Identification

Name
Sparteine
Accession Number
DB06727
Type
Small Molecule
Groups
Experimental
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
Categories
UNII
HPV1ED2WZQ
CAS number
90-39-1
Weight
Average: 234.3803
Monoisotopic: 234.209598842
Chemical Formula
C15H26N2
InChI Key
SLRCCWJSBJZJBV-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

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
Not Available
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
Toxicity
Not Available
Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
4-MethoxyamphetamineThe metabolism of 4-Methoxyamphetamine can be decreased when combined with Sparteine.
AbirateroneThe metabolism of Sparteine can be decreased when combined with Abiraterone.
AcebutololThe metabolism of Sparteine can be decreased when combined with Acebutolol.
AcetaminophenThe metabolism of Acetaminophen can be decreased when combined with Sparteine.
AlmotriptanThe metabolism of Almotriptan can be decreased when combined with Sparteine.
AlogliptinThe metabolism of Alogliptin can be decreased when combined with Sparteine.
AlprenololThe metabolism of Alprenolol can be decreased when combined with Sparteine.
AminophenazoneThe metabolism of Aminophenazone can be decreased when combined with Sparteine.
AmiodaroneAmiodarone may increase the QTc-prolonging activities of Sparteine.
AmitriptylineThe metabolism of Amitriptyline can be decreased when combined with Sparteine.
Food Interactions
Not 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 References
Not Available
External Links
KEGG Drug
D01041
KEGG Compound
C10783
PubChem Compound
168213
PubChem Substance
99443273
ChemSpider
147139
ChEBI
28827
PharmGKB
PA452610
Wikipedia
Sparteine
ATC Codes
C01BA04 — Sparteine

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
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
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
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

Taxonomy

Description
This compound belongs to the class of organic compounds 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.
Kingdom
Organic compounds
Super Class
Alkaloids and derivatives
Class
Lupin alkaloids
Sub Class
Sparteine, lupanine, and related alkaloids
Direct Parent
Sparteine, lupanine, and related alkaloids
Alternative Parents
Quinolizidines / Piperidines / Trialkylamines / Azacyclic compounds / Organopnictogen compounds / Hydrocarbon derivatives
Substituents
Sparteine-lupanine skeleton / Quinolizidine / Piperidine / Tertiary aliphatic amine / Tertiary amine / Azacycle / Organoheterocyclic compound / Organic nitrogen compound / Organopnictogen compound / Hydrocarbon derivative
Molecular Framework
Aliphatic heteropolycyclic compounds
External Descriptors
Not Available

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
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...
Gene Name
CYP2D6
Uniprot ID
P10635
Uniprot Name
Cytochrome P450 2D6
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. Halling J, Petersen MS, Damkier P, Nielsen F, Grandjean P, Weihe P, Lundgren S, Lundblad MS, Brosen K: Polymorphism of CYP2D6, CYP2C19, CYP2C9 and CYP2C8 in the Faroese population. Eur J Clin Pharmacol. 2005 Aug;61(7):491-7. doi: 10.1007/s00228-005-0938-1. Epub 2005 Jul 16. [PubMed:16025294]
  3. Damkier P, Hansen LL, Brosen K: Effect of diclofenac, disulfiram, itraconazole, grapefruit juice and erythromycin on the pharmacokinetics of quinidine. Br J Clin Pharmacol. 1999 Dec;48(6):829-38. [PubMed:10594487]
  4. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]

Drug created on August 18, 2010 14:01 / Updated on November 02, 2018 06:19