Tetrahydropalmatine

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

Identification

Generic Name
Tetrahydropalmatine
DrugBank Accession Number
DB12093
Background

Tetrahydropalmatine is under investigation in clinical trial NCT02118610 (Treatment of Schizophrenia With L-tetrahydropalmatine (l-THP): a Novel Dopamine Antagonist With Anti-inflammatory and Antiprotozoal Activity).

Type
Small Molecule
Groups
Investigational
Structure
Thumb
Weight
Average: 355.434
Monoisotopic: 355.178358289
Chemical Formula
C21H25NO4
Synonyms
Not Available

Pharmacology

Indication

Not Available

Pharmacology
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Contraindications & Blackbox Warnings
Contraindications
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UDopamine D1 receptor
antagonist
Humans
UDopamine D2 receptor
antagonist
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
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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
1,2-BenzodiazepineThe risk or severity of adverse effects can be increased when Tetrahydropalmatine is combined with 1,2-Benzodiazepine.
AbametapirThe serum concentration of Tetrahydropalmatine can be increased when it is combined with Abametapir.
AcarboseThe risk or severity of hypoglycemia can be increased when Tetrahydropalmatine is combined with Acarbose.
AcebutololThe risk or severity of bradycardia can be increased when Tetrahydropalmatine is combined with Acebutolol.
AceclofenacThe therapeutic efficacy of Tetrahydropalmatine can be decreased when used in combination with Aceclofenac.
AcemetacinThe therapeutic efficacy of Tetrahydropalmatine can be decreased when used in combination with Acemetacin.
AcetazolamideThe risk or severity of adverse effects can be increased when Acetazolamide is combined with Tetrahydropalmatine.
AcetohexamideThe risk or severity of hypoglycemia can be increased when Tetrahydropalmatine is combined with Acetohexamide.
AcetophenazineThe risk or severity of adverse effects can be increased when Acetophenazine is combined with Tetrahydropalmatine.
AcetyldigitoxinTetrahydropalmatine may increase the arrhythmogenic activities of Acetyldigitoxin.
Interactions
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Food Interactions
Not Available

Products

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Product Ingredients
IngredientUNIICASInChI Key
Tetrahydropalmatine HydrochlorideRH72T8K75E4880-82-4MGSZZQQRTPWMEI-LMOVPXPDSA-N

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as protoberberine alkaloids and derivatives. These are alkaloids with a structure based on a protoberberine moiety, which consists of a 5,6-dihydrodibenzene moiety fused to a quinolizinium and forming 5,6-Dihydrodibenzo(a,g)quinolizinium skeleton.
Kingdom
Organic compounds
Super Class
Alkaloids and derivatives
Class
Protoberberine alkaloids and derivatives
Sub Class
Not Available
Direct Parent
Protoberberine alkaloids and derivatives
Alternative Parents
Tetrahydroisoquinolines / Anisoles / Aralkylamines / Alkyl aryl ethers / Trialkylamines / Azacyclic compounds / Organopnictogen compounds / Hydrocarbon derivatives
Substituents
Alkyl aryl ether / Amine / Anisole / Aralkylamine / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Ether / Hydrocarbon derivative / Organic nitrogen compound
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
organic heterotetracyclic compound, berberine alkaloid (CHEBI:16563) / Isoquinoline alkaloids (C02890)
Affected organisms
Not Available

Chemical Identifiers

UNII
3X69CO5I79
CAS number
483-14-7
InChI Key
AEQDJSLRWYMAQI-KRWDZBQOSA-N
InChI
InChI=1S/C21H25NO4/c1-23-18-6-5-13-9-17-15-11-20(25-3)19(24-2)10-14(15)7-8-22(17)12-16(13)21(18)26-4/h5-6,10-11,17H,7-9,12H2,1-4H3/t17-/m0/s1
IUPAC Name
(12bS)-3,4,10,11-tetramethoxy-7,8,12b,13-tetrahydro-5H-6-azatetraphene
SMILES
COC1=CC=C2C[C@@H]3N(CCC4=CC(OC)=C(OC)C=C34)CC2=C1OC

References

General References
Not Available
KEGG Compound
C02890
PubChem Compound
72301
PubChem Substance
347828397
ChemSpider
65252
BindingDB
50424077
ChEBI
16563
ChEMBL
CHEMBL487182
ZINC
ZINC000019535049
Wikipedia
Tetrahydropalmatine

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2WithdrawnTreatmentCocaine Use1
1CompletedTreatmentCocaine Use1
Not AvailableCompletedTreatmentSchizophrenia1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0246 mg/mLALOGPS
logP3.09ALOGPS
logP3.15ChemAxon
logS-4.2ALOGPS
pKa (Strongest Basic)5.34ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area40.16 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity101.36 m3·mol-1ChemAxon
Polarizability39.97 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Targets

Drugtargets
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Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Antagonist
General Function
G-protein coupled amine receptor activity
Specific Function
Dopamine receptor whose activity is mediated by G proteins which activate adenylyl cyclase.
Gene Name
DRD1
Uniprot ID
P21728
Uniprot Name
D(1A) dopamine receptor
Molecular Weight
49292.765 Da
References
  1. Mantsch JR, Li SJ, Risinger R, Awad S, Katz E, Baker DA, Yang Z: Levo-tetrahydropalmatine attenuates cocaine self-administration and cocaine-induced reinstatement in rats. Psychopharmacology (Berl). 2007 Jul;192(4):581-91. Epub 2007 Mar 15. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Antagonist
General Function
Potassium channel regulator activity
Specific Function
Dopamine receptor whose activity is mediated by G proteins which inhibit adenylyl cyclase.
Gene Name
DRD2
Uniprot ID
P14416
Uniprot Name
D(2) dopamine receptor
Molecular Weight
50618.91 Da
References
  1. Mantsch JR, Li SJ, Risinger R, Awad S, Katz E, Baker DA, Yang Z: Levo-tetrahydropalmatine attenuates cocaine self-administration and cocaine-induced reinstatement in rats. Psychopharmacology (Berl). 2007 Jul;192(4):581-91. Epub 2007 Mar 15. [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]

Drug created on October 20, 2016 21:20 / Updated on June 12, 2020 16:53