Verapamil Hydrochloride

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Cat Number

API0232223

CAS Number

152-11-4

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CAS Number

152-11-4

EINECS

205-800-5

Storage

Store at room temperature, protected from light

Synonyms

Verapamil HCl; Verelan; Covera; Isoptin SR; Verelan PM; Calan SR; DTXSID2034095; NSC-272366

Molecular Formula

C27H39ClN2O4

Molecular Weight

491.1

Smiles

CC(C)C(CCCN(C)CCC1=CC(=C(C=C1)OC)OC)(C#N)C2=CC(=C(C=C2)OC)OC.Cl

Appearance

White or practically white crystalline powder

Melting Point

143°C

General Description

Verapamil hydrochloride is a synthetic phenylalkylamine calcium channel blocker with a nitrile group and a isopropylamine side chain. Its chemical structure is 2-(3,4-dimethoxyphenyl)-5-[2-(3,4-dimethoxyphenyl)ethyl-methylamino]-2-propan-2-ylpentanenitrile hydrochloride.

Mechanism of Action

Verapamil acts as a calcium channel blocker by binding to the alpha-1 subunit of the L-type calcium channels in the heart and vascular smooth muscle, reducing calcium influx. It has a greater effect on cardiac tissue than on vascular smooth muscle, leading to a decrease in heart rate, atrioventricular conduction, and myocardial contractility. The drug also has a mild alpha-adrenergic blocking effect.

Application

Verapamil is indicated for the treatment of hypertension, angina pectoris (including Prinzmetal's variant), and cardiac arrhythmias, particularly supraventricular tachycardias. It is also used for the prevention of migraine headaches and for the treatment of cluster headaches.

In mice with non-alcoholic fatty liver, verapamil (25 mg/kg IP for 10 days) enhanced autophagy, reduced liver weight, improved liver function and regeneration after 50% hepatectomy. Autophagy peaked at 48h in normal/mild fatty liver, and at 48–72h in severe fatty liver. Verapamil promotes hepatocyte regeneration through mTOR-independent autophagy induction.

Fig. 1 Autophagy changes of mice in HFD2m and HFD4m after 50% hepatectomy after injection of verapamil. (Lai JL, et al., 2021)

References

Lai JL, et al. Verapamil induces autophagy to improve liver regeneration in non-alcoholic fatty liver mice. Adipocyte. 2021;10(1):532-545.

In ureteral stricture patients and a TGF‑β1‑treated fibroblast model, verapamil activated autophagy and inhibited inflammation/fibrosis by repressing CaMKIIδ‑mediated STAT3 activation. STAT3 activated PAF1 transcription and PAF1 upregulation abolished verapamil's effects. In vivo, verapamil mitigated ureteral stricture. Verapamil acts through the CaMKIIδ/STAT3/PAF1 axis to reduce fibrosis.

Fig. 2 CaMK IIδ, STAT3 And PAF1 were markedly upregulated in ureteral scar tissues. (Zeng M, et al., 2024)

References

Zeng M, et al. Verapamil inhibits inflammation and promotes autophagy to alleviate ureteral scar by regulation of CaMK IIδ/STAT3 axis. Ren Fail. 2024;46(2):2387432.

Does Verapamil Hydrochloride require protection from light during long-term storage?

Yes, it is photosensitive. UV exposure can cause photodegradation and discoloration of the benzeneacetonitrile ring. Store in light-resistant containers, preferably amber glass.

What is the recommended storage humidity for Verapamil Hydrochloride?

It is slightly hygroscopic. Under high humidity (>70% RH), it may absorb moisture and clump. Store in tightly sealed containers with desiccant.

Is Verapamil Hydrochloride stable in injectable and oral solution formulations?

Aqueous solutions are stable when protected from light and stored at room temperature for up to 24 months.

How is the impurity verapamil N-oxide (an oxidative degradation product) monitored?

This degradation product is quantified using a stability-indicating HPLC method, ensuring it remains within pharmacopoeial limits.