Identification
- Generic Name
- Sparteine
- DrugBank Accession Number
- DB06727
- Background
Sparteine is a plant alkaloid derived from Cytisus scoparius and Lupinus mutabilis which may chelate calcium and magnesium. It is a sodium channel blocker, so it falls in the category of class 1a antiarrhythmic agents. Sparteine is not currently FDA-approved for human use, and its salt, sparteine sulfate, is one of the products that have been withdrawn or removed from the market for reasons of safety or effectiveness.1
- Type
- Small Molecule
- Groups
- Experimental, Withdrawn
- Structure
Structure for Sparteine (DB06727)
- Weight
- Average: 234.387
Monoisotopic: 234.209598845 - Chemical Formula
- C15H26N2
- Synonyms
- (-)-sparteine
- 6β,7α,9α,11α-pachycarpine
- Esparteina
- Lupinidine
- Sparteina
- Sparteine
- Sparteinum
Pharmacology
- Indication
Not Available
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Avoid life-threatening adverse drug eventsImprove clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events & improve clinical decision support.- 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
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.Improve decision support & research outcomes with our structured adverse effects data.- 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAbatacept The metabolism of Sparteine can be increased when combined with Abatacept. Abiraterone The metabolism of Sparteine can be decreased when combined with Abiraterone. Acebutolol Acebutolol may increase the arrhythmogenic activities of Sparteine. Acetaminophen The metabolism of Acetaminophen can be decreased when combined with Sparteine. Acetyldigitoxin Acetyldigitoxin may increase the arrhythmogenic activities of Sparteine. Adagrasib The metabolism of Sparteine can be decreased when combined with Adagrasib. Adalimumab The metabolism of Sparteine can be increased when combined with Adalimumab. Adenosine Adenosine may increase the arrhythmogenic activities of Sparteine. Ajmaline Ajmaline may increase the arrhythmogenic activities of Sparteine. Almotriptan The metabolism of Almotriptan can be decreased when combined with Sparteine. 
Identify potential medication risksEasily compare up to 40 drugs with our drug interaction checker.Get severity rating, description, and management advice.Learn more - Food Interactions
- Not Available
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Sparteine sulfate GQ3J2TLZ7E Not Available Not applicable
Categories
- ATC Codes
- C01BA04 — Sparteine
- Drug Categories
- Alkaloids
- Antiarrhythmic agents
- Antiarrhythmics, Class I
- Antiarrhythmics, Class Ia
- Cardiac Therapy
- Cardiovascular Agents
- Cytochrome P-450 CYP2D6 Inhibitors
- Cytochrome P-450 CYP2D6 Inhibitors (strength unknown)
- Cytochrome P-450 CYP2D6 Substrates
- Cytochrome P-450 Enzyme Inhibitors
- Cytochrome P-450 Substrates
- Heterocyclic Compounds, Fused-Ring
- Quinolizidine Alkaloids
- Quinolizidines
- Quinolizines
- Reproductive Control Agents
- Classification
- Not classified
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 298897D62S
- CAS number
- 90-39-1
- InChI Key
- SLRCCWJSBJZJBV-ZQDZILKHSA-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,2R,9S,10S)-7,15-diazatetracyclo[7.7.1.0^{2,7}.0^{10,15}]heptadecane
- SMILES
- [H][C@@]12CCCCN1C[C@@H]1C[C@H]2CN2CCCC[C@]12[H]
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
- Code of Federal Regulations 216.24: Drug products withdrawn or removed from the market for reasons of safety or effectiveness. [Link]
- External Links
- KEGG Drug
- D01041
- KEGG Compound
- C10783
- PubChem Compound
- 168213
- PubChem Substance
- 99443273
- ChemSpider
- 559096
- ChEBI
- 28827
- ChEMBL
- CHEMBL1908847
- ZINC
- ZINC000001408502
- PharmGKB
- PA452610
- Wikipedia
- Sparteine
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 30.5 °C PhysProp boiling point (°C) 325 °C PhysProp water solubility 3040 mg/L (at 22 °C) YALKOWSKY,SH & DANNENFELSER,RM (1992) - Predicted Properties
Property Value Source Water Solubility 0.931 mg/mL ALOGPS logP 2.98 ALOGPS logP 2.03 Chemaxon logS -2.4 ALOGPS pKa (Strongest Basic) 9.16 Chemaxon Physiological Charge 2 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 6.48 Å2 Chemaxon Rotatable Bond Count 0 Chemaxon Refractivity 71.82 m3·mol-1 Chemaxon Polarizability 28.37 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9757 Blood Brain Barrier + 0.9606 Caco-2 permeable + 0.6725 P-glycoprotein substrate Substrate 0.55 P-glycoprotein inhibitor I Non-inhibitor 0.6379 P-glycoprotein inhibitor II Non-inhibitor 0.8742 Renal organic cation transporter Inhibitor 0.7785 CYP450 2C9 substrate Non-substrate 0.884 CYP450 2D6 substrate Substrate 0.8919 CYP450 3A4 substrate Non-substrate 0.6969 CYP450 1A2 substrate Non-inhibitor 0.9045 CYP450 2C9 inhibitor Non-inhibitor 0.9576 CYP450 2D6 inhibitor Non-inhibitor 0.9231 CYP450 2C19 inhibitor Non-inhibitor 0.9576 CYP450 3A4 inhibitor Non-inhibitor 0.9518 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.6629 Ames test Non AMES toxic 0.6586 Carcinogenicity Non-carcinogens 0.9538 Biodegradation Not ready biodegradable 0.9974 Rat acute toxicity 2.4193 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.7831 hERG inhibition (predictor II) Non-inhibitor 0.7092
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Enzymes
- Kind
- Protein
- Organism
- Humans
- 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...
- Gene Name
- CYP2D6
- Uniprot ID
- P10635
- Uniprot Name
- Cytochrome P450 2D6
- Molecular Weight
- 55768.94 Da
References
- 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. [Article]
- 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. [Article]
- Flockhart Table of Drug Interactions [Link]
Drug created at August 18, 2010 20:01 / Updated at December 13, 2022 10:46