Nhận Dạng Quốc Tế & Đặc Tính Hóa Học
Monoisotopic mass
454.283157714
InChI
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
InChI Key
InChIKey=SGTNSNPWRIOYBX-UHFFFAOYSA-N
IUPAC Name
2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile
Traditional IUPAC Name
verapamil
SMILES
COC1=C(OC)C=C(CCN(C)CCCC(C#N)(C(C)C)C2=CC(OC)=C(OC)C=C2)C=C1
Độ sôi
243-246 °C at 1.00E-02 mm Hg
pKa (Strongest Basic)
9.68
Refractivity
132.65 m3·mol-1
Dược Lực Học :
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.
Cơ Chế Tác Dụng :
A calcium channel blocker that is a class IV anti-arrhythmia agent. [PubChem]
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.
Dược Động Học :
▧ Absorption :
90%
▧ Protein binding :
90%
▧ Route of Elimination :
Approximately 70% of an administered dose is excreted as metabolites in the urine and 16% or more in the feces within 5 days. About 3% to 4% is excreted in the urine as unchanged drug.
▧ Half Life :
2.8-7.4 hours
Độc Tính :
LD50=8 mg/kg (i.v. in mice)
Chỉ Định :
For the treatment of hypertension, angina, and cluster headache prophylaxis.
Tương Tác Thuốc :
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Acebutolol
Increased effect of both drugs
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Aliskiren
Monitor therapy due to increased concentration of aliskiren.
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Amifostine
Verapamil may enhance the hypotensive effect of Amifostine. At chemotherapeutic doses of Amifostine, Verapamil should be withheld for 24 hours prior to Amifostine administration. Caution should be used at lower Amifostine doses used during radiotherapy, but routine interruption of Verapamil therapy is not recommended.
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Aminophylline
Verapamil increases the effect of theophylline
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Amiodarone
Additive bradycardic effects may occur. One case report of sinus arrest has been reported. Monitor for changes in the therapeutic effect and signs of Verapamil toxicity if Amiodarone is initiated, discontinued or dose changed.
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Amobarbital
Amobarbital, a CYP3A4 inducer, may increase the serum concentration of Verapamil, a CYP3A4 substrate. Monitor for changes in the therapeutic/adverse effects of Verapamil if Amobarbital is initiated, discontinued or dose changed.
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Amprenavir
Amprenavir, a strong CYP3A4 inhibitor, may increase the serum concentration of Veramapil, a CYP3A4 substrate, by decreasing its metabolism and clearance. Consider alternate therapy or monitor for changes in the therapeutic/adverse effects of Verapamil if Amprenavir is initiated, discontinued or dose changed.
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Atazanavir
Atazanavir, a strong CYP3A4 inhibitor, may increase the serum concentration of Veramapil, a CYP3A4 substrate, by decreasing its metabolism and clearance. Consider alternate therapy or monitor for changes in the therapeutic/adverse effects of Verapamil if Atazanavir is initiated, discontinued or dose changed.
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Atenolol
Increased effect of both drugs
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Atorvastatin
Verapamil, a moderate CYP3A4 inhibitor, may increase the serum concentration of Atorvastatin by decreasing its metabolism. Avoid concurrent use if possible or reduce lovastatin dose during concomitant therapy. Monitor for changes in the therapeutic/adverse effects of Atorvastatin if Verapamil is initiated, discontinued or dose changed.
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Bisoprolol
Increased effect of both drugs
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Bromazepam
Verapamil may increase the serum concentration of bromazepam by decreasing its metabolism. Consider alternate therapy or a reductin in the bromazepam dose. Monitor for changes in the therapeutic and adverse effects of bromazepam if verapamil is initiated, discontinued or dose changed.
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Buspirone
Verapamil may increase the serum concentration of Buspirone. The likely occurs via Verapamil-mediated CYP3A4 inhibition resulting in decreased Buspirone metabolism. Monitor for changes in the therapeutic/adverse effects of Buspirone if Verpamil is initiated, discontinued or dose changed.
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Butabarbital
Butabarbital, a CYP3A4 inducer, may increase the serum concentration of Verapamil, a CYP3A4 substrate. Monitor for changes in the therapeutic/adverse effects of Verapamil if Butabarbital is initiated, discontinued or dose changed.
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Butalbital
Butalbital, a CYP3A4 inducer, may increase the serum concentration of Verapamil, a CYP3A4 substrate. Monitor for changes in the therapeutic/adverse effects of Verapamil if Butalbital is initiated, discontinued or dose changed.
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Carbamazepine
Verapamil may increase the serum concentration of Carbamazepine by decreasing its metabolism. Monitor for changes in the therapeutic/adverse effects of Carbamazepine if Verapamil is initiated, discontinued or dose changed.
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Carvedilol
Increased effect of both drugs
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Clarithromycin
Clarithromycin, a strong CYP3A4 inhibitor, may increase the serum concentration of Veramapil, a CYP3A4 substrate, by decreasing its metabolism and clearance. Consider alternate therapy or monitor for changes in the therapeutic/adverse effects of Verapamil if Clarithromycin is initiated, discontinued or dose changed.
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Colchicine
Verapamil may increase the serum concentration of Colchicine. This likely occurs via Verapamil-mediated inhibition of CYP3A4 and p-glycoprotein-mediated transport. Monitor for changes in the therapeutic/adverse effects of Colchicine if Verapamil is initiated, discontinued or dose changed.
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Conivaptan
Conivaptan, a strong CYP3A4 inhibitor, may increase the serum concentration of Veramapil, a CYP3A4 substrate, by decreasing its metabolism and clearance. Consider alternate therapy or monitor for changes in the therapeutic/adverse effects of Verapamil if Conivaptan is initiated, discontinued or dose changed.
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Cyclosporine
Verapamil may increase the serum concentration of cyclosporine by inhibiting CYP3A4-mediated metabolism of cyclosporine. Monitor for changes in the therapeutic/adverse effects of cyclosporine if verapamil is initiated, discontinued or dose changed.
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Dabigatran etexilate
Verapamil may increase serum concentrations of the active metabolite(s) of dabigatran etexilate, resulting in an increased risk of bleeding. It is also a strong p-glycoprotein inhibitor. Therapy modification should be considered.
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Darunavir
Darunavir, a strong CYP3A4 inhibitor, may increase the serum concentration of Veramapil, a CYP3A4 substrate, by decreasing its metabolism and clearance. Consider alternate therapy or monitor for changes in the therapeutic/adverse effects of Verapamil if Darunavir is initiated, discontinued or dose changed.
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Delavirdine
Delavirdine, a strong CYP3A4 inhibitor, may increase the serum concentration of Veramapil, a CYP3A4 substrate, by decreasing its metabolism and clearance. Consider alternate therapy or monitor for changes in the therapeutic/adverse effects of Verapamil if Delavirdine is initiated, discontinued or dose changed.
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Digitoxin
Verapamil may increase the serum concentration of Digitoxin by decreasing its metabolism and clearance. Monitor for changes in the therapeutic/adverse effects of Digitoxin if Verpamail is initiated, discontinued or dose changed.
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Digoxin
Verapamil may increase the serum concentration of Digoxin by decreasing its metabolism and clearance. Monitor for changes in the therapeutic/adverse effects of Digoxin if Verpamail is initiated, discontinued or dose changed.
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Dofetilide
Verapamil may increase the plamsa levels of Dofetilide. Increased risk of torsade de pointes. Concomitant therapy is contraindicated.
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Dronedarone
Verapamil is a moderate CYP3A4 inhibitor and will increase dronedarone levels 1.4-1.7 fold. Decrease doses of non-dihyropyridinic calcium-channel blocker.
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Eplerenone
This CYP3A4 inhibitor increases the effect and toxicity of eplerenone
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Erythromycin
Erythromycin, a moderate CYP3A4 inhibitor, may increase the serum concentration of veramapil, a CYP3A4 substrate, by decreasing its metabolism and clearance. Monitor for changes in the therapeutic/adverse effects of verapamil if erythromycin is initiated, discontinued or dose changed.
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Esmolol
Increased effect of both drugs
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Everolimus
Concomitant administration may increase the serum concentrations of both agents. Concurrent use should be avoided.
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Fluconazole
Fluconazole may increase the serum concentration of Verapamil by decreasing Verapamil metabolism. This likely occurs via Fluconazole-mediated CYP3A4 inhibition. Monitor for changes in the therapeutic/adverse effects of Verapamil if Fluconazole is initiated, discontinued, or dose changed.
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Fosamprenavir
Fosamprenavir, a strong CYP3A4 inhibitor, may increase the serum concentration of Veramapil, a CYP3A4 substrate, by decreasing its metabolism and clearance. Consider alternate therapy or monitor for changes in the therapeutic/adverse effects of Verapamil if Fosamprenavir is initiated, discontinued or dose changed.
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Halofantrine
Verapamil, a moderate CYP3A4 inhibitor, may increase the serum concentration of Halofantrine by decreasing its metabolism. Extreme caution with increased cardiac status monitoring should be used during concomitant therapy.
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Imatinib
Imatinib, a strong CYP3A4 inhibitor, may increase the serum concentration of Veramapil, a CYP3A4 substrate, by decreasing its metabolism and clearance. Consider alternate therapy or monitor for changes in the therapeutic/adverse effects of Verapamil if Imatinib is initiated, discontinued or dose changed.
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Indacaterol
Strong inhibitors of CYP3A4 may increase levels of indacaterol. Monitor closely for adverse events.
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Indinavir
Indinavir, a strong CYP3A4 inhibitor, may increase the serum concentration of Veramapil, a CYP3A4 substrate, by decreasing its metabolism and clearance. Consider alternate therapy or monitor for changes in the therapeutic/adverse effects of Verapamil if Indinavir is initiated, discontinued or dose changed.
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Isoniazid
Isoniazid, a strong CYP3A4 inhibitor, may increase the serum concentration of Veramapil, a CYP3A4 substrate, by decreasing its metabolism and clearance. Consider alternate therapy or monitor for changes in the therapeutic/adverse effects of Verapamil if Isoniazid is initiated, discontinued or dose changed.
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Itraconazole
Itraconazole, a strong CYP3A4 inhibitor, may increase the serum concentration of Veramapil, a CYP3A4 substrate, by decreasing its metabolism and clearance. Consider alternate therapy or monitor for changes in the therapeutic/adverse effects of Verapamil if Itraconazole is initiated, discontinued or dose changed.
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Ketoconazole
Ketoconazole, a strong CYP3A4 inhibitor, may increase the serum concentration of Veramapil, a CYP3A4 substrate, by decreasing its metabolism and clearance. Consider alternate therapy or monitor for changes in the therapeutic/adverse effects of Verapamil if Ketoconazole is initiated, discontinued or dose changed.
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Labetalol
Increased effect of both drugs
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Lithium
Signs of lithium toxicity
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Lopinavir
Lopinavir, a strong CYP3A4 inhibitor, may increase the serum concentration of Veramapil, a CYP3A4 substrate, by decreasing its metabolism and clearance. Consider alternate therapy or monitor for changes in the therapeutic/adverse effects of Verapamil if Lopinavir is initiated, discontinued or dose changed.
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Lovastatin
Verapamil, a moderate CYP3A4 inhibitor, may increase the serum concentration of Lovastatin by decreasing its metabolism. Avoid concurrent use if possible or reduce lovastatin dose during concomitant therapy. Monitor for changes in the therapeutic/adverse effects of Lovastatin if Verapamil is initiated, discontinued or dose changed.
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Methohexital
Methohexital, a CYP3A4 inducer, may increase the serum concentration of Verapamil, a CYP3A4 substrate. Monitor for changes in the therapeutic/adverse effects of Verapamil if Methohexital is initiated, discontinued or dose changed.
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Methylphenobarbital
Methylphenobarbital, a CYP3A4 inducer, may increase the serum concentration of Verapamil, a CYP3A4 substrate. Monitor for changes in the therapeutic/adverse effects of Verapamil if Methylphenobarbital is initiated, discontinued or dose changed.
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Metoprolol
Increased effect of both drugs
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Miconazole
Miconazole, a strong CYP3A4 inhibitor, may increase the serum concentration of Veramapil, a CYP3A4 substrate, by decreasing its metabolism and clearance. Consider alternate therapy or monitor for changes in the therapeutic/adverse effects of Verapamil if Miconazole is initiated, discontinued or dose changed.
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Midazolam
Verapamil may increase the serum concentration of Midazolam by decreasing its metabolism. Avoid concomitant therapy if possible or consider a dose reduction in the initial dose of Midazolam.
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Nadolol
Increased effect of both drugs
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Nafcillin
Nafcillin may decrease the serum concentration of Verapamil by increasing its metabolism via CYP3A4. Monitor for changes in the therapeutic/adverse effects of Verapamil if Nafcillin is initiated, discontinued or dose changed.
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Nefazodone
Nefazodone, a strong CYP3A4 inhibitor, may increase the serum concentration of Veramapil, a CYP3A4 substrate, by decreasing its metabolism and clearance. Consider alternate therapy or monitor for changes in the therapeutic/adverse effects of Verapamil if Nefazodone is initiated, discontinued or dose changed.
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Nelfinavir
Nelfinavir, a strong CYP3A4 inhibitor, may increase the serum concentration of Veramapil, a CYP3A4 substrate, by decreasing its metabolism and clearance. Consider alternate therapy or monitor for changes in the therapeutic/adverse effects of Verapamil if Nelfinavir is initiated, discontinued or dose changed.
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Nicardipine
Nicardipine, a strong CYP3A4 inhibitor, may increase the serum concentration of Veramapil, a CYP3A4 substrate, by decreasing its metabolism and clearance. Consider alternate therapy or monitor for changes in the therapeutic/adverse effects of Verapamil if Nicardipine is initiated, discontinued or dose changed.
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Oxprenolol
Increased effect of both drugs
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Oxtriphylline
Verapamil increases the effect of theophylline
-
Pentobarbital
Pentobarbital, a CYP3A4 inducer, may increase the serum concentration of Verapamil, a CYP3A4 substrate. Monitor for changes in the therapeutic/adverse effects of Verapamil if Pentobarbital is initiated, discontinued or dose changed.
-
Phenobarbital
Phenobarbital, a CYP3A4 inducer, may increase the serum concentration of Verapamil, a CYP3A4 substrate. Monitor for changes in the therapeutic/adverse effects of Verapamil if Phenobarbital is initiated, discontinued or dose changed.
-
Phenytoin
Verapamil may increase the serum concentration of Phenytoin by decreasing its metabolism. Monitor for changes in the therapeutic/adverse effects of Phenytoin if Verapamil is initiated, discontinued or dose changed.
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Pindolol
Increased effect of both drugs
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Posaconazole
Posaconazole, a strong CYP3A4 inhibitor, may increase the serum concentration of Veramapil, a CYP3A4 substrate, by decreasing its metabolism and clearance. Consider alternate therapy or monitor for changes in the therapeutic/adverse effects of Verapamil if Posaconazole is initiated, discontinued or dose changed.
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Prazosin
Risk of hypotension at the beginning of therapy
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Primidone
The barbiturate, primidone, decreases the effect of the calcium channel blocker, verapamil.
-
Propranolol
Increased effect of both drugs
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Quinidine
Concurrent therapy may result in increased serum levels of both agents. Both agents are CYP3A4 inhibitors and substrates. Consider alternate therapy or monitor for changes in the therapeutic/adverse effects of the agent if the other is initiated, discontinued or dose changed.
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Quinupristin
This combination presents an increased risk of toxicity
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Ranolazine
Verapamil, a CYP3A4 inhibitor, may increase the serum concentration of Ranolazine. Concomitant therapy is contraindicated.
-
Rifabutin
Rifabutin, a CYP3A4 inducer, may decrease the serum concentration of Verapamil by increasing its metabolism (particularly in the intestinal mucosa) and decreasing its absorption. Monitor for changes in the therapeutic/adverse effects of Verapamil if Rifabutin is initiated, discontinued or dose changed.
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Rifampicin
Rifampin, a CYP3A4 inducer, may decrease the serum concentration of Verapamil by increasing its metabolism (particularly in the intestinal mucosa) and decreasing its absorption. Monitor for changes in the therapeutic/adverse effects of Verapamil if Rifampin is initiated, discontinued or dose changed.
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Rifapentine
Rifapentine, a CYP3A4 inducer, may decrease the serum concentration of Verapamil by increasing its metabolism (particularly in the intestinal mucosa) and decreasing its absorption. Monitor for changes in the therapeutic/adverse effects of Verapamil if Rifapentine is initiated, discontinued or dose changed.
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Ritonavir
Ritonavir, a strong CYP3A4 inhibitor, may increase the serum concentration of Veramapil, a CYP3A4 substrate, by decreasing its metabolism and clearance. Consider alternate therapy or monitor for changes in the therapeutic/adverse effects of Verapamil if Ritonavir is initiated, discontinued or dose changed.
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Rituximab
Verapamil may increase the hypotensive effects of Rituximab. Consider withholding Verapamil therapy for 12 hours prior to Rituximab infusion.
-
Saquinavir
Saquinavir, a strong CYP3A4 inhibitor, may increase the serum concentration of Veramapil, a CYP3A4 substrate, by decreasing its metabolism and clearance. Consider alternate therapy or monitor for changes in the therapeutic/adverse effects of Verapamil if Saquinavir is initiated, discontinued or dose changed.
-
Secobarbital
Secobarbital, a CYP3A4 inducer, may increase the serum concentration of Verapamil, a CYP3A4 substrate. Monitor for changes in the therapeutic/adverse effects of Verapamil if Secobarbital is initiated, discontinued or dose changed.
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Silodosin
Verapamil is a moderate inhibitor of CYP3A4 and inhibits P-glycoprotein thus increasing the potential for adverse effects
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Simvastatin
Verapamil, a moderate CYP3A4 inhibitor, may increase the serum concentration of Simvastatin by decreasing its metabolism. Avoid concurrent use if possible or reduce Simvastatin dose during concomitant therapy. Monitor for changes in the therapeutic/adverse effects of Simvastatin if Verapamil is initiated, discontinued or dose changed.
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Tacrolimus
The calcium channel blocker, Verapamil, may increase the blood concentration of Tacrolimus. Monitor for changes in the therapeutic/toxic effects of Tacrolimus if Verapamil therapy is initiated, discontinued or altered.
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Tamsulosin
Verapamil, a CYP3A4 inhibitor, may decrease the metabolism and clearance of Tamsulosin, a CYP3A4 substrate. Monitor for changes in therapeutic/adverse effects of Tamsulosin if Verapamil is initiated, discontinued, or dose changed.
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Telithromycin
Telithromycin, a CYP3A4 and p-glycoprotein inhibitor, may increase the Vinblastine serum concentration and distribution in certain cells. Consider alternate therapy to avoid Vinblastine toxicity. Monitor for changes in the therapeutic/adverse effects of Vinblastine if Telithromycin is initiated, discontinued or dose changed.
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Terfenadine
Increased risk of cardiotoxicity and arrhythmias
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Theophylline
Verapamil increases the effect of theophylline
-
Thiopental
Thiopental, a CYP3A4 inducer, may increase the serum concentration of Verapamil, a CYP3A4 substrate. Monitor for changes in the therapeutic/adverse effects of Verapamil if Thiopental is initiated, discontinued or dose changed.
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Timolol
Additive effects of decreased heart rate and contractility may occur. Increased risk of heart block.
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Tipranavir
Tipranavir, co-administered with Ritonavir, may alter the concentration of Verapamil. Monitor for efficacy and adverse/toxic effects of Verapamil.
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Tolterodine
Verapamil may decrease the metabolism and clearance of Tolterodine. Adjust Tolterodine dose and monitor for efficacy and toxicity.
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Tolvaptan
Verapamil, a moderate CYP3A4 inhibitor, may increase the serum concentration of Tolvaptan. Concomitant therapy is contraindicated.
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Topotecan
The p-glycoprotein inhibitor, Verapamil, may increase the bioavailability of oral Topotecan. A clinically significant effect is also expected with IV Topotecan. Concomitant therapy should be avoided.
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Tramadol
Verapamil may increase Tramadol toxicity by decreasing Tramadol metabolism and clearance.
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Trazodone
The CYP3A4 inhibitor, Verapamil, may increase Trazodone efficacy/toxicity by decreasing Trazodone metabolism and clearance. Monitor for changes in Trazodone efficacy/toxicity if Verapamil is initiated, discontinued or dose changed.
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Treprostinil
Additive hypotensive effect. Monitor antihypertensive therapy during concomitant use.
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Triazolam
Verapamil may increase the serum concentration of Triazolam by decreasing its metabolism. Avoid concomitant therapy if possible or consider a dose reduction in the initial dose of Triazolam.
-
Voriconazole
Voriconazole, a strong CYP3A4 inhibitor, may increase the serum concentration of verapamil by decreasing its metabolism. Monitor for changes in the therapeutic and adverse effects of verapamil if voriconazole is initiated, discontinued or dose changed.
Liều Lượng & Cách Dùng :
Capsule, extended release - Oral
Liquid - Intravenous
Solution - Intravenous
Tablet - Oral
Tablet, extended release - Oral
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Nhà Sản Xuất
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Sản phẩm biệt dược : Bosoptin
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Sản phẩm biệt dược : Calan
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Sản phẩm biệt dược : Calan SR
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Sản phẩm biệt dược : Covera-HS
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Sản phẩm biệt dược : Isoptin
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Sản phẩm biệt dược : Isoptin SR
-
Sản phẩm biệt dược : Verelan
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Sản phẩm biệt dược : Verelan PM
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Sản phẩm biệt dược : Verisop
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Sản phẩm biệt dược : Vermin
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Sản phẩm biệt dược : Vermine
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Sản phẩm biệt dược : Verogalid
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Sản phẩm biệt dược : Verogalid ER
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Sản phẩm biệt dược : Verpamil
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Sản phẩm biệt dược : Vertab
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Sản phẩm biệt dược : Vetrimil
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Sản phẩm biệt dược : Zolvera
Tài Liệu Tham Khảo Thêm
National Drug Code Directory