RACEMETYROSINE HYDROCHLORIDE

Investigational

Details

Stereochemistry	RACEMIC
Molecular Formula	C10H13NO3.ClH
Molecular Weight	231.676
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of RACEMETYROSINE HYDROCHLORIDE

SMILES

Cl.CC(N)(CC1=CC=C(O)C=C1)C(O)=O

InChI

InChIKey=BVYZLEHNLQKCHO-UHFFFAOYSA-N

InChI=1S/C10H13NO3.ClH/c1-10(11,9(13)14)6-7-2-4-8(12)5-3-7;/h2-5,12H,6,11H2,1H3,(H,13,14);1H

HIDE SMILES / InChI

Molecular Formula	ClH
Molecular Weight	36.461
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	C10H13NO3
Molecular Weight	195.2151
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Description

Racemetirosine is an orally active inhibitor of the enzyme tyrosine 3-monooxygenase, and consequently of the synthesis of catecholamine. At dosages of 600 to 3500mg daily, it is effective in controlling the hypertensive episodes and symptoms of catecholamine excess in phaeochromocytoma during preparation for surgery. Oral Racemetirosine is well absorbed and absorption appears constant in each individual over a wide dosage range. The drug is largely excreted via the kidneys, but extrarenal elimination has not been studied. Case reports on the clinical use of Racemetirosine in phaeochromocytoma indicate that the drug controls hypertension and symptoms of catecholamine excess in most patients during preparation for surgical removal of a tumor. In some cases, the addition of Racemetirosine to phenoxybenzamine plus propranolol has resulted in adequate control of symptoms previously unresponsive to the adrenergic blocking regimen. Drowsiness and sedation have been the most frequently reported side effects of Racemetirosine treatment.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Tyrosine 3-hydroxylase 6	Inhibitor 8,504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Pheochromocytoma 14	Primary		Not Provided 511	Unknown

PubMed

Show entries

Title	Date	PubMed
Biochemical and pharmacologic effects of alpha-methyltyrosine in man.	1968 Mar	5637145
Noradrenergic content and turnover rate in kidney and heart shows gender and strain differences.	2002 Feb	11796665
The L-DOPA-sparing effect of R-(-)-1-(benzofuran-2-yl)-2-propylaminopentane hydrochloride [(-)-BPAP] in reserpine-pretreated rats.	2003 Feb 7	12527038
The partial dopamine D2-like receptor agonist terguride functions as an agonist in preweanling rats after a 5-day reserpine regimen.	2006 Mar	16447063
alpha(2)-Adrenoceptors mediate the acute inhibitory effect of fluoxetine on locus coeruleus noradrenergic neurons.	2009 May-Jun	19298831

Showing 1 to 5 of 5 entries

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Patents

Sample Use Guides

In Vivo Use Guide

The initial dose in adults and children 12 years of age and older is 250mg 4 times daily. This may be increased by 250 or 500mg daily to a maximum of 4g daily in divided doses, but the individual dose should be titrated by monitoring clinical symptoms and urinary catecholamine excretion.

Route of Administration: Oral

In Vitro Use Guide

Human mixed synoviocytes were incubated under hypoxic and normoxic conditions for 24 h with specific tyrosine hydroxylase (TH) cofactors BH4 (6R-5,6,7,8-tetrahydrobiopterin dihydrochloride), bivalent iron (Fe2+ sulfate heptahydrate), α-methyl-para-tyrosine (αmpT; a competitive TH blocker), monoaminooxidase (MAO) inhibitor bifemelane hydrochloric acid (HCL) and catechol-O-methyltransferase (COMT) inhibitor OR-486 Supernatant was collected and concentrations of interleukin (IL)-6, IL-8 and tumour necrosis factor (TNF) were determined by ELISA or Luminex technology. For catecholamine determination high pressure liquid chromatography (HPLC) was performed. Expression of TH was analysed by immunocytochemistry in chamber slides and via western blotting.