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

Identification

Generic Name
Tetrandrine
DrugBank Accession Number
DB14066
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Thumb
Weight
Average: 622.762
Monoisotopic: 622.30428708
Chemical Formula
C38H42N2O6
Synonyms
  • (+)-Tetrandrine
  • (S,S)-Tetrandrine
  • D-Tetrandrine
  • Fanchinine
  • Hanjisong
  • Sinomenine A

Pharmacology

Indication

Not Available

Pharmacology
Reduce drug development failure rates
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Contraindications & Blackbox Warnings
Contraindications
Avoid life-threatening adverse drug events
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Avoid life-threatening adverse drug events & improve clinical decision support.
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UP-glycoprotein 1
inhibitor
Humans
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

Adverse Effects
Adverseeffects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AbametapirThe serum concentration of Tetrandrine can be increased when it is combined with Abametapir.
AbataceptThe risk or severity of adverse effects can be increased when Abatacept is combined with Tetrandrine.
AbirateroneThe metabolism of Tetrandrine can be decreased when combined with Abiraterone.
AcarboseThe risk or severity of hypoglycemia can be increased when Tetrandrine is combined with Acarbose.
AcebutololAcebutolol may increase the arrhythmogenic activities of Tetrandrine.
AceclofenacThe risk or severity of hyperkalemia can be increased when Aceclofenac is combined with Tetrandrine.
AcemetacinThe risk or severity of hyperkalemia can be increased when Acemetacin is combined with Tetrandrine.
AcetohexamideThe risk or severity of hypoglycemia can be increased when Tetrandrine is combined with Acetohexamide.
AcetophenazineThe risk or severity of QTc prolongation can be increased when Tetrandrine is combined with Acetophenazine.
AcetyldigitoxinAcetyldigitoxin may increase the arrhythmogenic activities of Tetrandrine.
Interactions
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Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as lignans, neolignans and related compounds. These are plant products of low molecular weight formed primarily from oxidative coupling of two p-propylphenol moieties. They can also be described as micromolecules with two phenylpropanoid units coupled together. They can be attached in various manners, like C5-C5', C8-C8'. Most known natural lignans are oxidized at C9 and C9´ and, based upon the way in which oxygen is incorporated into the skeleton and on the cyclization patterns, a wide range of lignans of very different structural types can be formed.
Kingdom
Organic compounds
Super Class
Lignans, neolignans and related compounds
Class
Not Available
Sub Class
Not Available
Direct Parent
Lignans, neolignans and related compounds
Alternative Parents
Diarylethers / Tetrahydroisoquinolines / Anisoles / Aralkylamines / Alkyl aryl ethers / Trialkylamines / Oxacyclic compounds / Azacyclic compounds / Organopnictogen compounds / Hydrocarbon derivatives
Substituents
Alkyl aryl ether / Amine / Anisole / Aralkylamine / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Diaryl ether / Ether / Hydrocarbon derivative
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
isoquinolines (CHEBI:49) / Isoquinoline alkaloids (C09654)
Affected organisms
Not Available

Chemical Identifiers

UNII
29EX23D5AJ
CAS number
518-34-3
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

References

General References
Not Available
KEGG Compound
C09654
ChemSpider
65868
ChEBI
49
ChEMBL
CHEMBL176045
ZINC
ZINC000028116057
Wikipedia
Tetrandrine

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4Enrolling by InvitationTreatmentCoronavirus Disease 2019 (COVID‑19)1

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

Targets

Drugtargets2
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Kind
Protein
Organism
Humans
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. [Article]
  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. [Article]
  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. [Article]

Enzymes

Kind
Protein
Organism
Humans
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. [Article]

Transporters

Kind
Protein
Organism
Humans
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. [Article]
  2. Sun YF, Wink M: Tetrandrine and fangchinoline, bisbenzylisoquinoline alkaloids from Stephania tetrandra can reverse multidrug resistance by inhibiting P-glycoprotein activity in multidrug resistant human cancer cells. Phytomedicine. 2014 Jul-Aug;21(8-9):1110-9. doi: 10.1016/j.phymed.2014.04.029. Epub 2014 May 22. [Article]

Drug created at June 14, 2018 20:08 / Updated at June 12, 2020 16:53