metyrosine
Trade name: demser
Approved
Oct 3, 1979
Metirosine is an antihypertensive drug. Metyrosine inhibits tyrosine hydroxylase, which catalyzes the first transformation in catecholamine biosynthesis, i.e., the conversion of tyrosine to dihydroxyphenylalanine (DOPA). Because the first step is also the rate-limiting step, blockade of tyrosine hydroxylase activity results in decreased endogenous levels of catecholamines and their synthesis. This consequently, depletes the levels of the catecholamines dopamine, adrenaline and noradrenaline in the body,usually measured as decreased urinary excretion of catecholamines and their metabolites. One main end result of the catecholamine depletion is a decrease in blood presure. Metirosine is used for the treatment of patients with pheochromocytoma, for preoperative preparation of patients for surgery, management of patients when surgery is contraindicated, and chronic treatment of patients with malignant pheochromocytoma. — NCATS
Clinical trial activity
4 trials · 8 clinical orgs · 7 marketing orgs
Earliest trial started Jan 1, 2004 (NCT00581477)
Timeline
1970s
- Oct 3, 1979
Merck — Earliest FDA Approval
- Oct 3, 1979
Aton — NDA Secondary Org
- Oct 3, 1979
Merck — NDA Organization
- Oct 3, 1979
Bausch Health Companies — NDA Secondary Org
2000s
- Jan 1, 2004
Earliest Phase 3 Sponsor(trial)
2010s
- Jan 1, 2010
Bausch Health Companies — Earliest Phase 2 Sponsor(trial)
2020s
- Jul 24, 2020
Amneal Pharmaceuticals — Marketing Organization
- Sep 17, 2024
Leading Pharma Llc — Marketing Organization
- Apr 9, 2025
Cerovene — Marketing Organization
- Apr 9, 2025
Dr. Reddy's Laboratories — Marketing Organization
Indications
Approved for
Mechanism of action
- Tyrosine 3-hydroxylaseINHIBITOR
TH inhibitor
Approval history
- approvedPriority reviewOct 3, 1979
Chemistry & pharmacology
SMILES
C[C@](N)(CC1=CC=C(O)C=C1)C(O)=O- Mol. weight
- 195.2151 g/mol
- Lipinski Ro5
- Pass
- Rule of 3
- No
- Chirality
- Single Stereoisomer
- Inorganic
- No
- Polymer
- No
- Delivery
- Oral
- Availability
- Prescription Only
Oral
Yes
Parenteral
No
Topical
No
Sources
- WikipediaMetirosine ↗
- NCATSDOQ0J0TPF7 ↗
- ChEMBLCHEMBL1200862 ↗
Also known as
- (-)-alpha-methyl-l-tyrosine
- (-)-alpha-methyl-l-tyrosine
- alpha-methyl-paratyrosine
- alpha-methyl-paratyrosine
- demser
- demser
- demser
- demser
- l-588357-0
- l-588357-0
- l-metyrosine
- methyltyrosine
- methyltyrosine
- metirosin
- metirosin
- metirosina
- metirosina
- metirosine
- metirosine
- metirosine
- metirosine
- metirosine
- metirosine
- metirosine
- métirosine
- métirosine
- metirosinum
- metirosinum
- metyrosine
- metyrosine
- metyrosine
- metyrosine
- metyrosine
- metyrosine
- metyrosine
- metyrosine
- mk-781
- mk-781
- (s)-alpha-methyltyrosine
- (s)-alpha-methyltyrosine
- α-methyl-l-p-tyrosine
- α-methyl-l-p-tyrosine
- (–)-α-methyl-l-tyrosine
- (–)-α-methyl-l-tyrosine
- α-methyl-para-tyrosine
- α-methyl-para-tyrosine
- α-methyl-p-tyrosine
- α-methyl-p-tyrosine
- α-mpt
- α-mpt
Clinical trials
| NCT ID | Phase | Start date | Sponsor(s) |
|---|---|---|---|
| NCT03778996 | Phase 2 | May 31, 2019 | Joseph Ahmed Foundation (JAF), Sarcoma Oncology Research Center, LLC, Tyme, Inc |
| NCT02179814 | N/A | Feb 1, 2012 | University of Bern, University of Zurich |
| NCT01127503 | Phase 2 | Jun 1, 2010 | Bausch Health Companies, State University of New York, Syracuse |
| NCT00581477 | Phase 3 | Jan 1, 2004 | Vanderbilt University |
Organizations
Research & Development (8)
| Organization | Org type | Trials | As lead sponsor | Phases | Earliest year |
|---|---|---|---|---|---|
| Bausch Health Companies | For profit | 1 | 1 | 1 | 2010 |
| Joseph Ahmed Foundation (JAF) | Academic/Hospital | 1 | 0 | 1 | 2019 |
| Sarcoma Oncology Research Center, LLC | Academic/Hospital | 1 | 1 | 1 | 2019 |
| State University of New York, Syracuse | Academic/Hospital | 1 | 0 | 1 | 2010 |
| Tyme, Inc | For profit | 1 | 0 | 1 | 2019 |
| University of Bern | Academic/Hospital | 1 | 1 | 1 | 2012 |
| University of Zurich | Academic/Hospital | 1 | 0 | 1 | 2012 |
| Vanderbilt University | Academic/Hospital | 1 | 1 | 1 | 2004 |
Marketing (7)
| Organization | Org type | Relationship | Date |
|---|---|---|---|
| Amneal Pharmaceuticals | For profit | MKTG | Jul 24, 2020 |
| Aton | For profit | NDA2 | Oct 3, 1979 |
| Bausch Health Companies | For profit | NDA2 | Oct 3, 1979 |
| Cerovene | For profit | MKTG | Apr 9, 2025 |
| Dr. Reddy's Laboratories | For profit | MKTG | Apr 9, 2025 |
| Leading Pharma Llc | For profit | MKTG | Sep 17, 2024 |
| Merck | For profit | NDA | Oct 3, 1979 |