518-34-3 Usage
Description
D-Tetrandrine is a bis-benzylisoquinoline alkaloid derived from the roots of the R. stephania plant. It exhibits diverse biological activities, including anti-inflammatory, anti-nociceptive, and antihypertensive properties. D-Tetrandrine has been found to induce autophagy in various cell types and inhibit platelet aggregation. It also has the potential to increase glucose transporter 4 levels and decrease plasma glucose levels in diabetic models.
Uses
Used in Pharmaceutical Applications:
D-Tetrandrine is used as an anti-inflammatory agent for reducing the production of bacterial inflammatory mediators and suppressing lipopolysaccharide-induced microglial activity.
Used in Pain Management:
D-Tetrandrine is used as an analgesic for its pain-relieving properties.
Used in Anticancer Applications:
D-Tetrandrine is used as an antineoplastic agent, inducing autophagy in cancer cells such as HeLa, MCF-7, and human foreskin fibroblast (HFF) cells.
Used in Hypertension Treatment:
D-Tetrandrine is used as an antihypertensive drug for treating high blood pressure in China.
Used in Infection Control:
D-Tetrandrine is used as a potential blocker of the TPC2 calcium channel required for the Ebola infection process.
Used in Inflammation Treatment:
D-Tetrandrine is used as a lymphotoxin for its anti-inflammatory effects.
Physical Properties:
D-Tetrandrine appears as needle-like crystals (ether) and is a white powder in its chemical form. It is hardly soluble in water and petroleum ether but is soluble in ether and some organic solvents. The melting point of D-Tetrandrine is between 219–222°C, and its specific optical rotation is 285° (c=1, CHCl3), with sensitivity to light.
History
Recent 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.
Indications
This 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.
Pharmacology
Tetrandrine 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 Use
Tetrandrine 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.
References
Gralla, Coleman, Jonas, Cancer Chemother. Rep., Pt. 3, 5(1), 79 (1974)
Check Digit Verification of cas no
The CAS Registry Mumber 518-34-3 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,1 and 8 respectively; the second part has 2 digits, 3 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 518-34:
(5*5)+(4*1)+(3*8)+(2*3)+(1*4)=63
63 % 10 = 3
So 518-34-3 is a valid CAS Registry Number.
InChI:InChI=1/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
518-34-3Relevant articles and documents
Total synthesis method of optically pure Tetrandrine
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Paragraph 0052; 0057-0059; 0061; 0066-0068; 0069; 0074-0076, (2020/08/30)
The invention discloses a total synthesis method of optically pure tetrandrine, and belongs to the technical field of drug synthesis. The method comprises the following steps: (1) under the action ofa catalyst (1), carrying out intermolecular Ullmann reaction on a compound (1) and a compound (2) under alkaline and high-temperature conditions to synthesize a compound 3; (2) removing a hydroxyl protecting group from the compound (3) under an acidic condition to synthesize a compound (4); (3) carrying out intramolecular Ullmann reaction on the compound (4) under the action of a catalyst (2) under alkaline and high-temperature conditions to synthesize a compound (5), namely the optically pure tetrandrine. A convergent synthesis strategy is adopted, and only three steps are needed from the compound (1) to the synthesis of optically pure tetrandrine so that the reaction steps are greatly reduced, and the time and the material cost are saved; the yield can be as high as 28.7%-38.9%, and theyield is increased by dozens of times; the target product can be obtained on the gram scale, 1.3 g-1. 5 g of final optically pure product is synthesized, and the method has better industrialization potential.
Anti-inflammatory effects of the partially purified extract of radix stephaniae tetrandrae
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, (2008/06/13)
This invention relates to inflammatory responses in isolated peripheral human neutrophils that studied in the presence or absence of specially processed Radix Stephaniae tetrandrae (SPRST). We conclude that SPRST exerts anti-inflammatory effects by interf
ALKALOIDS OF DEHAASIA TRIANDRA
Lu, Sheng-Teh,Tsai, Ian-Lih,Leou, Shiow-Piaw
, p. 615 - 620 (2007/10/02)
Separation of the basic fraction from Dehaasia triandra afforded two new bisbenzylisoquinoline alkaloids, dehatridine and dehatrine, along with six known alkaloids, isocorydine, corytuberine, atheroline, nantenine, obaberine and a quaternary aporphine alkaloid, xanthoplanine (5). - Keywords: Dehaasia triandra; Lauraceae; Iau-Guoo-Nan; bisbenzylisoquinoline alkaloids; dehatridine; dehatrine.