関: alpha-methyltyrosine、metirosine

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2014/02/09 12:04:51」(JST)

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Metirosine (α-Methyltyrosine, Metyrosine, AMPT) is an antihypertensive drug. It inhibits the enzyme tyrosine hydroxylase and, therefore, catecholamine synthesis, which, as a consequence, depletes the levels of the catecholamines dopamine, adrenaline and noradrenaline in the body.

Clinical use[edit]

Metirosine has been used in the treatment of pheochromocytoma.^[1] It is contra-indicated for the treatment of essential hypertension.

However it is now rarely used in medicine, and its main use is in scientific research, to investigate the effects of catecholamine depletion on behaviour.^[2]

Chemistry[edit]

Metyrosine, (−)α-methyltyrosine, is synthesized in a few different ways, the simplest of which is the synthesis from 4-methoxyphenylacetone, which is reacted with potassium cyanide in the presence of ammonium carbonate to give the hydantoin. Treating this with hydrogen iodide removes the methyl-protecting group on the phenyl hydroxyl group and the product is hydrolyzed by barium hydroxide into a racemic mixture of α-methyl-D,L-tyrosine, from which the desired L-isomer is isolated.

Stein, G. A.; Bronner, H. A.; Pfister, K. (1955). Journal of the American Chemical Society 77 (3): 700. doi:10.1021/ja01608a046. edit
K. Potts, J. Chem. Soc., 1632 (1955).
Saari, W. S. (1967). "Reaction of nitro anions with N,N-dimethyl-p-hydroxybenzylamine. A new synthesis of alpha-methyltyrosine". Journal of Organic Chemistry 32 (12): 4074–4076. doi:10.1021/jo01287a087. PMID 5622474. edit
G.A. Stein, I.K. Pfister, U.S. Patent 2,868,818 (1959).

References[edit]

^ Green KN, Larsson SK, Beevers DG, Bevan PG, Hayes B (August 1982). "Alpha-methyltyrosine in the management of phaeochromocytoma". Thorax 37 (8): 632–3. doi:10.1136/thx.37.8.632. PMC 459390. PMID 7179194.
^ O'Leary OF, Bechtholt AJ, Crowley JJ, Hill TE, Page ME, Lucki I. Depletion of serotonin and catecholamines block the acute behavioral response to different classes of antidepressant drugs in the mouse tail suspension test. Psychopharmacology (Berlin). 2007 Jun;192(3):357-71. PMID 17318507

UpToDate Contents

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1. 成人における褐色細胞腫の治療 treatment of pheochromocytoma in adults
2. 小児における褐色細胞腫 pheochromocytoma in children
3. 褐色細胞腫を有する成人に対する麻酔 anesthesia for the adult with pheochromocytoma
4. 傍神経節腫：限局性疾患の治療 paragangliomas treatment of locoregional disease
5. 小児における高血圧緊急症および高血圧性急迫症のマネージメント management of hypertensive emergencies and urgencies in children

English Journal

Coronary bypass surgery in the presence of metastatic pheochromocytoma.

Seery K1, Ilsin B, Kulik A.
Journal of cardiac surgery.J Card Surg.2015 May;30(5):419-20. doi: 10.1111/jocs.12533. Epub 2015 Mar 10.
The hemodynamic management of a patient with a pheochromocytoma presents special challenges due to the episodic release of catecholamines from the tumor, which threatens to provoke a hypertensive crisis. We present a patient with metastatic pheochromocytoma (bone, lung, lymph nodes) who underwent su
PMID 25756842

Differentiation of malignant tumours from granulomas by using dynamic [(18)F]-fluoro-L-α-methyltyrosine positron emission tomography.

Yamaguchi A1, Hanaoka H1, Fujisawa Y2, Zhao S3, Suzue K4, Morita A2, Tominaga H5, Higuchi T6, Hisaeda H4, Tsushima Y6, Kuge Y7, Iida Y8.
EJNMMI research.EJNMMI Res.2015 Apr 30;5:29. doi: 10.1186/s13550-015-0109-z. eCollection 2015.
BACKGROUND: Previous clinical studies have revealed the potential of [(18)F]-fluoro-L-α-methyltyrosine ((18)F-FAMT) for the differential diagnosis of malignant tumours from sarcoidosis. However, one concern regarding the differential diagnosis with (18)F-FAMT is the possibility of false negatives g
PMID 25977883

Effects of intratumoral inflammatory process on 18F-FDG uptake: pathologic and comparative study with 18F-fluoro-α-methyltyrosine PET/CT in oral squamous cell carcinoma.

Kim M1, Achmad A2, Higuchi T3, Arisaka Y3, Yokoo H4, Yokoo S5, Tsushima Y3.
Journal of nuclear medicine : official publication, Society of Nuclear Medicine.J Nucl Med.2015 Jan;56(1):16-21. doi: 10.2967/jnumed.114.144014. Epub 2014 Dec 4.
The accurate depiction of both biologic and anatomic profiles of tumors has long been a challenge in PET imaging. An inflammation, which is innate in the carcinogenesis of oral squamous cell carcinoma (OSCC), frequently complicates the image analysis because of the limitations of (18)F-FDG and maxim
PMID 25476535

Japanese Journal

Surgical management of pheochromocytoma with the use of metyrosine

PERRY RR.
Ann Surg 212, 621-628, 1990
NAID 30018716624

Optical Resolution of (±)-Metyrosine (Organic Chemistry)

SAITO Hiroyuki,TAHARA Yoshiyuki
Agricultural and Biological Chemistry 52(9), 2349-2350, 1988-09-23
NAID 110006324008

Related Pictures

★リンクテーブル★

リンク元	「メチロシン」「metirosine」「alpha-methyltyrosine」

「メチロシン」

Metyrosine
Systematic (IUPAC) name
	(2S)-2-amino- 3-(4-hydroxyphenyl)- 2-methylpropanoic acid
Clinical data
Trade names	Demser
AHFS/Drugs.com	Consumer Drug Information
Legal status	?
Pharmacokinetic data
Half-life	3.4–3.7 hours
Identifiers
CAS number	672-87-7
ATC code	C02KB01
PubChem	CID 10123
DrugBank	DB00765
ChemSpider	390103
UNII	DOQ0J0TPF7
KEGG	D00762
ChEMBL	CHEMBL1200862
Chemical data
Formula	C10H13NO3
Mol. mass	195.215 g/mol
	SMILES O=C(O)[C@@](N)(Cc1ccc(O)cc1)C;
	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 ; Key:NHTGHBARYWONDQ-JTQLQIEISA-N ;
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