U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C10H13NO4
Molecular Weight 211.2145
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of METHYLDOPA ANHYDROUS

SMILES

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

InChI

InChIKey=CJCSPKMFHVPWAR-JTQLQIEISA-N
InChI=1S/C10H13NO4/c1-10(11,9(14)15)5-6-2-3-7(12)8(13)4-6/h2-4,12-13H,5,11H2,1H3,(H,14,15)/t10-/m0/s1

HIDE SMILES / InChI

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
Some side-effects of alpha-methyldopa.
1976 Apr 10
Dementia induced by methyldopa with haloperidol.
1976 May 27
Cardiac hypertrophy and antihypertensive therapy.
1977 Sep
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
Antihypertensive treatment decreased serum leptin levels in severe preeclampsia during pregnancy.
2001
[Drug-induced hemolytic anemia].
2001 Aug
Effect of phenobarbital and spironolactone treatment on the oxidative metabolism of antipyrine by rat liver microsomes.
2001 Jan-Feb
Juxtaglomerular cell tumor in pregnancy.
2001 Nov
Catechol-O-methyltransferase (COMT) genetic polymorphism in a Turkish population.
2001 Sep
Involvement of imidazoline receptors in the baroreflex effects of rilmenidine in conscious rabbits.
2001 Sep
The immune haemolytic anaemias: a century of exciting progress in understanding.
2001 Sep
Excretion of antihypertensive medication into human breast milk: a systematic review.
2002
Methyldopa versus no drug treatment in the management of mild pre-eclampsia.
2002 Apr
Liddle syndrome in a newborn infant.
2002 Aug
Effects of six anti-hypertensive medications on cognitive performance.
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
Rapid-eye-movement sleep in jittery infants.
2002 Jan
Hypertension/preeclampsia.
2002 Jan-Feb
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
Antihypertensive medication compliance in a Veterans Affairs Healthcare System.
2002 Jun
The treatment of hypertension in pregnancy.
2002 May
The effect of antihypertensive drugs on the fetus.
2002 May
Nephropathic cystinosis associated with cardiomyopathy: a 27-year clinical follow-up.
2002 Nov 9
Spectrophotometric investigations of the assay of physiologically active catecholamines in pharmaceutical formulations.
2002 Nov-Dec
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
Pharmacokinetic profile of methyldopa in the brain of sinaortic-denervated rats.
2003 Jul
Antihypertensive efficacy of moxonidine in primary care: a 'real-life' study.
2003 Jul-Aug
Blood pressure response to out-patient drug treatment of hypertension in 1973-1993 at Korle-Bu Teaching Hospital, Accra, Ghana.
2003 Jun
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
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
Name Type Language
METHYLDOPA ANHYDROUS
Common Name English
J9.247I
Code English
ANHYDROUS METHYLDOPA
MART.  
Common Name English
(-)-.ALPHA.-METHYLDOPA
Common Name English
L-.ALPHA.-METHYL-3-(3,4)-DIHYDROXYPHENYLALANINE
Common Name English
L-TYROSINE, 3-HYDROXY-.ALPHA.-METHYL-
Systematic Name English
METHYLDOPA (LEVOROTATORY)
Common Name English
BAYER-1440L
Code English
(-)-METHYLDOPA
Systematic Name English
ANHYDROUS METHYLDOPA [MART.]
Common Name English
(-)-.ALPHA.-METHYL-3,4-DIHYDROXYPHENYLALANINE
Systematic Name English
L-.ALPHA.-METHYLDOPA
Common Name English
(2S)-2-AMINO-3-(3,4-DIHYDROXYPHENYL)-2-METHYLPROPANOIC ACID
Systematic Name English
.ALPHA.-METHYL-L-DOPA
Brand Name English
METHYLDOPA [WHO-DD]
Common Name English
L-3-(3,4-DIHYDROXYPHENYL)-2-METHYLALANINE
Common Name English
METHYL DOPA
Systematic Name English
METHYLDOPA [INN]
Common Name English
METHYLDOPA [MI]
Common Name English
CARBIDOPA IMPURITY A [EP]
Common Name English
LEDERDOPA
Brand Name English
METHYLDOPA [HSDB]
Common Name English
NSC-169916
Code English
METHYLDOPA, ANHYDROUS
Common Name English
.ALPHA.-METHYL-L-3,4-DIHYDROXYPHENYLALANINE
Common Name English
(S)-(-)-.ALPHA.-METHYLDOPA
Common Name English
Classification Tree Code System Code
WHO-ATC C02AB01
Created by admin on Mon Oct 21 22:33:25 UTC 2019 , Edited by admin on Mon Oct 21 22:33:25 UTC 2019
NDF-RT N0000175554
Created by admin on Mon Oct 21 22:33:25 UTC 2019 , Edited by admin on Mon Oct 21 22:33:25 UTC 2019
WHO-ATC C02LB01
Created by admin on Mon Oct 21 22:33:25 UTC 2019 , Edited by admin on Mon Oct 21 22:33:25 UTC 2019
NDF-RT N0000009918
Created by admin on Mon Oct 21 22:33:25 UTC 2019 , Edited by admin on Mon Oct 21 22:33:25 UTC 2019
WHO-ATC C02AB
Created by admin on Mon Oct 21 22:33:25 UTC 2019 , Edited by admin on Mon Oct 21 22:33:25 UTC 2019
Code System Code Type Description
PUBCHEM
38853
Created by admin on Mon Oct 21 22:33:25 UTC 2019 , Edited by admin on Mon Oct 21 22:33:25 UTC 2019
PRIMARY
ECHA (EC/EINECS)
209-089-2
Created by admin on Mon Oct 21 22:33:25 UTC 2019 , Edited by admin on Mon Oct 21 22:33:25 UTC 2019
PRIMARY
RXCUI
1545996
Created by admin on Mon Oct 21 22:33:25 UTC 2019 , Edited by admin on Mon Oct 21 22:33:25 UTC 2019
PRIMARY RxNorm
EVMPD
SUB08867MIG
Created by admin on Mon Oct 21 22:33:25 UTC 2019 , Edited by admin on Mon Oct 21 22:33:25 UTC 2019
PRIMARY
INN
1110
Created by admin on Mon Oct 21 22:33:25 UTC 2019 , Edited by admin on Mon Oct 21 22:33:25 UTC 2019
PRIMARY
HSDB
555-30-6
Created by admin on Mon Oct 21 22:33:25 UTC 2019 , Edited by admin on Mon Oct 21 22:33:25 UTC 2019
PRIMARY
EPA CompTox
555-30-6
Created by admin on Mon Oct 21 22:33:25 UTC 2019 , Edited by admin on Mon Oct 21 22:33:25 UTC 2019
PRIMARY
LactMed
555-30-6
Created by admin on Mon Oct 21 22:33:25 UTC 2019 , Edited by admin on Mon Oct 21 22:33:25 UTC 2019
PRIMARY
EVMPD
SUB26433
Created by admin on Mon Oct 21 22:33:25 UTC 2019 , Edited by admin on Mon Oct 21 22:33:25 UTC 2019
PRIMARY
MERCK INDEX
M7397
Created by admin on Mon Oct 21 22:33:25 UTC 2019 , Edited by admin on Mon Oct 21 22:33:25 UTC 2019
PRIMARY Merck Index
CAS
555-30-6
Created by admin on Mon Oct 21 22:33:25 UTC 2019 , Edited by admin on Mon Oct 21 22:33:25 UTC 2019
PRIMARY
DRUG BANK
DB00968
Created by admin on Mon Oct 21 22:33:25 UTC 2019 , Edited by admin on Mon Oct 21 22:33:25 UTC 2019
PRIMARY
WIKIPEDIA
METHYLDOPA
Created by admin on Mon Oct 21 22:33:25 UTC 2019 , Edited by admin on Mon Oct 21 22:33:25 UTC 2019
PRIMARY