This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Name
Tetrandrine
Accession Number
DB14066
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
  • (+)-Tetrandrine
  • (S,S)-Tetrandrine
  • D-Tetrandrine
  • Fanchinine
  • Hanjisong
  • Sinomenine A
Categories
UNII
29EX23D5AJ
CAS number
518-34-3
Weight
Average: 622.762
Monoisotopic: 622.30428708
Chemical Formula
C38H42N2O6
InChI Key
WVTKBKWTSCPRNU-KYJUHHDHSA-N
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
IUPAC Name
(1S,14S)-9,20,21,25-tetramethoxy-15,30-dimethyl-7,23-dioxa-15,30-diazaheptacyclo[22.6.2.2^{3,6}.1^{8,12}.1^{14,18}.0^{27,31}.0^{22,33}]hexatriaconta-3,5,8(34),9,11,18(33),19,21,24(32),25,27(31),35-dodecaene
SMILES
COC1=CC=C2C[C@@H]3N(C)CCC4=C3C(OC3=CC5=C(CCN(C)[C@H]5CC5=CC=C(OC1=C2)C=C5)C=C3OC)=C(OC)C(OC)=C4

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UMultidrug resistance protein 1
inhibitor
Human
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
2-MethoxyethanolThe risk or severity of adverse effects can be increased when 2-Methoxyethanol is combined with Tetrandrine.
9-(N-methyl-L-isoleucine)-cyclosporin AThe risk or severity of adverse effects can be increased when 9-(N-methyl-L-isoleucine)-cyclosporin A is combined with Tetrandrine.
AbafunginThe therapeutic efficacy of Abafungin can be increased when used in combination with Tetrandrine.
AbataceptThe risk or severity of adverse effects can be increased when Abatacept is combined with Tetrandrine.
AbemaciclibThe serum concentration of Abemaciclib can be increased when it is combined with Tetrandrine.
AbetimusThe risk or severity of adverse effects can be increased when Abetimus is combined with Tetrandrine.
AcebutololThe serum concentration of Acebutolol can be increased when it is combined with Tetrandrine.
AcepromazineThe risk or severity of QTc prolongation can be increased when Tetrandrine is combined with Acepromazine.
AceprometazineThe risk or severity of QTc prolongation can be increased when Tetrandrine is combined with Aceprometazine.
AcetophenazineThe risk or severity of QTc prolongation can be increased when Tetrandrine is combined with Acetophenazine.
Food Interactions
Not Available

References

General References
Not Available
External Links
KEGG Compound
C09654
ChemSpider
65868
ChEBI
49
ChEMBL
CHEMBL176045
Wikipedia
Tetrandrine

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00296 mg/mLALOGPS
logP5.55ALOGPS
logP6.48ChemAxon
logS-5.3ALOGPS
pKa (Strongest Basic)8.28ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area61.86 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity180.11 m3·mol-1ChemAxon
Polarizability68.3 Å3ChemAxon
Number of Rings7ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
Not Available

Taxonomy

Classification
Not classified

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Xenobiotic-transporting atpase activity
Specific Function
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name
ABCB1
Uniprot ID
P08183
Uniprot Name
Multidrug resistance protein 1
Molecular Weight
141477.255 Da
References
  1. Fu L, Liang Y, Deng L, Ding Y, Chen L, Ye Y, Yang X, Pan Q: Characterization of tetrandrine, a potent inhibitor of P-glycoprotein-mediated multidrug resistance. Cancer Chemother Pharmacol. 2004 Apr;53(4):349-56. doi: 10.1007/s00280-003-0742-5. Epub 2003 Dec 10. [PubMed:14666379]
  2. Lu Y, Li F, Xu T, Sun J: Tetrandrine prevents multidrug resistance in the osteosarcoma cell line, U-2OS, by preventing Pgp overexpression through the inhibition of NF-kappaB signaling. Int J Mol Med. 2017 Apr;39(4):993-1000. doi: 10.3892/ijmm.2017.2895. Epub 2017 Feb 17. [PubMed:28260091]
  3. Chen Y, Xiao X, Wang C, Jiang H, Hong Z, Xu G: Beneficial effect of tetrandrine on refractory epilepsy via suppressing P-glycoprotein. Int J Neurosci. 2015;125(9):703-10. doi: 10.3109/00207454.2014.966821. Epub 2014 Oct 22. [PubMed:25233150]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
No
Actions
Substrate
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Uesawa Y, Takeuchi T, Mohri K: Integrated analysis on the physicochemical properties of dihydropyridine calcium channel blockers in grapefruit juice interactions. Curr Pharm Biotechnol. 2012 Jul;13(9):1705-17. [PubMed:22039822]

Drug created on June 14, 2018 14:08 / Updated on August 26, 2018 02:07