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Details

Stereochemistry ABSOLUTE
Molecular Formula C32H49NO9
Molecular Weight 591.7328
Optical Activity UNSPECIFIED
Defined Stereocenters 14 / 14
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of CEVADINE

SMILES

C\C=C(\C)C(=O)O[C@H]1CC[C@@]2(C)[C@@H]3CC[C@H]4[C@]5(O)C[C@H](O)[C@@]6(O)[C@@H](CN7C[C@@H](C)CC[C@H]7[C@@]6(C)O)[C@]5(O)C[C@]24O[C@]13O

InChI

InChIKey=DBUCFOVFALNEOO-HWBIYQLFSA-N
InChI=1S/C32H49NO9/c1-6-18(3)25(35)41-24-11-12-26(4)19-8-9-20-28(37)13-23(34)31(39)21(29(28,38)16-30(20,26)42-32(19,24)40)15-33-14-17(2)7-10-22(33)27(31,5)36/h6,17,19-24,34,36-40H,7-16H2,1-5H3/b18-6-/t17-,19-,20-,21-,22-,23-,24-,26-,27+,28+,29+,30+,31-,32-/m0/s1

HIDE SMILES / InChI

Description

Cevadine, veratridine, and related lipophilic ceveratrum alkaloids cause activation of the voltage-sensitive Na+ channels of nerve, heart, and skeletal muscle cell membranes similar to pyrethrins. Both veratridine and cevadine alter the ion selectivity of Na+ channels and cause persistent activation. The receptor for these alkaloids has not been isolated, but experiments indicate it is distinct from that of pyrethrin. Structurally, veratridine and cevadine differ only in their acyl group. Cevadine has been used as an insecticide, acting as a paralytic agent with higher toxicity to insects than to mammals. It has been used to study Na+ channel blockers such as vincamine and vincanol by inducing Na+ channels in the presence and absence of the drugs being tested.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
Mouse:LD50 = 300mg/kg; oral Rat: LD50 = 980 mg/kg; oral
Route of Administration: Oral
In Vitro Use Guide
Cevadine sensitivity of sartorius muscles incubated in glutamate Ringer was about five times greater than that of muscles incubated in normal Ringer. Therefore, even 0.005 mmol/l cevadine could induce depolarization and membrane potential oscillations.