Tetrandrine
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This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.
Explore a selection of our essential drug information below, or:
Identification
- Generic Name
- Tetrandrine
- DrugBank Accession Number
- DB14066
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental
- Structure
- 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
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- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UATP-dependent translocase ABCB1 inhibitorHumans - 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
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAbametapir The serum concentration of Tetrandrine can be increased when it is combined with Abametapir. Abatacept The risk or severity of adverse effects can be increased when Abatacept is combined with Tetrandrine. Acarbose The risk or severity of hypoglycemia can be increased when Tetrandrine is combined with Acarbose. Acebutolol Acebutolol may increase the arrhythmogenic activities of Tetrandrine. Aceclofenac The risk or severity of hyperkalemia can be increased when Aceclofenac is combined with Tetrandrine. - Food Interactions
- Not Available
Categories
- Drug Categories
- Agents causing hyperkalemia
- Alkaloids
- Anti-Infective Agents
- Antiarrhythmic agents
- Antimalarials
- Antineoplastic Agents
- Antineoplastic Agents, Phytogenic
- Antiparasitic Agents
- Antiprotozoals
- Bradycardia-Causing Agents
- Calcium Channel Blockers
- Calcium-Regulating Hormones and Agents
- Cardiovascular Agents
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 Substrates
- Drugs, Chinese Herbal
- Heterocyclic Compounds, Fused-Ring
- Immunologic Factors
- Immunosuppressive Agents
- Isoquinolines
- Membrane Transport Modulators
- P-glycoprotein inhibitors
- Plant Extracts
- 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
- External Links
- KEGG Compound
- C09654
- ChemSpider
- 65868
- ChEBI
- 49
- ChEMBL
- CHEMBL176045
- ZINC
- ZINC000028116057
- Wikipedia
- Tetrandrine
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample dataNot Available Unknown Status Treatment Rheumatoid Arthritis 1 somestatus stop reason just information to hide 4 Unknown Status Treatment Coronavirus Disease 2019 (COVID‑19) 1 somestatus stop reason just information to hide 4 Withdrawn Treatment Coronavirus Disease 2019 (COVID‑19) 1 somestatus stop reason just information to hide
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
Property Value Source Water Solubility 0.00296 mg/mL ALOGPS logP 5.55 ALOGPS logP 6.48 Chemaxon logS -5.3 ALOGPS pKa (Strongest Basic) 8.28 Chemaxon Physiological Charge 2 Chemaxon Hydrogen Acceptor Count 6 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 61.86 Å2 Chemaxon Rotatable Bond Count 4 Chemaxon Refractivity 180.11 m3·mol-1 Chemaxon Polarizability 68.3 Å3 Chemaxon Number of Rings 7 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 250.2186121 predictedDarkChem Lite v0.1.0 [M-H]- 248.3975121 predictedDarkChem Lite v0.1.0 [M+H]+ 250.1056121 predictedDarkChem Lite v0.1.0 [M+H]+ 249.0426121 predictedDarkChem Lite v0.1.0 [M+Na]+ 251.3396121 predictedDarkChem Lite v0.1.0 [M+Na]+ 248.8253121 predictedDarkChem Lite v0.1.0
Targets
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1. DetailsATP-dependent translocase ABCB1
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Translocates drugs and phospholipids across the membrane (PubMed:2897240, PubMed:35970996, PubMed:8898203, PubMed:9038218). Catalyzes the flop of phospholipids from the cytoplasmic to the exoplasmic leaflet of the apical membrane. Participates mainly to the flop of phosphatidylcholine, phosphatidylethanolamine, beta-D-glucosylceramides and sphingomyelins (PubMed:8898203). Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells (PubMed:2897240, PubMed:35970996, PubMed:9038218)
- Specific Function
- ABC-type xenobiotic transporter activity
- Gene Name
- ABCB1
- Uniprot ID
- P08183
- Uniprot Name
- ATP-dependent translocase ABCB1
- Molecular Weight
- 141477.255 Da
References
- 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]
- 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]
- 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
1. DetailsCytochrome P450 3A4
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Substrate
- General Function
- A cytochrome P450 monooxygenase involved in the metabolism of sterols, steroid hormones, retinoids and fatty acids (PubMed:10681376, PubMed:11093772, PubMed:11555828, PubMed:12865317, PubMed:14559847, PubMed:15373842, PubMed:15764715, PubMed:19965576, PubMed:20702771, PubMed:21490593, PubMed:21576599). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase). Catalyzes the hydroxylation of carbon-hydrogen bonds (PubMed:12865317, PubMed:14559847, PubMed:15373842, PubMed:15764715, PubMed:21490593, PubMed:21576599, PubMed:2732228). Exhibits high catalytic activity for the formation of hydroxyestrogens from estrone (E1) and 17beta-estradiol (E2), namely 2-hydroxy E1 and E2, as well as D-ring hydroxylated E1 and E2 at the C-16 position (PubMed:11555828, PubMed:12865317, PubMed:14559847). Plays a role in the metabolism of androgens, particularly in oxidative deactivation of testosterone (PubMed:15373842, PubMed:15764715, PubMed:22773874, PubMed:2732228). Metabolizes testosterone to less biologically active 2beta- and 6beta-hydroxytestosterones (PubMed:15373842, PubMed:15764715, PubMed:2732228). Contributes to the formation of hydroxycholesterols (oxysterols), particularly A-ring hydroxylated cholesterol at the C-4beta position, and side chain hydroxylated cholesterol at the C-25 position, likely contributing to cholesterol degradation and bile acid biosynthesis (PubMed:21576599). Catalyzes bisallylic hydroxylation of polyunsaturated fatty acids (PUFA) (PubMed:9435160). Catalyzes the epoxidation of double bonds of PUFA with a preference for the last double bond (PubMed:19965576). Metabolizes endocannabinoid arachidonoylethanolamide (anandamide) to 8,9-, 11,12-, and 14,15-epoxyeicosatrienoic acid ethanolamides (EpETrE-EAs), potentially modulating endocannabinoid system signaling (PubMed:20702771). Plays a role in the metabolism of retinoids. Displays high catalytic activity for oxidation of all-trans-retinol to all-trans-retinal, a rate-limiting step for the biosynthesis of all-trans-retinoic acid (atRA) (PubMed:10681376). Further metabolizes atRA toward 4-hydroxyretinoate and may play a role in hepatic atRA clearance (PubMed:11093772). Responsible for oxidative metabolism of xenobiotics. Acts as a 2-exo-monooxygenase for plant lipid 1,8-cineole (eucalyptol) (PubMed:11159812). Metabolizes the majority of the administered drugs. Catalyzes sulfoxidation of the anthelmintics albendazole and fenbendazole (PubMed:10759686). Hydroxylates antimalarial drug quinine (PubMed:8968357). Acts as a 1,4-cineole 2-exo-monooxygenase (PubMed:11695850). Also involved in vitamin D catabolism and calcium homeostasis. Catalyzes the inactivation of the active hormone calcitriol (1-alpha,25-dihydroxyvitamin D(3)) (PubMed:29461981)
- Specific Function
- 1,8-cineole 2-exo-monooxygenase activity
- Gene Name
- CYP3A4
- Uniprot ID
- P08684
- Uniprot Name
- Cytochrome P450 3A4
- Molecular Weight
- 57342.67 Da
References
- 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
1. DetailsATP-dependent translocase ABCB1
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Translocates drugs and phospholipids across the membrane (PubMed:2897240, PubMed:35970996, PubMed:8898203, PubMed:9038218). Catalyzes the flop of phospholipids from the cytoplasmic to the exoplasmic leaflet of the apical membrane. Participates mainly to the flop of phosphatidylcholine, phosphatidylethanolamine, beta-D-glucosylceramides and sphingomyelins (PubMed:8898203). Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells (PubMed:2897240, PubMed:35970996, PubMed:9038218)
- Specific Function
- ABC-type xenobiotic transporter activity
- Gene Name
- ABCB1
- Uniprot ID
- P08183
- Uniprot Name
- ATP-dependent translocase ABCB1
- Molecular Weight
- 141477.255 Da
References
- 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]
- 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 January 14, 2023 19:02