Methyldopa hydrochlorideProduct ingredient for Methyldopa

Name
Methyldopa hydrochloride
Drug Entry
Methyldopa

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

Accession Number
DBSALT001139
Structure
Synonyms
Methyldopa HCl / methyldopate hydrochloride
UNII
7PX435DN5A
CAS Number
2508-79-4
Weight
Average: 275.73
Monoisotopic: 275.0924358
Chemical Formula
C12H18ClNO4
InChI Key
QSRVZCCJDKYRRF-YDALLXLXSA-N
InChI
InChI=1S/C12H17NO4.ClH/c1-3-17-11(16)12(2,13)7-8-4-5-9(14)10(15)6-8;/h4-6,14-15H,3,7,13H2,1-2H3;1H/t12-;/m0./s1
IUPAC Name
ethyl (2S)-2-amino-3-(3,4-dihydroxyphenyl)-2-methylpropanoate hydrochloride
SMILES
Cl.CCOC(=O)[C@@](C)(N)CC1=CC(O)=C(O)C=C1
ChemSpider
16350
ChEMBL
CHEMBL1200432
Predicted Properties
PropertyValueSource
Water Solubility1.18 mg/mLALOGPS
logP0.61ALOGPS
logP1.41Chemaxon
logS-2.3ALOGPS
pKa (Strongest Acidic)9.29Chemaxon
pKa (Strongest Basic)7.22Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area92.78 Å2Chemaxon
Rotatable Bond Count5Chemaxon
Refractivity63.31 m3·mol-1Chemaxon
Polarizability24.97 Å3Chemaxon
Number of Rings1Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon