For research use only. Not for therapeutic Use.
Metyrosine is an inhibitor of the enzyme TYROSINE 3-MONOOXYGENASE, and consequently of the synthesis of catecholamines. It is used to control the symptoms of excessive sympathetic stimulation in patients with PHEOCHROMOCYTOMA. Metyrosine competitively inhibits tyrosine 3-monooxygenase, an enzyme that activates molecular oxygen to catalyze the hydroxylation of tyrosine to dihydroxyphenylalanine (Dopa), an intermediate to catecholamine (dopamine, norepinephrine, and epinephrine) production. This agent reduces the elevated levels of catecholamines associated with pheochromocytoma, thereby preventing hypertension.
| Catalog Number | R000665 |
| CAS Number | 672-87-7 |
| Synonyms | (S)-2-(4-Hydroxybenzyl)-2-aminopropanoic Acid; (S)-α-Methyltyrosine; Demser; L(-)-Metyrosine; L-Metyrosine; L-α-MT; L-α-Methyl-p-tyrosine; L-α-Methyltyrosine; MK 781; Metirosine; Metyrosine; |
| Molecular Formula | C10H13NO3 |
| Purity | ≥95% |
| Storage | Store at RT |
| IUPAC Name | (2S)-2-amino-3-(4-hydroxyphenyl)-2-methylpropanoic acid |
| 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 |
| SMILES | CC(CC1=CC=C(C=C1)O)(C(=O)O)N |
| Reference | </br>1:Preparation and biological evaluation of 3-[(76)Br]bromo-α-methyl-L-tyrosine, a novel tyrosine analog for positron emission tomography imaging of tumors. Ohshima Y, Hanaoka H, Watanabe S, Sugo Y, Watanabe S, Tominaga H, Oriuchi N, Endo K, Ishioka NS.Nucl Med Biol. 2011 Aug;38(6):857-65. doi: 10.1016/j.nucmedbio.2011.02.001. Epub 2011 Apr 21. PMID: 21843782 </br>2:Uptake of 3-[125I]iodo-alpha-methyl-L-tyrosine into colon cancer DLD-1 cells: characterization and inhibitory effect of natural amino acids and amino acid-like drugs. Shikano N, Ogura M, Okudaira H, Nakajima S, Kotani T, Kobayashi M, Nakazawa S, Baba T, Yamaguchi N, Kubota N, Iwamura Y, Kawai K.Nucl Med Biol. 2010 Feb;37(2):197-204. doi: 10.1016/j.nucmedbio.2009.10.011. Epub 2009 Nov 26. PMID: 20152719 </br>3:Stimulation of 125I-3-iodo-alpha-methyl-L-tyrosine uptake in Chinese hamster ovary (CHO-K1) cells by tyrosine esters. Shikano N, Ogura M, Sagara J, Nakajima S, Kobayashi M, Baba T, Yamaguchi N, Iwamura Y, Kubota N, Kawai K.Nucl Med Biol. 2010 Feb;37(2):189-96. doi: 10.1016/j.nucmedbio.2009.10.003. Epub 2009 Nov 3. PMID: 20152718 </br>4:Pharmacokinetics of 3-[125I]iodo-alpha-methyl-L-tyrosine, a tumor imaging agent, after probenecid loading in mice implanted with colon cancer DLD-1 cells. Nakajima S, Shikano N, Kotani T, Ogura M, Nishii R, Yoshimoto M, Yamaguchi N, Iwamura Y, Kubota N, Ishikawa N, Kawai K.Nucl Med Biol. 2007 Nov;34(8):1003-8. Epub 2007 Sep 4. PMID: 17998105 </br>5:Detection of maleate-induced Fanconi syndrome by decreasing accumulation of 125I-3-iodo-alpha-methyl-L-tyrosine in the proximal tubule segment-1 region of renal cortex in mice: a trial of separate evaluation of reabsorption. Shikano N, Nakajima S, Kotani T, Itoh Y, Nishii R, Yoshimoto M, Flores LG 2nd, Saji H, Ishikawa N, Kawai K.Ann Nucl Med. 2006 Apr;20(3):175-81. PMID: 16715947 </br>6:Renal accumulation and excretion of radioiodinated 3-iodo-alpha-methyl-L-tyrosine. Shikano N, Kawai K, Nakajima S, Nishii R, Flores LG 2nd, Kubodera A, Kubota N, Ishikawa N, Saji H.Ann Nucl Med. 2004 May;18(3):263-70. PMID: 15233289 </br>7:Transcellular transport of radioiodinated 3-iodo-alpha-methyl-L-tyrosine across monolayers of kidney epithelial cell line LLC-PK1. Shikano N, Kawai K, Nakajima S, Kubodera A, Kubota N, Ishikawa N, Saji H.Ann Nucl Med. 2004 May;18(3):227-34. PMID: 15233284 </br>8:Characterization of uptake of 3-[(131)I]iodo-alpha-methyl-L-tyrosine in human monocyte-macrophages. Prante O, Deichen JT, Hocke C, Kuwert T.Nucl Med Biol. 2004 Apr;31(3):365-72. PMID: 15028249 </br>9:Comparison of O-(2-18F-fluoroethyl)-L-tyrosine PET and 3-123I-iodo-alpha-methyl-L-tyrosine SPECT in brain tumors. Pauleit D, Floeth F, Tellmann L, Hamacher K, Hautzel H, Müller HW, Coenen HH, Langen KJ.J Nucl Med. 2004 Mar;45(3):374-81. PMID: 15001676 Free Article</br>10:Isoform selectivity of 3-125I-iodo-alpha-methyl-L-tyrosine membrane transport in human L-type amino acid transporters. Shikano N, Kanai Y, Kawai K, Inatomi J, Kim DK, Ishikawa N, Endou H.J Nucl Med. 2003 Feb;44(2):244-6. PMID: 12571216 Free Article |
