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Details

Stereochemistry ABSOLUTE
Molecular Formula C12H17NO4
Molecular Weight 239.2677
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of METHYLDOPATE

SMILES

CCOC(=O)[C@@](C)(N)CC1=CC(O)=C(O)C=C1

InChI

InChIKey=SVEBYYWCXTVYCR-LBPRGKRZSA-N
InChI=1S/C12H17NO4/c1-3-17-11(16)12(2,13)7-8-4-5-9(14)10(15)6-8/h4-6,14-15H,3,7,13H2,1-2H3/t12-/m0/s1

HIDE SMILES / InChI

Molecular Formula C12H17NO4
Molecular Weight 239.2677
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Methyldopate hydrochloride [levo-3-(3,4-dihydroxyphenyl)-2-methylalanine, ethyl ester hydrochloride] is the ethyl ester of methyldopa, supplied as the hydrochloride salt with a molecular weight of 275.73. Methyldopate hydrochloride is more soluble and stable in solution than methyldopa and is the preferred form for intravenous use. Methyldopate hydrochloride is an alpha adrenergic agonist that has both central and peripheral nervous system effects. Its primary clinical use is as an antihypertensive agent.

CNS Activity

Originator

Approval Year

PubMed

PubMed

TitleDatePubMed
[Use of alpha-methyldopa in the treatment of arterial hypertension].
1975 Aug 31
Delayed hepatotoxicity from methyldopa.
1975 Dec
Dihydroergotamine: an effective treatment for postural hypotension due to antihypertensive drugs (ganglion-blocking agents excepted).
1976
Some side-effects of alpha-methyldopa.
1976 Apr 10
Dementia induced by methyldopa with haloperidol.
1976 May 27
Development and trends in the drug treatment of essential hypertension.
1992 Dec
Autoantibodies associated with lupus induced by diverse drugs target a similar epitope in the (H2A-H2B)-DNA complex.
1992 Jul
Acute reactive hepatitis in pregnancy induced by alpha-methyldopa.
1997 Oct
Pregnancy and renal failure: the case for application of dosage guidelines.
2001
Drugs in pregnancy. Antihypertensives.
2001 Dec
Effect of phenobarbital and spironolactone treatment on the oxidative metabolism of antipyrine by rat liver microsomes.
2001 Jan-Feb
Pharmacokinetic and pharmacodynamic alterations of methyldopa in rats with aortic coarctation. A study using microdialysis.
2001 Nov
Juxtaglomerular cell tumor in pregnancy.
2001 Nov
Catechol-O-methyltransferase (COMT) genetic polymorphism in a Turkish population.
2001 Sep
Hepatotoxicity of commonly used drugs: nonsteroidal anti-inflammatory drugs, antihypertensives, antidiabetic agents, anticonvulsants, lipid-lowering agents, psychotropic drugs.
2002
Methyldopa versus no drug treatment in the management of mild pre-eclampsia.
2002 Apr
Immune-mediated drug-induced liver disease.
2002 Aug
[Primary aldosteronism and pregnancy: report of 2 cases].
2002 Dec
Calcium channel blocker, nimodipine, for the treatment of bipolar disorder during pregnancy.
2002 Dec
The effect of methyldopa treatment on uterine, umblical and fetal middle cerebral artery blood flows in preeclamptic patients.
2002 Jul
C4 deficiency state in antiphospholipid antibody-related recurrent preeclampsia evolving into systemic lupus erythematosus.
2002 Jul
Detection of alpha-methyldopa on thin-layer plates using pi-acceptors in 1,4-dioxane.
2002 Jul-Aug
The treatment of hypertension in pregnancy.
2002 May
The effect of antihypertensive drugs on the fetus.
2002 May
Pathophysiology and treatment of hot flashes.
2002 Nov
Nephropathic cystinosis associated with cardiomyopathy: a 27-year clinical follow-up.
2002 Nov 9
Oral beta-blockers for mild to moderate hypertension during pregnancy.
2003
Determination of antioxidant activity of some drugs using high-pressure liquid chromatography.
2003
Shifting trends in the pharmacologic treatment of hypertension in a Nigerian tertiary hospital: a real-world evaluation of the efficacy, safety, rationality and pharmaco-economics of old and newer antihypertensive drugs.
2003 Apr
Antihypertensive drug-associated sexual dysfunction: a prescription analysis-based study.
2003 Apr-May
Methyldopa supplement for resistant essential hypertension: a prospective randomized placebo control crossover study.
2003 Dec
Binding site of salsolinol: its properties in different regions of the brain and the pituitary gland of the rat.
2003 Jan
Pharmacokinetic profile of methyldopa in the brain of sinaortic-denervated rats.
2003 Jul
[Circadian blood pressure rhythm in preeclampsia as a predictor of maternal and obstetrical outcome].
2003 Jul-Aug
Antihypertensive efficacy of moxonidine in primary care: a 'real-life' study.
2003 Jul-Aug
Catechol-O-methyltransferase inhibition in erythrocytes and liver by BIA 3-202 (1-[3,4-dibydroxy-5-nitrophenyl]-2-phenyl-ethanone).
2003 Jun
Replacement of antipsychotic and antiepileptic medication by L-alpha-methyldopa in a woman with velocardiofacial syndrome.
2003 Mar
The aggressive treatment of hypertension.
2003 May 3
A survey of Canadian practitioners regarding the management of the hypertensive disorders of pregnancy.
2004
Preeclampsia with abnormal liver function tests is associated with cholestasis in a subgroup of cases.
2004
[Methyldopa in therapy of hypertension in pregnant women].
2004 Feb
Pheochromocytoma during pregnancy: laparoscopic and conventional surgical treatment of two cases.
2004 Feb
[Dementia induced by cardiokinetic and anti-hypertensive drugs].
2004 Jan
Liquid chromatography-tandem mass spectrometry method for the determination of tranexamic acid in human plasma.
2004 Jun 15
[Centrally-acting antihypertensive drugs].
2004 Mar
[Hypertension in pregnancy].
2004 Mar
Mediated exodus of L-dopa from human epidermal Langerhans cells.
2004 Mar
Drug-induced liver injury.
2004 Mar 1
Differential modulation by estrogen of alpha2-adrenergic and I1-imidazoline receptor-mediated hypotension in female rats.
2004 Oct
Inadequate control of blood pressure in Nigerians with diabetes.
2004 Winter
Patents

Sample Use Guides

In Vivo Use Guide
Initial: 250 mg PO q8-12hr for 2 days, increase q2Days PRN Maintenance: 250-1000 mg/day divided q6-12hr PO, usually no more than 3 g/day IV (methyldopate): 250-1000 mg infusion over 30-60 minutes q6-8hr PRN; no more than 4 g/day
Route of Administration: Intravenous; Oral
In Vitro Use Guide
Human uterine microvascular endothelial cells (UtMVEC) (PromoCell, Heidelberg, Germany) were cultured in EGM-2- MV medium (Lonza, Basel, Switzerland) until about 80% confluent. Cells from passage 4-8 were used in this study. Tissue culture plates (24-wells) were coated with undiluted Matrigel (300 μL/well; In Vitro Technologies, Noble Park, Vic., Australia) and polymerized for 30 minutes at 37°C. UtMVECs (100 000 cells/well) were seeded into each well and endothelial cell tubular networks formed within 4 hours of further incubation at 37°C. HTR-8/ SVneo cells (100 000 cells/well) were then added to each well with or without a low dose of TNF-α (0.5 ng/mL) together with methyldopa (5 μg/ mL), labetalol (0.5 μg/mL), hydralazine (10 μg/mL) or clonidine (1.0 μg/ mL) and co-cultured with the endothelial cellular networks. The control co-cultured cells had neither TNF-α nor medications added. After 24 hours of culture, the cells were retrieved from the cellular networks in Matrigel with Cell Recovery Solution (CRS) (In Vitro Technologies) for RNA extraction
Substance Class Chemical
Created
by admin
on Tue Oct 22 00:25:24 UTC 2019
Edited
by admin
on Tue Oct 22 00:25:24 UTC 2019
Record UNII
2579Z4P04J
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
METHYLDOPATE
VANDF   WHO-DD  
Common Name English
METHYLDOPATE [VANDF]
Common Name English
METHYLDOPATE [WHO-DD]
Common Name English
L-TYROSINE, 3-HYDROXY-.ALPHA.-METHYL-, ETHYL ESTER
Common Name English
L-3-(3,4-DIHYDROXYPHENYL)-2-METHYLALANINE ETHYL ESTER
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29709
Created by admin on Tue Oct 22 00:25:24 UTC 2019 , Edited by admin on Tue Oct 22 00:25:24 UTC 2019
Code System Code Type Description
ChEMBL
CHEMBL1201233
Created by admin on Tue Oct 22 00:25:24 UTC 2019 , Edited by admin on Tue Oct 22 00:25:24 UTC 2019
PRIMARY
RXCUI
6877
Created by admin on Tue Oct 22 00:25:24 UTC 2019 , Edited by admin on Tue Oct 22 00:25:24 UTC 2019
PRIMARY RxNorm
CAS
2544-09-4
Created by admin on Tue Oct 22 00:25:24 UTC 2019 , Edited by admin on Tue Oct 22 00:25:24 UTC 2019
PRIMARY
NCI_THESAURUS
C75041
Created by admin on Tue Oct 22 00:25:24 UTC 2019 , Edited by admin on Tue Oct 22 00:25:24 UTC 2019
PRIMARY
EPA CompTox
2544-09-4
Created by admin on Tue Oct 22 00:25:24 UTC 2019 , Edited by admin on Tue Oct 22 00:25:24 UTC 2019
PRIMARY
PUBCHEM
17277
Created by admin on Tue Oct 22 00:25:24 UTC 2019 , Edited by admin on Tue Oct 22 00:25:24 UTC 2019
PRIMARY
EVMPD
SUB08867MIG
Created by admin on Tue Oct 22 00:25:24 UTC 2019 , Edited by admin on Tue Oct 22 00:25:24 UTC 2019
PRIMARY
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