Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C20H24N2O2.2ClH |
| Molecular Weight | 397.339 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 5 / 5 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.Cl.COC1=CC2=C(C=CN=C2C=C1)[C@@H](O)[C@H]3C[C@@H]4CC[N@]3C[C@@H]4C=C
InChI
InChIKey=NNKXWRRDHYTHFP-FPYWIVBFSA-N
InChI=1S/C20H24N2O2.2ClH/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;2*1H/t13-,14-,19+,20+;;/m0../s1
| Molecular Formula | C20H24N2O2 |
| Molecular Weight | 324.4168 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 4 / 4 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
| Molecular Formula | ClH |
| Molecular Weight | 36.461 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
DescriptionCurator's Comment: The description was created based on several sources, including
https://link.springer.com/article/10.1023/A:1012220606675
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.
Approval Year
Sample Use Guides
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.
| Substance Class |
Chemical
Created
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Edited
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| Record UNII |
L53B7TOS4O
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| Record Status |
Validated (UNII)
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