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Identification
NameHuperzine B
Accession NumberDB03348  (EXPT01794)
TypeSmall Molecule
GroupsInvestigational
Description

Huperzine B is a novel acetylcholinesterase inhibitor.

Structure
Thumb
Synonyms
HUB
HupB
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
UNIINot Available
CAS number103548-82-9
WeightAverage: 256.3428
Monoisotopic: 256.157563272
Chemical FormulaC16H20N2O
InChI KeyInChIKey=YYWGABLTRMRUIT-UHFFFAOYSA-N
InChI
InChI=1S/C16H20N2O/c1-10-7-11-8-14-13(4-5-15(19)18-14)16(9-10)12(11)3-2-6-17-16/h4-5,7,11-12,17H,2-3,6,8-9H2,1H3,(H,18,19)
IUPAC Name
16-methyl-6,14-diazatetracyclo[7.5.3.0¹,¹⁰.0²,⁷]heptadeca-2(7),3,16-trien-5-one
SMILES
CC1=CC2CC3=C(C=CC(=O)N3)C3(C1)NCCCC23
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as phenanthrolines. These are aromatic polycyclic compounds containing the phenanthroline skeleton, which is a derivative of phenanthrene, and consists of two pyridine rings non-linearly joined by a benzene ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPhenanthrolines
Sub ClassNot Available
Direct ParentPhenanthrolines
Alternative Parents
Substituents
  • 1,7-phenanthroline
  • Quinolone
  • Aralkylamine
  • Pyridinone
  • Pyridine
  • Piperidine
  • Heteroaromatic compound
  • Lactam
  • Azacycle
  • Secondary amine
  • Secondary aliphatic amine
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationUnder investigation for the treatment of Alzheimer's disease.
PharmacodynamicsHuperzine B 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 B is comparably effective to the drugs currently on the market, and may even be somewhat safer in terms of side effects.
Mechanism of actionHuperzine B 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+0.9953
Blood Brain Barrier+0.9465
Caco-2 permeable-0.537
P-glycoprotein substrateSubstrate0.8401
P-glycoprotein inhibitor INon-inhibitor0.6301
P-glycoprotein inhibitor IINon-inhibitor0.8246
Renal organic cation transporterNon-inhibitor0.5913
CYP450 2C9 substrateNon-substrate0.8044
CYP450 2D6 substrateNon-substrate0.7676
CYP450 3A4 substrateSubstrate0.6455
CYP450 1A2 substrateNon-inhibitor0.5655
CYP450 2C9 inhibitorNon-inhibitor0.5898
CYP450 2D6 inhibitorNon-inhibitor0.7528
CYP450 2C19 inhibitorNon-inhibitor0.5068
CYP450 3A4 inhibitorNon-inhibitor0.8313
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.5088
Ames testNon AMES toxic0.682
CarcinogenicityNon-carcinogens0.9566
BiodegradationNot ready biodegradable0.9931
Rat acute toxicity2.7113 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9721
hERG inhibition (predictor II)Inhibitor0.5546
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 PropertiesNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.188 mg/mLALOGPS
logP1.31ALOGPS
logP0.67ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)11.22ChemAxon
pKa (Strongest Basic)9.77ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area41.13 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity78.06 m3·mol-1ChemAxon
Polarizability28.43 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis ReferenceNot Available
General References
  1. Zhang HY, Tang XC: Huperzine B, a novel acetylcholinesterase inhibitor, attenuates hydrogen peroxide induced injury in PC12 cells. Neurosci Lett. 2000 Sep 29;292(1):41-4. [PubMed:10996445 ]
  2. Feng S, Xia Y, Han D, Zheng C, He X, Tang X, Bai D: Synthesis and acetylcholinesterase inhibition of derivatives of huperzine B. Bioorg Med Chem Lett. 2005 Feb 1;15(3):523-6. [PubMed:15664805 ]
  3. He XC, Feng S, Wang ZF, Shi Y, Zheng S, Xia Y, Jiang H, Tang XC, Bai D: Study on dual-site inhibitors of acetylcholinesterase: Highly potent derivatives of bis- and bifunctional huperzine B. Bioorg Med Chem. 2007 Feb 1;15(3):1394-408. Epub 2006 Nov 9. [PubMed:17126020 ]
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
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. He XC, Feng S, Wang ZF, Shi Y, Zheng S, Xia Y, Jiang H, Tang XC, Bai D: Study on dual-site inhibitors of acetylcholinesterase: Highly potent derivatives of bis- and bifunctional huperzine B. Bioorg Med Chem. 2007 Feb 1;15(3):1394-408. Epub 2006 Nov 9. [PubMed:17126020 ]
  2. 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 June 13, 2005 07:24 / Updated on August 17, 2016 12:23