An active quinidine metabolite
Related Products
Isomer(s)
23410(3R)-hydroxy Quinidine
Parent Compound(s)
20356Quinidine
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(3S)-hydroxy Quinidine

Item No. 23411

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
6'-methoxy-cinchonan-3,9S-diol
CAS Number
53467-23-5
Molecular Formula
C20H24N2O3
Formula Weight
340.4
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: SolubleDMSO: SolubleMethanol: Soluble
SMILES
COC1=CC=C2C(C([C@H](O)[C@@]3([H])C[C@H]4[C@](C=C)(O)C[N@@]3CC4)=CC=N2)=C1
InChi Code
InChI=1S/C20H24N2O3/c1-3-20(24)12-22-9-7-13(20)10-18(22)19(23)15-6-8-21-17-5-4-14(25-2)11-16(15)17/h3-6,8,11,13,18-19,23-24H,1,7,9-10,12H2,2H3/t13-,18+,19-,20+/m0/s1
InChi Key
BSRUJCFCZKMFMB-LGWHJFRWSA-N
Shipping & Storage Information
Storage
4°C
Shipping
Room temperature in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

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    500 µg

    $208

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    1 mg

    $395

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    Product Description

    (3S)-hydroxy Quinidine is an active quinidine metabolite.1 Quinidine, an antiarrhythmic agent, undergoes rapid first-pass metabolism by the cytochrome P450 (CYP) isoforms CYP3A4, CYP2C9, CYP2E1, and CYP3A5, with CYP3A4 being the most active enzyme in the (3S)-hydroxy quinidine formation. (3S)-hydroxy Quinidine prolongs repolarization of canine Purkinje fibers in vitro and prevents ventricular fibrillation and ventricular tachycardia after coronary reperfusion in isolated rat hearts in a dose-dependent manner.2,3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Nielsen, T.L., Rasmussen, B.B., Flinois, J.-P., et al. In vitro metabolism of quinidine: the (3S)-3-hydroxylation of quinidine is a specific marker reaction for cytochrome P-4503A4 activity in human liver microsomes. J. Pharmacol. Exp. Ther. 289(1), 31-37 (1999).

    2. Vozeh, S., Oti-Amoako, K., Uematsu, T., et al. Antiarrhythmic activity of two quinidine metabolites in experimental reperfusion arrhythmia: Relative potency and pharmacodynamic interaction with the parent drug. J. Pharmacol. Exp. Ther. 243(1), 297-301 (1987).

    3. Thompson, K.A., Blair, I.A., Woosley, R.L., et al. Comparative in vitro electrophysiology of quinidine, its major metabolites and dihydroquinidine. J. Pharmacol. Exp. Ther. 24(1), 84-90 (1987).