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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
Structure of TETRANDRINE, (+)-

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

HIDE SMILES / InChI

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.

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
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
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 Jun 26 00:31:54 UTC 2021
Edited
by admin
on Sat Jun 26 00:31:54 UTC 2021
Record UNII
29EX23D5AJ
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TETRANDRINE, (+)-
Common Name English
SINOMENINE A
Common Name English
(S,S)-TETRANDRINE
Common Name English
NSC-77037
Code English
TETRANDRINE [WHO-DD]
Common Name English
(1.BETA.)-6,6',7,12-TETRAMETHOXY-2,2'-DIMETHYLBERBAMAN
Common Name English
TETRANDRINE [INCI]
Common Name English
TETRANDRIN
Common Name English
D-TETRANDRINE
Common Name English
TETRANDRINE
DASH   INCI   MI   WHO-DD  
INCI  
Official Name English
TETRANDRINE, D-
Common Name English
(+)-TETRANDRINE
Common Name English
TETRANDRINE [MI]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C333
Created by admin on Sat Jun 26 00:31:54 UTC 2021 , Edited by admin on Sat Jun 26 00:31:54 UTC 2021
FDA ORPHAN DRUG 518916
Created by admin on Sat Jun 26 00:31:54 UTC 2021 , Edited by admin on Sat Jun 26 00:31:54 UTC 2021
NCI_THESAURUS C574
Created by admin on Sat Jun 26 00:31:54 UTC 2021 , Edited by admin on Sat Jun 26 00:31:54 UTC 2021
FDA ORPHAN DRUG 545716
Created by admin on Sat Jun 26 00:31:54 UTC 2021 , Edited by admin on Sat Jun 26 00:31:54 UTC 2021
Code System Code Type Description
DRUG BANK
DB14066
Created by admin on Sat Jun 26 00:31:54 UTC 2021 , Edited by admin on Sat Jun 26 00:31:54 UTC 2021
PRIMARY
NCI_THESAURUS
C28952
Created by admin on Sat Jun 26 00:31:54 UTC 2021 , Edited by admin on Sat Jun 26 00:31:54 UTC 2021
PRIMARY
FDA UNII
29EX23D5AJ
Created by admin on Sat Jun 26 00:31:54 UTC 2021 , Edited by admin on Sat Jun 26 00:31:54 UTC 2021
PRIMARY
MESH
C009438
Created by admin on Sat Jun 26 00:31:54 UTC 2021 , Edited by admin on Sat Jun 26 00:31:54 UTC 2021
PRIMARY
CAS
916770-74-6
Created by admin on Sat Jun 26 00:31:54 UTC 2021 , Edited by admin on Sat Jun 26 00:31:54 UTC 2021
SUPERSEDED
MERCK INDEX
M10649
Created by admin on Sat Jun 26 00:31:54 UTC 2021 , Edited by admin on Sat Jun 26 00:31:54 UTC 2021
PRIMARY Merck Index
CAS
607379-81-7
Created by admin on Sat Jun 26 00:31:54 UTC 2021 , Edited by admin on Sat Jun 26 00:31:54 UTC 2021
SUPERSEDED
PUBCHEM
73078
Created by admin on Sat Jun 26 00:31:54 UTC 2021 , Edited by admin on Sat Jun 26 00:31:54 UTC 2021
PRIMARY
CAS
518-34-3
Created by admin on Sat Jun 26 00:31:54 UTC 2021 , Edited by admin on Sat Jun 26 00:31:54 UTC 2021
PRIMARY
WIKIPEDIA
TETRANDRINE
Created by admin on Sat Jun 26 00:31:54 UTC 2021 , Edited by admin on Sat Jun 26 00:31:54 UTC 2021
PRIMARY
CAS
5990-67-0
Created by admin on Sat Jun 26 00:31:54 UTC 2021 , Edited by admin on Sat Jun 26 00:31:54 UTC 2021
SUPERSEDED
CAS
6490-80-8
Created by admin on Sat Jun 26 00:31:54 UTC 2021 , Edited by admin on Sat Jun 26 00:31:54 UTC 2021
SUPERSEDED
Related Record Type Details
ENANTIOMER -> ENANTIOMER
DIASTEREOISOMER -> DIASTEREOISOMER
DIASTEREOISOMER -> DIASTEREOISOMER
RACEMATE -> ENANTIOMER
TARGET -> INHIBITOR
Related Record Type Details
ACTIVE MOIETY