SPARTEINE

First marketed in 1921

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C15H26N2
Molecular Weight	234.3809
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C1CCN2C[C@]3([H])C[C@@]([H])(CN4CCCC[C@]34[H])[C@]2([H])C1

InChI

InChIKey=SLRCCWJSBJZJBV-ZQDZILKHSA-N

InChI=1S/C15H26N2/c1-3-7-16-11-13-9-12(14(16)5-1)10-17-8-4-2-6-15(13)17/h12-15H,1-11H2/t12-,13-,14-,15+/m0/s1

HIDE SMILES / InChI

Molecular Formula	C15H26N2
Molecular Weight	234.3809
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	4 / 4
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: http://www.drugbank.ca/drugs/DB06727
Curator's Comment:: Description was created based on several sources, including http://www.ndrugs.com/?s=spal

Sparteine is a class 1a antiarrhythmic agent; a sodium channel blocker. It is the predominant alkaloid in Lupinus mutabilis, and is thought to chelate the bivalents calcium and magnesium. It is not FDA approved for human use as an antiarrhythmic agent. It is also used as a chiral base in organic chemistry, and as a ligand in organic chemical synthesis. Marketed under the brand name Spal in Taiwan and Sparteine in Brazil.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
sodium ion transport 13 Target ID: GO:0006814 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9781689	Inhibitor 7687		168.8 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Arrhythmia 37 Sources: http://www.ndrugs.com/?s=spal	Primary		Approved 7968	Spal Approved Use Indications: arrhythmias

T_1/2

Value	Dose	Co-administered	Analyte	Population
117.8 min EXPERIMENT https://link.springer.com/article/10.1007/BF00404298	200 mg single, intravenous dose: 200 mg route of administration: Intravenous experiment type: SINGLE co-administered:		SPARTEINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED
117.45 min EXPERIMENT https://link.springer.com/article/10.1007/BF00404298	200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered:		SPARTEINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED

F_unbound

Value	Dose	Co-administered	Analyte	Population
50% EXPERIMENT https://link.springer.com/article/10.1007/BF00404298	single, unknown		SPARTEINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
		substrate 1038	inhibitor 1359

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	OCT1 294 OCT2 304 OCT3 70 MATE1 123

Drug as victim

Target	Modality	Activity
CYP2D6 1038	substrate 2751 Sources: https://pubmed.ncbi.nlm.nih.gov/9731719/ \| https://pubmed.ncbi.nlm.nih.gov/21297307/ \| https://pubmed.ncbi.nlm.nih.gov/8513845/	yes
MATE1 123	substrate 2751 Sources: https://pubmed.ncbi.nlm.nih.gov/33434947/	yes
OCT1 294	substrate 2751 Sources: https://pubmed.ncbi.nlm.nih.gov/33434947/	yes
OCT2 304	substrate 2751 Sources: https://pubmed.ncbi.nlm.nih.gov/33434947/	yes
OCT3 70	substrate 2751 Sources: https://pubmed.ncbi.nlm.nih.gov/33434947/	yes

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 1391	inhibitor 1373 Sources: https://edoc.unibas.ch/34476/1/PhD%20thesis_Anja%20Schramm.pdf Page: 45.0

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:28827	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:28827
ChemicalBook	CB4674283	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB4674283
MolPort	MolPort-003-987-414	https://www.molport.com/shop/molecule-link/MolPort-003-987-414
ZINC	ZINC000001408502	http://zinc15.docking.org/substances/ZINC000001408502
eMolecules	1936017	https://www.emolecules.com/cgi-bin/more?vid=1936017

PubMed

Title	Date	PubMed
Cytochrome P450 2D6.1 and cytochrome P450 2D6.10 differ in catalytic activity for multiple substrates.	2001 Aug	11505218
Scope of enantioselective palladium(II)-catalyzed aerobic alcohol oxidations with (-)-sparteine.	2003 May 30	12762783

Patents

Sample Use Guides

In Vivo Use Guide

A single 100 mg oral dose of sparteine and a single 40 mg oral dose of dextromethorphan were administered on two occasions to 12 patients

Route of Administration: Oral

In Vitro Use Guide

Sparteine (20 uM) produced also remarkable inhibitions in the uptake of [3H]-histamine by astrocytes from rat brain.

Substance Class	Chemical Created by `admin` on `Sat Jun 26 03:19:23 UTC 2021` Edited by `admin` on `Sat Jun 26 03:19:23 UTC 2021`
Record UNII	298897D62S
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

SPARTEINE

Official Name

English

SPARTEINE [WHO-DD]

Common Name

English

7,14-METHANO-2H,6H-DIPYRIDO(1,2-A:1',2'-E)(1,5)DIAZOCINE, DODECAHYDRO-, (7S,7AR,14S,14AS)

Common Name

English

6-BETA,7-ALPHA,9-ALPHA,11-ALPHA-PACHYCARPINE

Common Name

English

SPARTEINE [MI]

Common Name

English

SPARTEINE [INN]

Common Name

English

Classification Tree Code System Code

WHO-ATC

C01BA04