U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula 2C32H49NO9.H2O4S
Molecular Weight 1281.544
Optical Activity UNSPECIFIED
Defined Stereocenters 28 / 28
E/Z Centers 2
Charge 0

SHOW SMILES / InChI
Structure of CEVADINE SULFATE

SMILES

OS(O)(=O)=O.[H][C@@]12CC[C@@]3([H])[C@]4(O)C[C@H](O)[C@@]5(O)[C@@]([H])(CN6C[C@@H](C)CC[C@@]6([H])[C@@]5(C)O)[C@]4(O)C[C@@]37O[C@]1(O)[C@H](CC[C@@]27C)OC(=O)C(\C)=C/C.[H][C@@]89CC[C@@]%10([H])[C@]%11(O)C[C@H](O)[C@@]%12(O)[C@@]([H])(CN%13C[C@@H](C)CC[C@@]%13([H])[C@@]%12(C)O)[C@]%11(O)C[C@@]%10%14O[C@]8(O)[C@H](CC[C@@]9%14C)OC(=O)C(\C)=C/C

InChI

InChIKey=LVNNUOZILAFQRM-OERGDMKHSA-N
InChI=1S/2C32H49NO9.H2O4S/c2*1-6-18(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;1-5(2,3)4/h2*6,17,19-24,34,36-40H,7-16H2,1-5H3;(H2,1,2,3,4)/b2*18-6-;/t2*17-,19-,20-,21-,22-,23-,24-,26-,27+,28+,29+,30+,31-,32-;/m00./s1

HIDE SMILES / InChI
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.

Approval Year

PubMed

PubMed

TitleDatePubMed
Neuroprotective action of a novel compound--M50463--in primary cultured neurons.
1999 Jan 2
Patents

Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment: Rats: veratrine (0.6 mg/kg, s.c.) significantly increased the plasma concentration of corticosterone, an endogenous biomarker for anxiety, compared to vehicle. https://www.ncbi.nlm.nih.gov/pubmed/26099814
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.
Name Type Language
CEVADINE SULFATE
Common Name English
CEVANE-3,4,12,14,16,17,20-HEPTOL, 4,9-EPOXY-, 3-(2-METHYL-2-BUTENOATE), (3.BETA.(Z),4.ALPHA.,16.BETA.)-, SULFATE (2:1) (SALT)
Systematic Name English
VERATRINE SULFATE
Common Name English
NSC-36572
Code English
Code System Code Type Description
CAS
7770-31-2
Created by admin on Sat Dec 16 08:56:54 GMT 2023 , Edited by admin on Sat Dec 16 08:56:54 GMT 2023
PRIMARY
NSC
36572
Created by admin on Sat Dec 16 08:56:54 GMT 2023 , Edited by admin on Sat Dec 16 08:56:54 GMT 2023
PRIMARY
CAS
15585-38-3
Created by admin on Sat Dec 16 08:56:54 GMT 2023 , Edited by admin on Sat Dec 16 08:56:54 GMT 2023
NO STRUCTURE GIVEN
PUBCHEM
119057566
Created by admin on Sat Dec 16 08:56:54 GMT 2023 , Edited by admin on Sat Dec 16 08:56:54 GMT 2023
PRIMARY
FDA UNII
3TU82R4MEV
Created by admin on Sat Dec 16 08:56:54 GMT 2023 , Edited by admin on Sat Dec 16 08:56:54 GMT 2023
PRIMARY