Tetrandrine

Modify Date: 2024-01-03 08:20:48

Tetrandrine structure	Common Name	Tetrandrine
	CAS Number	518-34-3	Molecular Weight	622.750
	Density	1.2±0.1 g/cm3	Boiling Point	710.5±60.0 °C at 760 mmHg
	Molecular Formula	C₃₈H₄₂N₂O₆	Melting Point	219-222ºC
	MSDS	Chinese USA	Flash Point	175.8±30.1 °C

Use of Tetrandrine

Tetrandrine is a bis-benzyl-isoquinoline alkaloid, which inhibits voltage-gated Ca2+ current (ICa) and Ca2+-activated K+ current.

Name	D-Tetrandrine
Synonym	More Synonyms

Description	Tetrandrine is a bis-benzyl-isoquinoline alkaloid, which inhibits voltage-gated Ca2+ current (ICa) and Ca2+-activated K+ current.
Related Catalog	Signaling Pathways >> Membrane Transporter/Ion Channel >> Calcium Channel Signaling Pathways >> Membrane Transporter/Ion Channel >> Potassium Channel Research Areas >> Cancer Research Areas >> Inflammation/Immunology
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

diazomethane

CAS#:186581-53-3

Penduline (Cocculus)

CAS#:26137-45-1

~98%

Tetrandrine

CAS#:518-34-3

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

Precursor 2
CAS#:186581-53-3 diazomethane CAS#:26137-45-1 Penduline (Cocculus)
DownStream 9
CAS#:83113-25-1 Tetrakis-(O-dem... CAS#:83087-72-3 6',7-Bis-(O-dem... CAS#:436-77-1 Fangchinoline CAS#:26137-45-1 Penduline (Cocculus)
CAS#:83113-24-0 (1β)-6-Methoxy-... CAS#:18251-36-0 Thalidezine CAS#:93-51-6 Creosol CAS#:75-50-3 Trimethylamine
CAS#:3423-07-2 1α-(4-Hydroxybe...

HS Code	2942000000

Cheminformatics analysis of assertions mined from literature that describe drug-induced liver injury in different species.

Chem. Res. Toxicol. 23 , 171-83, (2010)

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[Anti-tumor effect of tanshinone II A, tetrandrine, honokiol, curcumin, oridonin and paeonol on leukemia cell lines].

Sichuan Da Xue Xue Bao. Yi Xue Ban 43(3) , 362-6, (2012)

To study the anti-tumor effect of tanshinon II A, tetrandrine, honokiol, curcumin, oridonin and paeonol on leukemia cell lines SUP-B15, K562, CEM, HL-60 and NB4.To study the anti-tumor effect of tansh...

Precision-cut liver slices as a model for the early onset of liver fibrosis to test antifibrotic drugs.

Toxicol. Appl. Pharmacol. 274(2) , 328-38, (2014)

Induction of fibrosis during prolonged culture of precision-cut liver slices (PCLS) was reported. In this study, the use of rat PCLS was investigated to further characterize the mechanism of early ons...

(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

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