TETRANDRINE, (±)-

Possibly Marketed Outside US

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 Search

SMILES

COC1=CC2=C3C=C1OC4=C(OC)C(OC)=CC5=C4[C@H](CC6=CC(OC7=CC=C(C[C@@H]3N(C)CC2)C=C7)=C(OC)C=C6)N(C)CC5

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

Description
Sources: http://cbapharma.com/CBT1/cbt1.html | https://www.ncbi.nlm.nih.gov/pubmed/29334999 | https://www.ncbi.nlm.nih.gov/pubmed/29101806 | https://www.ncbi.nlm.nih.gov/pubmed/29061791

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
Multidrug resistance protein 1 9 Target ID: P08183 Gene ID: 5243.0 Gene Symbol: ABCB1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/14666379 \| https://www.ncbi.nlm.nih.gov/pubmed/26548759	Inhibitor 8504
Multidrug resistance-associated protein 1 15 Target ID: P33527\|\|\|Q9UQ99 Gene ID: 4363.0 Gene Symbol: ABCC1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/26548759	Inhibitor 8504

Conditions

Condition	Modality	Highest Phase	Product
Non-small cell lung cancer 211 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23675254	Palliative	Phase III 665	Unknown Approved Use Unknown
Nasopharyngeal carcinoma 8 Sources: https://www.ncbi.nlm.nih.gov/pubmed/29061791	Palliative	Phase II 1147	Unknown Approved Use Unknown
Tuberculosis 83 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25887373	Palliative	Basic research	Unknown Approved Use Unknown
Osteosarcoma 22 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26548759	Palliative	Phase I 438	Unknown Approved Use Unknown

C_max

Value	Dose	Co-administered	Analyte	Population
67.26 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29100757/	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:		TETRANDRINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
33.24 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29100757/	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:		BERBAMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

AUC

Value	Dose	Co-administered	Analyte	Population
1554.16 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29100757/	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:		TETRANDRINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
756.73 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29100757/	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:		BERBAMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
22.34 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29100757/	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:		TETRANDRINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
39.25 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29100757/	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:		BERBAMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

Doses

Dose	Population	Adverse events
2 % 2 times / day multiple, topical Studied dose Dose: 2 %, 2 times / day Route: topical Route: multiple Dose: 2 %, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/21725874/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/21725874/	Sources: https://pubmed.ncbi.nlm.nih.gov/21725874/

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
activator 150 inhibitor 2252			inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
P-gp 1741 OATP1B1 1079 OATP1B3 961	BCRP 697 P-gp 2052 CYP 303

Drug as perpetrator

Target	Modality	Activity
CYP3A4 2633	activator 342 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/73078#section=BioAssay-Results Page: 86.0	no
CYP3A4 2633	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/73078#section=BioAssay-Results Page: 87.0	no
P-gp 1932	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkw0MzAyIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDQ0OTY5MCJ9fQ==	yes [Inhibition 1 uM]
OATP1B1 1095	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/73078#section=BioAssay-Results Page: 326.0	yes [Inhibition 10 uM]
OATP1B3 970	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/73078#section=BioAssay-Results Page: 326.0	yes [Inhibition 10 uM]

Drug as victim

Target	Modality	Activity
P-gp 2052	substrate 4014 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/73078#section=BioAssay-Results Page: 313.0	inconclusive [Inhibition 10 uM]
BCRP 697	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/23742976/	no
CYP 303	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/32942071/	yes

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/73078#section=BioAssay-Results Page: 257.0

PubMed

Title	Date	PubMed
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.	2017-01	26822499
CYP3A5 mediates bioactivation and cytotoxicity of tetrandrine.	2016-07	26302866
Pulmonary toxicity and metabolic activation of tetrandrine in CD-1 mice.	2011-12-19	21992520
Tetrandrine down-regulates ERK/NF-κB signaling and inhibits activation of mesangial cells.	2011-12	22001142
Protective effect of tetrandrine on doxorubicin-induced cardiotoxicity in rats.	2010-09-18	20845809
Pretreatment with tetrandrine has protective effects against isoproterenol-induced myocardial infarction in rabbits.	2010-06-18	20554997
[Effect of tetrandrine combined with daunorubicin on expressions of P21 and P-gp in K562/A02 cells].	2009-10	19840446
Anticancer effect of tetrandrine on primary cancer cells isolated from ascites and pleural fluids.	2008-09-08	18495333
Studies on alkaloids binding to GC-rich human survivin promoter DNA using positive and negative ion electrospray ionization mass spectrometry.	2008-03	17968851
Tetrandrine achieved plasma concentrations capable of reversing MDR in vitro and had no apparent effect on doxorubicin pharmacokinetics in mice.	2007-10	17273824
Antifibrotic effects of tetrandrine on hepatic stellate cells and rats with liver fibrosis.	2007-01	17201889
Combination of tetrandrine as a potential-reversing agent with daunorubicin, etoposide and cytarabine for the treatment of refractory and relapsed acute myelogenous leukemia.	2006-04	16219352
Effects of tetrandrine and fangchinoline on experimental thrombosis in mice and human platelet aggregation.	1999-03	10193204
Effect of tetrandrine on proto-oncogene c-fos expression in rat cerebrum.	1997-07	10072926
Studies on the calcium antagonistic action of tetrandrine: XIII. Protective effect of tetrandrine on myocardial hypoxia and necrosis induced by isoproterenol in rats.	1986	3712522

Patents

Sample Use Guides

In Vivo Use Guide

(50 mg caps) 500 mg/m2/day x 7 + paclitaxel 135 mg/m2 + carboplatin AUC 6

Route of Administration: Oral

In Vitro Use Guide

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 `Tue Apr 01 16:39:37 GMT 2025` Edited by `admin` on `Tue Apr 01 16:39:37 GMT 2025`
Record UNII	VS4W77H3SD
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NSC-91771

Preferred Name

English

TETRANDRINE, (±)-

Common Name

English

DL-TETRANDRINE

Common Name

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 Tue Apr 01 16:39:37 GMT 2025 , Edited by admin on Tue Apr 01 16:39:37 GMT 2025

PRIMARY

NSC

91771

Created by admin on Tue Apr 01 16:39:37 GMT 2025 , Edited by admin on Tue Apr 01 16:39:37 GMT 2025

PRIMARY

CAS

23495-89-8

Created by admin on Tue Apr 01 16:39:37 GMT 2025 , Edited by admin on Tue Apr 01 16:39:37 GMT 2025

PRIMARY

EPA CompTox

DTXSID70881383

Created by admin on Tue Apr 01 16:39:37 GMT 2025 , Edited by admin on Tue Apr 01 16:39:37 GMT 2025

PRIMARY

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TETRANDRINE, (-)-

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Tetrandrine

ENANTIOMER -> RACEMATE

Details

SMILES

InChI

DescriptionSources: http://cbapharma.com/CBT1/cbt1.html | https://www.ncbi.nlm.nih.gov/pubmed/29334999 | https://www.ncbi.nlm.nih.gov/pubmed/29101806 | https://www.ncbi.nlm.nih.gov/pubmed/29061791

CNS Activity

Approval Year

Targets

Conditions

Approved Use

Approved Use

Approved Use

Approved Use

Cmax

AUC

T1/2

Doses

Overview

OverviewOther

Drug as perpetrator​

Drug as victim

Tox targets

PubMed

Patents

Sample Use Guides

Description
Sources: http://cbapharma.com/CBT1/cbt1.html | https://www.ncbi.nlm.nih.gov/pubmed/29334999 | https://www.ncbi.nlm.nih.gov/pubmed/29101806 | https://www.ncbi.nlm.nih.gov/pubmed/29061791

C_max

T_1/2

Drug as perpetrator