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Chemical Structure| 52-53-9 Chemical Structure| 52-53-9

Structure of Verapamil
CAS No.: 52-53-9

Chemical Structure| 52-53-9

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Verapamil ((±)-Verapamil) is a calcium channel blocker and a potent, orally active first-generation P-glycoprotein (P-gp) inhibitor that also inhibits CYP3A4. Verapamil has potential for research in high blood pressure, heart arrhythmias, and angina.

Synonyms: CP-16533-1; (±)-Verapamil; NSC 135784

4.5 *For Research Use Only !

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Product Citations

Product Citations

Haroon, Muhammad ; Sultana, Sharmin ; Najibi, Seyedeh A ; Wang, Emily T ; Michaelson, Abbey ; Al Muied, Pranto SM , et al.

Abstract: The imidazoquinoline family of toll-like receptor (TLR) immune cell agonists has long demonstrated moderate anticancer immunogenic effects by activating tumoricidal immune cells and depleting immunosuppressive cells within the tumor microenvironment. At a molecular level, we have also established that several imidazoquinolines traffic from within cancer cells to the extracellular space via P-glycoprotein (P-gp)-mediated efflux, a process commonly upregulated as multidrug-resistant (MDR) cancers acquire chemoresistance. However, imidazoquinoline P-gp efflux has never been deliberately enhanced to exploit this process. This study pioneers efforts to optimize imidazoquinoline efflux, ultimately balancing immunogenic potency alongside functional efflux susceptibility. Starting from an established imidazoquinoline scaffold previously optimized for potency, efflux was significantly enhanced by elaborating the N1 benzylic position with amide- and sulfonamide-linked P-gp affinity fragments consisting of empirically established P-gp substrates as well as computationally predicted P-gp binders. Lead compounds were identified from this series that exhibited enhanced P-gp efflux with functional retention of TLR agonism. Similar to the parent imidazoquinoline scaffold, leads had limited direct cytotoxicity in both treatment-naive and MDR B16 melanoma models and did not significantly affect the efficacy or trafficking of the chemotherapeutic doxorubicin. Efflux-enhanced imidazoquinolines were preferentially expelled from MDR-B16 cells relative to treatment-naive cells, resulting in immunogenicity that was enhanced as a consequence of the acquired MDR phenotype. Because enhanced P-gp-mediated efflux is common to most MDR cancer types, we envision that these results could inspire the design of immunotherapeutic drugs with mechanisms of action that are broadly enhanced in MDR cancers that have failed treatment or acquired resistance to chemotherapeutics.

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Product Details of Verapamil

CAS No. :52-53-9
Formula : C27H38N2O4
M.W : 454.60
SMILES Code : N#CC(CCCN(C)CCC1=CC(OC)=C(OC)C=C1)(C2=CC(OC)=C(OC)C=C2)C(C)C
Synonyms :
CP-16533-1; (±)-Verapamil; NSC 135784
MDL No. :MFCD00056240
InChI Key :SGTNSNPWRIOYBX-UHFFFAOYSA-N
Pubchem ID :2520

Safety of Verapamil

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338

Isoform Comparison

Biological Activity

Clinical Trial:

NCT Number Conditions Phases Recruitment Completion Date Locations
NCT02235558 Ischemic Stroke PHASE1 COMPLETED 2016-03-21 University of Kentucky Deparme... More >>nt of Neurosurgery, UK Chandler Hospital, Lexington, Kentucky, 40536, United States Less <<
NCT05847413 Type 1 Diabetes EARLY_PHASE1 COMPLETED 2021-12-10 Benaroya Research Institute, S... More >>eattle, Washington, 98101, United States Less <<
NCT03033537 Erectile Dysfunction COMPLETED 2016-01-20 -
NCT01607073 Dravet Syndrome PHASE2 COMPLETED 2025-01-15 Children's Memorial Hospital, ... More >>Chicago, Illinois, 60614, United States|Mayo Clinic, Rochester, Minnesota, 55905, United States|Gillette Children's Specialty Healthcare, Saint Paul, Minnesota, 55101, United States|Mary Hitchcock Memorial Hospital, Lebanon, New Hampshire, 03756, United States Less <<
NCT06447688 Radial Artery Spasm PHASE4 COMPLETED 2024-11-15 VM Medicalpark, Mersin, 33010,... More >> Turkey Less <<
NCT04406259 Cluster Headache PHASE4 RECRUITING 2025-03-01 CHU de Nice, NICE Cedex 1, Chu... More >>n, 06003, France|AP-HP H?pital la Timone, Marseille, 13005, France Less <<
NCT01655316 Paroxysmal Supraventricular Ta... More >>chycardia Less << PHASE4 COMPLETED 2025-08-11 -
NCT00348530 Systolic Heart Failure|Myocard... More >>ial Disease|Cardiomyopathy Less << PHASE4 UNKNOWN 2025-12-07 Silesian Center for Heart Dise... More >>ase, IIIrd Department of Cardiology, Silesian Medical University, Zabrze, 41-800, Poland Less <<

Protocol

Bio Calculators
Preparing Stock Solutions 1mg 5mg 10mg

1 mM

5 mM

10 mM

2.20mL

0.44mL

0.22mL

11.00mL

2.20mL

1.10mL

22.00mL

4.40mL

2.20mL

Dissolving Methods
Please choose the appropriate dissolution scheme according to your animal administration guide.For the following dissolution schemes, clear stock solution should be prepared according to in vitro experiments, and then cosolvent should be added in turn:

in order to ensure the reliability of the experimental results, the clarified stock solution can be properly preserved according to the storage conditions; The working fluid for in vivo experiment is recommended to be prepared now and used on the same day;

The percentage shown in front of the following solvent refers to the volume ratio of the solvent in the final solution; If precipitation or precipitation occurs in the preparation process, it can be assisted by heating and/or ultrasound.
Protocol 1
Protocol 2

References

 

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