phenylacetic acid
Trade name: ucephan
Approved
Jul 1, 1987
Phenylacetic acid (abr. PAA and synonyms are: α-toluic acid, benzeneacetic acid, alpha tolylic acid, 2-phenylacetic acid, β-phenylacetic acid) is an organic compound containing a phenyl functional group and acarboxylic acid functional group. Because it is used in the illicit production of phenylacetone (used in the manufacture of substituted amphetamines), it is subject to controls in countries including the United States and China Phenylacetic acid is used in some perfumes, possessing a honey-like odor in low concentrations, and is also used in penicillin G production. It is also employed to treat type II hyperammonemia to help reduce the amounts of ammonia in a patient's bloodstream by forming phenylacetyl-CoA, which then reacts with nitrogen-rich glutamine to form phenylacetylglutamine. This compound is then secreted by the patient's body. In Phase 2 of clinical research it investigated in the treatment of Brain and Central Nervous System Tumors. — NCATS
Clinical trial activity
47 trials · 7 clinical orgs · 7 marketing orgs
Earliest trial started Jan 1, 1985 (NCT00004767)
Timeline
1980s
- Jan 1, 1985
Earliest Phase 2 Sponsor(trial)
- Jan 21, 1986
Orphan Drug Designation
- Jul 1, 1987
Earliest FDA Approval
- Dec 23, 1987
Kendall McGaw Laboratories — First NDA Organization
- Dec 23, 1987
B. Braun — NDA Secondary Org
- Dec 23, 1987
Kendall McGaw Laboratories — NDA Organization
2000s
- Jan 1, 2005
Earliest Phase 1 Sponsor(trial)
- Feb 17, 2005
Medicis — NDA Secondary Org
- Feb 17, 2005
Bausch Health Companies — NDA Secondary Org
2010s
- Feb 24, 2016
Ailex Pharmaceuticals — Marketing Organization
- Aug 4, 2016
Navinta — Marketing Organization
- May 8, 2017
Maia Pharms Inc — Marketing Organization
2020s
- Jun 10, 2021
Maia Pharms Inc — NDA Secondary Org
Indications
Approved for
Studied for
- Adenocarcinoma · Phase 2
- Adrenocortical Carcinoma · Phase 2
- Amino Acid Metabolism, Inborn Errors · Phase 2
- Astrocytoma · Phase 2
- Brain Neoplasms · Phase 2
- Breast Neoplasms · Phase 2
- Carcinoma · Phase 2
- Carcinoma, Islet Cell · Phase 2
- Carcinoma, Merkel Cell · Phase 2
- Carcinoma, Neuroendocrine · Phase 2
- Carcinoma, Non-Small-Cell Lung · Phase 2
- Colonic Neoplasms · Phase 2
- Esophageal Neoplasms · Phase 2
- Glioblastoma · Phase 2
- Glioma · Phase 2
- Head and Neck Neoplasms · Phase 2
- Healthy Volunteers · Phase 1
- Hepatic Encephalopathy · Phase 2
- Intestinal Neoplasms · Phase 2
- Kidney Neoplasms · Phase 2
- Lung Neoplasms · Phase 2
- Lymphoma · Phase 2
- Lymphoma, Mantle-Cell · Phase 2
- Lymphoma, Non-Hodgkin · Phase 2
- Melanoma · Phase 2
- Mesothelioma, Malignant · Phase 2
- Multiple Myeloma · Phase 2
- Neoplasms · Phase 2
- Neuroblastoma · Phase 2
- Neuroectodermal Tumors, Primitive · Phase 2
- Oligodendroglioma · Phase 2
- Ovarian Neoplasms · Phase 2
- Pancreatic Neoplasms · Phase 2
- Pituitary Neoplasms · Phase 2
- Prostatic Neoplasms · Phase 2
- Sarcoma · Phase 2
- Small Cell Lung Carcinoma · Phase 2
- Stomach Neoplasms · Phase 2
- Urinary Bladder Neoplasms · Phase 2
- Uterine Cervical Neoplasms · Phase 2
- Vulvar Neoplasms · Phase 2
- Waldenstrom Macroglobulinemia · Phase 2
Mechanism of action
- GlutamineSEQUESTERING AGENT
Glutamine sequestering agent
Removes excess nitrogen, caused by enzyme deficiency
Combination products
ucephan
with sodium benzoate
Also known as ammonul
Approval history
- approvedJul 1, 1987
Chemistry & pharmacology
SMILES
OC(=O)CC1=CC=CC=C1- Mol. weight
- 136.1479 g/mol
- Lipinski Ro5
- Pass
- Rule of 3
- Yes
- Chirality
- Achiral Molecule
- Inorganic
- No
- Polymer
- No
- Availability
- Prescription Only
Oral
No
Parenteral
No
Topical
No
Sources
- WikipediaPhenylacetic acid ↗
- NCATSER5I1W795A ↗
- ChEMBLCHEMBL1200358 ↗
- ChEMBLCHEMBL1044 ↗
Also known as
- benzeneacetic acid
- benzeneacetic acid
- benzeneacetic acid
- benzeneacetic acid
- benzeneacetic acid
- phenylacetate
- phenylacetate
- phenylacetate
- phenylacetate
- phenylacetic acid
- phenylacetic acid
- phenylacetic acid
- phenylacetic acid
- phenylacetic acid, ammonium salt
- phenylacetic acid, calcium salt
- phenylacetic acid, cesium salt
- phenylacetic acid, lithium salt
- phenylacetic acid, mercury salt
- phenylacetic acid, potassium salt
- phenylacetic acid, rubidium salt
- phenylacetic acid, sodium salt
- phenylacetic acid, sodium salt , carboxy-(11)c-labeled cpd
- phenylethanoic acid
- sodium phenylacetate
- sodium phenylacetate
- sodium phenylacetate
- sodium phenylacetate
- sodium phenylacetate
- ucephan
- ucephan
Clinical trials
| NCT ID | Phase | Start date | Sponsor(s) |
|---|---|---|---|
| NCT00597909 | Phase 2 | Dec 1, 2007 | Horizon Pharma |
| NCT00977600 | Phase 1 | Mar 1, 2005 | Horizon Pharma, Ucyclyd |
| NCT00003455 | Phase 2 | Nov 1, 1999 | Burzynski Research Institute |
| NCT00003502 | Phase 2 | Nov 1, 1999 | Burzynski Research Institute |
| NCT00003517 | Phase 2 | Nov 1, 1999 | Burzynski Research Institute |
| NCT00003505 | Phase 2 | Nov 1, 1999 | Burzynski Research Institute |
| NCT00003514 | Phase 2 | Nov 1, 1999 | Burzynski Research Institute |
| NCT00003486 | Phase 2 | Nov 1, 1999 | Burzynski Research Institute |
| NCT00003456 | Phase 2 | Nov 1, 1998 | Burzynski Research Institute |
| NCT00003471 | Phase 2 | Aug 1, 1998 | Burzynski Research Institute |
| NCT00003491 | Phase 2 | Aug 1, 1998 | Burzynski Research Institute |
| NCT00003489 | Phase 2 | Aug 1, 1998 | Burzynski Research Institute |
| NCT00003512 | Phase 2 | Aug 1, 1998 | Burzynski Research Institute |
| NCT00003494 | Phase 2 | Aug 1, 1998 | Burzynski Research Institute |
| NCT00003500 | Phase 2 | Aug 1, 1998 | Burzynski Research Institute |
| NCT00003501 | Phase 2 | Aug 1, 1998 | Burzynski Research Institute |
| NCT00003485 | Phase 2 | Aug 1, 1998 | Burzynski Research Institute |
| NCT00003497 | Phase 2 | Aug 1, 1998 | Burzynski Research Institute |
| NCT00003496 | Phase 2 | Aug 1, 1998 | Burzynski Research Institute |
| NCT00003495 | Phase 2 | Aug 1, 1998 | Burzynski Research Institute |
Organizations
Research & Development (7)
| Organization | Org type | Trials | As lead sponsor | Phases | Earliest year |
|---|---|---|---|---|---|
| Burzynski Research Institute | Academic/Hospital | 43 | 43 | 1 | 1993 |
| Horizon Pharma | For profit | 2 | 2 | 2 | 2005 |
| Baylor University | Academic/Hospital | 1 | 1 | 1 | 1998 |
| Johns Hopkins University | Academic/Hospital | 1 | 0 | 1 | 1985 |
| National Cancer Institute (NCI) | Government | 1 | 0 | 1 | 1998 |
| National Center for Research Resources (NCRR) | Government | 1 | 1 | 1 | 1985 |
| Ucyclyd | For profit | 1 | 0 | 1 | 2005 |
Marketing (8)
| Organization | Org type | Relationship | Date |
|---|---|---|---|
| Ailex Pharmaceuticals | For profit | MKTG | Feb 24, 2016 |
| B. Braun | For profit | NDA2 | Dec 23, 1987 |
| Bausch Health Companies | For profit | NDA2 | Feb 17, 2005 |
| Kendall McGaw Laboratories | For profit | NDA | Dec 23, 1987 |
| Maia Pharms Inc | For profit | MKTG | May 8, 2017 |
| Maia Pharms Inc | For profit | NDA2 | Jun 10, 2021 |
| Medicis | For profit | NDA2 | Feb 17, 2005 |
| Navinta | For profit | MKTG | Aug 4, 2016 |