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Identification
NameHuperzine A
Accession NumberDB04864  (EXPT01795, DB01928)
TypeSmall Molecule
GroupsInvestigational
DescriptionHuperzine A, is a naturally occurring sesquiterpene alkaloid found in the extracts of the firmoss Huperzia serrata. The botanical has been used in China for centuries for the treatment of swelling, fever and blood disorders. Recently in clinical trials in China, it has demonstrated neuroprotective effects. It is currently being investigated as a possible treatment for diseases characterized by neurodegeneration – particularly Alzheimer’s disease. [Wikipedia]
Structure
Thumb
Synonyms
(−)-huperazine A
(−)-selagine
L-huperzine A
selagine
External Identifiers 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
SaltsNot Available
Categories
UNII0111871I23
CAS number102518-79-6
WeightAverage: 242.3162
Monoisotopic: 242.141913208
Chemical FormulaC15H18N2O
InChI KeyZRJBHWIHUMBLCN-YQEJDHNASA-N
InChI
InChI=1S/C15H18N2O/c1-3-11-10-6-9(2)8-15(11,16)12-4-5-14(18)17-13(12)7-10/h3-6,10H,7-8,16H2,1-2H3,(H,17,18)/b11-3+/t10-,15+/m0/s1
IUPAC Name
(1R,9R,13E)-1-amino-13-ethylidene-11-methyl-6-azatricyclo[7.3.1.0²,⁷]trideca-2(7),3,10-trien-5-one
SMILES
[H][C@@]12CC3=C(C=CC(=O)N3)[C@@](N)(CC(C)=C1)\C2=C\C
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as quinolones and derivatives. These are compounds containing a quinoline moiety which bears a ketone group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassQuinolines and derivatives
Sub ClassQuinolones and derivatives
Direct ParentQuinolones and derivatives
Alternative Parents
Substituents
  • Quinolone
  • Aralkylamine
  • Pyridinone
  • Pyridine
  • Heteroaromatic compound
  • Lactam
  • Azacycle
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Pharmacology
IndicationFor the treatment of Alzheimer's disease.
PharmacodynamicsHuperzine A is an alkaloid derived from Huperzia serrata (which is available as an herbal product in the US). It is under investigation as an acetylcholinesterase inhibitor. Clinical trials in China have shown that huperzine A is comparably effective to the drugs currently on the market, and may even be somewhat safer in terms of side effects.
Mechanism of actionHuperzine A has been found to be an inhibitor of the enzyme acetylcholinesterase. This is the same mechanism of action of pharmaceutical drugs such as galantamine and donepezil used to treat Alzheimer's disease.
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
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9809
Blood Brain Barrier+0.9053
Caco-2 permeable+0.5
P-glycoprotein substrateSubstrate0.6843
P-glycoprotein inhibitor INon-inhibitor0.7767
P-glycoprotein inhibitor IINon-inhibitor0.7828
Renal organic cation transporterNon-inhibitor0.82
CYP450 2C9 substrateNon-substrate0.8177
CYP450 2D6 substrateNon-substrate0.8258
CYP450 3A4 substrateSubstrate0.6804
CYP450 1A2 substrateInhibitor0.5759
CYP450 2C9 inhibitorInhibitor0.6166
CYP450 2D6 inhibitorNon-inhibitor0.7873
CYP450 2C19 inhibitorInhibitor0.5397
CYP450 3A4 inhibitorNon-inhibitor0.831
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.8312
Ames testNon AMES toxic0.6062
CarcinogenicityNon-carcinogens0.9234
BiodegradationNot ready biodegradable0.9967
Rat acute toxicity3.5096 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.993
hERG inhibition (predictor II)Non-inhibitor0.6042
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point217-219 °CNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.166 mg/mLALOGPS
logP1.78ALOGPS
logP0.62ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)11.11ChemAxon
pKa (Strongest Basic)9.09ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area55.12 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity75.79 m3·mol-1ChemAxon
Polarizability26.87 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
References
Synthesis ReferenceNot Available
General References
  1. Li WM, Kan KK, Carlier PR, Pang YP, Han YF: East meets West in the search for Alzheimer's therapeutics - novel dimeric inhibitors from tacrine and huperzine A. Curr Alzheimer Res. 2007 Sep;4(4):386-96. [PubMed:17908041 ]
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Interactions
Drug Interactions
Drug
4-AndrostenedioneThe risk or severity of adverse effects can be increased when 4-Androstenedione is combined with Huperzine A.
AcebutololHuperzine A may increase the bradycardic activities of Acebutolol.
AcetylcholineThe risk or severity of adverse effects can be increased when Huperzine A is combined with Acetylcholine.
AclidiniumThe therapeutic efficacy of Aclidinium can be decreased when used in combination with Huperzine A.
AlclometasoneThe risk or severity of adverse effects can be increased when Alclometasone is combined with Huperzine A.
AldosteroneThe risk or severity of adverse effects can be increased when Aldosterone is combined with Huperzine A.
AlprenololHuperzine A may increase the bradycardic activities of Alprenolol.
AmcinonideThe risk or severity of adverse effects can be increased when Amcinonide is combined with Huperzine A.
Anisotropine MethylbromideThe therapeutic efficacy of Anisotropine Methylbromide can be decreased when used in combination with Huperzine A.
ArecolineThe risk or severity of adverse effects can be increased when Huperzine A is combined with Arecoline.
ArotinololHuperzine A may increase the bradycardic activities of Arotinolol.
AtenololHuperzine A may increase the bradycardic activities of Atenolol.
Atracurium besylateThe therapeutic efficacy of Atracurium besylate can be decreased when used in combination with Huperzine A.
AtropineThe therapeutic efficacy of Atropine can be decreased when used in combination with Huperzine A.
Beclomethasone dipropionateThe risk or severity of adverse effects can be increased when Beclomethasone dipropionate is combined with Huperzine A.
BefunololHuperzine A may increase the bradycardic activities of Befunolol.
BenactyzineThe therapeutic efficacy of Benactyzine can be decreased when used in combination with Huperzine A.
BenzatropineThe therapeutic efficacy of Benzatropine can be decreased when used in combination with Huperzine A.
BetamethasoneThe risk or severity of adverse effects can be increased when Betamethasone is combined with Huperzine A.
BetaxololHuperzine A may increase the bradycardic activities of Betaxolol.
BethanecholThe risk or severity of adverse effects can be increased when Huperzine A is combined with Bethanechol.
BevantololHuperzine A may increase the bradycardic activities of Bevantolol.
BiperidenThe therapeutic efficacy of Biperiden can be decreased when used in combination with Huperzine A.
BisoprololHuperzine A may increase the bradycardic activities of Bisoprolol.
BopindololHuperzine A may increase the bradycardic activities of Bopindolol.
BudesonideThe risk or severity of adverse effects can be increased when Budesonide is combined with Huperzine A.
BufuralolHuperzine A may increase the bradycardic activities of Bufuralol.
BupranololHuperzine A may increase the bradycardic activities of Bupranolol.
CarbacholThe risk or severity of adverse effects can be increased when Huperzine A is combined with Carbachol.
CarteololHuperzine A may increase the bradycardic activities of Carteolol.
CarvedilolHuperzine A may increase the bradycardic activities of Carvedilol.
CeliprololHuperzine A may increase the bradycardic activities of Celiprolol.
CevimelineThe risk or severity of adverse effects can be increased when Huperzine A is combined with Cevimeline.
ChlorphenoxamineThe therapeutic efficacy of Chlorphenoxamine can be decreased when used in combination with Huperzine A.
CiclesonideThe risk or severity of adverse effects can be increased when Ciclesonide is combined with Huperzine A.
Clobetasol propionateThe risk or severity of adverse effects can be increased when Clobetasol propionate is combined with Huperzine A.
ClocortoloneThe risk or severity of adverse effects can be increased when Clocortolone is combined with Huperzine A.
Cortisone acetateThe risk or severity of adverse effects can be increased when Cortisone acetate is combined with Huperzine A.
CyclopentolateThe therapeutic efficacy of Cyclopentolate can be decreased when used in combination with Huperzine A.
DarifenacinThe therapeutic efficacy of Darifenacin can be decreased when used in combination with Huperzine A.
DehydroepiandrosteroneThe risk or severity of adverse effects can be increased when Dehydroepiandrosterone is combined with Huperzine A.
dehydroepiandrosterone sulfateThe risk or severity of adverse effects can be increased when dehydroepiandrosterone sulfate is combined with Huperzine A.
DesloratadineThe therapeutic efficacy of Desloratadine can be decreased when used in combination with Huperzine A.
DesoximetasoneThe risk or severity of adverse effects can be increased when Desoximetasone is combined with Huperzine A.
Desoxycorticosterone acetateThe risk or severity of adverse effects can be increased when Desoxycorticosterone acetate is combined with Huperzine A.
DexamethasoneThe risk or severity of adverse effects can be increased when Dexamethasone is combined with Huperzine A.
Dexamethasone isonicotinateThe risk or severity of adverse effects can be increased when Dexamethasone isonicotinate is combined with Huperzine A.
DexetimideThe therapeutic efficacy of Dexetimide can be decreased when used in combination with Huperzine A.
DicyclomineThe therapeutic efficacy of Dicyclomine can be decreased when used in combination with Huperzine A.
DiflorasoneThe risk or severity of adverse effects can be increased when Diflorasone is combined with Huperzine A.
DifluocortoloneThe risk or severity of adverse effects can be increased when Difluocortolone is combined with Huperzine A.
DifluprednateThe risk or severity of adverse effects can be increased when Difluprednate is combined with Huperzine A.
DipyridamoleThe therapeutic efficacy of Huperzine A can be decreased when used in combination with Dipyridamole.
EPIBATIDINEThe risk or severity of adverse effects can be increased when Huperzine A is combined with EPIBATIDINE.
EquileninThe risk or severity of adverse effects can be increased when Equilenin is combined with Huperzine A.
EquilinThe risk or severity of adverse effects can be increased when Equilin is combined with Huperzine A.
EsmololHuperzine A may increase the bradycardic activities of Esmolol.
EstroneThe risk or severity of adverse effects can be increased when Estrone is combined with Huperzine A.
EthopropazineThe therapeutic efficacy of Ethopropazine can be decreased when used in combination with Huperzine A.
FesoterodineThe therapeutic efficacy of Fesoterodine can be decreased when used in combination with Huperzine A.
FludrocortisoneThe risk or severity of adverse effects can be increased when Fludrocortisone is combined with Huperzine A.
FlumethasoneThe risk or severity of adverse effects can be increased when Flumethasone is combined with Huperzine A.
FlunisolideThe risk or severity of adverse effects can be increased when Flunisolide is combined with Huperzine A.
Fluocinolone AcetonideThe risk or severity of adverse effects can be increased when Fluocinolone Acetonide is combined with Huperzine A.
FluocinonideThe risk or severity of adverse effects can be increased when Fluocinonide is combined with Huperzine A.
FluocortoloneThe risk or severity of adverse effects can be increased when Fluocortolone is combined with Huperzine A.
FluorometholoneThe risk or severity of adverse effects can be increased when Fluorometholone is combined with Huperzine A.
FluprednideneThe risk or severity of adverse effects can be increased when Fluprednidene is combined with Huperzine A.
FluprednisoloneThe risk or severity of adverse effects can be increased when Fluprednisolone is combined with Huperzine A.
FlurandrenolideThe risk or severity of adverse effects can be increased when Flurandrenolide is combined with Huperzine A.
Fluticasone furoateThe risk or severity of adverse effects can be increased when Fluticasone furoate is combined with Huperzine A.
Fluticasone PropionateThe risk or severity of adverse effects can be increased when Fluticasone Propionate is combined with Huperzine A.
Gallamine TriethiodideThe therapeutic efficacy of Gallamine Triethiodide can be decreased when used in combination with Huperzine A.
GlycopyrroniumThe therapeutic efficacy of Glycopyrronium can be decreased when used in combination with Huperzine A.
GTS-21The risk or severity of adverse effects can be increased when Huperzine A is combined with GTS-21.
HexamethoniumThe therapeutic efficacy of Hexamethonium can be decreased when used in combination with Huperzine A.
HomatropineThe therapeutic efficacy of Homatropine can be decreased when used in combination with Huperzine A.
HydrocortisoneThe risk or severity of adverse effects can be increased when Hydrocortisone is combined with Huperzine A.
HyoscyamineThe therapeutic efficacy of Hyoscyamine can be decreased when used in combination with Huperzine A.
IndenololHuperzine A may increase the bradycardic activities of Indenolol.
Ipratropium bromideThe therapeutic efficacy of Ipratropium bromide can be decreased when used in combination with Huperzine A.
LabetalolHuperzine A may increase the bradycardic activities of Labetalol.
LobelineThe risk or severity of adverse effects can be increased when Huperzine A is combined with Lobeline.
MecamylamineThe therapeutic efficacy of Mecamylamine can be decreased when used in combination with Huperzine A.
MedrysoneThe risk or severity of adverse effects can be increased when Medrysone is combined with Huperzine A.
MelengestrolThe risk or severity of adverse effects can be increased when Melengestrol is combined with Huperzine A.
MethacholineThe risk or severity of adverse effects can be increased when Huperzine A is combined with Methacholine.
MethanthelineThe therapeutic efficacy of Methantheline can be decreased when used in combination with Huperzine A.
MethylprednisoloneThe risk or severity of adverse effects can be increased when Methylprednisolone is combined with Huperzine A.
MetixeneThe therapeutic efficacy of Metixene can be decreased when used in combination with Huperzine A.
MetoprololHuperzine A may increase the bradycardic activities of Metoprolol.
MivacuriumHuperzine A may decrease the neuromuscular blocking activities of Mivacurium.
MometasoneThe risk or severity of adverse effects can be increased when Mometasone is combined with Huperzine A.
N-butylscopolammonium bromideThe therapeutic efficacy of N-butylscopolammonium bromide can be decreased when used in combination with Huperzine A.
NadololHuperzine A may increase the bradycardic activities of Nadolol.
NicotineThe risk or severity of adverse effects can be increased when Huperzine A is combined with Nicotine.
Nicotine bitartrateThe risk or severity of adverse effects can be increased when Huperzine A is combined with Nicotine bitartrate.
NVA237The therapeutic efficacy of NVA237 can be decreased when used in combination with Huperzine A.
OrphenadrineThe therapeutic efficacy of Orphenadrine can be decreased when used in combination with Huperzine A.
OxprenololHuperzine A may increase the bradycardic activities of Oxprenolol.
OxybutyninThe therapeutic efficacy of Oxybutynin can be decreased when used in combination with Huperzine A.
OxyphenoniumThe therapeutic efficacy of Oxyphenonium can be decreased when used in combination with Huperzine A.
PancuroniumThe therapeutic efficacy of Pancuronium can be decreased when used in combination with Huperzine A.
ParamethasoneThe risk or severity of adverse effects can be increased when Paramethasone is combined with Huperzine A.
PenbutololHuperzine A may increase the bradycardic activities of Penbutolol.
PentoliniumThe therapeutic efficacy of Pentolinium can be decreased when used in combination with Huperzine A.
PilocarpineThe risk or severity of adverse effects can be increased when Huperzine A is combined with Pilocarpine.
PindololHuperzine A may increase the bradycardic activities of Pindolol.
PipecuroniumThe therapeutic efficacy of Pipecuronium can be decreased when used in combination with Huperzine A.
PirenzepineThe therapeutic efficacy of Pirenzepine can be decreased when used in combination with Huperzine A.
PractololHuperzine A may increase the bradycardic activities of Practolol.
PrednicarbateThe risk or severity of adverse effects can be increased when Prednicarbate is combined with Huperzine A.
PrednisoloneThe risk or severity of adverse effects can be increased when Prednisolone is combined with Huperzine A.
PrednisoneThe risk or severity of adverse effects can be increased when Prednisone is combined with Huperzine A.
PregnenoloneThe risk or severity of adverse effects can be increased when Pregnenolone is combined with Huperzine A.
ProcyclidineThe therapeutic efficacy of Procyclidine can be decreased when used in combination with Huperzine A.
PropanthelineThe therapeutic efficacy of Propantheline can be decreased when used in combination with Huperzine A.
PropranololHuperzine A may increase the bradycardic activities of Propranolol.
QuinidineThe therapeutic efficacy of Quinidine can be decreased when used in combination with Huperzine A.
RapacuroniumHuperzine A may decrease the neuromuscular blocking activities of Rapacuronium.
RimexoloneThe risk or severity of adverse effects can be increased when Rimexolone is combined with Huperzine A.
ScopolamineThe therapeutic efficacy of Scopolamine can be decreased when used in combination with Huperzine A.
Scopolamine butylbromideThe therapeutic efficacy of Scopolamine butylbromide can be decreased when used in combination with Huperzine A.
SolifenacinThe therapeutic efficacy of Solifenacin can be decreased when used in combination with Huperzine A.
SotalolHuperzine A may increase the bradycardic activities of Sotalol.
SuccinylcholineThe serum concentration of Succinylcholine can be increased when it is combined with Huperzine A.
TimololHuperzine A may increase the bradycardic activities of Timolol.
TiotropiumThe therapeutic efficacy of Tiotropium can be decreased when used in combination with Huperzine A.
TixocortolThe risk or severity of adverse effects can be increased when Tixocortol is combined with Huperzine A.
TolterodineThe therapeutic efficacy of Tolterodine can be decreased when used in combination with Huperzine A.
TriamcinoloneThe risk or severity of adverse effects can be increased when Triamcinolone is combined with Huperzine A.
TrihexyphenidylThe therapeutic efficacy of Trihexyphenidyl can be decreased when used in combination with Huperzine A.
TrimethaphanThe therapeutic efficacy of Trimethaphan can be decreased when used in combination with Huperzine A.
TropicamideThe therapeutic efficacy of Tropicamide can be decreased when used in combination with Huperzine A.
TrospiumThe therapeutic efficacy of Trospium can be decreased when used in combination with Huperzine A.
TubocurarineThe therapeutic efficacy of Tubocurarine can be decreased when used in combination with Huperzine A.
UmeclidiniumThe therapeutic efficacy of Umeclidinium can be decreased when used in combination with Huperzine A.
VareniclineThe risk or severity of adverse effects can be increased when Huperzine A is combined with Varenicline.
VecuroniumThe therapeutic efficacy of Vecuronium can be decreased when used in combination with Huperzine A.
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Serine hydrolase activity
Specific Function:
Terminates signal transduction at the neuromuscular junction by rapid hydrolysis of the acetylcholine released into the synaptic cleft. Role in neuronal apoptosis.
Gene Name:
ACHE
Uniprot ID:
P22303
Molecular Weight:
67795.525 Da
References
  1. Zangara A: The psychopharmacology of huperzine A: an alkaloid with cognitive enhancing and neuroprotective properties of interest in the treatment of Alzheimer's disease. Pharmacol Biochem Behav. 2003 Jun;75(3):675-86. [PubMed:12895686 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Serine hydrolase activity
Specific Function:
Terminates signal transduction at the neuromuscular junction by rapid hydrolysis of the acetylcholine released into the synaptic cleft. Role in neuronal apoptosis.
Gene Name:
ACHE
Uniprot ID:
P22303
Molecular Weight:
67795.525 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]
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Drug created on October 19, 2007 17:03 / Updated on August 17, 2016 12:24