导航

Methyldopa

Identification

Summary

Methyldopais 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
药物Bank Accession Number
DB00968
Background

Methyldopa, or α-methyldopa, is a centrally acting sympatholytic agent and an antihypertensive agent.4It 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.1Methyldopa 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;4however, it is still used as monotherapy11or in combination withhydrochlorothiazide.12Methyldopa 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
乡村小道cture
 3D
Similar Structures
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

Pharmacology

Indication

Methyldopa is indicated for the management of hypertension as monotherapy11or in combination with hydrochlorothiazide.12Methyldopa injection is used to manage hypertensive crises.13

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Associated Conditions
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.11Stimulation of alpha-adrenergic receptors leads to decreased peripheral sympathetic tone and reduced arterial pressure.3Methyldopa 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.11Following 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.2Methyldopa is metabolized to α‐methylnorepinephrine via dopamine beta-hydroxylase activity and, consequently, alpha-methylepinephrine via phenylethanolamine-N-methyltransferase activity.9,8,10Mediating 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.11Inhibiting 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.5In healthy individuals, the inactive D-isomer is less readily absorbed than the active L-isomer.7The mean bioavailability of methyldopa is 25%, ranging from eight to 62%.5Following oral administration, about 50% of the dose is absorbed and Tmaxis 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-soluble4, 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.5Following 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.7L-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.11After 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

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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%),6,11with 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.4After 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,4possibly leading to more profound and prolonged hypotensive effects in these patients.5

Half-life

The plasma half-life of methyldopa is 105 minutes.11Following 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 LD50is 5000 mg/kg in rats and 5300 mg/kg in mice. Intraperitoneal LD50is 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.
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Abacavir Methyldopa may decrease the excretion rate of Abacavir which could result in a higher serum level.
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.
Acetaminophen Acetaminophen may decrease the excretion rate of Methyldopa which could result in a higher serum level.
Acetazolamide Acetazolamide may increase the excretion rate of Methyldopa which could result in a lower serum level and potentially a reduction in efficacy.
Acetylsalicylic acid Acetylsalicylic acid may decrease the antihypertensive activities of Methyldopa.
Acipimox The risk or severity of myopathy, rhabdomyolysis, and myoglobinuria can be increased when Methyldopa is combined with Acipimox.
Aclidinium Methyldopa may decrease the excretion rate of Aclidinium which could result in a higher serum level.
Acrivastine Methyldopa may decrease the excretion rate of Acrivastine which could result in a higher serum level.
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Food Interactions
  • Take with or without food. Drug pharmacokinetics is unaffected.

Products

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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
International/Other Brands
Aldomet/Aldometil/Aldomin/Dopamet/Hypolag/Medomet/Medopren/Novomedopa/Nu-Medopa
Brand Name Prescription Products
名字 Dosage Strength Route Labeller Marketing Start Marketing End 地区 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 Canada flag
Aldomet Tab 125mg Tablet 125 mg Oral Merck Frosst Canada & Cie, Merck Frosst Canada & Co. 1971-12-31 1998-08-14 Canada flag
Aldomet Tab 250mg Tablet 250 mg Oral Merck Frosst Canada & Cie, Merck Frosst Canada & Co. 1963-12-31 2004-11-12 Canada flag
Aldomet Tab 500mg Tablet 500 mg Oral Merck Frosst Canada & Cie, Merck Frosst Canada & Co. 1971-12-31 1998-08-14 Canada flag
Dopamet Tab 125mg Tablet 125 mg Oral Icn Pharmaceuticals 1976-12-31 2005-04-26 Canada flag
Dopamet Tab 250mg Tablet 250 mg Oral Icn Pharmaceuticals 1972-12-31 2005-04-26 Canada flag
Dopamet Tab 500mg Tablet 500 mg Oral Icn Pharmaceuticals 1976-12-31 2005-04-26 Canada flag
Medimet 250tab Tablet 250 mg Oral Medic Laboratory LtÉe 1976-12-31 1996-09-09 Canada flag
Methyldopa Tablet 250 mg Oral Aa Pharma Inc 1976-12-31 Not applicable Canada flag
Methyldopa Tablet 125 mg Oral Aa Pharma Inc 1980-04-02 Not applicable Canada flag
Generic Prescription Products
名字 Dosage Strength Route Labeller Marketing Start Marketing End 地区 Image
Methyldopa Tablet, film coated 250 mg/1 Oral Rebel Distributors 2009-02-23 Not applicable US flag
Methyldopa Tablet, film coated 500 mg/1 Oral Avera McKennan Hospital 2016-04-18 2017-05-24 US flag
Methyldopa Tablet, film coated 500 mg/1 Oral Teva Pharmaceuticals USA, Inc. 2009-04-28 2018-02-28 US flag
Methyldopa Tablet, film coated 250 mg/1 Oral IVAX Pharmaceuticals, Inc. 1986-02-20 2010-09-30 US flag
Methyldopa Tablet 250 mg/1 Oral Mylan Institutional Inc. 1998-09-01 2020-01-31 US flag
Methyldopa Tablet, film coated 500 mg/1 Oral Physicians Total Care, Inc. 1996-07-26 Not applicable US flag
Methyldopa Tablet, film coated 125 mg/1 Oral Accord Healthcare Inc. 2012-06-27 2012-06-27 US flag
Methyldopa Tablet, film coated 250 mg/1 Oral Carilion Materials Management 2012-07-24 Not applicable US flag
Methyldopa Tablet, film coated 500 mg/1 Oral A S Medication Solutions 2009-04-28 Not applicable US flag
Methyldopa Tablet, film coated 500 mg/1 Oral Rebel Distributors 1984-02-20 Not applicable US flag
Mixture Products
名字 Ingredients Dosage Route Labeller Marketing Start Marketing End 地区 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 US flag
Aldoril Methyldopa sesquihydrate(500 mg/1)+Hydrochlorothiazide(50 mg/1) Tablet, film coated Oral Merck Sharp & Dohme Limited 1962-12-20 2006-03-31 US flag
Aldoril Methyldopa sesquihydrate(250 mg/1)+Hydrochlorothiazide(15 mg/1) Tablet, film coated Oral Merck Sharp & Dohme Limited 1962-12-20 2006-03-31 US flag
Aldoril Methyldopa sesquihydrate(500 mg/1)+Hydrochlorothiazide(30 mg/1) Tablet, film coated Oral Merck Sharp & Dohme Limited 1962-12-20 2006-03-31 US flag
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 Canada flag
Aldoril 25 Tab Methyldopa(250 mg)+Hydrochlorothiazide(25 mg) Tablet Oral Merck Frosst Canada & Cie, Merck Frosst Canada & Co. 1963-12-31 1999-03-02 Canada flag
Apo Methazide 15 Methyldopa(250 mg)+Hydrochlorothiazide(15 mg) Tablet Oral Apotex Corporation 1984-12-31 2019-05-04 Canada flag
Apo Methazide 25 Methyldopa(250 mg)+Hydrochlorothiazide(25 mg) Tablet Oral Apotex Corporation 1984-12-31 2019-05-04 Canada flag
甲基多巴和Hydrochlorothiazide Methyldopa sesquihydrate(250 mg/1)+Hydrochlorothiazide(25 mg/1) Tablet Oral Physicians Total Care, Inc. 1986-02-15 2012-06-30 US flag
甲基多巴和Hydrochlorothiazide Methyldopa sesquihydrate(250 mg/1)+Hydrochlorothiazide(25 mg/1) Tablet Oral Mylan Pharmaceuticals Inc. 1986-01-23 Not applicable US flag

Categories

ATC Codes
C02AB01 — Methyldopa (levorotatory)
药物Categories
Chemical TaxonomyProvided by类yfire
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
类
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
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Substituents
1-hydroxy-2-unsubstituted benzenoid/1-hydroxy-4-unsubstituted benzenoid/3-phenylpropanoic-acid/Alpha-amino酸/Alpha-amino酸or derivatives/Amine/Amino acid/Amino acid or derivatives/Amphetamine or derivatives/Aralkylamine
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
一般引用
  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]
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
药物s.com
药物s.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Methyldopa
FDA label
Download (155 KB)
MSDS
Download (53.4 KB)

Clinical Trials

Clinical TrialsLearn More" title="" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count
4 Completed Treatment Hypertension in Pregnancy/Prophylaxis of preeclampsia 1
4 Enrolling by Invitation Treatment Postpartum Hypertension (PPHT) 1
4 招募ing Prevention Pregnancy Induced Hypertension (PIH)/Prophylaxis of preeclampsia 1
4 Unknown Status Diagnostic Prophylaxis of preeclampsia 1
4 Unknown Status Treatment Diabetes/Hypertensive Diseases 1
4 Unknown Status Treatment Prophylaxis of preeclampsia 1
2 Completed Treatment Pregnant Women With Mild Preeclampsia 1
2 Withdrawn Prevention Type 1 Diabetes Mellitus 1
1 Completed Not Available Myalgic Encephalomyelitis (ME)/Orthostatic Intolerance/Postural Orthostatic Tachycardia Syndrome (POTS) 1
1 Completed Other Healthy Subjects (HS) 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, coated Oral 250 MG
Tablet, coated Oral 500 MG
Tablet, film coated Oral 500 MG
Tablet Oral 283 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 500 mg/1
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 500 mg
Tablet Oral 250 mg
Tablet Oral
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 0.39美元 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
药物Bank 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规则 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 没有准备好可生物降解 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 usingadmetSAR, 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 Not Available
GC-MS Spectrum - GC-EI-TOF GC-MS splash10-001i-0690000000-f54d986a8144f4a79b82
Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
质/女士Spectrum - LC-ESI-qTof , Positive 质/女士 Not Available
MS/MS Spectrum - , positive 质/女士 splash10-0g5i-2900000000-2d1c0ec9ad93e208b620

Targets

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Details 1.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
监护系统
Uniprot ID
P20711
Uniprot Name
Aromatic-L-amino-acid decarboxylase
分子量
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]
Details 2.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
分子量
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]

Enzymes

Details 1.Catechol O-methyltransferase
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
O-methyltransferase activity
Specific Function
Catalyzes the O-methylation, and thereby the inactivation, of catecholamine neurotransmitters and catechol hormones. Also shortens the biological half-lives of certain neuroactive drugs, like L-DOP...
Gene Name
COMT
Uniprot ID
P21964
Uniprot Name
Catechol O-methyltransferase
分子量
30036.77 Da
References
  1. Alazizi A, Liu MY, Williams FE, Kurogi K, Sakakibara Y, Suiko M, Liu MC: Identification, characterization, and ontogenic study of a catechol O-methyltransferase from zebrafish. Aquat Toxicol. 2011 Mar;102(1-2):18-23. doi: 10.1016/j.aquatox.2010.12.016. Epub 2010 Dec 29. [Article]
  2. Ameyaw MM, Syvanen AC, Ulmanen I, Ofori-Adjei D, McLeod HL: Pharmacogenetics of catechol-O-methyltransferase: frequency of low activity allele in a Ghanaian population. Hum Mutat. 2000 Nov;16(5):445-6. [Article]
  3. 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]
Details 2.Aromatic-L-amino-acid decarboxylase
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
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
监护系统
Uniprot ID
P20711
Uniprot Name
Aromatic-L-amino-acid decarboxylase
分子量
53925.815 Da
References
  1. 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]
Details 3.Sulfotransferase (Protein Group)
Kind
Protein group
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Sulfotransferase activity
Specific Function
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfonation of steroids and bile acids in the liver and adrenal glands.
Components:
名字 UniProt ID
Bile salt sulfotransferase Q06520
Sulfotransferase 1A1 P50225
Sulfotransferase 1A2 P50226
Sulfotransferase 1A3 P0DMM9
Sulfotransferase 1A4 P0DMN0
Sulfotransferase 1C2 O00338
Sulfotransferase 1C3 Q6IMI6
Sulfotransferase 1C4 O75897
Sulfotransferase 4A1 Q9BR01
Sulfotransferase 6B1 Q6IMI4
Sulfotransferase family cytosolic 1B member 1 O43704
References
  1. 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]
Details 4.Dopamine beta-hydroxylase
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
L-ascorbic acid binding
Specific Function
Conversion of dopamine to noradrenaline.
Gene Name
DBH
Uniprot ID
P09172
Uniprot Name
Dopamine beta-hydroxylase
分子量
69064.45 Da
References
  1. 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]
Details 5.Phenylethanolamine N-methyltransferase
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Phenylethanolamine n-methyltransferase activity
Specific Function
Converts noradrenaline to adrenaline.
Gene Name
PNMT
Uniprot ID
P11086
Uniprot Name
Phenylethanolamine N-methyltransferase
分子量
30854.745哒
References
  1. 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]

Carriers

Details 1.Serum albumin
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Binder
General Function
Toxic substance binding
Specific Function
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
Serum albumin
分子量
69365.94 Da
References
  1. Hubbard AK, Lohr CL, Hastings K, Clarke JB, Gandolfi AJ: Immunogenicity studies of a synthetic antigen of alpha methyl dopa. Immunopharmacol Immunotoxicol. 1993 Nov;15(5):621-37. doi: 10.3109/08923979309019734. [Article]

Transporters

Details 1.Solute carrier family 15 member 1
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Proton-dependent oligopeptide secondary active transmembrane transporter activity
Specific Function
Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides. May constitute a major route for the absorption of protein digestion end-products.
Gene Name
SLC15A1
Uniprot ID
P46059
Uniprot Name
Solute carrier family 15 member 1
分子量
78805.265 Da
References
  1. Han HK, Rhie JK, Oh DM, Saito G, Hsu CP, Stewart BH, Amidon GL: CHO/hPEPT1 cells overexpressing the human peptide transporter (hPEPT1) as an alternative in vitro model for peptidomimetic drugs. J Pharm Sci. 1999 Mar;88(3):347-50. [Article]

药物created at June 13, 2005 13:24 / Updated at August 02, 2022 05:13