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
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
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/3207434 | https://www.ncbi.nlm.nih.gov/pubmed/26242116http://www.rlsnet.ru/mnn_index_id_2749.htm
Curator's Comment: Penetrates through the BBB.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL220 |
6.13 µM [IC50] | ||
Target ID: GO:0005272 |
14.1 µM [IC50] | ||
Target ID: CHEMBL4824 |
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Target ID: CHEMBL1980 |
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Target ID: CHEMBL1980 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
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| Primary | Unknown Approved UseUnknown |
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| Palliative | Unknown Approved UseUnknown |
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| Primary | ALLAPININ Approved UseExcerts 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. |
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| Primary | ALLAPININ Approved UseExcerts 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 | ALLAPININ Approved UseExcerts 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 | ALLAPININ Approved UseExcerts 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 | ALLAPININ Approved UseExcerts 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
| Title | Date | PubMed |
|---|---|---|
| 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
Sample Use Guides
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
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.
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3W1334H51X
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767350-42-5
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90479694
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PARENT (SALT/SOLVATE)
SUBSTANCE RECORD
