Identification
NameSparteine
Accession NumberDB06727
TypeSmall Molecule
GroupsExperimental
Description

Sparteine is a class 1a antiarrhythmic agent; a sodium channel blocker. It is an alkaloid and can be extracted from scotch broom. 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, and it is not included in the Vaughn Williams classification of antiarrhythmic drugs.

Structure
Thumb
Synonyms
(-)-sparteine
d-Sparteine
Esparteina
Genisteine
lupinidine
Pachycarpine
Sparteinum
Sparteinum sulfuricum
External IDs Not Available
Product Ingredients Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
Categories
UNII298897D62S
CAS number90-39-1
WeightAverage: 234.3803
Monoisotopic: 234.209598842
Chemical FormulaC15H26N2
InChI KeySLRCCWJSBJZJBV-AJNGGQMLSA-N
InChI
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
IUPAC Name
(1S,2S,9S,10S)-7,15-diazatetracyclo[7.7.1.0²,⁷.0¹⁰,¹⁵]heptadecane
SMILES
C1CCN2C[C@@H]3C[C@@H](CN4CCCC[C@@H]34)[C@@H]2C1
Pharmacology
IndicationNot Available
Structured Indications Not Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
Pharmacogenomic Effects/ADRs Not Available
Interactions
Drug Interactions
DrugInteractionDrug group
AbirateroneThe serum concentration of Sparteine can be increased when it is combined with Abiraterone.Approved
AmiodaroneAmiodarone may increase the QTc-prolonging activities of Sparteine.Approved, Investigational
ArtemetherThe metabolism of Sparteine can be decreased when combined with Artemether.Approved
AtomoxetineThe metabolism of Sparteine can be decreased when combined with Atomoxetine.Approved
BetaxololThe metabolism of Sparteine can be decreased when combined with Betaxolol.Approved
BupropionThe metabolism of Sparteine can be decreased when combined with Bupropion.Approved
Carboprost TromethamineThe risk or severity of adverse effects can be increased when Carboprost Tromethamine is combined with Sparteine.Approved
CelecoxibThe metabolism of Sparteine can be decreased when combined with Celecoxib.Approved, Investigational
ChloroquineThe metabolism of Sparteine can be decreased when combined with Chloroquine.Approved, Vet Approved
ChlorpromazineThe metabolism of Sparteine can be decreased when combined with Chlorpromazine.Approved, Vet Approved
CholecalciferolThe metabolism of Sparteine can be decreased when combined with Cholecalciferol.Approved, Nutraceutical
CimetidineThe metabolism of Sparteine can be decreased when combined with Cimetidine.Approved
CinacalcetThe metabolism of Sparteine can be decreased when combined with Cinacalcet.Approved
CitalopramThe metabolism of Sparteine can be decreased when combined with Citalopram.Approved
ClemastineThe metabolism of Sparteine can be decreased when combined with Clemastine.Approved
ClobazamThe metabolism of Sparteine can be decreased when combined with Clobazam.Approved, Illicit
ClomipramineThe metabolism of Sparteine can be decreased when combined with Clomipramine.Approved, Vet Approved
ClotrimazoleThe metabolism of Sparteine can be decreased when combined with Clotrimazole.Approved, Vet Approved
ClozapineThe metabolism of Sparteine can be decreased when combined with Clozapine.Approved
CobicistatThe serum concentration of Sparteine can be increased when it is combined with Cobicistat.Approved
CocaineThe metabolism of Sparteine can be decreased when combined with Cocaine.Approved, Illicit
DarifenacinThe metabolism of Sparteine can be decreased when combined with Darifenacin.Approved, Investigational
DarunavirThe serum concentration of Sparteine can be increased when it is combined with Darunavir.Approved
DelavirdineThe metabolism of Sparteine can be decreased when combined with Delavirdine.Approved
DesipramineThe metabolism of Sparteine can be decreased when combined with Desipramine.Approved
DiphenhydramineThe metabolism of Sparteine can be decreased when combined with Diphenhydramine.Approved
DronedaroneThe metabolism of Sparteine can be decreased when combined with Dronedarone.Approved
DuloxetineThe metabolism of Sparteine can be decreased when combined with Duloxetine.Approved
EliglustatThe metabolism of Sparteine can be decreased when combined with Eliglustat.Approved
FesoterodineThe serum concentration of the active metabolites of Fesoterodine can be increased when Fesoterodine is used in combination with Sparteine.Approved
FingolimodFingolimod may increase the arrhythmogenic activities of Sparteine.Approved, Investigational
FluoxetineThe metabolism of Sparteine can be decreased when combined with Fluoxetine.Approved, Vet Approved
FluvoxamineThe metabolism of Sparteine can be decreased when combined with Fluvoxamine.Approved, Investigational
HaloperidolThe metabolism of Sparteine can be decreased when combined with Haloperidol.Approved
ImipramineThe metabolism of Sparteine can be decreased when combined with Imipramine.Approved
IndinavirThe metabolism of Sparteine can be decreased when combined with Indinavir.Approved
IsoniazidThe metabolism of Sparteine can be decreased when combined with Isoniazid.Approved
KetoconazoleThe metabolism of Sparteine can be decreased when combined with Ketoconazole.Approved, Investigational
LopinavirThe metabolism of Sparteine can be decreased when combined with Lopinavir.Approved
LorcaserinThe metabolism of Sparteine can be decreased when combined with Lorcaserin.Approved
LumefantrineThe metabolism of Sparteine can be decreased when combined with Lumefantrine.Approved
MethadoneThe metabolism of Sparteine can be decreased when combined with Methadone.Approved
MethotrimeprazineThe metabolism of Sparteine can be decreased when combined with Methotrimeprazine.Approved
MetoprololThe serum concentration of Metoprolol can be increased when it is combined with Sparteine.Approved, Investigational
MirabegronThe metabolism of Sparteine can be decreased when combined with Mirabegron.Approved
NevirapineThe metabolism of Sparteine can be decreased when combined with Nevirapine.Approved
NicardipineThe metabolism of Sparteine can be decreased when combined with Nicardipine.Approved
NilotinibThe metabolism of Sparteine can be decreased when combined with Nilotinib.Approved, Investigational
PanobinostatThe serum concentration of Sparteine can be increased when it is combined with Panobinostat.Approved, Investigational
ParoxetineThe metabolism of Sparteine can be decreased when combined with Paroxetine.Approved, Investigational
Peginterferon alfa-2bThe serum concentration of Sparteine can be decreased when it is combined with Peginterferon alfa-2b.Approved
PromazineThe metabolism of Sparteine can be decreased when combined with Promazine.Approved, Vet Approved
PropafenonePropafenone may increase the arrhythmogenic activities of Sparteine.Approved
QuinidineThe metabolism of Sparteine can be decreased when combined with Quinidine.Approved
QuinineThe metabolism of Sparteine can be decreased when combined with Quinine.Approved
RanolazineThe metabolism of Sparteine can be decreased when combined with Ranolazine.Approved, Investigational
RitonavirThe metabolism of Sparteine can be decreased when combined with Ritonavir.Approved, Investigational
RolapitantThe metabolism of Sparteine can be decreased when combined with Rolapitant.Approved
RopiniroleThe metabolism of Sparteine can be decreased when combined with Ropinirole.Approved, Investigational
SertralineThe metabolism of Sparteine can be decreased when combined with Sertraline.Approved
StiripentolThe metabolism of Sparteine can be decreased when combined with Stiripentol.Approved
TerbinafineThe metabolism of Sparteine can be decreased when combined with Terbinafine.Approved, Investigational, Vet Approved
ThioridazineThe serum concentration of Thioridazine can be increased when it is combined with Sparteine.Withdrawn
TiclopidineThe metabolism of Sparteine can be decreased when combined with Ticlopidine.Approved
TipranavirThe metabolism of Sparteine can be decreased when combined with Tipranavir.Approved, Investigational
TranylcypromineThe metabolism of Sparteine can be decreased when combined with Tranylcypromine.Approved
VenlafaxineThe metabolism of Sparteine can be decreased when combined with Venlafaxine.Approved
ZiprasidoneThe metabolism of Sparteine can be decreased when combined with Ziprasidone.Approved
Food InteractionsNot Available
References
Synthesis Reference

Bernd Hachmeister, "Process for the production of 17-hydroxysparteine by oxidation of sparteine with a permanganate." U.S. Patent US4237295, issued June, 1975.

US4237295
General ReferencesNot Available
External Links
ATC CodesC01BA04 — Sparteine
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Clinical Trials
Clinical Trials Not Available
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point (°C)30.5 °CPhysProp
boiling point (°C)325 °CPhysProp
water solubility3040 mg/L (at 22 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
Predicted Properties
PropertyValueSource
Water Solubility0.931 mg/mLALOGPS
logP2.98ALOGPS
logP2.03ChemAxon
logS-2.4ALOGPS
pKa (Strongest Basic)9.46ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area6.48 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity71.82 m3·mol-1ChemAxon
Polarizability28.4 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9757
Blood Brain Barrier+0.9606
Caco-2 permeable+0.6725
P-glycoprotein substrateSubstrate0.55
P-glycoprotein inhibitor INon-inhibitor0.6379
P-glycoprotein inhibitor IINon-inhibitor0.8742
Renal organic cation transporterInhibitor0.7785
CYP450 2C9 substrateNon-substrate0.884
CYP450 2D6 substrateSubstrate0.8919
CYP450 3A4 substrateNon-substrate0.6969
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.9576
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9576
CYP450 3A4 inhibitorNon-inhibitor0.9518
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6629
Ames testNon AMES toxic0.6586
CarcinogenicityNon-carcinogens0.9538
BiodegradationNot ready biodegradable0.9974
Rat acute toxicity2.4193 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.7831
hERG inhibition (predictor II)Non-inhibitor0.7092
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as sparteine, lupanine, and related alkaloids. These are alkaloids with a structure based on either sparteine, lupanine, or derivatives thereof. These are tetracyclic compounds made of two fused quinolizidine ring systems.
KingdomChemical entities
Super ClassOrganic compounds
ClassAlkaloids and derivatives
Sub ClassLupin alkaloids
Direct ParentSparteine, lupanine, and related alkaloids
Alternative ParentsQuinolizidines / Piperidines / Trialkylamines / Azacyclic compounds / Organopnictogen compounds / Hydrocarbon derivatives
SubstituentsSparteine-lupanine skeleton / Quinolizidine / Piperidine / Tertiary aliphatic amine / Tertiary amine / Azacycle / Organoheterocyclic compound / Organic nitrogen compound / Organopnictogen compound / Hydrocarbon derivative
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrateinhibitor
General Function:
Steroid hydroxylase activity
Specific Function:
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:
CYP2D6
Uniprot ID:
P10635
Molecular Weight:
55768.94 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
  2. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Drug created on August 18, 2010 14:01 / Updated on June 11, 2017 21:02