
No
Topical
No
Sources
- WikipediaAcenocoumarol ↗
- NCATSI6WP63U32H ↗
- ChEMBLCHEMBL397420 ↗
Also known as
- 3-(alpha-(4'-nitrophenyl)-beta-acetylethyl)-4-hydroxycoumarin
- 3-(alpha-(4'-nitrophenyl)-beta-acetylethyl)-4-hydroxycoumarin
- 3-(alpha-acetonyl-4-nitrobenzyl)-4-hydroxycoumarin
- 3-(alpha-acetonyl-4-nitrobenzyl)-4-hydroxycoumarin
- 3-(alpha-acetonyl-p-nitrobenzyl)-4-hydroxycoumarin
- 3-(alpha-acetonyl-p-nitrobenzyl)-4-hydroxycoumarin
- 3-(alpha-(p-nitrophenol)-beta-acetylethyl)-4-hydroxycoumarin
- 3-(alpha-(p-nitrophenol)-beta-acetylethyl)-4-hydroxycoumarin
- 3-(alpha-p-nitrophenyl-beta-acetylethyl)-4-hydroxycoumarin
- 3-(alpha-p-nitrophenyl-beta-acetylethyl)-4-hydroxycoumarin
- 4-hydroxy-3-(1-(4-nitrophenyl)-3-oxobutyl)-2h-1-benzopyran-2-one
- 4-hydroxy-3-(1-(4-nitrophenyl)-3-oxobutyl)-2h-1-benzopyran-2-one
- 4-hydroxy-3-[1-(4-nitrophenyl)-3-oxobutyl]-2h-chromen-2-one
- 4-hydroxy-3-[1-(4-nitrophenyl)-3-oxobutyl]-2h-chromen-2-one
- acenocoumarin
- acenocoumarin
- acenocoumarin
- acenocoumarin
- acenocoumarol
- acenocoumarol
- acenocoumarol
- acenocoumarol
- acenocoumarol
- acenocoumarol
- acenocoumarolum
- acenocoumarolum
- acenocumarol
- acenocumarol
- acenocumarolo
- acenocumarolo
- acenokumarin
- acenokumarin
- g 23350
- g 23350
- g 23350
- g 23350
- g 23350
- g 23350
- g-23350
- nicoumalone
- nicoumalone
- nicoumalone
- nicoumalone
- nicumalon
- nicumalon
- nitrophenylacetylethyl-4-hydroxycoumarine
- nitrophenylacetylethyl-4-hydroxycoumarine
- nitrovarfarian
- nitrovarfarian
- nitrowarfarin
- nitrowarfarin
- sinthrome
- sinthrome
- sintrom
Clinical trials
| NCT ID | Phase | Start date | Sponsor(s) |
|---|---|---|---|
| NCT05515120 | Phase 2/Phase 3 (Phase 3) | Jan 3, 2021 | Instituto Mexicano del Seguro Social |
| NCT03153150 | Phase 3 | Jul 3, 2017 | NHS Lothian, University of Edinburgh |
| NCT02981472 | Phase 2 | Jan 4, 2017 | Bristol-Myers Squibb, Pfizer |
| NCT02826200 | Phase 4 | Jul 1, 2016 | Semmelweis University, University of London |
| NCT02935855 | Phase 4 | Sep 1, 2015 | University of Pavia |
| NCT01851824 | Phase 1 | Aug 1, 2013 | Roche |
| NCT01830543 | Phase 3 | May 1, 2013 | Bayer, Janssen Pharmaceutica NV, Johnson and Johnson |
| NCT02926170 | Phase 3 | Mar 1, 2013 | Universidad Autonoma de Barcelona |
| NCT01674647 | Phase 3 | Oct 1, 2012 | Bayer, Johnson and Johnson |
| NCT01631877 | N/A | Jun 1, 2012 | Institute of Liver and Biliary Sciences, India |
| NCT01556659 | N/A | Mar 1, 2012 | Erasmus University Rotterdam, University of Amsterdam |
| NCT01164046 | Phase 3 | Aug 1, 2010 | University of Amsterdam, University of Groningen |
| NCT01141153 | Phase 4 | Jun 1, 2010 | Universidad Autonoma de Barcelona |
| NCT00512928 | N/A | Sep 1, 2007 | Maastricht University |
| NCT00711308 | Phase 4 | Apr 1, 2005 | Complejo Hospitalario Xeral Calde, Hospital do Meixoeiro, Vigo, Hospital Xeral Cies de Vigo, Leo Pharma |
| NCT00070655 | Phase 3 | Sep 1, 2003 | Sanofi |
| NCT00062803 | Phase 3 | Jun 1, 2003 | Sanofi |
| NCT00067093 | Phase 3 | May 1, 2003 | Sanofi |
| NCT00966290 | Phase 4 | Feb 1, 2003 | Jean Monnet University, University of Toulouse |
| NCT00689520 | Phase 4 | Jan 1, 2002 | Hospital Creu Roja de l'Hospitalet, Leo Pharma, University of Barcelona |
Showing 20 of 20 trials
Page 1 / 1
Organizations
Research & Development (27)
| Organization | Org type | Trials | As lead sponsor | Phases | Earliest year |
|---|---|---|---|---|---|
| Sanofi | For profit | 3 | 3 | 1 | 2003 |
| Bayer | For profit | 2 | 1 | 1 | 2012 |
| Johnson and Johnson | For profit | 2 | 1 | 1 | 2012 |
| Leo Pharma | For profit | 2 | 0 | 1 | 2002 |
| Universidad Autonoma de Barcelona | Academic/Hospital | 2 | 2 | 2 | 2010 |
| University of Amsterdam | Academic/Hospital | 2 | 1 | 2 | 2010 |
| Bristol-Myers Squibb | For profit | 1 | 1 | 1 | 2017 |
| Complejo Hospitalario Xeral Calde | Academic/Hospital | 1 | 1 | 1 | 2005 |
| Erasmus University Rotterdam | Academic/Hospital | 1 | 0 | 1 | 2012 |
| Hospital Creu Roja de l'Hospitalet | Academic/Hospital | 1 | 0 | 1 | 2002 |
| Hospital do Meixoeiro, Vigo | Academic/Hospital | 1 | 0 | 1 | 2005 |
| Hospital Xeral Cies de Vigo | Academic/Hospital | 1 | 0 | 1 | 2005 |
| Institute of Liver and Biliary Sciences, India | Academic/Hospital | 1 | 1 | 1 | 2012 |
| Instituto Mexicano del Seguro Social | Government | 1 | 1 | 1 | 2021 |
| Janssen Pharmaceutica NV | For profit | 1 | 0 | 1 | 2013 |
| Jean Monnet University | Academic/Hospital | 1 | 0 | 1 | 2003 |
| Maastricht University | Academic/Hospital | 1 | 1 | 1 | 2007 |
| NHS Lothian | Academic/Hospital | 1 | 0 | 1 | 2017 |
| Pfizer | For profit | 1 | 0 | 1 | 2017 |
| Roche | For profit | 1 | 1 | 1 | 2013 |
27 organizations
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