Nitrendipine

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Nitrendipine
Skeletal formula of nitrendipine
Ball-and-stick model of the nitrendipine molecule
Clinical data
Trade namesBaypress
AHFS/Drugs.comInternational Drug Names
Routes of
administration
By mouth
ATC code
Pharmacokinetic data
Bioavailability60–70%
Protein binding98%
MetabolismHepatic (completely)
Onset of action1–2 hours
Elimination half-life8–24 hours
ExcretionUrine (30%)
Identifiers
  • (RS)-3-Ethyl 5-methyl 2,6-dimethyl-4-(m-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate
JSmol)
ChiralityRacemic mixture
Melting point158 °C (316 °F)
  • O=C(OCC)\C1=C(\N/C(=C(/C(=O)OC)C1c2cccc([N+]([O-])=O)c2)C)C
  • InChI=1S/C18H20N2O6/c1-5-26-18(22)15-11(3)19-10(2)14(17(21)25-4)16(15)12-7-6-8-13(9-12)20(23)24/h6-9,16,19H,5H2,1-4H3 checkY
  • Key:PVHUJELLJLJGLN-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Nitrendipine is a

dihydropyridine calcium channel blocker. It is used in the treatment of primary (essential) hypertension to decrease blood pressure and can reduce the cardiotoxicity of cocaine.[1]

It was patented in 1971 and approved for medical use in 1985.[2]

Medical uses

Nitrendipine is given to hypertensive individuals in 20 mg oral tablets every day.

hepatic metabolism, 80% of the 20 mg dose can be recovered in the first 96 hours as inactive polar metabolites. The specific volume of distribution of the drug is 2-6 L/kg. In terms of drug half-life, nitrendipine has a half-life of 12–24 hours.[3]
The reported side effects include: headache, flushing, edema and palpitations. These side effects can all be attributed to the vasodilation effect of this drug.[3]

Mechanism of action

Once nitrendipine is ingested, it is absorbed by the gut and metabolized by the liver before it goes into the systemic circulation and reaches the cells of the

total peripheral resistance
, which decreases the workload on the heart and prevents scarring of the heart or heart failure.

Nitrendipine has additionally been found to act as an

antimineralocorticoid.[5]

Stereochemistry

Nitrendipine contains a stereocenter and can exist as either of two

racemate, an equal mixture of (R)- and the (S)-forms.[6]

Enantiomers of Nitrendipine

(R)-(+)-Nitrendipine
CAS number: 80890-07-9

(S)-(-)-Nitrendipine
CAS number: 80873-62-7

References