Stereochemistry | RACEMIC |
Molecular Formula | C27H38N2O4 |
Molecular Weight | 454.6016 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
COC1=C(OC)C=C(CCN(C)CCCC(C#N)(C(C)C)C2=CC(OC)=C(OC)C=C2)C=C1
InChI
InChIKey=SGTNSNPWRIOYBX-UHFFFAOYSA-N
InChI=1S/C27H38N2O4/c1-20(2)27(19-28,22-10-12-24(31-5)26(18-22)33-7)14-8-15-29(3)16-13-21-9-11-23(30-4)25(17-21)32-6/h9-12,17-18,20H,8,13-16H2,1-7H3
Verapamil is a FDA approved drug used to treat high blood pressure and to control chest pain. Verapamil is an L-type calcium channel blocker that also has antiarrythmic activity. The R-enantiomer is more effective at reducing blood pressure compared to the S-enantiomer. However, the S-enantiomer is 20 times more potent than the R-enantiomer at prolonging the PR interval in treating arrhythmias. Verapamil inhibits voltage-dependent calcium channels. Specifically, its effect on L-type calcium channels in the heart causes a reduction in ionotropy and chronotropy, thuis reducing heart rate and blood pressure. Verapamil's mechanism of effect in cluster headache is thought to be linked to its calcium-channel blocker effect, but which channel subtypes are involved is presently not known.
CNS Activity
Originator
Approval Year
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Drug as victim
Tox targets
Sourcing
Sample Use Guides
Angina: Clinical trials show that the usual dose is 80 mg to 120 mg three times a day.
However, 40 mg three times a day may be warranted in patients who may have an
increased response to verapamil (eg, decreased hepatic function, elderly, etc). Upward
titration should be based on therapeutic efficacy and safety evaluated approximately eight
hours after dosing. Dosage may be increased at daily (eg, patients with unstable angina)
or weekly intervals until optimum clinical response is obtained.
Arrhythmias: The dosage in digitalized patients with chronic atrial fibrillation (see
PRECAUTIONS) ranges from 240 to 320 mg/day in divided (t.i.d. or q.i.d.) doses. The
dosage for prophylaxis of PSVT (non-digitalized patients) ranges from 240 to
480 mg/day in divided (t.i.d. or q.i.d.) doses. In general, maximum effects for any given
dosage will be apparent during the first 48 hours of therapy.
Essential hypertension: Dose should be individualized by titration. The usual initial
monotherapy dose in clinical trials was 80 mg three times a day (240 mg/day). Daily
dosages of 360 and 480 mg have been used but there is no evidence that dosages beyond
360 mg provided added effect. Consideration should be given to beginning titration at
40 mg three times per day in patients who might respond to lower doses, such as the
elderly or people of small stature. The antihypertensive effects of CALAN are evident
within the first week of therapy. Upward titration should be based on therapeutic
efficacy, assessed at the end of the dosing interval.
Route of Administration:
Other