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Details

Stereochemistry RACEMIC
Molecular Formula C38H42N2O6
Molecular Weight 622.7499
Optical Activity ( + / - )
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TETRANDRINE, (±)-

SMILES

[H][C@]12CC3=CC=C(OC4=CC(C[C@]5([H])N(C)CCC6=CC(OC)=C(OC)C(OC7=CC1=C(CCN2C)C=C7OC)=C56)=CC=C4OC)C=C3

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

HIDE SMILES / InChI

Molecular Formula C38H42N2O6
Molecular Weight 622.7499
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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P08183
Gene ID: 5243.0
Gene Symbol: ABCB1
Target Organism: Homo sapiens (Human)
Target ID: P33527|||Q9UQ99
Gene ID: 4363.0
Gene Symbol: ABCC1
Target Organism: Homo sapiens (Human)
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
Unknown

Approved Use

Unknown
Palliative
Unknown

Approved Use

Unknown
Palliative
Unknown

Approved Use

Unknown
Palliative
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
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
Pulmonary toxicity and metabolic activation of tetrandrine in CD-1 mice.
2011 Dec 19
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

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
by admin
on Sat Dec 16 11:36:39 UTC 2023
Edited
by admin
on Sat Dec 16 11:36:39 UTC 2023
Record UNII
VS4W77H3SD
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TETRANDRINE, (±)-
Common Name English
DL-TETRANDRINE
Common Name English
NSC-91771
Code English
BERBAMAN, 6,6',7,12-TETRAMETHOXY-2,2'-DIMETHYL-, (1.BETA.)-(±)-
Common Name English
(±)-TETRANDRINE
Common Name English
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-TETRAMETHOXY-4,17-DIMETHYL-, (4AR,16AR)-REL-
Systematic Name English
Code System Code Type Description
FDA UNII
VS4W77H3SD
Created by admin on Sat Dec 16 11:36:39 UTC 2023 , Edited by admin on Sat Dec 16 11:36:39 UTC 2023
PRIMARY
NSC
91771
Created by admin on Sat Dec 16 11:36:39 UTC 2023 , Edited by admin on Sat Dec 16 11:36:39 UTC 2023
PRIMARY
PUBCHEM
73078
Created by admin on Sat Dec 16 11:36:39 UTC 2023 , Edited by admin on Sat Dec 16 11:36:39 UTC 2023
PRIMARY
CAS
23495-89-8
Created by admin on Sat Dec 16 11:36:39 UTC 2023 , Edited by admin on Sat Dec 16 11:36:39 UTC 2023
PRIMARY
EPA CompTox
DTXSID70881383
Created by admin on Sat Dec 16 11:36:39 UTC 2023 , Edited by admin on Sat Dec 16 11:36:39 UTC 2023
PRIMARY
Related Record Type Details
ENANTIOMER -> RACEMATE
ENANTIOMER -> RACEMATE