Details of the Drug

General Information of Drug (ID: DMAOJBX)

Drug Name
Tetrandrine
Synonyms Tetrandrine, Millenia Hope; Tetrandrine, West Virginia University; Tranex-18
Indication
Disease Entry ICD 11 Status REF
Sarcoma 2A60-2C35 Phase 1 [1]
Colorectal cancer 2B91.Z Discontinued in Phase 3 [2]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 2 Molecular Weight (mw) 622.7
Logarithm of the Partition Coefficient (xlogp) 6.4
Rotatable Bond Count (rotbonds) 4
Hydrogen Bond Donor Count (hbonddonor) 0
Hydrogen Bond Acceptor Count (hbondacc) 8
Chemical Identifiers
Formula
C38H42N2O6
IUPAC Name
(1S,14S)-9,20,21,25-tetramethoxy-15,30-dimethyl-7,23-dioxa-15,30-diazaheptacyclo[22.6.2.23,6.18,12.114,18.027,31.022,33]hexatriaconta-3(36),4,6(35),8,10,12(34),18,20,22(33),24,26,31-dodecaene
Canonical SMILES
CN1CCC2=CC(=C3C=C2[C@@H]1CC4=CC=C(C=C4)OC5=C(C=CC(=C5)C[C@H]6C7=C(O3)C(=C(C=C7CCN6C)OC)OC)OC)OC
InChI
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
InChIKey
WVTKBKWTSCPRNU-KYJUHHDHSA-N
Cross-matching ID
PubChem CID
73078
ChEBI ID
CHEBI:49
CAS Number
518-34-3
DrugBank ID
DB14066
TTD ID
D0G4ES
INTEDE ID
DR1570
Combinatorial Drugs (CBD) Click to Jump to the Detailed CBD Information of This Drug
Repurposed Drugs (RPD) Click to Jump to the Detailed RPD Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Calcium channel unspecific (CaC) TT5HONZ NOUNIPROTAC Antagonist [3]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 3A4 (CYP3A4) DE4LYSA CP3A4_HUMAN Substrate [4]
Cytochrome P450 3A5 (CYP3A5) DEIBDNY CP3A5_HUMAN Substrate [5]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
14-3-3 protein sigma (SFN) OTLJCZ1U 1433S_HUMAN Gene/Protein Processing [6]
5'-AMP-activated protein kinase catalytic subunit alpha-1 (PRKAA1) OT7TNF0L AAPK1_HUMAN Post-Translational Modifications [7]
Apoptosis regulator BAX (BAX) OTAW0V4V BAX_HUMAN Gene/Protein Processing [6]
Apoptosis regulator Bcl-2 (BCL2) OT9DVHC0 BCL2_HUMAN Gene/Protein Processing [8]
Apoptosis-inducing factor 1, mitochondrial (AIFM1) OTKPWB7Q AIFM1_HUMAN Gene/Protein Processing [6]
ATP-dependent translocase ABCB1 (ABCB1) OTEJROBO MDR1_HUMAN Gene/Protein Processing [9]
Autophagy protein 5 (ATG5) OT4T5SMS ATG5_HUMAN Gene/Protein Processing [10]
Baculoviral IAP repeat-containing protein 5 (BIRC5) OTILXZYL BIRC5_HUMAN Gene/Protein Processing [8]
Bcl-2 homologous antagonist/killer (BAK1) OTDP6ILW BAK_HUMAN Gene/Protein Processing [6]
Bcl-2-like protein 1 (BCL2L1) OTRC5K9O B2CL1_HUMAN Gene/Protein Processing [6]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

1 Clinical pipeline report, company report or official report of the Pharmaceutical Research and Manufacturers of America (PhRMA)
2 Trusted, scientifically sound profiles of drug programs, clinical trials, safety reports, and company deals, written by scientists. Springer. 2015. Adis Insight (drug id 800022136)
3 Tetrandrine: a novel calcium channel antagonist inhibits type I calcium channels in neuroblastoma cells. Neuropharmacology. 1991 Dec;30(12A):1325-31.
4 Integrated analysis on the physicochemical properties of dihydropyridine calcium channel blockers in grapefruit juice interactions. Curr Pharm Biotechnol. 2012 Jul;13(9):1705-17.
5 CYP3A5 mediates bioactivation and cytotoxicity of tetrandrine. Arch Toxicol. 2016 Jul;90(7):1737-48.
6 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. Environ Toxicol. 2017 Jan;32(1):329-343. doi: 10.1002/tox.22238. Epub 2016 Jan 29.
7 Antitumor activity of arsenite in combination with tetrandrine against human breast cancer cell line MDA-MB-231 in vitro and in vivo. Cancer Cell Int. 2018 Aug 13;18:113. doi: 10.1186/s12935-018-0613-0. eCollection 2018.
8 Anticancer effect of tetrandrine on primary cancer cells isolated from ascites and pleural fluids. Cancer Lett. 2008 Sep 8;268(1):166-75. doi: 10.1016/j.canlet.2008.03.059. Epub 2008 May 20.
9 [Effect of tetrandrine combined with daunorubicin on expressions of P21 and P-gp in K562/A02 cells]. Zhongguo Shi Yan Xue Ye Xue Za Zhi. 2009 Oct;17(5):1179-82.
10 Tetrandrine induces apoptosis Via caspase-8, -9, and -3 and poly (ADP ribose) polymerase dependent pathways and autophagy through beclin-1/ LC3-I, II signaling pathways in human oral cancer HSC-3 cells. Environ Toxicol. 2016 Apr;31(4):395-406. doi: 10.1002/tox.22053. Epub 2014 Sep 30.