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MedKoo Cat#: 318264 | Name: Metyrosine
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Metyrosine 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.

Chemical Structure

Metyrosine
Metyrosine
CAS#312753-06-3

Theoretical Analysis

MedKoo Cat#: 318264

Name: Metyrosine

CAS#: 312753-06-3

Chemical Formula: C24H28N2O3

Exact Mass: 392.2100

Molecular Weight: 392.49

Elemental Analysis: C, 73.44; H, 7.19; N, 7.14; O, 12.23

Price and Availability

Size Price Availability Quantity
100mg USD 350.00 2 weeks
250mg USD 650.00 2 weeks
500mg USD 1,050.00 2 weeks
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Related CAS #
No Data
Synonym
Metyrosine, Metirosine, α-Methyltyrosine, Indacaterol, Arcapta, Onbrez, QAB-149
IUPAC/Chemical Name
5-[(1R)-2-[(5,6-diethyl-2,3-dihydro-1H-inden-2-yl)amino]-1-hydroxyethyl]-8-hydroxy-1H-quinolin-2-one
InChi Key
QZZUEBNBZAPZLX-QFIPXVFZSA-N
InChi Code
InChI=1S/C24H28N2O3/c1-3-14-9-16-11-18(12-17(16)10-15(14)4-2)25-13-22(28)19-5-7-21(27)24-20(19)6-8-23(29)26-24/h5-10,18,22,25,27-28H,3-4,11-13H2,1-2H3,(H,26,29)/t22-/m0/s1
SMILES Code
O=C1NC2=C(C([C@@H](O)CNC3CC4=C(C=C(CC)C(CC)=C4)C3)=CC=C2O)C=C1
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO, not in water
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Indacaterol is an orally active ultra-long-acting β2 adrenergic receptor (ADRB2) agonist. Indacaterol inhibits NF-κB activity in a β-arrestin2-dependent manner.
In vitro activity:
Indacaterol significantly inhibits tumor necrosis factor-α (TNF-α)-induced NF-κB activity by reducing levels of both phosphorylated-IKK and -IκBα, thereby decreasing NF-κB nuclear translocation and the expression of MMP-9, an NF-κB target gene. Subsequently, this study shows that indacaterol significantly inhibits TNF-α/NF-κB-induced cell invasiveness and migration in a human cancer cell line. Reference: Mol Cells. 2014 Aug;37(8):585-91. https://pubmed.ncbi.nlm.nih.gov/25134539/
In vivo activity:
Eighteen albino Wistar male rats were divided into groups; gastric I/R (GIR), 50 mg/kg metyrosine+gastric I/R (MGIR), and sham (SG) groups. Metyrosine decreased the MDA and MPO and the increased the tGSH and SOD. In addition, it reduced inflammation by suppressing the decrease of COX-1 and the increase of COX-2. Histopathologically, metyrosine decreased symptoms caused by I/R such as mucosal necrosis, hemorrhage, edema, PMNL infiltration, and dilated congested blood vessels. Reference: Acta Cir Bras. 2018 Mar;33(3):259-267. https://pubmed.ncbi.nlm.nih.gov/29668781/
Solvent mg/mL mM comments
Solubility
DMF:PBS (pH 7.2) (1:3) 0.3 0.64
DMSO 43.2 109.98
Ethanol 10.5 26.75
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 392.49 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Lee SU, Ahn KS, Sung MH, Park JW, Ryu HW, Lee HJ, Hong ST, Oh SR. Indacaterol inhibits tumor cell invasiveness and MMP-9 expression by suppressing IKK/NF-κB activation. Mol Cells. 2014 Aug;37(8):585-91. doi: 10.14348/molcells.2014.0076. Epub 2014 Aug 18. PMID: 25134539; PMCID: PMC4145369. 2. Anderson R, Theron AJ, Steel HC, Durandt C, Tintinger GR, Feldman C. The beta-2-adrenoreceptor agonists, formoterol and indacaterol, but not salbutamol, effectively suppress the reactivity of human neutrophils in vitro. Mediators Inflamm. 2014;2014:105420. doi: 10.1155/2014/105420. Epub 2014 Mar 6. PMID: 24733958; PMCID: PMC3964838. 3. Çimen O, Çimen FK, Gülaboğlu M, Bilgin AÖ, Çekiç AB, Eken H, Süleyman Z, Bilgin Y, Altuner D. The effect of metyrosine on oxidative gastric damage induced by ischemia/reperfusion in rats. Biochemical and histopathological evaluation. Acta Cir Bras. 2018 Mar;33(3):259-267. doi: 10.1590/s0102-865020180030000008. Erratum in: Acta Cir Bras. 2019 Feb 14;34(1):e20180308ERRATUM. PMID: 29668781. 4. Albayrak A, Polat B, Cadirci E, Hacimuftuoglu A, Halici Z, Gulapoglu M, Albayrak F, Suleyman H. Gastric anti-ulcerative and anti-inflammatory activity of metyrosine in rats. Pharmacol Rep. 2010 Jan-Feb;62(1):113-9. doi: 10.1016/s1734-1140(10)70248-6. PMID: 20360621.
In vitro protocol:
1. Lee SU, Ahn KS, Sung MH, Park JW, Ryu HW, Lee HJ, Hong ST, Oh SR. Indacaterol inhibits tumor cell invasiveness and MMP-9 expression by suppressing IKK/NF-κB activation. Mol Cells. 2014 Aug;37(8):585-91. doi: 10.14348/molcells.2014.0076. Epub 2014 Aug 18. PMID: 25134539; PMCID: PMC4145369. 2. Anderson R, Theron AJ, Steel HC, Durandt C, Tintinger GR, Feldman C. The beta-2-adrenoreceptor agonists, formoterol and indacaterol, but not salbutamol, effectively suppress the reactivity of human neutrophils in vitro. Mediators Inflamm. 2014;2014:105420. doi: 10.1155/2014/105420. Epub 2014 Mar 6. PMID: 24733958; PMCID: PMC3964838.
In vivo protocol:
1. Çimen O, Çimen FK, Gülaboğlu M, Bilgin AÖ, Çekiç AB, Eken H, Süleyman Z, Bilgin Y, Altuner D. The effect of metyrosine on oxidative gastric damage induced by ischemia/reperfusion in rats. Biochemical and histopathological evaluation. Acta Cir Bras. 2018 Mar;33(3):259-267. doi: 10.1590/s0102-865020180030000008. Erratum in: Acta Cir Bras. 2019 Feb 14;34(1):e20180308ERRATUM. PMID: 29668781. 2. Albayrak A, Polat B, Cadirci E, Hacimuftuoglu A, Halici Z, Gulapoglu M, Albayrak F, Suleyman H. Gastric anti-ulcerative and anti-inflammatory activity of metyrosine in rats. Pharmacol Rep. 2010 Jan-Feb;62(1):113-9. doi: 10.1016/s1734-1140(10)70248-6. PMID: 20360621.
1: Wachtel H, Kennedy EH, Zaheer S, Bartlett EK, Fishbein L, Roses RE, Fraker DL, Cohen DL. Preoperative Metyrosine Improves Cardiovascular Outcomes for Patients Undergoing Surgery for Pheochromocytoma and Paraganglioma. Ann Surg Oncol. 2015 Dec;22 Suppl 3:646-54. doi: 10.1245/s10434-015-4862-z. Epub 2015 Sep 15. PubMed PMID: 26374407. 2: Thanapaalasingham K, Pollmann AS, Schelew B. Failure of metyrosine therapy for preoperative management of pheochromocytoma: a case report. Can J Anaesth. 2015 Dec;62(12):1303-7. doi: 10.1007/s12630-015-0480-2. Epub 2015 Sep 11. PubMed PMID: 26362800. 3: Ahiskalioglu A, Ince I, Aksoy M, Ahiskalioglu EO, Comez M, Dostbil A, Celik M, Alp HH, Coskun R, Taghizadehghalehjoughi A, Suleyman B. Comparative Investigation of Protective Effects of Metyrosine and Metoprolol Against Ketamine Cardiotoxicity in Rats. Cardiovasc Toxicol. 2015 Oct;15(4):336-44. doi: 10.1007/s12012-014-9301-z. PubMed PMID: 25503950. 4: Yilmaz M, Isaoglu U, Uslu T, Yildirim K, Seven B, Akcay F, Hacimuftuoglu A. Effect of methylprednisolone on bone mineral density in rats with ovariectomy-induced bone loss and suppressed endogenous adrenaline levels by metyrosine. Indian J Pharmacol. 2013 Jul-Aug;45(4):344-7. doi: 10.4103/0253-7613.115008. PubMed PMID: 24014908; PubMed Central PMCID: PMC3757601. 5: Yigiter M, Yildiz A, Polat B, Alp HH, Keles ON, Salman AB, Suleyman H. The protective effects of metyrosine, lacidipine, clonidine, and moxonidine on kidney damage induced by unilateral ureteral obstruction in rats. Surg Today. 2012 Nov;42(11):1051-60. doi: 10.1007/s00595-011-0074-8. Epub 2011 Dec 28. PubMed PMID: 22202971. 6: Salman S, Kumbasar S, Hacimuftuoglu A, Ozturk B, Seven B, Polat B, Gundogdu C, Demirci E, Yildirim K, Akcay F, Uslu T, Tuncel Daloglu F, Suleyman H. The effect of metyrosine/prednisolone combination to oophorectomy-induced osteoporosis. Iran J Reprod Med. 2012 Jul;10(4):363-72. PubMed PMID: 25246899; PubMed Central PMCID: PMC4165955. 7: Albayrak Y, Saglam MB, Yildirim K, Karatay S, Polat B, Uslu T, Suleyman H, Akcay F. Effects of epinephrine and cortisol on the analgesic activity of metyrosine in rats. Arch Pharm Res. 2011 Sep;34(9):1519-25. doi: 10.1007/s12272-011-0914-5. Epub 2011 Oct 6. PubMed PMID: 21975814. 8: Albayrak A, Polat B, Cadirci E, Hacimuftuoglu A, Halici Z, Gulapoglu M, Albayrak F, Suleyman H. Gastric anti-ulcerative and anti-inflammatory activity of metyrosine in rats. Pharmacol Rep. 2010 Jan-Feb;62(1):113-9. PubMed PMID: 20360621. 9: Carandang CG, Scholten MC. Metyrosine in psychosis associated with 22q11.2 deletion syndrome: case report. J Child Adolesc Psychopharmacol. 2007 Feb;17(1):115-20. PubMed PMID: 17343559. 10: Steinsapir J, Carr AA, Prisant LM, Bransome ED Jr. Metyrosine and pheochromocytoma. Arch Intern Med. 1997 Apr 28;157(8):901-6. PubMed PMID: 9129550. 11: Aly FA, Belal F, el-Brashy A. Polarographic determination of metyrosine through treatment with nitrous acid. Pharm World Sci. 1993 Oct 15;15(5):208-11. PubMed PMID: 7903059. 12: Perry RR, Keiser HR, Norton JA, Wall RT, Robertson CN, Travis W, Pass HI, Walther MM, Linehan WM. Surgical management of pheochromocytoma with the use of metyrosine. Ann Surg. 1990 Nov;212(5):621-8. PubMed PMID: 1978640; PubMed Central PMCID: PMC1358191. 13: Serri O, Comtois R, Bettez P, Dubuc G, Buu NT, Kuchel O. Reduction in the size of a pheochromocytoma pulmonary metastasis by metyrosine therapy. N Engl J Med. 1984 May 10;310(19):1264-5. PubMed PMID: 6709035. 14: Anton AH, Crumrine RS, Stern RC, Izant RJ Jr. Inhibition of catecholamine biosynthesis by carbidopa and metyrosine in neuroblastoma. Pediatr Pharmacol (New York). 1983;3(2):107-17. PubMed PMID: 6425794. 15: Triner L, Baer L, Gallagher R, Weitzman S. Use of metyrosine in the anaesthetic management of patients with catecholamine-secreting tumours. A case report. Br J Anaesth. 1982 Dec;54(12):1333-6. PubMed PMID: 6128992. 16: Metyrosine for pheochromocytoma. Med Lett Drugs Ther. 1980 Mar 21;22(6):28. PubMed PMID: 7360110. 17: Magelund G, Gerlach J, Casey DE. Neuroleptic-potentiating effect of metyrosine. Am J Psychiatry. 1979 May;136(5):732. PubMed PMID: 35016. 18: Scriabine A, Ludden CT, Sweet CS, Porter CC, Ulm EH, Stone CA, Watkins CJ, Wurtman RJ, Cronin BL. Antihypertensive activity of metyrosine in spontaneously hypertensive rats and its enhancement by carbidopa. Clin Sci Mol Med Suppl. 1978 Dec;4:255s-257s. PubMed PMID: 282064. 19: Nasrallah HA, Donnelly EF, Bigelow LB, Rivera-Calimlim L, Rogol A, Potkin S, Rauscher FP, Wyatt RJ. Inhibition of dopamine synthesis in chronic schizophrenia. Clinical ineffectiveness of metyrosine. Arch Gen Psychiatry. 1977 Jun;34(6):649-55. PubMed PMID: 17374. 20: Wålinder J, Skott A, Carlsson A, Roos BE. Potentiation by metyrosine of thioridazine effects in chronic schizophrenics. A long-term trial using double-blind crossover technique. Arch Gen Psychiatry. 1976 Apr;33(4):501-5. PubMed PMID: 779704.