Methyldopa sesquihydrateProduct ingredient for Methyldopa
- Name
- Methyldopa sesquihydrate
- 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
- DBSALT000988
- Structure
- Synonyms
- 3-Hydroxy-α-methyl-L-tyrosine hydrate (2:3) / L-3-(3,4-dihydroxyphenyl)-2-methylalanine sesquihydrate / Methyldopa / Methyldopa hydrate
- UNII
- 56LH93261Y
- CAS Number
- 41372-08-1
- Weight
- Average: 476.479
Monoisotopic: 476.200609858 - Chemical Formula
- C20H32N2O11
- InChI Key
- YKFCISHFRZHKHY-NGQGLHOPSA-N
- InChI
- 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
- IUPAC Name
- bis((2S)-2-amino-3-(3,4-dihydroxyphenyl)-2-methylpropanoic acid) trihydrate
- SMILES
- O.O.O.C[C@](N)(CC1=CC=C(O)C(O)=C1)C(O)=O.C[C@](N)(CC1=CC=C(O)C(O)=C1)C(O)=O
- External Links
- ChemSpider
- 35561
- ChEMBL
- CHEMBL1591707
- 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 6 Chemaxon Refractivity 53.79 m3·mol-1 Chemaxon Polarizability 20.78 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon