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V106

Sigma-Aldrich

R(+)-Verapamil monohydrochloride hydrate

≥98% (HPLC), powder

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About This Item

Empirical Formula (Hill Notation):
C27H38N2O4 · HCl · xH2O
CAS Number:
38176-02-2
Molecular Weight:
491.06 (anhydrous basis)
EC Number:
205-800-5
MDL number:
MFCD11046028
UNSPSC Code:
12161501
PubChem Substance ID:
24900706
NACRES:
NA.77

Quality Level

100

assay

≥98% (HPLC)

form

powder

optical activity

[α]22/D +9.6°, c = 0.5 in ethanol(lit.)

storage condition

desiccated

color

white

solubility

H2O: >30 mg/mL
ethanol: soluble

SMILES string

O.Cl.COc1ccc(CCN(C)CCC[C@@](C#N)(C(C)C)c2ccc(OC)c(OC)c2)cc1OC

InChI

1S/C27H38N2O4.ClH.H2O/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;1H;1H2/t27-;;/m1../s1

InChI key

ICKXRKHJKXMFLR-KFSCGDPASA-N

Application

R(+)-Verapamil monohydrochloride hydrate has been used as a P-glycoprotein (gp) inhibitor, to detect P-gp expression on the SK-OV-3 and SK-OV-3/DDP cell surface by flow cytometry. It has also been used as a calcium channel blocker, to evaluate its effect on doxorubicin (DOX) cytotoxicity.

Biochem/physiol Actions

Verapamil is a calcium channel blocker. Verapamil hydrochloride is a phenyl-alkyl amine derivative and is potentially used for treating hypertension, angina pectoris and arrhythmias. It is water soluble in nature.
Inhibitor of P-glycoprotein; less active enantiomer of (±)-verapamil.

Caution

hygroscopic

pictograms

Skull and crossbones
GHS06

signalword

Danger

Hazard Classifications

Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation - Acute Tox. 3 Oral

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Effect of formulation variables on verapamil hydrochloride release from hydrated HPMC matrices
Ramrez C, et al.
Journal of the Mexican Chemical Society, 48(4), 326-331 (2004)
E G Chikhale et al.
The Journal of pharmacology and experimental therapeutics, 273(1), 298-303 (1995-04-01)
When the blood-brain barrier (BBB) transport of a series of model peptides that varied in their physicochemical properties (lipophilicity, size and hydrogen-bonding potential) was determined using an in situ rat brain perfusion technique, an unexpected increase in flux with increasing
Assessment of the chemotherapeutic potential of a new camptothecin derivative, ZBH-1205
Wu D, et al.
Archives of Biochemistry and Biophysics, 604(1), 74-85 (2016)
J A Plumb et al.
Biochemical pharmacology, 39(4), 787-792 (1990-02-15)
The L-isomer of verapamil is a more potent calcium antagonist than the D-isomer. We have examined the two stereoisomers of verapamil for their ability to increase the chemosensitivity in vitro of three drug resistant cell lines (2780AD, MCF7/AdrR and H69LX10).
Formulation and evaluation of once daily sustained release matrix tablet of verapamil hydrochloride
Ray B and Gupta MM
Journal of Drug Delivery and Therapeutics, 3(1) (2013)
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