aminocaproic acid
Trade name: amicar
Approved
Jun 3, 1964
6-Aminocaproic acid (epsilon-aminocaproic acid, marketed as Amicar) is an ant fibrinolytic agent that acts by inhibiting plasminogen activators, which have fibrinolytic properties. It is useful in enhancing hemostasis when fibrinolysis contributes to bleeding. In life threatening situations, transfusion of appropriate blood products and other emergency measures may be required. Fibrinolytic bleeding may frequently be associated with surgical complications following heart surgery (with or without cardiac bypass procedures) and portacaval shunt; hematological disorders such as a megakaryocytic thrombocytopenia (accompanying aplastic anemia); hepatic cirrhosis; and neoplastic disease such as carcinoma of the prostate, lung, stomach, and cervix. Aminocaproic acid binds reversibly to the kringle domain of plasminogen and blocks the binding of plasminogen to fibrin and its activation to plasmin. With NO activation of plasmin, there is a reduction in fibrinolysis. The drug should NOT be administered without a definite diagnosis and/or laboratory finding indicative of hyperfibrinolysis (hyperplasminemia). Inhibition of fibrinolysis by aminocaproic acid may theoretically result in clotting or thrombosis. However, there is no definite evidence that administration of aminocaproic acid has been responsible for the few reported cases of intravascular clotting which followed this treatment. Rather, it appears that such intravascular clotting was most likely due to the patient's preexisting clinical condition, e.g., the presence of DIC. It has been postulated that extravascular clots formed in vivo may not undergo spontaneous lysis as do normal clots. Reports have appeared in the literature of an increased incidence of certain neurological deficits such as hydrocephalus, cerebral ischemia, or cerebral vasospasm associated with the use of ant fibrinolytic agents in the treatment of subarachnoid hemorrhage (SAH). All of these events have also been described as part of the natural course of SAH, or as a consequence of diagnostic procedures such as angiography. Drug relatedness remains unclear. Aminocaproic acid may change the conformation of apoliprotein, changing its binding properties and potentially preventing the formation of lipoprotein. — NCATS
Clinical trial activity
23 trials · 29 clinical orgs · 27 marketing orgs
Earliest trial started Sep 1, 2000 (NCT00320619)
Timeline
1960s
- Mar 6, 1964
Clover Biopharmaceuticals — First NDA Organization
- Mar 6, 1964
Clover Biopharmaceuticals — NDA Organization
- Jun 3, 1964
Earliest FDA Approval
- Jun 3, 1964
Clover Biopharmaceuticals — NDA Secondary Org
- Jun 3, 1964
Akorn, Inc. — NDA Secondary Org
- Jun 3, 1964
Hikma — Marketing Organization
- Jun 8, 1964
Epic Pharma Llc — Marketing Organization
1980s
1990s
- Sep 2, 1998
Akorn, Inc. — Marketing Organization
2010s
- Nov 27, 2018
Sunny Pharmtech Inc — Marketing Organization
- Aug 23, 2019
Amneal Pharmaceuticals — Marketing Organization
2020s
- Feb 26, 2020
VistaPharm, Inc. — Marketing Organization
- Aug 11, 2020
Tulex Pharmaceuticals — Marketing Organization
- Nov 6, 2020
MSN Laboratories — Marketing Organization
- Dec 14, 2020
Ani Pharmaceuticals — Marketing Organization
- Jan 26, 2021
Leading Pharma Llc — Marketing Organization
- Jan 26, 2021
CARNEGIE — Marketing Organization
- Apr 8, 2021
Airis Pharma Pvt Ltd — Marketing Organization
- Apr 8, 2021
Belcher Pharmaceuticals — Marketing Organization
- Jun 14, 2021
Edenbridge Pharms — Marketing Organization
- Mar 23, 2022
Lachman Consultants — Marketing Organization
- Sep 14, 2022
OPTIMUS PHARMA PRIVATE LTD — Marketing Organization
- Sep 26, 2022
Aurobindo Pharma — Marketing Organization
- Nov 4, 2022
Annora Pharma — Marketing Organization
- Mar 24, 2023
Taro Pharmaceuticals — Marketing Organization
- Mar 24, 2023
Sun Pharmaceuticals — Marketing Organization
- Jan 1, 2026
Earliest Phase 3 Sponsor(trial)
Indications
Approved for
Studied for
- Aminocaproic Acid · Phase 4
- Aortic Diseases · Early Phase 1
- Blood Circulation · Phase 4
- Blood Loss, Surgical · Phase 4
- Blood Transfusion · Phase 2
- Cardiopulmonary Bypass · Phase 2/Phase 3
- Cerebral Hemorrhage · Phase 1
- Craniosynostoses · Phase 2
- Fibrinolysis · Phase 2/Phase 3
- General Surgery · Phase 4
- Hematologic Neoplasms · Phase 2
- Hemorrhage · Phase 4
- Hypertension · Phase 3
- Inflammation · Phase 2/Phase 3
- Oral Hemorrhage · Phase 4
- Osteoarthritis · Phase 4
- Osteoarthritis, Hip · Phase 4
- Osteoarthritis, Knee · Phase 4
- Osteotomy · Phase 4
- Pathology · Phase 4
- Rosacea · Early Phase 1
- Scoliosis · Phase 4
- Thrombocytopenia · Phase 2
- Thrombosis · Phase 2
Mechanism of action
- Tissue-type plasminogen activatorINHIBITOR
PLAT inhibitor
- PlasminogenINHIBITOR
PLG inhibitor
Approval history
- approvedPriority reviewJun 3, 1964
Chemistry & pharmacology
SMILES
NCCCCCC(O)=O- Mol. weight
- 131.1729 g/mol
- Lipinski Ro5
- Pass
- Rule of 3
- No
- Chirality
- Achiral Molecule
- Inorganic
- No
- Polymer
- No
- Delivery
- Oral, Parenteral
- Availability
- Prescription Only
Oral
Yes
Parenteral
Yes
Topical
No
Sources
- WikipediaAminocaproic acid ↗
- NCATSU6F3787206 ↗
- ChEMBLCHEMBL1046 ↗
Also known as
- 177 j.d
- 177 j.d
- 177 j.d.
- 177 j.d.
- 6-aminocaproic acid
- 6-aminocaproic acid
- 6-aminocaproic acid
- 6-aminohexanoic acid
- 6-aminohexanoic acid
- 6-aminohexanoic acid
- acepramin
- acide aminocaproïque
- acide aminocaproïque
- acide aminocaproque
- acide aminocaproque
- ácido aminocapróico
- ácido aminocapróico
- acidum aminocaproicum
- acidum aminocaproicum
- ahx
- ahx
- amicar
- amicar
- amicar
- aminocaproic
- aminocaproic
- aminocaproic
- aminocaproic acid
- aminocaproic acid
- aminocaproic acid
- aminocaproic acid
- aminocaproic acid
- aminocaproic acid
- aminocaproic acid
- aminocaproic acid
- aminocaproic acid
- aminocaproic acid
- aminocapronsäure
- aminocapronsäure
- aminohexanoic acid
- aminohexanoic acid
- caproamin
- caproamin
- cl-10304
- cl-10304
- cy-116
- cy-116
- eaca
- eaca
- eaca
- epsicaprom
- epsicaprom
- epsikapron
- epsikapron
- epsilcapramine
- epsilcapramine
- epsilon-ahx
- epsilon-ahx
- epsilon aminocaproic acid
- epsilon aminocaproic acid
- epsilon-aminocaproic acid
- epsilon-aminocaproic acid
- epsilon-aminocaproic acid
- epsilon-aminocaproic acid
- epsilon-aminocaproic acid
- epsilon-aminohexanoic acid
- epsilon-aminohexanoic acid
- z
- ε-aminocaproic acid
- ε-aminocaproic acid
Clinical trials
| NCT ID | Phase | Start date | Sponsor(s) |
|---|---|---|---|
| NCT07030101 | Phase 3 | Nov 30, 2026 | EMS S/A |
| NCT04814433 | N/A | Mar 24, 2021 | New York University |
| NCT04187014 | Phase 2 | Jan 6, 2020 | Universidad Autonoma de Nuevo Leon |
| NCT03365999 | Phase 2 | Oct 15, 2017 | Universidad Autonoma de Nuevo Leon |
| NCT02639819 | Phase 1 | Jun 1, 2016 | University of Texas, San Antonio |
| NCT02656472 | Phase 4 | Feb 1, 2016 | Advocate Healthcare, Advocate Health Care |
| NCT02030821 | Phase 4 | Jan 1, 2015 | Duke University |
| NCT02257580 | Phase 4 | Jan 1, 2015 | Rockefeller University |
| NCT02229968 | Phase 2 | Oct 1, 2014 | Children's National Medical Center |
| NCT02074436 | Phase 2 | May 1, 2014 | Akorn, Inc., Emory University |
| NCT01873768 | Phase 4 | Jan 1, 2014 | CHI Health Mercy Hospital, Creighton University, Miller Orthopedic Specialists |
| NCT02238288 | Phase 4 | Dec 1, 2013 | Grupo de Estudos Multicentricos em Onco-Hematologia, Rio de Janeiro State University |
| NCT01981863 | Phase 4 | Jul 1, 2013 | Stanford University |
| NCT01965730 | Early Phase 1 (Phase 1) | Jan 1, 2013 | University of Pennsylvania |
| NCT01527968 | N/A | Apr 1, 2012 | Heekin Institute for Orthopedic Research, Heekin Orthopedic Research Institute |
| NCT01398280 | Early Phase 1 (Phase 1) | Jul 1, 2011 | University of California, San Diego |
| NCT01248104 | N/A | Mar 1, 2010 | Loma Linda University |
| NCT00912119 | Phase 1 | May 1, 2009 | Children's Anesthesiology Associates, Ltd., Thomas B. and Jeannette E. Laws McCabe Fund Pilot Award, University of Pennsylvania |
| NCT00958581 | Phase 4 | Dec 1, 2008 | New York University |
| NCT02655653 | N/A | Oct 1, 2008 | Yeshiva University |
Organizations
Research & Development (29)
Marketing (33)
| Organization | Org type | Relationship | Date |
|---|---|---|---|
| Abraxis | For profit | MKTG | Jun 17, 1986 |
| Airis Pharma Pvt Ltd | For profit | MKTG | Apr 8, 2021 |
| Akorn, Inc. | For profit | MKTG | Sep 2, 1998 |
| Akorn, Inc. | For profit | NDA2 | Jun 3, 1964 |
| Amneal Pharmaceuticals | For profit | SYN | Nov 26, 2019 |
| Amneal Pharmaceuticals | For profit | MKTG | Aug 23, 2019 |
| Amneal Pharmaceuticals | For profit | SYN | Nov 26, 2019 |
| Ani Pharmaceuticals | For profit | MKTG | Dec 14, 2020 |
| Ani Pharmaceuticals | For profit | MKTG | Dec 14, 2020 |
| Annora Pharma | For profit | MKTG | Nov 4, 2022 |
| Athenex, Inc. | For profit | MKTG | — |
| Aurobindo Pharma | For profit | MKTG | Sep 26, 2022 |
| Baxalta | For profit | NDA2 | Oct 29, 1982 |
| Baxter | For profit | NDA2 | Oct 29, 1982 |
| Belcher Pharmaceuticals | For profit | MKTG | Apr 8, 2021 |
| CARNEGIE | For profit | MKTG | Jan 26, 2021 |
| Clover Biopharmaceuticals | For profit | NDA | Mar 6, 1964 |
| Clover Biopharmaceuticals | For profit | NDA2 | Jun 3, 1964 |
| Edenbridge Pharms | For profit | MKTG | Jun 14, 2021 |
| Epic Pharma Llc | For profit | MKTG | Jun 8, 1964 |
| Hikma | For profit | MKTG | Jun 3, 1964 |
| Hospira | For profit | MKTG | Mar 9, 1987 |
| Lachman Consultants | For profit | MKTG | Mar 23, 2022 |
| Leading Pharma Llc | For profit | MKTG | Jan 26, 2021 |
| Lutipold | For profit | MKTG | Dec 1, 1987 |
| MSN Laboratories | For profit | MKTG | Nov 6, 2020 |
| OPTIMUS PHARMA PRIVATE LTD | For profit | MKTG | Sep 14, 2022 |
| Sun Pharmaceuticals | For profit | MKTG | Mar 24, 2023 |
| Sunny Pharmtech Inc | For profit | MKTG | Nov 27, 2018 |
| Sunny Pharmtech Inc | For profit | MKTG | Nov 27, 2018 |
| Taro Pharmaceuticals | For profit | MKTG | Mar 24, 2023 |
| Tulex Pharmaceuticals | For profit | MKTG | Aug 11, 2020 |
| VistaPharm, Inc. | For profit | MKTG | Feb 26, 2020 |