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
- Weight
- Average: 256.3428
Monoisotopic: 256.157563272 - Chemical Formula
- C16H20N2O
- Synonyms
- HupB
Pharmacology
- Indication
Under investigation for the treatment of Alzheimer's disease.
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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.
Target Actions Organism UAcetylcholinesterase Not Available Humans - 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. View sample adverse effects data in our new Data Library!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.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
- DC3Z5425Y5
- 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
- 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]
- 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]
- 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]
- External Links
- 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
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
Property Value Source logP 0.67 Chemaxon pKa (Strongest Acidic) 11.22 Chemaxon pKa (Strongest Basic) 9.77 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 41.13 Å2 Chemaxon Rotatable Bond Count 0 Chemaxon Refractivity 78.06 m3·mol-1 Chemaxon Polarizability 28.42 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9953 Blood Brain Barrier + 0.9465 Caco-2 permeable - 0.537 P-glycoprotein substrate Substrate 0.8401 P-glycoprotein inhibitor I Non-inhibitor 0.6301 P-glycoprotein inhibitor II Non-inhibitor 0.8246 Renal organic cation transporter Non-inhibitor 0.5913 CYP450 2C9 substrate Non-substrate 0.8044 CYP450 2D6 substrate Non-substrate 0.7676 CYP450 3A4 substrate Substrate 0.6455 CYP450 1A2 substrate Non-inhibitor 0.5655 CYP450 2C9 inhibitor Non-inhibitor 0.5898 CYP450 2D6 inhibitor Non-inhibitor 0.7528 CYP450 2C19 inhibitor Non-inhibitor 0.5068 CYP450 3A4 inhibitor Non-inhibitor 0.8313 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.5088 Ames test Non AMES toxic 0.682 Carcinogenicity Non-carcinogens 0.9566 Biodegradation Not ready biodegradable 0.9931 Rat acute toxicity 2.7113 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9721 hERG inhibition (predictor II) Inhibitor 0.5546
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key 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
Targets

- 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
- 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]
- 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 at June 13, 2005 13:24 / Updated at June 12, 2020 16:52