D-Tetrandrine

D-Tetrandrine Basic information
Product Name:D-Tetrandrine
Synonyms:[4aS-(4aR*,16aR*)]-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 98%;Conba;Jinake;(1β)-6,6',7,12-tetramethoxy-2,2'-dimethylberbaman;TETRANDRINE, (S,S)-(+)-(RG);Trandrine;16H-1,24:6,9-Dietheno-11,15-metheno-2H-pyrido[2',3':17,18][1,11]dioxacycloeicosino[2,3,4-ij]isoquinoline,3,4,4a,5, 16a,17,18,19-octahydro-12,21,22,26-
CAS:518-34-3
MF:C38H42N2O6
MW:622.75
EINECS:683-095-7
Product Categories:chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract;Inhibitors;Alkaloids;reference substance
Mol File:518-34-3.mol
D-Tetrandrine Structure
D-Tetrandrine Chemical Properties
Melting point 219-222 °C(lit.)
Boiling point 662.81°C (rough estimate)
alpha 285 º (c=1, CHCl3)
density 1.1528 (rough estimate)
refractive index 1.5300 (estimate)
storage temp. 2-8°C
solubility Chloroform (Slightly), Methanol (Slightly, Heated)
form solid
pka7.70±0.20(Predicted)
color Off-White
λmax283nm(EtOH)(lit.)
Merck 14,9231
LogP3.550 (est)
Safety Information
Hazard Codes Xi
Risk Statements 36/37/38
Safety Statements 22-24/25-36-26
WGK Germany 3
RTECS XE9350000
HS Code 29349990
MSDS Information
D-Tetrandrine Usage And Synthesis
DescriptionRecently it has been discovered that pronounced drug-dependence and related toxic effects occur in both dogs and rhesus monkeys with this alkaloid on intravenous injection with a dose of 10-150 mg/kg. When rapidly injected, the acute hypotensive effect is very marked and fatal at once. Following drug administration at toxic levels it is found that severe local tissue reaction heptaotoxicity and lymphoid necrosis occurs. At the highest dosage level there is a very definite nephrotoxicity in monkeys and some indications of this in dogs. The evidence available suggests that monkeys are less sensitive to hepatotoxicity with this drug than dogs.
DescriptionTetrandrine is a bis-benzylisoquinoline alkaloid that has been found in R. stephania roots and has diverse biological activities. It induces autophagy in HeLa, MCF-7, and human foreskin fibroblast (HFF) cells when used at a concentration of 5 μM, an effect that can be reversed by the autophagy inhibitor 3-methyladenine . Tetrandrine inhibits PAF-, thrombin-, collagen-, ADP-, or epinephrine-induced aggregation of isolated human platelets. Priming of mesenchymal stem cells (MSCs) with tetrandrine (5 and 10 μM) reduces TNF-α secretion by RAW 264.7 cells in co-culture. Ear skin transplantation of tetrandrine-primed MSCs decreases ear levels of TNF-α in a mouse model of ear skin inflammation. Tetrandrine (1 mg/kg) increases soleus muscle levels of glucose transporter 4 (Glut4) and decreases plasma glucose levels in a rat model of diabetes induced by streptozotocin .
Chemical PropertiesWhite powder
Physical propertiesAppearance: Needle-like crystals (ether). Solubility: Hardly soluble in water and petroleum ether; soluble in ether and some organic solvents. Melting point: 219– 222?°C. Specific optical rotation: 285° (c?=?1, CHCl3); sensitive to light.
HistoryRecent studies have shown that tetrandrine has a variety of biological effects and very good applicational prospects in the treatment of fibrosis and portal vein and pulmonary hypertension, the regulation of immunologic function, as well as the prevention and treatment of tumor.
As early as 1988, tetrandrine has been found having the effect on blocking the Ca2 + channel and was quickly applied into the pharmacological research in the field of cardiovascular and inflammatory diseases. Results from a large number of studies have shown that tetrandrine has good effects on antihypertension, arrhythmia, myocardial ischemia, inflammation, and so on. As a traditional Chinese calcium antagonist, tetrandrine has a broad prospects in clinical applications of cardiovascular and inflammatory diseases.In the early 1990s, the application of tetrandrine was extended. During that time, researchers conducted many studies about its protective effects on liver, lung, and mitochondria, which opened a new field for the treatment of liver disease. In 2002, it was found that tetrandrine can inhibit the synthesis of DNA and RNA in tumor cells, which provided a new method for the treatment of cancer. At present, the prevention and treatment effects of hypertension, fibrosis, digestive diseases, tumors, rheumatoid arthritis, and other autoimmune diseases of tetrandrine have been confirmed, as well as the function of reducing portal hypertension and pulmonary hypertension, while its other pharmacological effects are to be explored in further study.
UsesTetrandrine is a lipopolysaccharide-induced microglial suppressor, effectively reducing the production of bacterial inflammatory mediators. Anti-inflammatory, anti-nociceptive. Tetrandrine is used in China to treat high blood pressure. This drug blocked the TPC2 calcium channel required for the Ebola infection process (Robert A. Davey et al., Science 2015, DOI: 10.1126/science.1258758).
Usesanalgesic, antineoplastic, antihypertensive, lymphotoxin
IndicationsThis product is included in national standards for chemical drugs (Volume 14), British Pharmacopoeia (2017), and European Pharmacopoeia (9.0th ed.). Tetrandrine is used for the treatment of mild to moderate hypertension and hypertensive crisis, rheumatism, silicosis, etc.
DefinitionChEBI: (+)-Tetrandrine is a member of isoquinolines and a bisbenzylisoquinoline alkaloid.
PharmacologyTetrandrine has analgesic, anti-inflammatory, and anti-allergic effects and has a wide range of usage on the cardiovascular system owing to its antihypertensive, anti-myocardial ischemia/reperfusion injury and antiarrhythmic effects. It can inhibit the platelet aggregation induced by ADP, collagen, and arachidonic acid in?vitro and can also restrain the platelet adhesion and thrombosis (in rabbits). Tetrandrine also has anticancer effects. Studies have shown that tetrandrine has a strong inhibitory effect on the DNA and RNA synthesis in L7712 and S180 (cancer cells), which can significantly suppress the growth of Wacker sarcoma W256. Besides that, tetrandrine has the ability to relax the striated muscle, and its methyl iodide or methyl bromide derivatives can also affect the muscles. Notably, tetrandrine can prevent silicosis and has a preferable outcome on the clinical treatment of such disease. In addition, tetrandrine also owns antipyretic, diuretic, and antiallergic shock effects.
Clinical UseTetrandrine is used for the treatment of hypertension, angina, termination of paroxysmal supraventricular tachycardia, pulmonary fibrosis, and other diseases in clinical application, and it also has strong antitumor effects. Tetrandrine was also approved for lowering blood glucose and free radical damage; its treatment effect on silicosis is significant and superior to conventional immunosuppressive and cytotoxic drugs.
ReferencesGralla, Coleman, Jonas, Cancer Chemother. Rep., Pt. 3, 5(1), 79 (1974)
D-Tetrandrine Preparation Products And Raw materials
Preparation Products(+)-Atherospermoline-->Berbaman-6,6',7,12-tetrol, 2,2'-dimethyl-, (1β)- (9CI)
Rotundine Sophoricoside Dacthal Demethyl tetrandrine,Demethyl tetrandrine ETHANE AKOS NCG1-0047 RADIX STEPHANIAE TETRANDRAE PLANT EXTRACT TETRANDRINE3.15%,RADIX STEPHANIAE TETRANDRAE PLANT EXTRACT TETRANDRINE3.15% Berbamine hydrochloride BERBAMINE (r,s)-tetrandrin Dimethyl sulfide Dimethyl fumarate 7-O-ethyl fangchinoline (+/-)-Tetrahydropapaverine Dimethyl sebacate Dimethyl ether Dimethyl sulfate D-Tetrandrine

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