Methyldopa

Identification

Summary

Methyldopa is a centrally-acting alpha-2 adrenergic agonist used to manage hypertension alone or in combination with hydrochlorothiazide, and to treat hypertensive crises.

Generic Name

Methyldopa

DrugBank Accession Number

DB00968

Background

Methyldopa, or α-methyldopa, is a centrally acting sympatholytic agent and an antihypertensive agent.⁴ It is an analog of DOPA (3,4‐hydroxyphenylanine), and it is a prodrug, meaning that the drug requires biotransformation to an active metabolite for therapeutic effects. Methyldopa works by binding to alpha(α)-2 adrenergic receptors as an agonist, leading to the inhibition of adrenergic neuronal outflow and reduction of vasoconstrictor adrenergic signals.¹ Methyldopa exists in two isomers D-α-methyldopa and L-α-methyldopa, which is the active form.⁷

First introduced in 1960 as an antihypertensive agent, methyldopa was considered to be useful in certain patient populations, such as pregnant women and patients with renal insufficiency. Since then, methyldopa was largely replaced by newer, better-tolerated antihypertensive agents;⁴ however, it is still used as monotherapy ¹¹ or in combination with hydrochlorothiazide.¹² Methyldopa is also available as intravenous injection, which is used to manage hypertension when oral therapy is unfeasible and to treat hypertensive crisis.¹³

Type

Small Molecule

Groups

Approved

Structure

3D

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MOLSDF3D-SDFPDBSMILESInChI

Similar Structures

Structure for Methyldopa (DB00968)

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Weight

Average: 211.2145
Monoisotopic: 211.084457909

Chemical Formula

C₁₀H₁₃NO₄

Synonyms

• (S)-(-)-alpha-Methyldopa
• 3-Hydroxy-alpha-methyl-L-tyrosine
• Alpha medopa
• alpha-Methyl dopa
• alpha-methyl-L-dopa
• Alphamethyldopa
• AMD
• Anhydrous methyldopa
• L-alpha-Methyldopa
• L-Methyl Dopa
• Methyl dopa
• Methyldopa
• Methyldopa anhydrous
• metildopa
• α-Methyl dopa
• α-methyl-L-dopa

External IDs

• Bayer 1440L
• J9.247I

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Pharmacology

Indication

Methyldopa is indicated for the management of hypertension as monotherapy ¹¹ or in combination with hydrochlorothiazide.¹² Methyldopa injection is used to manage hypertensive crises.¹³

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Associated Conditions

Indication Type	Indication	Combined Product Details	Approval Level	Age Group	Patient Characteristics	Dose Form
Management of	High blood pressure (hypertension)		••••••••••••		•••••• •••••••• •••• •••••••	•••••••••• ••••••••
Used in combination to manage	Hypertension	Combination Product in combination with: Hydrochlorothiazide (DB00999)	••••••••••••			••••••
Management of	Hypertension		••••••••••••			••••••
Management of	Hypertensive crisis		••••••••••••		•••••• •••••••• •••• •••••••	•••••••••• ••••••••

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Contraindications & Blackbox Warnings

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Pharmacodynamics

Antihypertensive effects of methyldopa are mostly mediated by its pharmacologically active metabolite, alpha-methylnorepinephrine, which works as an agonist at central inhibitory alpha-adrenergic receptors.¹¹ Stimulation of alpha-adrenergic receptors leads to decreased peripheral sympathetic tone and reduced arterial pressure.³ Methyldopa causes a net reduction in the tissue concentration of serotonin, dopamine, norepinephrine, and epinephrine. Overall, methyldopa lowers both standing blood pressure and especially supine blood pressure, with infrequent symptomatic postural hypotension. Methyldopa also reduces plasma renin activity but has negligible effects on glomerular filtration rate, renal blood flow, or filtration fraction. It also has no direct effect on cardiac function but in some patients, a slowed heart rate may occur.¹¹

Following oral administration, blood-pressure-lowering effects are observed within 12 to 24 hours in most patients, and a maximum reduction in blood pressure occurs in 4 to 6 hours. Blood pressure returns to pre-treatment levels within 24 to 48 hours following drug discontinuation.¹¹ Following intravenous administration, the blood-pressure-lowering effects of methyldopa last for about 10 to 16 hours.⁴

Mechanism of action

The exact mechanism of methyldopa is not fully elucidated; however, the main mechanisms of methyldopa involve its actions on alpha-adrenergic receptor and the aromatic L-amino acid decarboxylase enzyme, to a lesser extent. The sympathetic outflow is regulated by alpha (α)-2 adrenergic receptors and imidazoline receptors expressed on adrenergic neurons within the rostral ventrolateral medulla.² Methyldopa is metabolized to α‐methylnorepinephrine via dopamine beta-hydroxylase activity and, consequently, alpha-methylepinephrine via phenylethanolamine-N-methyltransferase activity.^9,8,10 Mediating the therapeutic effects of methyldopa, α‐methylnorepinephrine and α-methylepinephrine active metabolites are agonists at presynaptic alpha-2 adrenergic receptors in the brainstem. Stimulating alpha-2 adrenergic receptors results in the inhibition of adrenergic neuronal outflow and attenuation of norepinephrine release in the brainstem. Consequently, the output of vasoconstrictor adrenergic signals to the peripheral sympathetic nervous system is reduced, leading to a reduction in blood pressure.¹

The L-isomer of alpha-methyldopa also reduces blood pressure by inhibiting aromatic L-amino acid decarboxylase, also known as DOPA decarboxylase, which is an enzyme responsible for the syntheses of dopamine and serotonin.¹¹ Inhibiting this enzyme leads to depletion of biogenic amines such as norepinephrine. However, inhibition of aromatic L-amino acid decarboxylase plays a minimal role in the blood-pressure‐lowering effect of methyldopa.^2,3

Target	Actions	Organism
AAromatic-L-amino-acid decarboxylase	inhibitor	Humans
AAlpha-2A adrenergic receptor	agonist	Humans

Absorption

Methyldopa is incompletely absorbed from the gastrointestinal tract following oral administration.⁵ In healthy individuals, the inactive D-isomer is less readily absorbed than the active L-isomer.⁷ The mean bioavailability of methyldopa is 25%, ranging from eight to 62%.⁵ Following oral administration, about 50% of the dose is absorbed and T_max is about three to six hours.^6,4

Volume of distribution

The apparent volume of distribution ranges between 0.19 and 0.32L/kg and the total volume of distribution ranges from 0.41 to 0.72L/kg. Since methyldopa is lipid-soluble ⁴, it crosses the placental barrier, appears in cord blood, and appears in breast milk.¹¹

Protein binding

Methyldopa is less than 15% bound to plasma proteins and its primary metabolite, O-sulfate metabolite, is about 50% protein bound.⁵ Following intravenous administration, approximately 17% of the dose in normal subjects were circulating in the plasma as free methyldopa.¹³

Metabolism

Two isomers of methyldopa undergo different metabolic pathways.⁷ L-α-methyldopa is biotransformed to its pharmacologically active metabolite, alpha-methylnorepinephrine. Methyldopa is extensively metabolized in the liver to form the main circulating metabolite in the plasma, alpha (α)-methyldopa mono-O-sulfate. Its other metabolites also include 3-O-methyl-α-methyldopa; 3,4-dihydroxyphenylacetone; α-methyldopamine; and 3-O-methyl-α-methyldopamine. These metabolites are further conjugated in the liver to form sulfate conjugates.¹¹ After intravenous administration, the most prominent metabolites are alpha-methyldopamine and the glucuronide of dihydroxyphenylacetone, along with other uncharacterized metabolites.⁵

D-α-methyldopa, which is the inactive isomer of methyldopa, is also metabolized to 3-O-methyl-α-methyldopa and 3,4-dihydroxyphenylacetone to a minimal extent; however, there are no amines (α-methyldopamine and 3-O-methyl-α-methyldopamine) formed.⁷

Hover over products below to view reaction partners

• Methyldopa
  • 3-O-methyl-alpha-methyldopa
    • 3-O-methyl-alpha-methyldopa sulfate
  • Alpha-methyldopamine
    • Alpha-methylnorepinephrine
      • Alpha-methylepinephrine
    • 3-O-methyl-alpha-methyldopamine
  • Alpha-methyldopa-mono-O-sulfate
  • 3,4-Dihydroxyphenylacetone
    • 3,4-Dihydroxyphenylacetone glucuronide

Route of elimination

Approximately 70% of absorbed methyldopa is excreted in the urine as unchanged parent drug (24%) and α-methyldopa mono-O-sulfate (64%),^6,11 with variability.3-O-methyl-α-methyldopa accounted for about 4% of urinary excretion products. Other metabolites like 3,4-dihydroxyphenylacetone, α-methyldopamine, and 3-O-methyl-α-methyldopamine are also excreted in urine.⁶

Unabsorbed drug is excreted in feces as the unchanged parent compound.⁴ After oral doses, excretion is essentially complete in 36 hours.¹²

Due to attenuated excretion in patients with renal failure, accumulation of the drug and its metabolites may occur,⁴ possibly leading to more profound and prolonged hypotensive effects in these patients.⁵

Half-life

The plasma half-life of methyldopa is 105 minutes.¹¹ Following intravenous injection, the plasma half-life of methyldopa ranges from 90 to 127 minutes.¹³

Clearance

The renal clearance is about 130 mL/min in normal subjects and is decreased in patients with renal insufficiency.¹¹

Adverse Effects

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Toxicity

The lowest published toxic dose via oral route is 44 gm/kg/3Y (intermittent) in a female. Oral LD₅₀ is 5000 mg/kg in rats and 5300 mg/kg in mice. Intraperitoneal LD₅₀ is 300 mg/kg in rats and 150 mg/kg in mice.¹⁴

Acute overdosage is characterized by acute hypotension and other presentations attributed to the brain and gastrointestinal dysfunction, such as excessive sedation, weakness, bradycardia, dizziness, light-headedness, constipation, distention, flatus, diarrhea, nausea, and vomiting. Symptomatic and supportive measures should be initiated in the event of methyldopa overdose. Overdosage following recent oral ingestion can be managed by gastric lavage or emesis, as well as infusions to limit further drug absorption. Cardiac rate and output, blood volume, electrolyte balance, paralytic ileus, urinary function and cerebral activity should be closely monitored. The use of sympathomimetic drugs such as levarterenol, epinephrine, and metaraminol bitartrate, or dialysis may be considered.¹¹

Pathways

Not Available

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Interactions

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This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.

• Approved
• Vet approved
• Nutraceutical
• Illicit
• Withdrawn
• Investigational
• Experimental
• All Drugs

Drug	Interaction
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Abacavir	Methyldopa may decrease the excretion rate of Abacavir which could result in a higher serum level.
Abaloparatide	The risk or severity of adverse effects can be increased when Methyldopa is combined with Abaloparatide.
Acebutolol	The therapeutic efficacy of Methyldopa can be decreased when used in combination with Acebutolol.
Aceclofenac	The therapeutic efficacy of Methyldopa can be decreased when used in combination with Aceclofenac.
Acemetacin	The therapeutic efficacy of Methyldopa can be decreased when used in combination with Acemetacin.

Food Interactions

• Take with or without food. Drug pharmacokinetics is unaffected.

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Product Ingredients

Ingredient	UNII	CAS	InChI Key
Methyldopa hydrochloride	7PX435DN5A	2508-79-4	QSRVZCCJDKYRRF-YDALLXLXSA-N
Methyldopa sesquihydrate	56LH93261Y	41372-08-1	YKFCISHFRZHKHY-NGQGLHOPSA-N

Product Images

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International/Other Brands

Aldomet / Aldometil / Aldomin / Dopamet / Hypolag / Medomet / Medopren / Novomedopa / Nu-Medopa

Brand Name Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End	Region	Image
Aldomet Ester HCl Inj	Liquid	250 mg / 5 mL	Intravenous	Merck Frosst Canada & Cie, Merck Frosst Canada & Co.	1963-12-31	2002-07-29
Aldomet Tab 125mg	Tablet	125 mg	Oral	Merck Frosst Canada & Cie, Merck Frosst Canada & Co.	1971-12-31	1998-08-14
Aldomet Tab 250mg	Tablet	250 mg	Oral	Merck Frosst Canada & Cie, Merck Frosst Canada & Co.	1963-12-31	2004-11-12
Aldomet Tab 500mg	Tablet	500 mg	Oral	Merck Frosst Canada & Cie, Merck Frosst Canada & Co.	1971-12-31	1998-08-14
Dopamet Tab 125mg	Tablet	125 mg	Oral	Icn Pharmaceuticals	1976-12-31	2005-04-26

Generic Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End	Region	Image
Methyldopa	Tablet, film coated	125 mg/1	Oral	Accord Healthcare Inc.	2012-06-27	2012-06-27
Methyldopa	Tablet	250 mg/1	Oral	Mylan Pharmaceuticals Inc.	1985-04-18	Not applicable
Methyldopa	Tablet, film coated	250 mg/1	Oral	Teva Pharmaceuticals USA, Inc.	2009-02-23	2018-02-28
Methyldopa	Tablet, film coated	250 mg/1	Oral	Rebel Distributors	2009-02-23	Not applicable
Methyldopa	Tablet, film coated	500 mg/1	Oral	Accord Healthcare Inc.	2012-07-24	2022-08-31

Mixture Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End	Region	Image
Aldoril	Methyldopa sesquihydrate (250 mg/1) + Hydrochlorothiazide (25 mg/1)	Tablet, film coated	Oral	Merck Sharp & Dohme Limited	1962-12-20	2006-03-31
Aldoril	Methyldopa sesquihydrate (500 mg/1) + Hydrochlorothiazide (50 mg/1)	Tablet, film coated	Oral	Merck Sharp & Dohme Limited	1962-12-20	2006-03-31
Aldoril	Methyldopa sesquihydrate (250 mg/1) + Hydrochlorothiazide (15 mg/1)	Tablet, film coated	Oral	Merck Sharp & Dohme Limited	1962-12-20	2006-03-31
Aldoril	Methyldopa sesquihydrate (500 mg/1) + Hydrochlorothiazide (30 mg/1)	Tablet, film coated	Oral	Merck Sharp & Dohme Limited	1962-12-20	2006-03-31
Aldoril 15 Tab	Methyldopa (250 mg) + Hydrochlorothiazide (15 mg)	Tablet	Oral	Merck Frosst Canada & Cie, Merck Frosst Canada & Co.	1967-12-31	1998-08-14

Categories

ATC Codes

C02AB01 — Methyldopa (levorotatory)

• C02AB — Methyldopa
• C02A — ANTIADRENERGIC AGENTS, CENTRALLY ACTING
• C02 — ANTIHYPERTENSIVES
• C — CARDIOVASCULAR SYSTEM

Drug Categories

• Adrenergic Agents
• Adrenergic Agonists
• Adrenergic alpha-2 Receptor Agonists
• Adrenergic alpha-Agonists
• Agents Causing Muscle Toxicity
• Amines
• Amino Acids
• Amino Acids, Aromatic
• Amino Acids, Cyclic
• Amino Acids, Peptides, and Proteins
• Antiadrenergic Agents, Centrally Acting
• Antihypertensive Agents
• Antihypertensive Agents Indicated for Hypertension
• Aromatic L-amino Acid Decarboxylase Inhibitors
• Autonomic Agents
• Benzene Derivatives
• Bradycardia-Causing Agents
• Cardiovascular Agents
• Catecholamines
• Catechols
• Central alpha-2 Adrenergic Agonist
• Central Alpha-agonists
• COMT Substrates
• Dihydroxyphenylalanine
• Drugs that are Mainly Renally Excreted
• Enzyme Inhibitors
• Hypotensive Agents
• Neurotransmitter Agents
• Peripheral Nervous System Agents
• Phenols
• Sympatholytics

Chemical TaxonomyProvided by Classyfire

Description

This compound belongs to the class of organic compounds known as phenylpropanoic acids. These are compounds with a structure containing a benzene ring conjugated to a propanoic acid.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Phenylpropanoic acids

Sub Class

Not Available

Direct Parent

Phenylpropanoic acids

Alternative Parents

D-alpha-amino acids / Amphetamines and derivatives / Phenylpropanes / Catechols / Aralkylamines / 1-hydroxy-4-unsubstituted benzenoids / 1-hydroxy-2-unsubstituted benzenoids / Amino acids / Monocarboxylic acids and derivatives / Carboxylic acids / Organopnictogen compounds / Organic oxides / Monoalkylamines / Hydrocarbon derivatives / Carbonyl compounds

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Substituents

1-hydroxy-2-unsubstituted benzenoid / 1-hydroxy-4-unsubstituted benzenoid / 3-phenylpropanoic-acid / Alpha-amino acid / Alpha-amino acid or derivatives / Amine / Amino acid / Amino acid or derivatives / Amphetamine or derivatives / Aralkylamine / Aromatic homomonocyclic compound / Benzenoid / Carbonyl group / Carboxylic acid / Carboxylic acid derivative / Catechol / D-alpha-amino acid / Hydrocarbon derivative / Monocarboxylic acid or derivatives / Monocyclic benzene moiety / Organic nitrogen compound / Organic oxide / Organic oxygen compound / Organonitrogen compound / Organooxygen compound / Organopnictogen compound / Phenol / Phenylpropane / Primary aliphatic amine / Primary amine

show 20 more

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

non-proteinogenic L-alpha-amino acid, L-tyrosine derivative (CHEBI:61058)

Affected organisms

• Humans and other mammals

Chemical Identifiers

UNII

M4R0H12F6M

CAS number

555-30-6

InChI Key

CJCSPKMFHVPWAR-JTQLQIEISA-N

InChI

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

IUPAC Name

(2S)-2-amino-3-(3,4-dihydroxyphenyl)-2-methylpropanoic acid

SMILES

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

References

Synthesis Reference

US2868818

General References

1. Mah GT, Tejani AM, Musini VM: Methyldopa for primary hypertension. Cochrane Database Syst Rev. 2009 Oct 7;(4):CD003893. doi: 10.1002/14651858.CD003893.pub3. [Article]
2. Sica DA: Centrally acting antihypertensive agents: an update. J Clin Hypertens (Greenwich). 2007 May;9(5):399-405. [Article]
3. van Zwieten PA: Pharmacology of centrally acting hypotensive drugs. Br J Clin Pharmacol. 1980;10 Suppl 1:13S-20S. [Article]
4. Gupta M, Al Khalili Y: Methyldopa . [Article]
5. Myhre E, Rugstad HE, Hansen T: Clinical pharmacokinetics of methyldopa. Clin Pharmacokinet. 1982 May-Jun;7(3):221-33. doi: 10.2165/00003088-198207030-00003. [Article]
6. BUHS RP, BECK JL, SPETH OC, SMITH JL, TRENNER NR, CANNON PJ, LARAGH JH: THE METABOLISM OF METHYLDOPA IN HYPERTENSIVE HUMAN SUBJECTS. J Pharmacol Exp Ther. 1964 Feb;143:205-14. [Article]
7. Au WY, Dring LG, Grahame-Smith DG, Isaac P, Williams RT: The metabolism of 14 C-labelled -methyldopa in normal and hypertensive human subjects. Biochem J. 1972 Aug;129(1):1-10. doi: 10.1042/bj1290001. [Article]
8. Tung CS, Goldberg MR, Hollister AS, Oates JA, Robertson D: Central and peripheral cardiovascular effects of alpha-methylepinephrine. J Pharmacol Exp Ther. 1983 Nov;227(2):484-90. [Article]
9. Goldberg MR, Gerkens JF, Oates JA, Robertson D: alpha-Methylepinephrine, a methyldopa metabolite that binds to alpha-receptors in rat brain. Eur J Pharmacol. 1981 Jan 5;69(1):95-9. doi: 10.1016/0014-2999(81)90606-3. [Article]
10. Robertson D, Tung CS, Goldberg MR, Hollister AS, Gerkens JF, Oates JA: Antihypertensive metabolites of alpha-methyldopa. Hypertension. 1984 Sep-Oct;6(5 Pt 2):II45-50. doi: 10.1161/01.hyp.6.5_pt_2.ii45. [Article]
11. DailyMed Label: METHYLDOPA oral tablet, film coated [Link]
12. DailyMed Label: METHYLDOPA AND HYDROCHLOROTHIAZIDE oral tablet [Link]
13. DailyMed Label: Methyldopate Intravenous Injection [Link]
14. Cayman Chemical: Methyldopa Safety Data Sheet [Link]

External Links

Human Metabolome Database

HMDB0011754

KEGG Drug

D08205

KEGG Compound

C07194

PubChem Compound

38853

PubChem Substance

46508535

ChemSpider

35562

BindingDB

48449

RxNav

1545996

ChEBI

61058

ChEMBL

CHEMBL459

ZINC

ZINC000000020255

Therapeutic Targets Database

DAP000226

PharmGKB

PA450453

RxList

RxList Drug Page

Drugs.com

Drugs.com Drug Page

PDRhealth

PDRhealth Drug Page

Wikipedia

Methyldopa

FDA label

Download (155 KB)

MSDS

Download (53.4 KB)

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">

Phase	Status	Purpose	Conditions	Count
4	Completed	Treatment	Hypertension in Pregnancy / Pre-Eclampsia	1
4	Completed	Treatment	Hypertension / Postpartum Pre-Eclampsia / Pregnancy-Induced Hypertension in Postpartum	1
4	Recruiting	Prevention	Gestational Hypertension / Pre-Eclampsia	1
4	Unknown Status	Diagnostic	Pre-Eclampsia	1
4	Unknown Status	Treatment	Diabetes / Hypertensive Diseases	1

Pharmacoeconomics

Manufacturers

Not Available

Packagers

• Advanced Pharmaceutical Services Inc.
• American Regent
• A-S Medication Solutions LLC
• Caremark LLC
• Central Texas Community Health Centers
• Direct Dispensing Inc.
• Dispensing Solutions
• Diversified Healthcare Services Inc.
• Emcure Pharmaceuticals Ltd.
• Endo Pharmaceuticals Inc.
• H and H Laboratories
• Heartland Repack Services LLC
• Hospira Inc.
• Ivax Pharmaceuticals
• Kaiser Foundation Hospital
• Luitpold Pharmaceuticals Inc.
• Major Pharmaceuticals
• Murfreesboro Pharmaceutical Nursing Supply
• Mylan
• Nucare Pharmaceuticals Inc.
• PCA LLC
• PD-Rx Pharmaceuticals Inc.
• Pharmedix
• Physicians Total Care Inc.
• Rebel Distributors Corp.
• Remedy Repack
• Sandhills Packaging Inc.
• Southwood Pharmaceuticals
• Teva Pharmaceutical Industries Ltd.
• UDL Laboratories
• United Research Laboratories Inc.
• Watson Pharmaceuticals

Dosage Forms

Form	Route	Strength
Tablet	Oral	500.0000 mg
Tablet, coated	Oral	250 MG
Tablet, coated	Oral	500 MG
Tablet	Oral	283 mg
Tablet	Oral	28300000 mg
Liquid	Intravenous	250 mg / 5 mL
Tablet, film coated	Oral
Tablet, film coated	Oral
Capsule
Tablet	Oral	125 mg
Tablet	Oral	250 mg/1
Tablet	Oral	250 mg
Tablet	Oral	500 mg/1
Tablet	Oral	500 mg
Tablet, film coated	Oral	125 mg/1
Tablet, film coated	Oral	250 mg/1
Tablet, film coated	Oral	500 mg/1
Tablet	Oral
Injection, solution	Intravenous	50 mg/1mL
Tablet	Oral
Tablet, film coated	Oral	500 mg
Tablet, delayed release	Oral	250 mg
Tablet, film coated	Oral	250 mg
Tablet, film coated	Oral	125 mg

Prices

Unit description	Cost	Unit
Aldoclor 250-250 mg tablet	0.67USD	tablet
Methyldopa 500 mg tablet	0.67USD	tablet
Methyldopa 250 mg tablet	0.39USD	tablet
Apo-Methyldopa 500 mg Tablet	0.27USD	tablet
Methyldopate 250 mg/5 ml vial	0.24USD	ml
Apo-Methyldopa 250 mg Tablet	0.15USD	tablet
Apo-Methyldopa 125 mg Tablet	0.1USD	tablet

DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.

Patents

Not Available

Properties

State

Solid

Experimental Properties

Property	Value	Source
melting point (°C)	>300	https://www.fishersci.ca/store/msds?partNumber=AAH5670403&productDescription=3-4-dihydroxy-alpha-methyl-l-phenylalanine-sesquihydrate-99&language=en&countryCode=CA
water solubility	1E+004 mg/L (at 25 °C)	MERCK INDEX (1996)

Predicted Properties

Property	Value	Source
Water Solubility	2.26 mg/mL	ALOGPS
logP	-2	ALOGPS
logP	-1.4	Chemaxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	1.73	Chemaxon
pKa (Strongest Basic)	9.85	Chemaxon
Physiological Charge	0	Chemaxon
Hydrogen Acceptor Count	5	Chemaxon
Hydrogen Donor Count	4	Chemaxon
Polar Surface Area	103.78 Å2	Chemaxon
Rotatable Bond Count	3	Chemaxon
Refractivity	53.79 m3·mol-1	Chemaxon
Polarizability	20.73 Å3	Chemaxon
Number of Rings	1	Chemaxon
Bioavailability	1	Chemaxon
Rule of Five	Yes	Chemaxon
Ghose Filter	No	Chemaxon
Veber's Rule	No	Chemaxon
MDDR-like Rule	No	Chemaxon

Predicted ADMET Features

Property	Value	Probability
Human Intestinal Absorption	+	0.9374
Blood Brain Barrier	-	0.9276
Caco-2 permeable	-	0.8957
P-glycoprotein substrate	Substrate	0.6066
P-glycoprotein inhibitor I	Non-inhibitor	0.9852
P-glycoprotein inhibitor II	Non-inhibitor	0.9895
Renal organic cation transporter	Non-inhibitor	0.9357
CYP450 2C9 substrate	Non-substrate	0.7757
CYP450 2D6 substrate	Non-substrate	0.8
CYP450 3A4 substrate	Non-substrate	0.6053
CYP450 1A2 substrate	Non-inhibitor	0.9045
CYP450 2C9 inhibitor	Non-inhibitor	0.9369
CYP450 2D6 inhibitor	Non-inhibitor	0.9491
CYP450 2C19 inhibitor	Non-inhibitor	0.9233
CYP450 3A4 inhibitor	Non-inhibitor	0.864
CYP450 inhibitory promiscuity	Low CYP Inhibitory Promiscuity	0.9551
Ames test	Non AMES toxic	0.8185
Carcinogenicity	Non-carcinogens	0.8997
Biodegradation	Not ready biodegradable	0.8077
Rat acute toxicity	1.6281 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Weak inhibitor	0.9939
hERG inhibition (predictor II)	Non-inhibitor	0.9629

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	splash10-00xu-4900000000-739bef9b92ae61fa3997
GC-MS Spectrum - GC-EI-TOF	GC-MS	splash10-001i-0690000000-f54d986a8144f4a79b82
LC-MS/MS Spectrum - LC-ESI-qTof , Positive	LC-MS/MS	splash10-0g5i-2900000000-2d1c0ec9ad93e208b620
MS/MS Spectrum - , positive	LC-MS/MS	splash10-0g5i-2900000000-2d1c0ec9ad93e208b620
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	splash10-03di-0980000000-db7d45cd09e0758893a7
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	splash10-0002-2930000000-46f8cd02027cf186b14c
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0002-1900000000-86b3d1abc851b64eaf9f
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	splash10-0002-0900000000-8b30987165a9e994ce58
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	splash10-05te-5900000000-684f3eaf7f328f05ac6f
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	splash10-014m-9200000000-39c570eafb042de39db3
Predicted 1H NMR Spectrum	1D NMR	Not Applicable
Predicted 13C NMR Spectrum	1D NMR	Not Applicable

Chromatographic Properties

Collision Cross Sections (CCS)

Adduct	CCS Value (Å2)	Source type	Source
[M-H]-	153.8856241	predicted	DarkChem Lite v0.1.0
[M-H]-	143.58476	predicted	DeepCCS 1.0 (2019)
[M+H]+	154.1786241	predicted	DarkChem Lite v0.1.0
[M+H]+	145.98033	predicted	DeepCCS 1.0 (2019)
[M+Na]+	153.7147241	predicted	DarkChem Lite v0.1.0
[M+Na]+	151.9368	predicted	DeepCCS 1.0 (2019)

Targets

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Details1. Aromatic-L-amino-acid decarboxylase

Kind

Protein

Organism

Humans

Pharmacological action

Yes

Actions

Inhibitor

General Function

Pyridoxal phosphate binding

Specific Function

Catalyzes the decarboxylation of L-3,4-dihydroxyphenylalanine (DOPA) to dopamine, L-5-hydroxytryptophan to serotonin and L-tryptophan to tryptamine.

Gene Name

DDC

Uniprot ID

P20711

Uniprot Name

Aromatic-L-amino-acid decarboxylase

Molecular Weight

53925.815 Da

References

1. SOURKES TL: Inhibition of dihydroxy-phenylalanine decarboxylase by derivatives of phenylalanine. Arch Biochem Biophys. 1954 Aug;51(2):444-56. [Article]
2. Campbell NR, Sundaram RS, Werness PG, Van Loon J, Weinshilboum RM: Sulfate and methyldopa metabolism: metabolite patterns and platelet phenol sulfotransferase activity. Clin Pharmacol Ther. 1985 Mar;37(3):308-15. doi: 10.1038/clpt.1985.45. [Article]

Details2. Alpha-2A adrenergic receptor

Kind

Protein

Organism

Humans

Pharmacological action

Yes

Actions

Agonist

General Function

Thioesterase binding

Specific Function

Alpha-2 adrenergic receptors mediate the catecholamine-induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is oxymetazo...

Gene Name

ADRA2A

Uniprot ID

P08913

Uniprot Name

Alpha-2A adrenergic receptor

Molecular Weight

48956.275 Da

References

1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
3. Sica DA: Centrally acting antihypertensive agents: an update. J Clin Hypertens (Greenwich). 2007 May;9(5):399-405. [Article]
4. Kawasaki H: [Centrally acting sympathetic inhibitors for therapy of patients with hypertension]. Nihon Rinsho. 1997 Aug;55(8):2081-5. [Article]
5. Head GA: Central imidazoline- and alpha 2-receptors involved in the cardiovascular actions of centrally acting antihypertensive agents. Ann N Y Acad Sci. 1999 Jun 21;881:279-86. [Article]
6. van Zwieten PA: New central mediators as targets of centrally acting antihypertensive drugs. Clin Exp Hypertens. 1996 Apr-May;18(3-4):291-303. [Article]
7. van Zwieten PA: Development and trends in the drug treatment of essential hypertension. J Hypertens Suppl. 1992 Dec;10(7):S1-12. [Article]
8. Velliquette RA, Ernsberger P: Contrasting metabolic effects of antihypertensive agents. J Pharmacol Exp Ther. 2003 Dec;307(3):1104-11. Epub 2003 Oct 13. [Article]

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Drug created at June 13, 2005 13:24 / Updated at February 20, 2024 23:55