Huperzine B

Identification

Generic Name
Huperzine B
DrugBank Accession Number
DB03348
Background

Huperzine B is a novel acetylcholinesterase inhibitor.

Type
Small Molecule
Groups
Investigational
Structure
Thumb
Weight
Average: 256.3428
Monoisotopic: 256.157563272
Chemical Formula
C16H20N2O
Synonyms
  • HupB

Pharmacology

Indication

Under investigation for the treatment of Alzheimer's disease.

Pharmacology
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Contraindications & Blackbox Warnings
Contraindications
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Pharmacodynamics

Huperzine 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 action

Huperzine 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.

TargetActionsOrganism
UAcetylcholinesteraseNot AvailableHumans
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
Medicalerrors
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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.
Not Available
Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This 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.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Phenanthrolines
Sub Class
Not Available
Direct Parent
Phenanthrolines
Alternative Parents
Quinolones and derivatives / Pyridinones / Aralkylamines / Piperidines / Heteroaromatic compounds / Lactams / Dialkylamines / Azacyclic compounds / Organooxygen compounds / Organic oxides
show 1 more
Substituents
1,7-phenanthroline / Amine / Aralkylamine / Aromatic heteropolycyclic compound / Azacycle / Heteroaromatic compound / Hydrocarbon derivative / Lactam / Organic nitrogen compound / Organic oxide
show 9 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
Not Available
CAS number
103548-82-9
InChI Key
YYWGABLTRMRUIT-HWWQOWPSSA-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)/t11-,12+,16+/m0/s1
IUPAC Name
(1R,9R,10R)-16-methyl-6,14-diazatetracyclo[7.5.3.0^{1,10}.0^{2,7}]heptadeca-2(7),3,16-trien-5-one
SMILES
[H][C@]12CCCN[C@]11CC(C)=C[C@H]2CC2=C1C=CC(=O)N2

References

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. [Article]
  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. [Article]
  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. [Article]
KEGG Compound
C09866
PubChem Compound
5462442
PubChem Substance
175426855
ChemSpider
16744040
BindingDB
50199518
ChEMBL
CHEMBL245079
ZINC
ZINC000003872828
PDBe Ligand
HUB
PDB Entries
1gpn

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
logP0.67ChemAxon
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
Polarizability28.42 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
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

Targets

Drugtargets
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Details
1. Acetylcholinesterase
Kind
Protein
Organism
Humans
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
Uniprot Name
Acetylcholinesterase
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. [Article]
  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. [Article]

Drug created on June 13, 2005 13:24 / Updated on June 12, 2020 16:52