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
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
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 |
DescriptionSources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2004/13400s086lbl.pdfhttps://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=f5f25053-a9f3-48b9-a412-078f5ee942fd&type=displayCurator's Comment: Description was created based on several sources, including
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2004/13400s086lbl.pdfhttps://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=f5f25053-a9f3-48b9-a412-078f5ee942fd&type=display
Curator's Comment: Description was created based on several sources, including
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
Sources: https://www.drugs.com/monograph/methyldopa.htmlhttps://www.drugs.com/ppa/methyldopa-and-methyldopate-hcl.html
Curator's Comment: Methyldopa and methyldopate cross the blood-brain
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL1843 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7136732 |
60.0 µM [IC50] | ||
Target ID: CHEMBL2095203 |
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Target ID: CHEMBL2094111 Sources: https://www.drugs.com/pro/methyldopa.html |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | ALDOMET Approved UseINDICATION AND USAGE: Hypertension. Launch Date1962 |
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Primary | ALDOMET Approved UseINDICATION AND USAGE: Hypertension. Launch Date1962 |
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Primary | ALDOMET Approved UseINDICATION AND USAGE: Hypertension. Launch Date1962 |
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Primary | Methyldopate hydrochloride Approved UseHypertension, when parenteral medication is indicated. The treatment of hypertensive crises may be initiated with Methyldopate HCl Injection. Launch Date1995 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
771.3 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/21125810 |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
5352.9 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/21125810 |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7047042 |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
12.6 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/21125810 |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7047042 |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
85% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7047042 |
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
Dose | Population | Adverse events |
---|---|---|
2.5 g single, oral |
unknown, 19 |
Other AEs: Coma... |
2326 mg multiple, oral Recommended Dose: 2326 mg Route: oral Route: multiple Dose: 2326 mg Sources: |
unhealthy, 36-68 |
Disc. AE: Depression, Tiredness... AEs leading to discontinuation/dose reduction: Depression (2 patients) Sources: Tiredness (2 patients) Diarrhoea (1 patient) Rash (1 patient) Blackout (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 |
Other AEs: Somnolence, Dry mouth... Other AEs: Somnolence (15 patients) Sources: 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) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Coma | grade 1 | 2.5 g single, oral |
unknown, 19 |
Blackout | 1 patient Disc. AE |
2326 mg multiple, oral Recommended Dose: 2326 mg Route: oral Route: multiple Dose: 2326 mg Sources: |
unhealthy, 36-68 |
Diarrhoea | 1 patient Disc. AE |
2326 mg multiple, oral Recommended Dose: 2326 mg Route: oral Route: multiple Dose: 2326 mg Sources: |
unhealthy, 36-68 |
Rash | 1 patient Disc. AE |
2326 mg multiple, oral Recommended Dose: 2326 mg Route: oral Route: multiple Dose: 2326 mg Sources: |
unhealthy, 36-68 |
Depression | 2 patients Disc. AE |
2326 mg multiple, oral Recommended Dose: 2326 mg Route: oral Route: multiple Dose: 2326 mg Sources: |
unhealthy, 36-68 |
Tiredness | 2 patients Disc. AE |
2326 mg multiple, oral Recommended Dose: 2326 mg Route: oral Route: multiple Dose: 2326 mg Sources: |
unhealthy, 36-68 |
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 |
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 |
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 |
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 |
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 |
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 |
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 |
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 |
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 |
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 |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://molpharm.aspetjournals.org/content/12/6/911 Page: abstract |
likely |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://www.scirp.org/pdf/JBiSE_2017112915210255.pdf Page: 10.0 |
PubMed
Title | Date | PubMed |
---|---|---|
[Use of alpha-methyldopa in the treatment of arterial hypertension]. | 1975 Aug 31 |
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Letter: Dementia associated with clonidine therapy. | 1975 Mar 15 |
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Dihydroergotamine: an effective treatment for postural hypotension due to antihypertensive drugs (ganglion-blocking agents excepted). | 1976 |
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Some side-effects of alpha-methyldopa. | 1976 Apr 10 |
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Dementia induced by methyldopa with haloperidol. | 1976 May 27 |
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Antihypertensive drug therapy for mild to moderate hypertension during pregnancy. | 2001 |
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[Drug-induced hemolytic anemia]. | 2001 Aug |
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Effect of alpha-methyldopa on pentoxyresorufin O-dealkylation in liver microsomes from rats treated with phenobarbital. | 2001 Aug 1 |
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Comparative bioavailability of alpha-methyldopa normal and film tablet formulations after single oral administration in healthy volunteers. | 2001 Jan-Jun |
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[Enantiomeric separation of drugs based on macrocyclic antibiotics]. | 2001 Jul |
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Drug interference in clinical chemistry: recommendation of drugs and their concentrations to be used in drug interference studies. | 2001 Jul |
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Pharmacological treatment of severe hypertension in pregnancy and the role of serotonin(2)-receptor blockers. | 2001 Mar |
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The effects of nitric oxide synthase inhibitors on the sedative effect of clonidine. | 2001 Nov |
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Excretion of antihypertensive medication into human breast milk: a systematic review. | 2002 |
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Hepatotoxicity of commonly used drugs: nonsteroidal anti-inflammatory drugs, antihypertensives, antidiabetic agents, anticonvulsants, lipid-lowering agents, psychotropic drugs. | 2002 |
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Methyldopa versus no drug treatment in the management of mild pre-eclampsia. | 2002 Apr |
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Antihypertensive medication compliance in a Veterans Affairs Healthcare System. | 2002 Jun |
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The effect of antihypertensive drugs on the fetus. | 2002 May |
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Physician gender and antihypertensive prescription pattern in primary care. | 2003 Nov |
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A survey of Canadian practitioners regarding the management of the hypertensive disorders of pregnancy. | 2004 |
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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 |
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27998008
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
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admin
on
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Mon Mar 31 18:14:40 GMT 2025
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Record UNII |
M4R0H12F6M
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Record Status |
Validated (UNII)
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Record Version |
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WHO-ATC |
C02AB01
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NDF-RT |
N0000175554
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WHO-ATC |
C02LB01
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NDF-RT |
N0000009918
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WHO-ATC |
C02AB
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38853
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209-089-2
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1545996
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SUB08867MIG
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1110
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M4R0H12F6M
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218
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DTXSID5023295
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C175729
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SUB26433
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m7397
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555-30-6
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M4R0H12F6M
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DB00968
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169916
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METHYLDOPA
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61058
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Related Record | Type | Details | ||
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SOLVATE->ANHYDROUS | |||
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TARGET -> INHIBITOR |
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SALT/SOLVATE -> PARENT | |||
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SUBSTANCE->BASIS OF STRENGTH |
Related Record | Type | Details | ||
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METABOLITE -> PARENT |
ACTIVE IN RATS
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METABOLITE -> PARENT |
URINE
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PARENT -> METABOLITE | |||
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METABOLITE -> PARENT |
URINE
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METABOLITE -> PARENT | |||
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METABOLITE -> PARENT |
URINE
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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
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Related Record | Type | Details | ||
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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Related Record | Type | Details | ||
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ACTIVE MOIETY |