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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(O)=C(O)C=C1)C(O)=O.C[C@](N)(CC2=CC(O)=C(O)C=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
MOL RATIO 3 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C10H13NO4
Molecular Weight 211.2145
Charge 0
Count
MOL RATIO 2 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
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

Targets

Primary TargetPharmacologyConditionPotency
60.0 µM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
ALDOMET
Primary
ALDOMET
Primary
ALDOMET
Primary
Methyldopate hydrochloride

Cmax

ValueDoseCo-administeredAnalytePopulation
771.3 ng/mL
250 mg single, oral
METHYLDOPA plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
4.54 μg × h/mL
100 mg single, intravenous
METHYLDOPA plasma
Homo sapiens
5352.9 ng × h/mL
250 mg single, oral
METHYLDOPA plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
1.28 h
100 mg single, intravenous
METHYLDOPA plasma
Homo sapiens
12.6 h
250 mg single, oral
METHYLDOPA plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
85%
100 mg single, intravenous
METHYLDOPA plasma
Homo sapiens

Doses

AEs

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as victim

Tox targets

PubMed

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: Other
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
Record UNII
56LH93261Y
Record Status Validated (UNII)
Record Version