D-Tetrandrine
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D-Tetrandrine
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CAS No:
518-34-3
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Formula:
C38H42N2O6
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Chemical Name:
D-Tetrandrine
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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-
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CAS No:
Description
Tetrandrine is a bis-benzyl-isoquinoline alkaloid, which inhibits voltage-gated Ca2+ current (ICa) and Ca2+-activated K+ current.
(+)-Tetrandrine is a member of isoquinolines and a bisbenzylisoquinoline alkaloid.|Tetrandrine is a natural, bis-benzylisoquinoline alkaloid isolated from the root of the plant Radix stephania tetrandrae. Tetrandrine non-selectively inhibits calcium channel activity and induces G1 blockade of the G1 phase of the cell cycle and apoptosis in various cell types, resulting in immunosuppressive, anti-proliferative and free radical scavenging effects. This agent also increases glucose utilization by enhancing hepatocyte glycogen synthesis, resulting in the lowering of plasma glucose. (NCI04)
Recently 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.
Tetrandrine is abis-benzylisoquinoline alkaloid that has been found inR. stephaniaroots 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 .
White powder
D-Tetrandrine Basic Attributes
622.75
622.75
683-095-7
29EX23D5AJ
91771|77037
DTXSID10178062
C28952
Off-White
29349990
Characteristics
283nm(EtOH)(lit.)
61.9
Appearance: 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.
6.4
solid
1.1528 (rough estimate)
219-222 °C(lit.)
662.81°C (rough estimate)
175.8±30.1 °C
1.5300 (estimate)
Keep container tightly closed. Keep container in a cool, well-ventilated area. Do not store above 20ºC.
285 º (c=1, CHCl3)
7.70±0.20(Predicted)
245.3 Ų [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]
2-8°C
Safety Information
NONH for all modes of transport
3
Xi
22-24/25-36-26
XE9350000
Xi
Stable at normal temperatures and pressures.
36/37/38
|Danger|H300 (50%): Fatal if swallowed [Danger Acute toxicity, oral]|P264, P270, P301+P310, P301+P312, P321, P330, P405, and P501|Aggregated GHS information provided by 2 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Drug Information
Agents used in the treatment of malaria. They are usually classified on the basis of their action against plasmodia at different stages in their life cycle in the human. (From AMA, Drug Evaluations Annual, 1992, p1585) (See all compounds classified as Antimalarials.)|A class of drugs that act by selective inhibition of calcium influx through cellular membranes. (See all compounds classified as Calcium Channel Blockers.)|Agents used in the prophylaxis or therapy of VIRUS DISEASES. Some of the ways they may act include preventing viral replication by inhibiting viral DNA polymerase; binding to specific cell-surface receptors and inhibiting viral penetration or uncoating; inhibiting viral protein synthesis; or blocking late stages of virus assembly. (See all compounds classified as Antiviral Agents.)|Agents obtained from higher plants that have demonstrable cytostatic or antineoplastic activity. (See all compounds classified as Antineoplastic Agents, Phytogenic.)|Agents that suppress immune function by one of several mechanisms of action. Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. Others may act through activation of T-CELLS or by inhibiting the activation of HELPER CELLS. While immunosuppression has been brought about in the past primarily to prevent rejection of transplanted organs, new applications involving mediation of the effects of INTERLEUKINS and other CYTOKINES are emerging. (See all compounds classified as Immunosuppressive Agents.)
(+)-tetrandrine
D-Tetrandrine Use and Manufacturing
analgesic, antineoplastic, antihypertensive, lymphotoxin.Anti-rheumatic and analgesic, this product is used to treat rheumatism, hypertension, lung cancer and other diseases
Tetrandrine 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).
analgesic, antineoplastic, antihypertensive, lymphotoxin
Computed Properties
Molecular Weight:622.7
XLogP3:6.4
Hydrogen Bond Acceptor Count:8
Rotatable Bond Count:4
Exact Mass:622.30428706
Monoisotopic Mass:622.30428706
Topological Polar Surface Area:61.9
Heavy Atom Count:46
Complexity:979
Defined Atom Stereocenter Count:2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
Drug Function and Efficacy
It can lower blood pressure, slow heart rate, counteract arrhythmias, reduce spontaneous activity, and work synergistically with sodium pentobarbital
Registered Holders
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Zhejiang Jinhua Conba BIO-PHARM. Co., Ltd.
Active![China]()
China
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Shiyao Group Jiangxi Jinfurong Pharmaceutical Co., Ltd.
Active![China]()
China
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Tongliao Huabang Pharmaceutical Co., Ltd.
Active![China]()
China
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