Details of the Drug

General Information of Drug (ID: DMBYCU0)

Drug Name

Metyrosine

Synonyms

Demser; Methyltyrosine; Metirosina; Metirosine; Metirosinum; Racemetirosina; Racemetirosine; Racemetirosinum; Metyrosine[USAN]; Racemetirosine [INN]; M 8131; MK 781; Alpha-MPT; Alpha-Methyltyrosine; Demser (TN); H 9/88; L 588357-0; L-AMPT; M-5185; MK-781; Metirosina [INN-Spanish]; Metirosine (INN); Metirosinum [INN-Latin]; Metyrosine (USP); Racemetirosina [INN-Spanish]; Racemetirosinum [INN-Latin]; DL-alpha-Methyltyrosine; L-588357-0; Alpha-Methyl-L-tyrosine; Alpha-Methyl-dl-tyrosine; Alpha-Methyl-p-tyrosine; Alpha-Methyl-para-tyrosine; A-methyl-L-p-tyrosine; Alpha-Methyl-L-P-Tyrosine; Alpha-Methyltyrosine, (L)-Isomer; DL-alpha-Methyl-p-tyrosine; L-alpha-Methyl-p-tyrosine; Alpha-Methyltyrosine, (D,L)-Isomer; DL-2-Methyl-3-(4-hydroxyphenyl)alanine; Alpha-Methyltyrosine, (+,-)-Isomer; L-2-Methyl-3-(4-hydroxy-phenyl)alanine; (+-)-alpha-Methyl-DL-tyrosine; (-)-(S)-2-Amino-3-(4-hydroxyphenyl)-2-methylpropionsaeure; (-)-alpha-Methyl-DL-tyrosine; (-)-alpha-Methyl-L-tyrosine; (2R)-2-amino-3-(4-hydroxyphenyl)-2-methylpropanoic acid; (2S)-2-amino-3-(4-hydroxyphenyl)-2-methylpropanoic acid; (R,S)-2-Amino-3-(4-hydroxyphenyl)-2-methylpropionsaeure; (S)-alpha-Methyltyrosine; 2-amino-3-(4-hydroxyphenyl)-2-methylpropanoic acid; 4-Hydroxy-alpha-methylphenylalanine

Indication

Disease Entry	ICD 11	Status	REF
Pheochromocytoma	5A75	Approved	[1], [2]

Therapeutic Class

Anticancer Agents

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

195.21

Topological Polar Surface Area (xlogp)

-1.6

Rotatable Bond Count (rotbonds)

3

Hydrogen Bond Donor Count (hbonddonor)

3

Hydrogen Bond Acceptor Count (hbondacc)

4

ADMET Property

Absorption: The drug is well absorbed from the gastrointestinal tract [3]
BDDCS Class: Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 4: low solubility and low permeability [4]
Half-life: The concentration or amount of drug in body reduced by one-half in 3.4 - 3.7 hours [5]

Chemical Identifiers

Formula: C10H13NO3
IUPAC Name: (2S)-2-amino-3-(4-hydroxyphenyl)-2-methylpropanoic acid
Canonical SMILES: C[C@](CC1=CC=C(C=C1)O)(C(=O)O)N
InChI: InChI=1S/C10H13NO3/c1-10(11,9(13)14)6-7-2-4-8(12)5-3-7/h2-5,12H,6,11H2,1H3,(H,13,14)/t10-/m0/s1
InChIKey: NHTGHBARYWONDQ-JTQLQIEISA-N

Cross-matching ID

PubChem CID: 441350
ChEBI ID: CHEBI:6912
CAS Number: 672-87-7
DrugBank ID: DB00765
TTD ID: D0B3QM
ACDINA ID: D00427

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Tyrosine 3-monooxygenase (TH)	TTUHP71	TY3H_HUMAN	Binder	[6]

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Molecular Interaction Atlas (MIA)

MIA Detail

Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease

Pheochromocytoma

ICD Disease Classification

5A75

Molecule Name	Molecule Type	Gene Name	p-value	Fold-Change	Z-score
Tyrosine 3-monooxygenase (TH)	DTT	TH	9.10E-04	-2.73	-1.55

Molecular Expression Atlas (MEA)

MEA Detail

Jump to Detail Molecular Expression Atlas of This Drug

Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Disease Different from Metyrosine (Comorbidity)

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Comorbidity	REF
Allopregnanolone	DMNLHAC	Moderate	Additive CNS depression effects by the combination of Metyrosine and Allopregnanolone.	Mental/behavioural/neurodevelopmental disorder [6E20-6E8Z]	[15]
Lasmiditan	DMXLVDT	Moderate	Additive CNS depression effects by the combination of Metyrosine and Lasmiditan.	Migraine [8A80]	[16]
Thalidomide	DM70BU5	Moderate	Additive CNS depression effects by the combination of Metyrosine and Thalidomide.	Multiple myeloma [2A83]	[17]
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Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG

DIG Name	DIG ID	PubChem CID	Functional Classification
FD&C blue no. 2	E00446	2723854	Colorant
Magnesium stearate	E00208	11177	lubricant
Silicon dioxide	E00670	Not Available	Anticaking agent; Opacifying agent; Viscosity-controlling agent
Titanium dioxide	E00322	26042	Coating agent; Colorant; Opacifying agent
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Pharmaceutical Formulation

Formulation Name	Drug Dosage	Dosage Form	Route
Metyrosine 250 mg capsule	250 mg	Oral Capsule	Oral

Jump to Detail Pharmaceutical Formulation Page of This Drug

References

1	URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 6956).
2	FDA Approved Drug Products from FDA Official Website. 2009. Application Number: (NDA) 017871.
3	FDA approval: ado-trastuzumab emtansine for the treatment of patients with HER2-positive metastatic breast cancer. Clin Cancer Res. 2014 Sep 1;20(17):4436-41.
4	BDDCS predictions, self-correcting aspects of BDDCS assignments, BDDCS assignment corrections, and classification for more than 175 additional drugs
5	Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
6	Dopamine beta-hydroxylase deficiency. A genetic disorder of cardiovascular regulation. Hypertension. 1991 Jul;18(1):1-8.
7	Selectivity and affinity determinants for ligand binding to the aromatic amino acid hydroxylases. Curr Med Chem. 2007;14(4):455-67.
8	Effect of metals and phenylalanine on the activity of human tryptophan hydroxylase-2: comparison with that on tyrosine hydroxylase activity. Neurosci Lett. 2006 Jul 3;401(3):261-5.
9	Biochemistry of postmortem brains in Parkinson's disease: historical overview and future prospects. J Neural Transm Suppl. 2007;(72):113-20.
10	Effect of L1-79 on Core Symptoms of Autism Spectrum Disorder: A Case Series. Clin Ther. 2019 Oct;41(10):1972-1981.
11	Clinical pipeline report, company report or official report of Oxford BioMedica.
12	Clinical pipeline report, company report or official report of Oxford BioMedica.
13	How many drug targets are there Nat Rev Drug Discov. 2006 Dec;5(12):993-6.
14	URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Target id: 1243).
15	Product Information. Zulresso (brexanolone). Sage Therapeutics, Inc., Cambridge, MA.
16	Product Information. Reyvow (lasmiditan). Lilly, Eli and Company, Indianapolis, IN.
17	Product Information. Thalomid (thalidomide). Celgene Corporation, Warren, NJ.