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
CHEMBL49
CAS Number
518-34-3
UNII
29EX23D5AJ
DrugBank ID
DB14066
TTD ID
D0G4ES
INTEDE ID
DR1570
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Drug Pharmacogenomic Perturbation (DPP)NEW Click to Jump to the Detailed DPP Information of This Drug
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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-inducing factor 1, mitochondrial (AIFM1) OTKPWB7Q AIFM1_HUMAN Gene/Protein Processing [6]
ATP-dependent translocase ABCB1 (ABCB1) OTEJROBO MDR1_HUMAN Gene/Protein Processing [8]
Autophagy protein 5 (ATG5) OT4T5SMS ATG5_HUMAN Gene/Protein Processing [9]
Baculoviral IAP repeat-containing protein 5 (BIRC5) OTILXZYL BIRC5_HUMAN Gene/Protein Processing [10]
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]
BH3-interacting domain death agonist (BID) OTOSHSHU BID_HUMAN Gene/Protein Processing [6]
Cadherin-1 (CDH1) OTFJMXPM CADH1_HUMAN Gene/Protein Processing [11]
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 [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.
9 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.
10 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.
11 Tetrandrine inhibits human brain glioblastoma multiforme GBM 8401 cancer cell migration and invasion in vitro. Environ Toxicol. 2019 Apr;34(4):364-374. doi: 10.1002/tox.22691. Epub 2018 Dec 13.