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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 No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

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

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
ALDOMET

Approved Use

INDICATION AND USAGE: Hypertension.

Launch Date

1962
Primary
ALDOMET

Approved Use

INDICATION AND USAGE: Hypertension.

Launch Date

1962
Primary
ALDOMET

Approved Use

INDICATION AND USAGE: Hypertension.

Launch Date

1962
Primary
Methyldopate hydrochloride

Approved Use

Hypertension, when parenteral medication is indicated. The treatment of hypertensive crises may be initiated with Methyldopate HCl Injection.

Launch Date

1995
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
771.3 ng/mL
250 mg single, oral
dose: 250 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
METHYLDOPA plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
5352.9 ng × h/mL
250 mg single, oral
dose: 250 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
METHYLDOPA plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
4.54 μg × h/mL
100 mg single, intravenous
dose: 100 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
METHYLDOPA plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
12.6 h
250 mg single, oral
dose: 250 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
METHYLDOPA plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
1.28 h
100 mg single, intravenous
dose: 100 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
METHYLDOPA plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
85%
100 mg single, intravenous
dose: 100 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
METHYLDOPA plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
2.5 g single, oral
Dose: 2.5 g
Route: oral
Route: single
Dose: 2.5 g
Sources:
unknown, 19
Health Status: unknown
Age Group: 19
Sex: M
Sources:
Other AEs: Coma...
Other AEs:
Coma (grade 1)
Sources:
2326 mg multiple, oral
Recommended
Dose: 2326 mg
Route: oral
Route: multiple
Dose: 2326 mg
Sources:
unhealthy, 36-68
Health Status: unhealthy
Age Group: 36-68
Sex: M+F
Sources:
Disc. AE: Depression, Tiredness...
AEs leading to
discontinuation/dose reduction:
Depression (2 patients)
Tiredness (2 patients)
Diarrhoea (1 patient)
Rash (1 patient)
Blackout (1 patient)
Sources:
250 mg 4 times / day multiple, oral
Recommended
Dose: 250 mg, 4 times / day
Route: oral
Route: multiple
Dose: 250 mg, 4 times / day
Sources:
unhealthy
Health Status: unhealthy
Sex: M+F
Sources:
Other AEs: Somnolence, Dry mouth...
Other AEs:
Somnolence (15 patients)
Dry mouth (12 patients)
Malaise (6 patients)
Constipation (5 patients)
Anorexia (5 patients)
Diarrhoea (3 patients)
Depression (2 patients)
Weight gain (2 patients)
Mental confusion (1 patient)
Postural hypotension (1 patient)
Sources:
AEs

AEs

AESignificanceDosePopulation
Coma grade 1
2.5 g single, oral
Dose: 2.5 g
Route: oral
Route: single
Dose: 2.5 g
Sources:
unknown, 19
Health Status: unknown
Age Group: 19
Sex: M
Sources:
Blackout 1 patient
Disc. AE
2326 mg multiple, oral
Recommended
Dose: 2326 mg
Route: oral
Route: multiple
Dose: 2326 mg
Sources:
unhealthy, 36-68
Health Status: unhealthy
Age Group: 36-68
Sex: M+F
Sources:
Diarrhoea 1 patient
Disc. AE
2326 mg multiple, oral
Recommended
Dose: 2326 mg
Route: oral
Route: multiple
Dose: 2326 mg
Sources:
unhealthy, 36-68
Health Status: unhealthy
Age Group: 36-68
Sex: M+F
Sources:
Rash 1 patient
Disc. AE
2326 mg multiple, oral
Recommended
Dose: 2326 mg
Route: oral
Route: multiple
Dose: 2326 mg
Sources:
unhealthy, 36-68
Health Status: unhealthy
Age Group: 36-68
Sex: M+F
Sources:
Depression 2 patients
Disc. AE
2326 mg multiple, oral
Recommended
Dose: 2326 mg
Route: oral
Route: multiple
Dose: 2326 mg
Sources:
unhealthy, 36-68
Health Status: unhealthy
Age Group: 36-68
Sex: M+F
Sources:
Tiredness 2 patients
Disc. AE
2326 mg multiple, oral
Recommended
Dose: 2326 mg
Route: oral
Route: multiple
Dose: 2326 mg
Sources:
unhealthy, 36-68
Health Status: unhealthy
Age Group: 36-68
Sex: M+F
Sources:
Mental confusion 1 patient
250 mg 4 times / day multiple, oral
Recommended
Dose: 250 mg, 4 times / day
Route: oral
Route: multiple
Dose: 250 mg, 4 times / day
Sources:
unhealthy
Health Status: unhealthy
Sex: M+F
Sources:
Postural hypotension 1 patient
250 mg 4 times / day multiple, oral
Recommended
Dose: 250 mg, 4 times / day
Route: oral
Route: multiple
Dose: 250 mg, 4 times / day
Sources:
unhealthy
Health Status: unhealthy
Sex: M+F
Sources:
Dry mouth 12 patients
250 mg 4 times / day multiple, oral
Recommended
Dose: 250 mg, 4 times / day
Route: oral
Route: multiple
Dose: 250 mg, 4 times / day
Sources:
unhealthy
Health Status: unhealthy
Sex: M+F
Sources:
Somnolence 15 patients
250 mg 4 times / day multiple, oral
Recommended
Dose: 250 mg, 4 times / day
Route: oral
Route: multiple
Dose: 250 mg, 4 times / day
Sources:
unhealthy
Health Status: unhealthy
Sex: M+F
Sources:
Depression 2 patients
250 mg 4 times / day multiple, oral
Recommended
Dose: 250 mg, 4 times / day
Route: oral
Route: multiple
Dose: 250 mg, 4 times / day
Sources:
unhealthy
Health Status: unhealthy
Sex: M+F
Sources:
Weight gain 2 patients
250 mg 4 times / day multiple, oral
Recommended
Dose: 250 mg, 4 times / day
Route: oral
Route: multiple
Dose: 250 mg, 4 times / day
Sources:
unhealthy
Health Status: unhealthy
Sex: M+F
Sources:
Diarrhoea 3 patients
250 mg 4 times / day multiple, oral
Recommended
Dose: 250 mg, 4 times / day
Route: oral
Route: multiple
Dose: 250 mg, 4 times / day
Sources:
unhealthy
Health Status: unhealthy
Sex: M+F
Sources:
Anorexia 5 patients
250 mg 4 times / day multiple, oral
Recommended
Dose: 250 mg, 4 times / day
Route: oral
Route: multiple
Dose: 250 mg, 4 times / day
Sources:
unhealthy
Health Status: unhealthy
Sex: M+F
Sources:
Constipation 5 patients
250 mg 4 times / day multiple, oral
Recommended
Dose: 250 mg, 4 times / day
Route: oral
Route: multiple
Dose: 250 mg, 4 times / day
Sources:
unhealthy
Health Status: unhealthy
Sex: M+F
Sources:
Malaise 6 patients
250 mg 4 times / day multiple, oral
Recommended
Dose: 250 mg, 4 times / day
Route: oral
Route: multiple
Dose: 250 mg, 4 times / day
Sources:
unhealthy
Health Status: unhealthy
Sex: M+F
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
likely
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
[Use of alpha-methyldopa in the treatment of arterial hypertension].
1975 Aug 31
Letter: Dementia associated with clonidine therapy.
1975 Mar 15
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
Antihypertensive drug therapy for mild to moderate hypertension during pregnancy.
2001
[Drug-induced hemolytic anemia].
2001 Aug
Effect of alpha-methyldopa on pentoxyresorufin O-dealkylation in liver microsomes from rats treated with phenobarbital.
2001 Aug 1
Comparative bioavailability of alpha-methyldopa normal and film tablet formulations after single oral administration in healthy volunteers.
2001 Jan-Jun
[Enantiomeric separation of drugs based on macrocyclic antibiotics].
2001 Jul
Drug interference in clinical chemistry: recommendation of drugs and their concentrations to be used in drug interference studies.
2001 Jul
Pharmacological treatment of severe hypertension in pregnancy and the role of serotonin(2)-receptor blockers.
2001 Mar
The effects of nitric oxide synthase inhibitors on the sedative effect of clonidine.
2001 Nov
Excretion of antihypertensive medication into human breast milk: a systematic review.
2002
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
Antihypertensive medication compliance in a Veterans Affairs Healthcare System.
2002 Jun
The effect of antihypertensive drugs on the fetus.
2002 May
Physician gender and antihypertensive prescription pattern in primary care.
2003 Nov
A survey of Canadian practitioners regarding the management of the hypertensive disorders of pregnancy.
2004
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
Oral enalapril-hydrochlorothiazide-methyldopa as first line treatment for severe hypertension in Nigerians.
2004 Jan
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
Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment: When control has been obtained, oral therapy with tablets may be substituted for intravenous therapy, starting with the same dosage schedule used for the parenteral route. The effectiveness and anticipated responses are described in the circular for tablets.
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: Other
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 Mar 31 18:14:40 GMT 2025
Edited
by admin
on Mon Mar 31 18:14:40 GMT 2025
Record UNII
M4R0H12F6M
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ANHYDROUS METHYLDOPA
MART.  
Preferred Name English
METHYLDOPA ANHYDROUS
Common Name English
J9.247I
Code 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
L-3-(3,4-DIHYDROXYPHENYL)-2-METHYLALANINE
Common Name English
Methyldopa [WHO-DD]
Common Name English
METHYL DOPA
Systematic Name English
methyldopa [INN]
Common Name English
METHYLDOPA [MI]
Common Name English
LEDERDOPA
Brand Name English
CARBIDOPA IMPURITY A [EP IMPURITY]
Common 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 Mar 31 18:14:40 GMT 2025 , Edited by admin on Mon Mar 31 18:14:40 GMT 2025
NDF-RT N0000175554
Created by admin on Mon Mar 31 18:14:40 GMT 2025 , Edited by admin on Mon Mar 31 18:14:40 GMT 2025
WHO-ATC C02LB01
Created by admin on Mon Mar 31 18:14:40 GMT 2025 , Edited by admin on Mon Mar 31 18:14:40 GMT 2025
NDF-RT N0000009918
Created by admin on Mon Mar 31 18:14:40 GMT 2025 , Edited by admin on Mon Mar 31 18:14:40 GMT 2025
WHO-ATC C02AB
Created by admin on Mon Mar 31 18:14:40 GMT 2025 , Edited by admin on Mon Mar 31 18:14:40 GMT 2025
Code System Code Type Description
PUBCHEM
38853
Created by admin on Mon Mar 31 18:14:40 GMT 2025 , Edited by admin on Mon Mar 31 18:14:40 GMT 2025
PRIMARY
ECHA (EC/EINECS)
209-089-2
Created by admin on Mon Mar 31 18:14:40 GMT 2025 , Edited by admin on Mon Mar 31 18:14:40 GMT 2025
PRIMARY
RXCUI
1545996
Created by admin on Mon Mar 31 18:14:40 GMT 2025 , Edited by admin on Mon Mar 31 18:14:40 GMT 2025
PRIMARY RxNorm
EVMPD
SUB08867MIG
Created by admin on Mon Mar 31 18:14:40 GMT 2025 , Edited by admin on Mon Mar 31 18:14:40 GMT 2025
PRIMARY
INN
1110
Created by admin on Mon Mar 31 18:14:40 GMT 2025 , Edited by admin on Mon Mar 31 18:14:40 GMT 2025
PRIMARY
DAILYMED
M4R0H12F6M
Created by admin on Mon Mar 31 18:14:40 GMT 2025 , Edited by admin on Mon Mar 31 18:14:40 GMT 2025
PRIMARY
HSDB
218
Created by admin on Mon Mar 31 18:14:40 GMT 2025 , Edited by admin on Mon Mar 31 18:14:40 GMT 2025
PRIMARY
EPA CompTox
DTXSID5023295
Created by admin on Mon Mar 31 18:14:40 GMT 2025 , Edited by admin on Mon Mar 31 18:14:40 GMT 2025
PRIMARY
NCI_THESAURUS
C175729
Created by admin on Mon Mar 31 18:14:40 GMT 2025 , Edited by admin on Mon Mar 31 18:14:40 GMT 2025
PRIMARY
EVMPD
SUB26433
Created by admin on Mon Mar 31 18:14:40 GMT 2025 , Edited by admin on Mon Mar 31 18:14:40 GMT 2025
PRIMARY
MERCK INDEX
m7397
Created by admin on Mon Mar 31 18:14:40 GMT 2025 , Edited by admin on Mon Mar 31 18:14:40 GMT 2025
PRIMARY Merck Index
CAS
555-30-6
Created by admin on Mon Mar 31 18:14:40 GMT 2025 , Edited by admin on Mon Mar 31 18:14:40 GMT 2025
PRIMARY
FDA UNII
M4R0H12F6M
Created by admin on Mon Mar 31 18:14:40 GMT 2025 , Edited by admin on Mon Mar 31 18:14:40 GMT 2025
PRIMARY
DRUG BANK
DB00968
Created by admin on Mon Mar 31 18:14:40 GMT 2025 , Edited by admin on Mon Mar 31 18:14:40 GMT 2025
PRIMARY
NSC
169916
Created by admin on Mon Mar 31 18:14:40 GMT 2025 , Edited by admin on Mon Mar 31 18:14:40 GMT 2025
PRIMARY
WIKIPEDIA
METHYLDOPA
Created by admin on Mon Mar 31 18:14:40 GMT 2025 , Edited by admin on Mon Mar 31 18:14:40 GMT 2025
PRIMARY
CHEBI
61058
Created by admin on Mon Mar 31 18:14:40 GMT 2025 , Edited by admin on Mon Mar 31 18:14:40 GMT 2025
PRIMARY
Related Record Type Details
SOLVATE->ANHYDROUS
TARGET -> INHIBITOR
SALT/SOLVATE -> PARENT
SUBSTANCE->BASIS OF STRENGTH
Related Record Type Details
METABOLITE -> PARENT
ACTIVE IN RATS
METABOLITE -> PARENT
URINE
PARENT -> METABOLITE
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