1. Membrane Transporter/Ion Channel Apoptosis
  2. P-glycoprotein Apoptosis
  3. (S)-Verapamil

(S)-Verapamil ((S)-(-)-Verapamil) is an orally active MRP1 (ABCC1) modulator with a Kd value of 113 nM for hamster MRP1. (S)-Verapamil regulates MRP1, promotes MRP1-mediated glutathione efflux and the transport of calcein and leukotriene C4, reverses glutathione-activated MRP1 ATPase activity, and ultimately depletes intracellular glutathione and induces cell death. (S)-Verapamil specifically induces apoptosis in MRP1-overexpressing tumor cells. (S)-Verapamil can be used in research related to cancer, cardiac diseases such as supraventricular arrhythmia, and hypertension.

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(S)-Verapamil

(S)-Verapamil Chemical Structure

CAS No. : 36622-29-4

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Description

(S)-Verapamil ((S)-(-)-Verapamil) is an orally active MRP1 (ABCC1) modulator with a Kd value of 113 nM for hamster MRP1. (S)-Verapamil regulates MRP1, promotes MRP1-mediated glutathione efflux and the transport of calcein and leukotriene C4, reverses glutathione-activated MRP1 ATPase activity, and ultimately depletes intracellular glutathione and induces cell death. (S)-Verapamil specifically induces apoptosis in MRP1-overexpressing tumor cells. (S)-Verapamil can be used in research related to cancer, cardiac diseases such as supraventricular arrhythmia, and hypertension[1][2].

In Vitro

(S)-Verapamil (72 h) potently induces cell death in MRP1-transfected BHK-21 cells[1].
(S)-Verapamil causes strong and rapid depletion of glutathione inside MRP1-transfected BHK-21 cells[1].
(S)-Verapamil (30 μM; 10 min) effectively inhibits MRP1-mediated calcein transport in MRP1-transfected BHK-21 cells[1].
(S)-Verapamil (1-256 μM; in the presence of 3 mM GSH), when combined with 3 mM GSH, potently inhibits ATP-dependent LTC4 transport in MRP1-transfected BHK-21 membrane vesicles[1].
(S)-Verapamil binds tightly to purified MRP1 with a Kd value of 113 nM, and induces significant conformational changes in purified MRP1[1].
(S)-Verapamil (4 h) slightly stimulates the basal ATPase activity of purified MRP1, and completely reverses the activation of ATPase activity induced by 5 mM GSH[1].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

In Vivo

(S)-Verapamil is up to 10 times more potent than (R)-verapamil for negative dromotropic effects on atrioventricular nodal conduction in healthy dogs[2].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Molecular Weight

454.61

Formula

C27H38N2O4

CAS No.
Appearance

Oil

SMILES

[C@@](CCCN(CCC1=CC(OC)=C(OC)C=C1)C)(C(C)C)(C#N)C2=CC(OC)=C(OC)C=C2

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Room temperature in continental US; may vary elsewhere.

Storage

4°C, protect from light

*In solvent : -80°C, 6 months; -20°C, 1 month (protect from light)

Solvent & Solubility
In Vitro: 

DMSO : ≥ 100 mg/mL (219.97 mM; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO)

*"≥" means soluble, but saturation unknown.

Preparing
Stock Solutions
Concentration Solvent Mass 1 mg 5 mg 10 mg
1 mM 2.1997 mL 10.9984 mL 21.9969 mL
5 mM 0.4399 mL 2.1997 mL 4.3994 mL
View the Complete Stock Solution Preparation Table

* Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month (protect from light). When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.

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Purity & Documentation
References

Complete Stock Solution Preparation Table

* Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month (protect from light). When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.

Optional Solvent Concentration Solvent Mass 1 mg 5 mg 10 mg 25 mg
DMSO 1 mM 2.1997 mL 10.9984 mL 21.9969 mL 54.9922 mL
5 mM 0.4399 mL 2.1997 mL 4.3994 mL 10.9984 mL
10 mM 0.2200 mL 1.0998 mL 2.1997 mL 5.4992 mL
15 mM 0.1466 mL 0.7332 mL 1.4665 mL 3.6661 mL
20 mM 0.1100 mL 0.5499 mL 1.0998 mL 2.7496 mL
25 mM 0.0880 mL 0.4399 mL 0.8799 mL 2.1997 mL
30 mM 0.0733 mL 0.3666 mL 0.7332 mL 1.8331 mL
40 mM 0.0550 mL 0.2750 mL 0.5499 mL 1.3748 mL
50 mM 0.0440 mL 0.2200 mL 0.4399 mL 1.0998 mL
60 mM 0.0367 mL 0.1833 mL 0.3666 mL 0.9165 mL
80 mM 0.0275 mL 0.1375 mL 0.2750 mL 0.6874 mL
100 mM 0.0220 mL 0.1100 mL 0.2200 mL 0.5499 mL
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  • Do most proteins show cross-species activity?

    Species cross-reactivity must be investigated individually for each product. Many human cytokines will produce a nice response in mouse cell lines, and many mouse proteins will show activity on human cells. Other proteins may have a lower specific activity when used in the opposite species.

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Product Name:
(S)-Verapamil
Cat. No.:
HY-136907
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