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Details

Stereochemistry ABSOLUTE
Molecular Formula 2C10H13NO4.3H2O
Molecular Weight 476.4749
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of METHYLDOPA

SMILES

O.O.O.C[C@](N)(CC1=CC=C(O)C(O)=C1)C(O)=O.C[C@](N)(CC2=CC=C(O)C(O)=C2)C(O)=O

InChI

InChIKey=YKFCISHFRZHKHY-NGQGLHOPSA-N
InChI=1S/2C10H13NO4.3H2O/c2*1-10(11,9(14)15)5-6-2-3-7(12)8(13)4-6;;;/h2*2-4,12-13H,5,11H2,1H3,(H,14,15);3*1H2/t2*10-;;;/m00.../s1

HIDE SMILES / InChI

Molecular Formula H2O
Molecular Weight 18.0153
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C10H13NO4
Molecular Weight 211.2145
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
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
Autoantibodies associated with lupus induced by diverse drugs target a similar epitope in the (H2A-H2B)-DNA complex.
1992 Jul
Centrally acting imidazoline I1-receptor agonists: do they have a place in the management of hypertension?
2001
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
Immune-mediated drug-induced liver disease.
2002 Aug
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
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
The effects of dopamine synthesis inhibitors and dopamine antagonists on regeneration in the hydra Hydra attenuata.
2002 May-Jun
Analysis of L-dopa in human serum.
2002 Nov
Pathophysiology and treatment of hot flashes.
2002 Nov
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
Comparative single- and multiple-dose pharmacokinetics of levodopa and 3-O-methyldopa following a new dual-release and a conventional slow-release formulation of levodopa and benserazide in healthy volunteers.
2003
Angiotensin II-receptor-antagonists: further evidence of fetotoxicity but not teratogenicity.
2003 Aug
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
Antihypertensive efficacy of moxonidine in primary care: a 'real-life' study.
2003 Jul-Aug
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
Physician gender and antihypertensive prescription pattern in primary care.
2003 Nov
[Clinical observation on the efficacy enhancing and toxicity attenuating effect of nuzhen yangyin granule to the anti-parkinsonism therapy mainly with Medopa].
2003 Nov
Nocturnal sleep, daytime sleepiness, and quality of life in stable patients on hemodialysis.
2003 Nov 21
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
Chronic ethanol administration attenuates imidazoline I1 receptor- or alpha 2-adrenoceptor-mediated reductions in blood pressure and hemodynamic variability in hypertensive rats.
2004 Feb 6
[Dementia induced by cardiokinetic and anti-hypertensive drugs].
2004 Jan
Oral enalapril-hydrochlorothiazide-methyldopa as first line treatment for severe hypertension in Nigerians.
2004 Jan
Treatment of menopause-associated vasomotor symptoms: position statement of The North American Menopause Society.
2004 Jan-Feb
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
Treating high blood pressure in Africans with type 2 diabetes.
2004 Winter
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 00:50:14 UTC 2019
Edited
by admin
on Tue Oct 22 00:50:14 UTC 2019
Record UNII
56LH93261Y
Record Status Validated (UNII)
Record Version
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Name Type Language
METHYLDOPA
EP   MART.   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-IP  
USAN  
Official Name English
METHYLDOPA [USP]
Common Name English
ALDORIL COMPONENT METHYLDOPA
Common Name English
L-3-(3,4-DIHYDROXYPHENYL)-2-METHYLALANINE SESQUIHYDRATE
Common Name English
ALPHA-METHYLDOPA
Common Name English
DOPEGYT
Brand Name English
METHYLDOPUM [WHO-IP LATIN]
Common Name English
L-TYROSINE, 3-HYDROXY-.ALPHA.-METHYL-, SESQUIHYDRATE
Common Name English
L-TYROSINE, 3-HYDROXY-.ALPHA.-METHYL-, HYDRATE (2:3)
Systematic Name English
PRESINOL
Brand Name English
METHYLDOPA [USAN]
Common Name English
METHYLDOPA [USP-RS]
Common Name English
METHYLDOPA [ORANGE BOOK]
Common Name English
METHYLDOPA [VANDF]
Common Name English
MK-351
Code English
METHYLDOPA SESQUIHYDRATE [WHO-DD]
Common Name English
METHYLDOPA SESQUIHYDRATE [MI]
Common Name English
METHYLDOPA SESQUIHYDRATE
MART.   MI   WHO-DD  
Common Name English
DOPAMET
Brand Name English
METHYLDOPA SESQUIHYDRATE [MART.]
Common Name English
METHYLDOPA [WHO-IP]
Common Name English
METHYLDOPA HYDRATE
JAN  
Systematic Name English
METHYLDOPA COMPONENT OF ALDORIL
Common Name English
METHYLDOPA [MART.]
Common Name English
MEDOPREN
Brand Name English
ALDOMET
Brand Name English
METHYLDOPA HYDRATE [JAN]
Common Name English
METHYLDOPA [EP]
Common Name English
Classification Tree Code System Code
WHO-VATC QC02AB01
Created by admin on Tue Oct 22 00:50:14 UTC 2019 , Edited by admin on Tue Oct 22 00:50:14 UTC 2019
LIVERTOX 624
Created by admin on Tue Oct 22 00:50:14 UTC 2019 , Edited by admin on Tue Oct 22 00:50:14 UTC 2019
NCI_THESAURUS C270
Created by admin on Tue Oct 22 00:50:14 UTC 2019 , Edited by admin on Tue Oct 22 00:50:14 UTC 2019
FDA ORPHAN DRUG 548616
Created by admin on Tue Oct 22 00:50:14 UTC 2019 , Edited by admin on Tue Oct 22 00:50:14 UTC 2019
WHO-VATC QC02LB01
Created by admin on Tue Oct 22 00:50:14 UTC 2019 , Edited by admin on Tue Oct 22 00:50:14 UTC 2019
NCI_THESAURUS C66884
Created by admin on Tue Oct 22 00:50:14 UTC 2019 , Edited by admin on Tue Oct 22 00:50:14 UTC 2019
NDF-RT N0000175554
Created by admin on Tue Oct 22 00:50:14 UTC 2019 , Edited by admin on Tue Oct 22 00:50:14 UTC 2019
WHO-ESSENTIAL MEDICINES LIST 12.3
Created by admin on Tue Oct 22 00:50:14 UTC 2019 , Edited by admin on Tue Oct 22 00:50:14 UTC 2019
Code System Code Type Description
WIKIPEDIA
METHYLDOPA
Created by admin on Tue Oct 22 00:50:14 UTC 2019 , Edited by admin on Tue Oct 22 00:50:14 UTC 2019
PRIMARY
EVMPD
SUB08867MIG
Created by admin on Tue Oct 22 00:50:14 UTC 2019 , Edited by admin on Tue Oct 22 00:50:14 UTC 2019
PRIMARY
EPA CompTox
41372-08-1
Created by admin on Tue Oct 22 00:50:14 UTC 2019 , Edited by admin on Tue Oct 22 00:50:14 UTC 2019
PRIMARY
PUBCHEM
38852
Created by admin on Tue Oct 22 00:50:14 UTC 2019 , Edited by admin on Tue Oct 22 00:50:14 UTC 2019
PRIMARY
ChEMBL
CHEMBL459
Created by admin on Tue Oct 22 00:50:14 UTC 2019 , Edited by admin on Tue Oct 22 00:50:14 UTC 2019
PRIMARY
NCI_THESAURUS
C47616
Created by admin on Tue Oct 22 00:50:14 UTC 2019 , Edited by admin on Tue Oct 22 00:50:14 UTC 2019
PRIMARY
RXCUI
6876
Created by admin on Tue Oct 22 00:50:14 UTC 2019 , Edited by admin on Tue Oct 22 00:50:14 UTC 2019
PRIMARY RxNorm
MESH
D008750
Created by admin on Tue Oct 22 00:50:14 UTC 2019 , Edited by admin on Tue Oct 22 00:50:14 UTC 2019
PRIMARY
MERCK INDEX
M7397
Created by admin on Tue Oct 22 00:50:14 UTC 2019 , Edited by admin on Tue Oct 22 00:50:14 UTC 2019
PRIMARY
CAS
41372-08-1
Created by admin on Tue Oct 22 00:50:14 UTC 2019 , Edited by admin on Tue Oct 22 00:50:14 UTC 2019
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
METHYLDOPA
Created by admin on Tue Oct 22 00:50:14 UTC 2019 , Edited by admin on Tue Oct 22 00:50:14 UTC 2019
PRIMARY Description: White to yellowish white, fine powder or lumps; odourless. Solubility: Slightly soluble in water and ethanol (~750 g/l) TS; practically insoluble in ether R. Category: Antihypertensive. Storage: Methyldopa should be kept in a well-closed container, protected from light. Definition: Methyldopa contains not less than 98.0% and not more than 101.0% of C10H13NO4, calculated with reference to the anhydrous substance.
EVMPD
SUB25993
Created by admin on Tue Oct 22 00:50:14 UTC 2019 , Edited by admin on Tue Oct 22 00:50:14 UTC 2019
PRIMARY
Related Record Type Details
BASIS OF STRENGTH->SUBSTANCE
ASSAY (TITRATION)
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BASIS OF STRENGTH->SUBSTANCE
ASSAY (TITRATION)
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PARENT -> SALT/SOLVATE
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For the calculation of contents, multiply the peak areas by 1.3
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IMPURITY -> PARENT
For the calculation of contents, multiply the peak areas by 2.6
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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ACTIVE MOIETY