Explore a selection of our essential drug information below, or:
Identification
- Generic Name
- Osanetant
- DrugBank Accession Number
- DB04872
- Background
Developed by Sanofi-Aventis (formerly Sanofi-Synthelabo), osanetant (SR-142801) is an NK3 receptor antagonist which was under development for the treatment of schizophrenia and other Central Nervous System (CNS) disorders. In a review of its R&D portfolio, the company announced in August 2005 that it would cease any further development of osanetant. This follows an earlier decision to discontinue development of eplivanserin for schizophrenia.
- Type
- Small Molecule
- Groups
- Investigational
- Structure
Structure for Osanetant (DB04872)
- Weight
- Average: 606.625
Monoisotopic: 605.257582985 - Chemical Formula
- C35H41Cl2N3O2
- Synonyms
- Osanetant
- External IDs
- SR 142801
- SR-142801
- SR142801
Pharmacology
- Indication
Potential therapy for schizophrenia, depression and visceral pain.
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Osanetant is a neurokinin-3 (NK3) receptor antagonist. Preliminary clinical trials have demonstrated that osanetant is superior to placebo on global assessment of efficacy and measures of positive symptoms in schizophrenia.
- Mechanism of action
The mechanism of action of osanetant is uncertain at this point. Various preclinical data indicate that activation of NK3 receptors enhances the release of biogenic amines, including dopamine and serotonin. NK3 receptor antagonists could block NK3-receptor-mediated activation of these systems.
Target Actions Organism ANeuromedin-K receptor antagonistHumans - 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.
Drug Interaction Integrate drug-drug
interactions in your software1,2-Benzodiazepine The risk or severity of CNS depression can be increased when Osanetant is combined with 1,2-Benzodiazepine. Acetazolamide The risk or severity of CNS depression can be increased when Acetazolamide is combined with Osanetant. Acetophenazine The risk or severity of CNS depression can be increased when Acetophenazine is combined with Osanetant. Agomelatine The risk or severity of CNS depression can be increased when Osanetant is combined with Agomelatine. Alfentanil The risk or severity of CNS depression can be increased when Alfentanil is combined with Osanetant. - Food Interactions
- Not Available
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as 1-benzoylpiperidines. These are compounds containing a piperidine ring substituted at the 1-position with a benzoyl group.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Benzene and substituted derivatives
- Sub Class
- Benzoyl derivatives
- Direct Parent
- 1-benzoylpiperidines
- Alternative Parents
- N-benzoylpiperidines / Phenylpiperidines / Phenylbutylamines / Benzamides / Dichlorobenzenes / Aralkylamines / Aryl chlorides / Tertiary carboxylic acid amides / Acetamides / Trialkylamines show 7 more
- Substituents
- 1,2-dichlorobenzene / 1-benzoylpiperidine / Acetamide / Amine / Amino acid or derivatives / Aralkylamine / Aromatic heteromonocyclic compound / Aryl chloride / Aryl halide / Azacycle show 25 more
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- K7G81N94DT
- CAS number
- 160492-56-8
- InChI Key
- DZOJBGLFWINFBF-UMSFTDKQSA-N
- InChI
- InChI=1S/C35H41Cl2N3O2/c1-27(41)38(2)35(29-13-7-4-8-14-29)19-23-39(24-20-35)21-9-17-34(30-15-16-31(36)32(37)25-30)18-10-22-40(26-34)33(42)28-11-5-3-6-12-28/h3-8,11-16,25H,9-10,17-24,26H2,1-2H3/t34-/m0/s1
- IUPAC Name
- N-(1-{3-[(3R)-1-benzoyl-3-(3,4-dichlorophenyl)piperidin-3-yl]propyl}-4-phenylpiperidin-4-yl)-N-methylacetamide
- SMILES
- CN(C(C)=O)C1(CCN(CCC[C@@]2(CCCN(C2)C(=O)C2=CC=CC=C2)C2=CC(Cl)=C(Cl)C=C2)CC1)C1=CC=CC=C1
References
- General References
- Kronenberg G, Berger P, Tauber RF, Bandelow B, Henkel V, Heuser I: Randomized, double-blind study of SR142801 (Osanetant). A novel neurokinin-3 (NK3) receptor antagonist in panic disorder with pre- and posttreatment cholecystokinin tetrapeptide (CCK-4) challenges. Pharmacopsychiatry. 2005 Jan;38(1):24-9. [Article]
- Kamali F: Osanetant Sanofi-Synthelabo. Curr Opin Investig Drugs. 2001 Jul;2(7):950-6. [Article]
- External Links
- PubChem Compound
- 219077
- PubChem Substance
- 175426879
- ChemSpider
- 189901
- BindingDB
- 50291261
- ChEMBL
- CHEMBL346178
- ZINC
- ZINC000003935475
- Wikipedia
- Osanetant
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample data1, 2 Completed Treatment Postmenopausal Vasomotor Symptoms 1 somestatus stop reason just information to hide 0 Terminated Treatment Adenocarcinoma of Prostate 1 somestatus stop reason just information to hide 0 Withdrawn Treatment Adenocarcinoma of Prostate 1 somestatus stop reason just information to hide
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 0.000154 mg/mL ALOGPS logP 6.47 ALOGPS logP 6.27 Chemaxon logS -6.6 ALOGPS pKa (Strongest Basic) 9.3 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 43.86 Å2 Chemaxon Rotatable Bond Count 8 Chemaxon Refractivity 172.73 m3·mol-1 Chemaxon Polarizability 66.14 Å3 Chemaxon Number of Rings 5 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9486 Blood Brain Barrier + 0.9882 Caco-2 permeable + 0.5767 P-glycoprotein substrate Substrate 0.6866 P-glycoprotein inhibitor I Inhibitor 0.7694 P-glycoprotein inhibitor II Inhibitor 0.837 Renal organic cation transporter Inhibitor 0.5525 CYP450 2C9 substrate Non-substrate 0.8013 CYP450 2D6 substrate Non-substrate 0.6861 CYP450 3A4 substrate Substrate 0.7427 CYP450 1A2 substrate Non-inhibitor 0.9532 CYP450 2C9 inhibitor Non-inhibitor 0.9439 CYP450 2D6 inhibitor Inhibitor 0.5109 CYP450 2C19 inhibitor Non-inhibitor 0.8248 CYP450 3A4 inhibitor Non-inhibitor 0.703 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.7353 Ames test Non AMES toxic 0.7977 Carcinogenicity Non-carcinogens 0.8292 Biodegradation Not ready biodegradable 0.994 Rat acute toxicity 2.8030 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9523 hERG inhibition (predictor II) Inhibitor 0.8584
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 227.06737 predictedDeepCCS 1.0 (2019) [M+H]+ 229.02464 predictedDeepCCS 1.0 (2019) [M+Na]+ 234.76506 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Antagonist
- General Function
- This is a receptor for the tachykinin neuropeptide neuromedin-K (neurokinin B). It is associated with G proteins that activate a phosphatidylinositol-calcium second messenger system. The rank order of affinity of this receptor to tachykinins is: neuromedin-K > substance K > substance P
- Specific Function
- tachykinin receptor activity
- Gene Name
- TACR3
- Uniprot ID
- P29371
- Uniprot Name
- Neuromedin-K receptor
- Molecular Weight
- 52201.35 Da
References
- Tian G, Wilkins D, Scott CW: Neurokinin-3 receptor-specific antagonists talnetant and osanetant show distinct mode of action in cellular Ca2+ mobilization but display similar binding kinetics and identical mechanism of binding in ligand cross-competition. Mol Pharmacol. 2007 Mar;71(3):902-11. Epub 2006 Dec 15. [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 20, 2007 10:46 / Updated at August 26, 2024 19:22