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

[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

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 8 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 8297
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 8297

Conditions

Condition	Modality	Highest Phase	Product
Non-small cell lung cancer 206 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23675254	Palliative	Phase III 656	Unknown Approved Use Unknown
Nasopharyngeal carcinoma 8 Sources: https://www.ncbi.nlm.nih.gov/pubmed/29061791	Palliative	Phase II 1132	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 428	Unknown Approved Use Unknown

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	3712522
Effect of tetrandrine on proto-oncogene c-fos expression in rat cerebrum.	1997 Jul	10072926
Pretreatment with tetrandrine has protective effects against isoproterenol-induced myocardial infarction in rabbits.	2010 May-Jun	20554997
Tetrandrine down-regulates ERK/NF-κB signaling and inhibits activation of mesangial cells.	2011 Dec	22001142

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 `Sat Dec 16 11:36:39 GMT 2023` Edited by `admin` on `Sat Dec 16 11:36:39 GMT 2023`
Record UNII	VS4W77H3SD
Record Status	`Validated (UNII)`
Record Version

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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