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Details

Stereochemistry ABSOLUTE
Molecular Formula C32H44N2O8.ClH
Molecular Weight 621.161
Optical Activity UNSPECIFIED
Defined Stereocenters 12 / 12
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LAPPACONITINE HYDROCHLORIDE

SMILES

Cl.[H][C@@]12C[C@H]3[C@H](OC)[C@]1(O)[C@](O)(C[C@@H]3OC)[C@H]4C[C@H]5[C@@]26[C@H](CC[C@]5(CN(CC)[C@]46[H])OC(=O)C7=C(NC(C)=O)C=CC=C7)OC

InChI

InChIKey=AFZPKUNOYLOCHW-IPZKEBFRSA-N
InChI=1S/C32H44N2O8.ClH/c1-6-34-16-29(42-28(36)18-9-7-8-10-21(18)33-17(2)35)12-11-25(40-4)31-23(29)14-20(26(31)34)30(37)15-22(39-3)19-13-24(31)32(30,38)27(19)41-5;/h7-10,19-20,22-27,37-38H,6,11-16H2,1-5H3,(H,33,35);1H/t19-,20+,22+,23-,24+,25+,26-,27+,29-,30+,31+,32+;/m1./s1

HIDE SMILES / InChI
Molecular Formula C32H44N2O8
Molecular Weight 584.7004
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 11 / 12
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

Description

Lappaconitine is an alkaloid isolated from the root of Aconltitum sinomantanum Nakai. It has a strong analgesic activity that does not involve the opioid receptor. It was shown to have class-I antiarrhythmic action and irreversibly blocks cloned human heart (hH1) channels by binding to the site 2 receptor.

CNS Activity

Originator

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
 6.13 µM [IC50]
Inhibitor
8297
 14.1 µM [IC50]
Antagonist
2778
Blocker
537
Blocker
537
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Phase I
428
Unknown

Approved Use

Unknown
Primary
Phase II
1132
Unknown

Approved Use

Unknown
Palliative
Phase II
1132
Unknown

Approved Use

Unknown
Primary
Approved
8429
ALLAPININ

Approved Use

Excerts membrane stabilizing action, influences sodium channels, belongs to IC class of antiarrhythmic agents. Causes slowing of atrioventricular and intraventricular condution, shortens the effective and functional refractory periods in the atria and ventricles. Does does not affect the duration of the interval QT, conductivity in the AV node anterograde direction, heart rate and blood pressure, myocardial contractility (in the absence of heart failure events). Provides moderate antispasmodic, vasodilating, cholinolytic and sedative effect.
Primary
Approved
8429
ALLAPININ

Approved Use

Excerts membrane stabilizing action, influences sodium channels, belongs to IC class of antiarrhythmic agents. Causes slowing of atrioventricular and intraventricular condution, shortens the effective and functional refractory periods in the atria and ventricles. Does does not affect the duration of the interval QT, conductivity in the AV node anterograde direction, heart rate and blood pressure, myocardial contractility (in the absence of heart failure events). Provides moderate antispasmodic, vasodilating, cholinolytic and sedative effect.
Primary
Approved
8429
ALLAPININ

Approved Use

Excerts membrane stabilizing action, influences sodium channels, belongs to IC class of antiarrhythmic agents. Causes slowing of atrioventricular and intraventricular condution, shortens the effective and functional refractory periods in the atria and ventricles. Does does not affect the duration of the interval QT, conductivity in the AV node anterograde direction, heart rate and blood pressure, myocardial contractility (in the absence of heart failure events). Provides moderate antispasmodic, vasodilating, cholinolytic and sedative effect.
Primary
Approved
8429
ALLAPININ

Approved Use

Excerts membrane stabilizing action, influences sodium channels, belongs to IC class of antiarrhythmic agents. Causes slowing of atrioventricular and intraventricular condution, shortens the effective and functional refractory periods in the atria and ventricles. Does does not affect the duration of the interval QT, conductivity in the AV node anterograde direction, heart rate and blood pressure, myocardial contractility (in the absence of heart failure events). Provides moderate antispasmodic, vasodilating, cholinolytic and sedative effect.
Primary
Approved
8429
ALLAPININ

Approved Use

Excerts membrane stabilizing action, influences sodium channels, belongs to IC class of antiarrhythmic agents. Causes slowing of atrioventricular and intraventricular condution, shortens the effective and functional refractory periods in the atria and ventricles. Does does not affect the duration of the interval QT, conductivity in the AV node anterograde direction, heart rate and blood pressure, myocardial contractility (in the absence of heart failure events). Provides moderate antispasmodic, vasodilating, cholinolytic and sedative effect.
PubMed

PubMed

TitleDatePubMed
Pharmacological studies of lappaconitine. Analgesic activities.
1988 Jul
Irreversible block of human heart (hH1) sodium channels by the plant alkaloid lappaconitine.
2001 Feb
Comparative metabolism of Lappaconitine in rat and human liver microsomes and in vivo of rat using ultra high-performance liquid chromatography-quadrupole/time-of-flight mass spectrometry.
2015 Jun 10
Selective dual cholinesterase inhibitors from Aconitum laeve.
2018 Feb
Patents

Patents

RU2513580C1
3
RU2518742C2
3
US5290784
3
US5547956
3

Sample Use Guides

In Vivo Use Guide
Lappaconitine (8 mg) was intravenously dripped to patients in the lappaconitine group 30 min before ending the operation. PCIA started as soon as the end of the surgery and the total dose of lappaconitine was 36 mg.
Route of Administration: Intravenous
In Vitro Use Guide
Right isolated guinea-pig atria became bradycardic at 3 uM lappaconitine, and at 4.5 uM one of six right atria ceased contracting. Asystolia was also observed in left atria at concentrations about 600 nM, but all of the asystolic atria resumed contraction as the stimulation current was increased, indicating an elevation of the excitation threshold.
Substance Class Chemical
Created
by admin
on Sat Dec 16 05:17:40 GMT 2023
Edited
by admin
on Sat Dec 16 05:17:40 GMT 2023
Record UNII
3W1334H51X
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
LAPPACONITINE HYDROCHLORIDE
Common Name English
ACONITANE-4,8,9-TRIOL, 20-ETHYL-1,14,16-TRIMETHOXY-, 4-(2-(ACETYLAMINO)BENZOATE), HYDROCHLORIDE (1:1), (1.ALPHA.,14.ALPHA.,16.BETA.)-
Systematic Name English
ACONITANE-4,8,9-TRIOL, 20-ETHYL-1,14,16-TRIMETHOXY-, 4-(2-(ACETYLAMINO)BENZOATE), MONOHYDROCHLORIDE, (1.ALPHA.,14.ALPHA.,16.BETA.)-
Systematic Name English
Code System Code Type Description
FDA UNII
3W1334H51X
Created by admin on Sat Dec 16 05:17:40 GMT 2023 , Edited by admin on Sat Dec 16 05:17:40 GMT 2023
PRIMARY
CAS
767350-42-5
Created by admin on Sat Dec 16 05:17:40 GMT 2023 , Edited by admin on Sat Dec 16 05:17:40 GMT 2023
PRIMARY
PUBCHEM
90479694
Created by admin on Sat Dec 16 05:17:40 GMT 2023 , Edited by admin on Sat Dec 16 05:17:40 GMT 2023
PRIMARY
Related Record Type Details
Structure of LAPPACONITINE
PARENT -> SALT/SOLVATE
NIH
NCATS
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