Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C38H42N2O6 |
| Molecular Weight | 622.7513 |
| Optical Activity | ( + ) |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CN1CCc2cc(c3cc2[C@]1([H])Cc4ccc(cc4)Oc5cc(ccc5OC)C[C@@]6([H])c7c(CCN6C)cc(c(c7O3)OC)OC)OC
InChI
InChIKey=WVTKBKWTSCPRNU-KYJUHHDHSA-N
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
| Molecular Formula | C38H42N2O6 |
| Molecular Weight | 622.7513 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
Tetrandrine, isolated from the root of Stephania tetrandra S Moore, is a traditional Chinese clinical agent for silicosis, autoimmune disorders, inflammatory pulmonary diseases, cardiovascular diseases and hypertension. Tetrandrine is a potent MDR-reversing agent and is an ABCB1/ABCC1 inhibitor. Tetrandrine (CBT-1) is being developed by CBA Pharma, as an adjunctive therapy to chemotherapy in various cancer types with multiple drug resistance (MDR), including acute myelogenous leukemia , Breast, Non-Hodgkin’s Lymphoma, Hodgkin’s disease, Non-Small Cell Lung Cancer, Multiple Myeloma, Gallbladder, Pancreatic, Gastrointestinal Tract, Small Cell Lung Cancer, Bladder, Head & Neck, and Sarcoma.
CNS Activity
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: P08183 Gene ID: 5243.0 Gene Symbol: ABCB1 Target Organism: Homo sapiens (Human) |
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Target ID: P33527|||Q9UQ99 Gene ID: 4363.0 Gene Symbol: ABCC1 Target Organism: Homo sapiens (Human) |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Palliative | Unknown Approved UseUnknown |
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| Palliative | Unknown Approved UseUnknown |
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| Palliative | Unknown Approved UseUnknown |
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| Palliative | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Studies on the calcium antagonistic action of tetrandrine: XIII. Protective effect of tetrandrine on myocardial hypoxia and necrosis induced by isoproterenol in rats. | 1986 |
|
| Effect of tetrandrine on proto-oncogene c-fos expression in rat cerebrum. | 1997 Jul |
|
| Effects of tetrandrine and fangchinoline on experimental thrombosis in mice and human platelet aggregation. | 1999 Mar |
|
| Combination of tetrandrine as a potential-reversing agent with daunorubicin, etoposide and cytarabine for the treatment of refractory and relapsed acute myelogenous leukemia. | 2006 Apr |
|
| Antifibrotic effects of tetrandrine on hepatic stellate cells and rats with liver fibrosis. | 2007 Jan |
|
| Tetrandrine achieved plasma concentrations capable of reversing MDR in vitro and had no apparent effect on doxorubicin pharmacokinetics in mice. | 2007 Oct |
|
| Studies on alkaloids binding to GC-rich human survivin promoter DNA using positive and negative ion electrospray ionization mass spectrometry. | 2008 Mar |
|
| Anticancer effect of tetrandrine on primary cancer cells isolated from ascites and pleural fluids. | 2008 Sep 8 |
|
| [Effect of tetrandrine combined with daunorubicin on expressions of P21 and P-gp in K562/A02 cells]. | 2009 Oct |
|
| Protective effect of tetrandrine on doxorubicin-induced cardiotoxicity in rats. | 2010 May-Jun |
|
| Pretreatment with tetrandrine has protective effects against isoproterenol-induced myocardial infarction in rabbits. | 2010 May-Jun |
|
| Tetrandrine down-regulates ERK/NF-κB signaling and inhibits activation of mesangial cells. | 2011 Dec |
|
| CYP3A5 mediates bioactivation and cytotoxicity of tetrandrine. | 2016 Jul |
|
| Tetrandrine induces programmed cell death in human oral cancer CAL 27 cells through the reactive oxygen species production and caspase-dependent pathways and associated with beclin-1-induced cell autophagy. | 2017 Jan |
Patents
Sample Use Guides
(50 mg caps) 500 mg/m2/day x 7 + paclitaxel 135 mg/m2 + carboplatin AUC 6
Route of Administration:
Oral
It was investigated the effect of combined treatment of irradiation and maximum non-cytotoxic doses of tetrandrine on the nasopharyngeal carcinoma cell lines CNE1 and CNE2. The maximum non-cytotoxic doses of tetrandrine in CNE1 and CNE2 cells were assessed using the MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide) assay. The maximum non-cytotoxic doses of tetrandrine in CNE1 and CNE2 cells were 1.5 μmol/L and 1.8 μmol/L, respectively. When cells were exposed to irradiation and the maximum non-cytotoxic doses of tetrandrine, the survival fraction was decreased.
| Substance Class |
Chemical
Created
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Sat Jun 26 00:31:54 UTC 2021
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Sat Jun 26 00:31:54 UTC 2021
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| Record UNII |
29EX23D5AJ
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| Record Status |
Validated (UNII)
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NCI_THESAURUS |
C333
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FDA ORPHAN DRUG |
518916
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NCI_THESAURUS |
C574
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FDA ORPHAN DRUG |
545716
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DB14066
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C28952
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29EX23D5AJ
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C009438
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916770-74-6
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M10649
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607379-81-7
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73078
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518-34-3
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TETRANDRINE
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5990-67-0
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6490-80-8
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ACTIVE MOIETY |
