Lappaconitine Hydrobromide

Names

[ Name ]:
Lappaconitine Hydrobromide

[Synonym ]:
Benzoic acid, 2-(acetylamino)-, (1α,14α,16β)-20-ethyl-8,9-dihydroxy-1,14,16-trimethoxyaconitan-4-yl ester, hydrobromide (1:1)
(1α,14α,16β)-20-Ethyl-8,9-dihydroxy-1,14,16-trimethoxyaconitan-4-yl 2-acetamidobenzoate hydrobromide (1:1)
(1a,14a,16b)-20-Ethyl-1,14,16-trimethyoxyaconitane-4,8,9-triol 4-(2-(Acetylamino)benzoate) Monohydrobromide
lappaconitine hydrobromide
(1α,14α,16β)-20-ethyl-8,9-dihydroxy-1,14,16-trimethoxyaconitan-4-yl 2-(acetylamino)benzoate hydrobromide (1:1)

Biological Activity

[Description]:

Lappaconitine hydrobromide, a diterpene alkaloid, is a drug for the treatment of cardiac arrhythmias.IC50 value:Target: A natural product for anti-cardiac arrhythmiasIn vitro: Lappaconitine hydrobromide was found to exert an inhibitory effect on inward tetrodotoxin-sensitive sodium currents without changing their voltage dependence [1]. In vivo: The effect of Lappaconitine hydrobromide on aconitine--induced arrhythmias is due to modulation of genes encoding Na(+)-, K(+)-, Ca(2+)-channels, conducting ionic currents (I(Na), I(to), I(Ks), I(K1), I(CaT)), which are involved in the formation of different phases of the action potential [2]. Lappaconitine hydrobromide was found to be beneficial both in ventricular and supraventricular premature beats. Oral allapinine usually showed its effect 40-60 minutes following its administration, its maximum action being 4-5 hours later, its duration was some 8 hours. The optimal dose of the drug amounted to 75 mg/day [3].

[Related Catalog]:

Signaling Pathways >> Others >> Others

Natural Products >> Alkaloid

Research Areas >> Cardiovascular Disease

[References]

[1]. A. E. Valeev, et al. Effects of allapinine on sodium currents in neurons isolated from the rat trigeminal ganglion and cardiomyocytes. Neurophysiology, 1990, 22 (2): 157-162.

[2]. Vakhitova IuV, et al. To the mechanisms of antiarrhythmic action of Allapinine. Bioorg Khim, 2013, 39 (1):105-16

[3]. Abdalla A., et al. Allapinine pharmacodynamics and potential adverse effects. Kardiologiya. 29(7): 29-32

[Related Small Molecules]

Chemical & Physical Properties

[ Boiling Point ]:
740.8ºC at 760 mmHg

[ Melting Point ]:
223-226ºC

[ Molecular Formula ]:
C₃₂H₄₅BrN₂O₈

[ Molecular Weight ]:
665.612

[ Flash Point ]:
401.8ºC

[ Exact Mass ]:
664.235901

[ PSA ]:
126.79000

[ LogP ]:
3.19060

[ Storage condition ]:
2-8°C

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: AR5569600

CHEMICAL NAME :: Aconitane-4,8,9-triol, 20-ethyl-1,14,16-trimethoxy-, 4-(2-(acetylamino)benzoate), monohydrobromide, (1-alpha,14-alpha,16-beta)-

CAS REGISTRY NUMBER :: 97792-45-5

LAST UPDATED :: 199606

DATA ITEMS CITED :: 7

MOLECULAR FORMULA :: C32-H44-N2-O8.Br-H

MOLECULAR WEIGHT :: 665.70

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 47500 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: GTPZAB Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. (V/O Mezhdunarodnaya Kniga, 113095 Moscow, USSR) V.1-36, 1957-1992. For publisher information, see MTPEEI Volume(issue)/page/year: 35(1),30,1991

TYPE OF TEST :: LC - Lethal concentration

ROUTE OF EXPOSURE :: Inhalation

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >400 mg/m3

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: GTPZAB Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. (V/O Mezhdunarodnaya Kniga, 113095 Moscow, USSR) V.1-36, 1957-1992. For publisher information, see MTPEEI Volume(issue)/page/year: 35(1),30,1991

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 35500 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 38,892,1988

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 11700 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: YHTPAD Yaoxue Tongbao. Bulletin of Pharmacology. (China International Book Trading Corp., POB 2820, Beijing, Peop. Rep. China) V.13-23, 1978-88. For publisher information, see ZYZAEU. Volume(issue)/page/year: 19,24,1984

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 8400 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: YHTPAD Yaoxue Tongbao. Bulletin of Pharmacology. (China International Book Trading Corp., POB 2820, Beijing, Peop. Rep. China) V.13-23, 1978-88. For publisher information, see ZYZAEU. Volume(issue)/page/year: 19,24,1984

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 16300 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: GTPZAB Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. (V/O Mezhdunarodnaya Kniga, 113095 Moscow, USSR) V.1-36, 1957-1992. For publisher information, see MTPEEI Volume(issue)/page/year: 35(1),30,1991 ** OTHER MULTIPLE DOSE TOXICITY DATA **

TYPE OF TEST :: TCLo - Lowest published toxic concentration

ROUTE OF EXPOSURE :: Inhalation

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 4800 ug/m3/17W-I

TOXIC EFFECTS :: Cardiac - other changes Kidney, Ureter, Bladder - other changes in urine composition Blood - pigmented or nucleated red blood cells

REFERENCE :: GTPZAB Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. (V/O Mezhdunarodnaya Kniga, 113095 Moscow, USSR) V.1-36, 1957-1992. For publisher information, see MTPEEI Volume(issue)/page/year: 35(1),30,1991

Safety Information

[ Hazard Codes ]:
T+: Very toxic;

[ Risk Phrases ]:
R28

[ Safety Phrases ]:
45

[ RIDADR ]:
UN 1544 6.1/PG 2

[ RTECS ]:
AR5569600

[ Packaging Group ]:
II

[ HS Code ]:
29399990

Related Compounds

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