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SML3048

Sigma-Aldrich

Tetrandrine

≥98% (HPLC)

Synonym(s):

(+)-Tetrandrine, (4aS,16aS)-3,4,4a,5,16a,17,18,19-Octahydro-12,21,22,26-tetramethoxy-4,17-dimethyl-16H-1,24:6,9-dietheno-11,15-metheno-2H-pyrido[2′,3′:17,18][1,11]dioxacycloeicosino[2,3,4-ij]isoquinoline, (S,S)-Tetrandrine, NSC 77037, Tetrandrin, (1β)-6,6′,7,12-Tetramethoxy-2,2′-dimethylberbaman

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About This Item

Empirical Formula (Hill Notation):
C38H42N2O6
CAS Number:
518-34-3
Molecular Weight:
622.75
MDL number:
MFCD08689909
UNSPSC Code:
12352200
NACRES:
NA.77

Quality Level

100

assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

2-8°C

SMILES string

COc1ccc2C[C@@H]3N(C)CCc4cc(OC)c(OC)c(Oc5cc6[C@H](Cc7ccc(Oc1c2)cc7)N(C)CCc6cc5OC)c34

InChI

1S/C38H42N2O6/c1-39-15-13-25-20-32(42-4)34-22-28(25)29(39)17-23-7-10-27(11-8-23)45-33-19-24(9-12-31(33)41-3)18-30-36-26(14-16-40(30)2)21-35(43-5)37(44-6)38(36)46-34/h7-12,19-22,29-30H,13-18H2,1-6H3/t29-,30-/m0/s1

InChI key

WVTKBKWTSCPRNU-KYJUHHDHSA-N

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Biochem/physiol Actions

Tetrandrine is bisbenzylisoquinoline alkaloid extracted from isolated from Stephania tetrandra S Moore that exhibits numerous pharmacological activities including anti-cancer, anti-inflammatory, negative ionotropic and chronotropic effects on myocardium, immunologic and antiallergenic effects. It has been used for treatment of tuberculosis, hyperglycemia, malaria, cancer and fever. Tetrandrine is potent calcium channel blocker. Tetrandrine targets multiple signaling pathways controlling cell cycle, apoptosis. Tetrandrine is an inhibitor of efflux pumps that reversed the clarithromycin resistance phenotype of some Mycobacterium avium complex clinical isolates.

pictograms

Skull and crossbones
GHS06

signalword

Danger

hcodes

H300

Hazard Classifications

Acute Tox. 2 Oral

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Bhagya N et al.
Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie, 97, 624-632 (2017-11-05)
Tetrandrine has been known in the treatment of tuberculosis, hyperglycemia, negative ionotropic and chronotropic effects on myocardium, malaria, cancer and fever since years together. It has been known that, tetrandrine could modulate multiple signaling molecules such as kinases of cell
Melissa Menichini et al.
The Journal of antibiotics, 73(2), 128-132 (2019-10-19)
In this study we aimed to evaluate the effect of the combination of clarithromycin and four inhibitors of efflux pumps (EPIs), including berberine (BER), carbonyl cyanide m-chlorophenylhydrazone (CCCP), piperine (PIP) and tetrandrine (TET), against 12 Mycobacterium avium complex clinical isolates.

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