CANADINE

Details

Stereochemistry	RACEMIC
Molecular Formula	C20H21NO4
Molecular Weight	339.385
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC1=C(OC)C2=C(CC3N(CCC4=CC5=C(OCO5)C=C34)C2)C=C1

InChI

InChIKey=VZTUIEROBZXUFA-UHFFFAOYSA-N

InChI=1S/C20H21NO4/c1-22-17-4-3-12-7-16-14-9-19-18(24-11-25-19)8-13(14)5-6-21(16)10-15(12)20(17)23-2/h3-4,8-9,16H,5-7,10-11H2,1-2H3

HIDE SMILES / InChI

Molecular Formula	C20H21NO4
Molecular Weight	339.385
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/21659472 | https://www.ncbi.nlm.nih.gov/pubmed/8010106

Canadine (tetrahydroberberine,THB) is an isoquinoline alkaloid (5,8,13,13a-tetrahydro-9,10-dimethoxy-6H-benzo[g]-1,3-benzodioxolo[5,6-a]quinolizine) from Corydalis tuber, it has micromolar affinity for dopamine D(2) (pK(i) = 6.08) and 5-HT(1A) (pK(i) = 5.38) receptors but moderate to no affinity for other relevant serotonin receptors (i.e., 5-HT(1B), 5-HT(1D), 5-HT(3), and 5-HT(4). Canadine enhances gastrointestinal motor function. THB, with D(2) receptor antagonist and 5-HT(1A) receptor agonist properties, has significant potential as a therapeutic for treatment of functional dyspepsia. THB is a potent inhibitor of platelet aggregation in vitro and in vivo and is a promising antithrombotic drug.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Dopamine D2 receptor 297 Target ID: CHEMBL217 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21659472 \| https://www.ncbi.nlm.nih.gov/pubmed/2530755 \|	Antagonist 2778	119.0 nM [Ki]
Serotonin 1a (5-HT1a) receptor 172 Target ID: CHEMBL214 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21659472	Agonist 2678	5.38 null [pKi]
platelet aggregation 76 Target ID: GO:0070527 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8010106	Inhibitor 8297	0.86 mM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Functional dyspepsia 12 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21659472	Primary	Preclinical	Unknown Approved Use Unknown
Thrombosis 22 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8010106	Primary	Preclinical	Unknown Approved Use Unknown
Myocardial ischemia 15 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8352004 https://www.ncbi.nlm.nih.gov/pubmed/1598835	Preventing	Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Chlorobenzylidine-calf thymus DNA interaction II: circular dichroism and nuclear magnetic resonance studies.	2004 Nov	15477134
Chiral high-performance liquid chromatographic separation of the enantiomers of tetrahydropalmatine and tetrahydroberberine, isolated from Corydalis yanhusuo.	2006 Feb	16402177
Tetrahydroberberine blocks ATP-sensitive potassium channels in dopamine neurons acutely-dissociated from rat substantia nigra pars compacta.	2010 Dec	20804776
Simultaneous determination of active xanthone glycosides, timosaponins and alkaloids in rat plasma after oral administration of Zi-Shen Pill extract for the pharmacokinetic study by liquid chromatography-tandem mass spectrometry.	2010 Jul 1	20541984
Structural optimization of berberine as a synergist to restore antifungal activity of fluconazole against drug-resistant Candida albicans.	2014 Jan	24376206
Non-nucleoside reverse transcriptase inhibitor (NNRTI) cross-resistance: implications for preclinical evaluation of novel NNRTIs and clinical genotypic resistance testing.	2014 Jan	23934770

Patents

Sample Use Guides

In Vivo Use Guide

Rats: Oral administration of Canadine not only resulted in the significantly accelerated gastric emptying of normal rats in a bell-shaped relationship, with a maximal efficacy at a dose of 30 ug/kg, but also restored the delayed gastric emptying caused by apomorphine, which might be mediated by an antidopaminergic effect.

Route of Administration: Oral

In Vitro Use Guide

Canadine (tetrahydroberberine,THB) (0.1-10 uM/L) shifted the dose-response curves to the right in a nonparallel fashion and decreased the maximal response (Emax) of both the fenoldopam(FODA, a selective DA1 agonist)-induced and the propyl-butyl-dopamine(PBDA, a selective DA2 agonist)-induced vasorelaxation, showing a non-competitive antagonistic action. The pD'2 values of THB for FODA in the renal, pulmonary and mesenteric arteries were 5.29, 5.37 and 5.46, respectively, while for PBDA in the mesenteric and femoral arteries were 5.53 and 5.48, respectively.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 02:10:55 GMT 2023` Edited by `admin` on `Sat Dec 16 02:10:55 GMT 2023`
Record UNII	V2SSH085X8
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CANADINE

Common Name

English

XANTHOPUCCINE

Common Name

English

(±)-CANADINE

Common Name

English

5,8,13,13A-TETRAHYDRO-9,10-DIMETHOXY-6H-BENZO(G)-1,3-BENZODIOXOLO(5,6-A)QUINOLIZINE

Common Name

English

CANADINE, (±)-

Common Name

English

CANADINE [MI]

Common Name

English

DL-TETRAHYDROBERBERINE

Common Name

English

CANADINE DL-FORM [MI]

Common Name

English

NSC-94918

Code

English

CANADINE DL-FORM

Common Name

English

TETRAHYDROBERBERINE

Common Name

English

NSC-36351

Code

English

Code System Code Type Description

WIKIPEDIA

CANADINE