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518-34-3

518-34-3 structure
518-34-3 structure
  • Name: Tetrandrine
  • Chemical Name: D-Tetrandrine
  • CAS Number: 518-34-3
  • Molecular Formula: C38H42N2O6
  • Molecular Weight: 622.750
  • Catalog: API Antipyretic analgesics Analgesic
  • Create Date: 2018-06-08 13:37:51
  • Modify Date: 2024-01-03 08:20:48
  • Tetrandrine is a bis-benzyl-isoquinoline alkaloid, which inhibits voltage-gated Ca2+ current (ICa) and Ca2+-activated K+ current.
Name D-Tetrandrine
Synonyms (1S,14S)-9,20,21,25-Tetramethoxy-15,30-dimethyl-7,23-dioxa-15,30-diazaheptacyclo[22.6.2.2.1.1.0.0]hexatriaconta-3,5,8(34),9,11,18(33),19,21,24,26,31,35-dodecaene
Tetrandrine
(1S,14S)-9,20,21,25-Tetramethoxy-15,30-dimethyl-7,23-dioxa-15,30-diazaheptacyclo[22.6.2.2.1.1.0.0]hexatriaconta-3,5,8(34),9,11,18(33),19,21,24,26,31,35-dodecaen
Trandrine
Conba
MFCD08689909
(1β)-6,6',7,12-Tetramethoxy-2,2'-dimethylberbaman
sinomeninea
6,6',7,12-Tetramethoxy-2,2'-dimethylberbaman
hanfangchin A
TETRANDRIN
fanchinine
Jinake
6,6',7,12-tetramethoxy-2,2'-dimethyl-berbaman
(1S,14S)-9,20,21,25-Tétraméthoxy-15,30-diméthyl-7,23-dioxa-15,30-diazaheptacyclo[22.6.2.2.1.1.0.0]hexatriaconta-3,5,8(34),9,11,18(33),19,21,24,26,31,35-dodécaène
(1b)-6,6',7,12-Tetramethoxy-2,2'-dimethylberbaman
(S,S)-(+)-Tetrandrine
iso-tetrandrine
(1β,1'β)-6,6',7,12-Tetramethoxy-2,2'-dimethylberbaman
Description Tetrandrine is a bis-benzyl-isoquinoline alkaloid, which inhibits voltage-gated Ca2+ current (ICa) and Ca2+-activated K+ current.
Related Catalog
Target

Ca2+ current[1] K+ current[1]

In Vitro The effects of Tetrandrine, a bis-benzyl-isoquinoline alkaloid, on voltage-gated Ca2+ currents (ICa) and on Ca2+-activated K+ current (IK(Ca)) and channels in isolated nerve terminals of the rat neurohypophysis are investigated using patch-clamp techniques. The non-inactivating component of ICa is inhibited by external Tetrandrine in a voltage- and dose-dependent manner, with an IC50=10.1μM. Tetrandrine decreases the channel-open probability, within bursts, with an IC50=0.21 μM[1]. To evaluate the effects of Tetrandrine on HCC cells, Huh7, HCCLM9 and Hep3B cells are treated with 0 (DMSO), 0.5, 1, 2 or 4 μM of Tetrandrine for 24 h. The cell proliferation assay indicates that Tetrandrine exhibits almost no effect on the inhibition of HCC cell proliferation at 0.5-2 μM. However, Tetrandrine inhibits HCC cell migration in a dose-dependent manner. Furthermore, a wound-healing and transwell assay shows that 2 μM Tetrandrine significantly inhibits HCC cell migration and invasion[2].
In Vivo To evaluate the effect of Tetrandrine on the inhibition of tumor metastasis in vivo, HCCLM9 subcutaneous tumor xenograft models is established with athymic nude mice. When the tumor volume reach approximately 50 mm3, nude mice are orally administered vehicle or Tetrandrine (30 mg/kg) every other day for 37 days. Tetrandrine treatment inhibits tumor growth by reducing the tumor volume and weight[2].
Cell Assay Huh7, HCCLM9 and Hep3B cells are seeded in a 96-well plate at a cell density of 5 × 103 cells/well. The cells are treated with the indicated concentrations (0-4 μM) of Tetrandrine for 24 h. The cells are subsequently stained with 20 μL of MTS for 1-2 h, and the plates are read at 490 nm on a BioTek ELx800[2].
Animal Admin Mice[2] Four-week-old male athymic BALB/c nu/nu SPF mice (body weight range from 18 g to 20 g) are used. HCCLM9 WT and HCCLM9 ATG7 KO cells (5 million) resuspended in 0.2 mL of PBS are subcutaneously implanted into the right flank of each mouse. When the tumor volume reach approximately 50 mm3, the tumor-bearing mice are randomly divided into control and treatment groups (n = 6). The control and treatment groups are administered oral injection of vehicle (0.5% methylcellulose) and Tetrandrine at 30 mg/kg of body weight every other day for 37 days. During the treatment, the tumor volumes are measured every day and are calculated.
References

[1]. Wang G, et al. Tetrandrine blocks a slow, large-conductance, Ca(2+)-activated potassium channel besides inhibiting a non-inactivating Ca2+ current in isolated nerve terminals of the rat neurohypophysis. Pflugers Arch. 1992 Sep;421(6):558-65.

[2]. Zhang Z, et al. The plant alkaloid tetrandrine inhibits metastasis via autophagy-dependent Wnt/β-catenin and metastatic tumor antigen 1 signaling in human liver cancer cells. J Exp Clin Cancer Res. 2018 Jan 15;37(1):7.
Density 1.2±0.1 g/cm3
Boiling Point 710.5±60.0 °C at 760 mmHg
Melting Point 219-222ºC
Molecular Formula C38H42N2O6
Molecular Weight 622.750
Flash Point 175.8±30.1 °C
Exact Mass 622.304260
PSA 61.86000
LogP 3.55
Vapour Pressure 0.0±2.3 mmHg at 25°C
Index of Refraction 1.586

CHEMICAL IDENTIFICATION

RTECS NUMBER :
XE9350000
CHEMICAL NAME :
Tetrandrine
CAS REGISTRY NUMBER :
518-34-3
BEILSTEIN REFERENCE NO. :
0877811
LAST UPDATED :
199612
DATA ITEMS CITED :
9
MOLECULAR FORMULA :
C38-H42-N2-O6
MOLECULAR WEIGHT :
622.82

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
41300 ug/kg
TOXIC EFFECTS :
Behavioral - convulsions or effect on seizure threshold
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
37500 ug/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Mammal - cat
DOSE/DURATION :
40 mg/kg
TOXIC EFFECTS :
Behavioral - tremor Cardiac - other changes Lungs, Thorax, or Respiration - other changes
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rabbit
DOSE/DURATION :
15 mg/kg
TOXIC EFFECTS :
Behavioral - convulsions or effect on seizure threshold Cardiac - other changes Lungs, Thorax, or Respiration - other changes
TYPE OF TEST :
Sister chromatid exchange

MUTATION DATA

TYPE OF TEST :
Sister chromatid exchange
TEST SYSTEM :
Rodent - hamster Lung
DOSE/DURATION :
80 mg/L
REFERENCE :
MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 224,5,1989
Personal Protective Equipment Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter
Hazard Codes Xi
Risk Phrases R36/37/38
Safety Phrases S22-S24/25
RIDADR NONH for all modes of transport
WGK Germany 3
RTECS XE9350000
HS Code 2942000000
186581-53-3 structure

186581-53-3

26137-45-1 structure

26137-45-1

~98%

518-34-3 structure

518-34-3

Literature: Kashiwaba, Noriaki; Morooka, Shigeo; Kimura, Michiko; Ono, Minoru; Murakoshi, Yoshie; et al. Heterocycles, 1995 , vol. 41, # 9 p. 2043 - 2048
HS Code 2942000000

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title: CAS No. 518-34-3 | Chemsrc address: https://www.chemsrc.com/en/baike/314542.html

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