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Details

Stereochemistry ABSOLUTE
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
Tetrandrine achieved plasma concentrations capable of reversing MDR in vitro and had no apparent effect on doxorubicin pharmacokinetics in mice.
2007 Oct
Anticancer effect of tetrandrine on primary cancer cells isolated from ascites and pleural fluids.
2008 Sep 8
Tetrandrine down-regulates ERK/NF-κB signaling and inhibits activation of mesangial cells.
2011 Dec
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 11:54:12 GMT 2023
Edited
by admin
on Sat Dec 16 11:54:12 GMT 2023
Record UNII
29EX23D5AJ
Record Status Validated (UNII)
Record Version
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Name Type Language
TETRANDRINE, (+)-
Common Name English
SINOMENINE A
Common Name English
Tetrandrine [WHO-DD]
Common Name English
(S,S)-TETRANDRINE
Common Name English
NSC-77037
Code 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 Dec 16 11:54:13 GMT 2023 , Edited by admin on Sat Dec 16 11:54:13 GMT 2023
FDA ORPHAN DRUG 518916
Created by admin on Sat Dec 16 11:54:13 GMT 2023 , Edited by admin on Sat Dec 16 11:54:13 GMT 2023
NCI_THESAURUS C574
Created by admin on Sat Dec 16 11:54:13 GMT 2023 , Edited by admin on Sat Dec 16 11:54:13 GMT 2023
FDA ORPHAN DRUG 545716
Created by admin on Sat Dec 16 11:54:13 GMT 2023 , Edited by admin on Sat Dec 16 11:54:13 GMT 2023
Code System Code Type Description
DRUG BANK
DB14066
Created by admin on Sat Dec 16 11:54:13 GMT 2023 , Edited by admin on Sat Dec 16 11:54:13 GMT 2023
PRIMARY
SMS_ID
100000174928
Created by admin on Sat Dec 16 11:54:13 GMT 2023 , Edited by admin on Sat Dec 16 11:54:13 GMT 2023
PRIMARY
NCI_THESAURUS
C28952
Created by admin on Sat Dec 16 11:54:13 GMT 2023 , Edited by admin on Sat Dec 16 11:54:13 GMT 2023
PRIMARY
FDA UNII
29EX23D5AJ
Created by admin on Sat Dec 16 11:54:13 GMT 2023 , Edited by admin on Sat Dec 16 11:54:13 GMT 2023
PRIMARY
MESH
C009438
Created by admin on Sat Dec 16 11:54:13 GMT 2023 , Edited by admin on Sat Dec 16 11:54:13 GMT 2023
PRIMARY
CAS
916770-74-6
Created by admin on Sat Dec 16 11:54:13 GMT 2023 , Edited by admin on Sat Dec 16 11:54:13 GMT 2023
SUPERSEDED
NSC
77037
Created by admin on Sat Dec 16 11:54:13 GMT 2023 , Edited by admin on Sat Dec 16 11:54:13 GMT 2023
PRIMARY
EPA CompTox
DTXSID10178062
Created by admin on Sat Dec 16 11:54:13 GMT 2023 , Edited by admin on Sat Dec 16 11:54:13 GMT 2023
PRIMARY
MERCK INDEX
m10649
Created by admin on Sat Dec 16 11:54:13 GMT 2023 , Edited by admin on Sat Dec 16 11:54:13 GMT 2023
PRIMARY Merck Index
CAS
607379-81-7
Created by admin on Sat Dec 16 11:54:13 GMT 2023 , Edited by admin on Sat Dec 16 11:54:13 GMT 2023
SUPERSEDED
PUBCHEM
73078
Created by admin on Sat Dec 16 11:54:13 GMT 2023 , Edited by admin on Sat Dec 16 11:54:13 GMT 2023
PRIMARY
CAS
518-34-3
Created by admin on Sat Dec 16 11:54:13 GMT 2023 , Edited by admin on Sat Dec 16 11:54:13 GMT 2023
PRIMARY
WIKIPEDIA
TETRANDRINE
Created by admin on Sat Dec 16 11:54:13 GMT 2023 , Edited by admin on Sat Dec 16 11:54:13 GMT 2023
PRIMARY
CAS
5990-67-0
Created by admin on Sat Dec 16 11:54:13 GMT 2023 , Edited by admin on Sat Dec 16 11:54:13 GMT 2023
SUPERSEDED
CAS
6490-80-8
Created by admin on Sat Dec 16 11:54:13 GMT 2023 , Edited by admin on Sat Dec 16 11:54:13 GMT 2023
SUPERSEDED
Related Record Type Details
ENANTIOMER -> ENANTIOMER
DIASTEREOISOMER -> DIASTEREOISOMER
TRANSPORTER -> INHIBITOR
DIASTEREOISOMER -> DIASTEREOISOMER
RACEMATE -> ENANTIOMER
TARGET -> INHIBITOR
Related Record Type Details
ACTIVE MOIETY