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Identification
- Generic Name
- Zanapezil
- DrugBank Accession Number
- DB04859
- Background
Zanapezil (TAK-147) is a selective acetylcholine (ACh) esterase inhibitor under investigation as a drug for Alzheimer's disease (AD) treatment.
- Type
- Small Molecule
- Groups
- Investigational
- Structure
Structure for Zanapezil (DB04859)
- Weight
- Average: 376.5344
Monoisotopic: 376.251463656 - Chemical Formula
- C25H32N2O
- Synonyms
- Zanapezil
- Zanepezil
- External IDs
- TAK-147
Pharmacology
- Indication
For the treatment of dementia in subjects with Alzheimer’s disease.
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Zanapezil is an acetylcholinesterase inhibitor being developed by Takeda for the treatment of dementia in subjects with Alzheimer’s disease. In May 2003, the company discontinued development of the compound due to a lack of a dose-dependent effect in the trials.
- Mechanism of action
Zanapezil inhibits the degradation of acetylcholine, a neurotransmitter, to prevent the reduction of cerebral acetylcholine levels and to enhance the mental function of patients with dementia. It is expected to act selectively on the central nervous system, resulting in fewer peripheral adverse reactions.
Target Actions Organism AAcetylcholinesterase inhibitorHumans - 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 n-benzylpiperidines. These are heterocyclic Compounds containing a piperidine ring conjugated to a benzyl group through one nitrogen ring atom.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Piperidines
- Sub Class
- Benzylpiperidines
- Direct Parent
- N-benzylpiperidines
- Alternative Parents
- Butyrophenones / Benzazepines / Phenylmethylamines / Benzylamines / Aryl alkyl ketones / Secondary alkylarylamines / Azepines / Aralkylamines / Trialkylamines / Azacyclic compounds show 3 more
- Substituents
- Amine / Aralkylamine / Aromatic heteropolycyclic compound / Aryl alkyl ketone / Aryl ketone / Azacycle / Azepine / Benzazepine / Benzenoid / Benzylamine show 16 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 0A0800O89N
- CAS number
- 142852-50-4
- InChI Key
- PMBLXLOXUGVTGB-UHFFFAOYSA-N
- InChI
- InChI=1S/C25H32N2O/c28-25(23-11-10-22-8-4-5-15-26-24(22)18-23)12-9-20-13-16-27(17-14-20)19-21-6-2-1-3-7-21/h1-3,6-7,10-11,18,20,26H,4-5,8-9,12-17,19H2
- IUPAC Name
- 3-(1-benzylpiperidin-4-yl)-1-(2,3,4,5-tetrahydro-1H-1-benzazepin-8-yl)propan-1-one
- SMILES
- O=C(CCC1CCN(CC2=CC=CC=C2)CC1)C1=CC2=C(CCCCN2)C=C1
References
- General References
- Hatip-Al-Khatib I, Takashi A, Egashira N, Iwasaki K, Fujiwara M: Comparison of the effect of TAK-147 (zanapezil) and E-2020 (donepezil) on extracellular acetylcholine level and blood flow in the ventral hippocampus of freely moving rats. Brain Res. 2004 Jun 25;1012(1-2):169-76. [Article]
- Hatip-Al-Khatib I, Iwasaki K, Yoshimitsu Y, Arai T, Egashira N, Mishima K, Ikeda T, Fujiwara M: Effect of oral administration of zanapezil (TAK-147) for 21 days on acetylcholine and monoamines levels in the ventral hippocampus of freely moving rats. Br J Pharmacol. 2005 Aug;145(8):1035-44. [Article]
- External Links
- PubChem Compound
- 198752
- PubChem Substance
- 175426869
- ChemSpider
- 172025
- BindingDB
- 50037157
- ChEMBL
- CHEMBL75013
Clinical Trials
- Clinical Trials
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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 Water Solubility 0.000615 mg/mL ALOGPS logP 5.15 ALOGPS logP 4.78 Chemaxon logS -5.8 ALOGPS pKa (Strongest Acidic) 16.97 Chemaxon pKa (Strongest Basic) 9.24 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 32.34 Å2 Chemaxon Rotatable Bond Count 6 Chemaxon Refractivity 118.68 m3·mol-1 Chemaxon Polarizability 45.36 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 Yes Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.982 Blood Brain Barrier + 0.9946 Caco-2 permeable + 0.5583 P-glycoprotein substrate Substrate 0.7921 P-glycoprotein inhibitor I Inhibitor 0.9285 P-glycoprotein inhibitor II Non-inhibitor 0.5815 Renal organic cation transporter Inhibitor 0.7487 CYP450 2C9 substrate Non-substrate 0.8537 CYP450 2D6 substrate Substrate 0.781 CYP450 3A4 substrate Non-substrate 0.5592 CYP450 1A2 substrate Inhibitor 0.642 CYP450 2C9 inhibitor Non-inhibitor 0.9477 CYP450 2D6 inhibitor Inhibitor 0.8139 CYP450 2C19 inhibitor Non-inhibitor 0.9217 CYP450 3A4 inhibitor Non-inhibitor 0.5365 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.6221 Ames test Non AMES toxic 0.7535 Carcinogenicity Non-carcinogens 0.9435 Biodegradation Not ready biodegradable 0.9824 Rat acute toxicity 2.8114 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.5952 hERG inhibition (predictor II) Inhibitor 0.8697
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-004i-0009000000-d4617b3799943ec6c259 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-004i-0019000000-b60c6c6f94392bdf83fa Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-004i-0309000000-4b8635e72d084a79411a Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-004i-0009000000-89f04d7bfe9ebf9d9b12 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0006-6395000000-3aace9ae337aa3ab251a Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-05be-1922000000-a6dfd7e0d29fb21e11ef Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 192.9204 predictedDeepCCS 1.0 (2019) [M+H]+ 195.2784 predictedDeepCCS 1.0 (2019) [M+Na]+ 202.34438 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Hydrolyzes rapidly the acetylcholine neurotransmitter released into the synaptic cleft allowing to terminate the signal transduction at the neuromuscular junction. Role in neuronal apoptosis.
- Specific Function
- acetylcholine binding
- Gene Name
- ACHE
- Uniprot ID
- P22303
- Uniprot Name
- Acetylcholinesterase
- Molecular Weight
- 67795.525 Da
References
- Hatip-Al-Khatib I, Iwasaki K, Yoshimitsu Y, Arai T, Egashira N, Mishima K, Ikeda T, Fujiwara M: Effect of oral administration of zanapezil (TAK-147) for 21 days on acetylcholine and monoamines levels in the ventral hippocampus of freely moving rats. Br J Pharmacol. 2005 Aug;145(8):1035-44. [Article]
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
Drug created at October 19, 2007 00:46 / Updated at August 26, 2024 19:22