EPIQUINIDINE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C20H24N2O2
Molecular Weight	324.4168
Optical Activity	UNSPECIFIED
Defined Stereocenters	5 / 5
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@@]1(C[C@@H]2CC[N@]1C[C@@H]2C=C)[C@H](O)C3=CC=NC4=CC=C(OC)C=C34

InChI

InChIKey=LOUPRKONTZGTKE-AFHBHXEDSA-N

InChI=1S/C20H24N2O2/c1-3-13-12-22-9-7-14(13)10-19(22)20(23)16-6-8-21-18-5-4-15(24-2)11-17(16)18/h3-6,8,11,13-14,19-20,23H,1,7,9-10,12H2,2H3/t13-,14-,19+,20+/m0/s1

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/23114754
Curator's Comment: The description was created based on several sources, including https://link.springer.com/article/10.1023/A:1012220606675

Epiquinidine is an alkaloid derived from the bark of the cinchona tree. The most abundant constituents of the Cinchona barks are two pairs of erythro diastereoisomers: quinineand quinidine, which are active antimalarials. Their threo epimers, epiquinine and epiquinidine, are practically inactive. Compared to quinine and quinidine, the 9-epimers had significantly reduced hemozoin inhibition efficiency and did not affect pH-dependent aggregation of ferriprotoporphyrin IX (FPIX) heme. Magnetic susceptibility measurements showed that the 9-epimers perturb FPIX monomer-dimer equilibrium in favor of monomer, and UV-visible (VIS) titrations showed that Epiquinine and Epiquinidine bind monomer with similar affinity relative to quinine and quinidine. However, unique ring proton shifts in the presence of zinc(II) protoporphyrin IX (ZnPIX) indicate that binding of the 9-epimers to monomeric heme is via a distinct geometry.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Ferriprotoporphyrin IX 43 Target ID: CHEMBL613897 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23114754	Binding Agent 1064

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2578

PubMed

Title	Date	PubMed

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

Antiplasmodial cytocidal and cytostatic activity was assessed against the CQS HB3 strain, CQR Dd2 strain, and CQR K76I line. he cytocidal assay utilizes a 6-h bolus dose with high concentrations of drug (Epiquinidine), followed by washing drug away and growth in the absence of drug for 48 h, while the cytostatic assay utilizes continuous growth for 48 h in the constant presence of low concentrations of drug. Test compounds were dissolved in deionized water, 50% EtOH, or DMSO. Serial drug dilutions were made using complete medium, and 100-mkl aliquots were transferred to 96-well clear-bottom black plates. Following addition of 100 mkl of asynchronous or sorbitol-synchronized culture (1% final parasitemia, 2% final hematocrit), plates were transferred to an airtight chamber gassed with 5% CO2–5% O2–90% N2 and incubated at 37°C.

Name

Type

Language

EPIQUINIDINE

Common Name

English

(9R)-6'-METHOXYCINCHONAN-9-OL

Common Name

English

ICQ-12

Code

English

CINCHONAN-9-OL, 6'-METHOXY-, (9R)-

Common Name

English

9-EPI-QUINIDINE

Common Name

English

9-EPIQUINIDINE

Common Name

English

EPIQUINIDINE [MI]

Common Name

English

Code System Code Type Description

MERCK INDEX

m4945