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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

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
Dihydroergotamine: an effective treatment for postural hypotension due to antihypertensive drugs (ganglion-blocking agents excepted).
1976
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
Centrally acting imidazoline I1-receptor agonists: do they have a place in the management of hypertension?
2001
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
Detection of alpha-methyldopa on thin-layer plates using pi-acceptors in 1,4-dioxane.
2002 Jul-Aug
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
Determination of antioxidant activity of some drugs using high-pressure liquid chromatography.
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
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
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
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
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
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 Mon Oct 21 22:33:25 UTC 2019
Edited
by admin
on Mon Oct 21 22:33:25 UTC 2019
Record UNII
M4R0H12F6M
Record Status Validated (UNII)
Record Version
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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
Related Record Type Details
TARGET -> INHIBITOR
SALT/SOLVATE -> PARENT
SUBSTANCE->BASIS OF STRENGTH
Related Record Type Details
PARENT -> METABOLITE
URINE
METABOLITE -> PARENT
ACTIVE IN RATS
METABOLITE -> PARENT
URINE
METABOLITE -> PARENT
URINE
METABOLITE -> PARENT
METABOLITE -> PARENT
URINE
METABOLITE -> PARENT
Approximately 70 percent of the drug which is absorbed is excreted in the urine as methyldopa and its mono-0-sulfate conjugate
MAJOR
PLASMA; URINE
Related Record Type Details
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Related Record Type Details
ACTIVE MOIETY