Minaprine
Identification
- Generic Name
- Minaprine
- DrugBank Accession Number
- DB00805
- Background
Minaprine is a psychotropic drug which has proved to be effective in the treatment of various depressive states. Like most antidepressants minaprine antagonizes behavioral despair. Minaprine is an amino-phenylpyridazine antidepressant reported to be relatively free of cardiotoxicity, drowsiness, and weight gain.
- Type
- Small Molecule
- Groups
- Approved
- Structure
- Weight
- Average: 298.3828
Monoisotopic: 298.179361346 - Chemical Formula
- C17H22N4O
- Synonyms
- 4-(2-((4-Methyl-6-phenyl-3-pyridazinyl)amino)ethyl)morpholine
- 4-Methyl-3-(2-morpholinoethylamino)-6-phenylpyridazin
- Minaprina
- Minaprine
- Minaprinum
- N-(4-Methyl-6-phenyl-3-pyridazinyl)-4-morpholineethanamine
- External IDs
- AGR-1240
- CB-30038
Pharmacology
- Indication
For the treatment of depression
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- Pharmacodynamics
Minaprine is an amino-phenylpyridazine antidepressant reported to be relatively free of cardiotoxicity, drowsiness, and weight gain. Similar to other antidepressant treatments, minaprine attenuates the beta-adrenergic receptor function. Studies have also shown that minaprine improves memory consolidation and that repeated drug administration leads to potentiation of this effect. Moreover, the effects of minaprine on memory consolidation are related to its dopaminergic action.
- Mechanism of action
Minaprine binds to serotonin type 2 receptors and to dopamine D1 and D2 type receptors. It also binds to the serotonin reuptake pump. Therefore, minaprine blocks the reuptake of both dopamine and serotonin. It is also, to a slight degree, cholinomimetic. Thus it may exhibit both mood-brightening and nootropic properties. It also acts as a reversible inhibitor of MAO-A (RIMA).It has also been found to inhibit acetylcholinesterase.
Target Actions Organism AAmine oxidase [flavin-containing] A inhibitorHumans A5-hydroxytryptamine receptor 2B antagonistHumans A5-hydroxytryptamine receptor 2A antagonistHumans A5-hydroxytryptamine receptor 2C antagonistHumans AAcetylcholinesterase inhibitorHumans USodium-dependent serotonin transporter inhibitorHumans UDopamine D1 receptor agonistHumans UDopamine D2 receptor agonistHumans UMuscarinic acetylcholine receptor M1 agonistHumans - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
Hepatic. Cytochrome P4502D is responsible for the 4-hydroxylation of minaprine to 4-hydroxyminaprine.
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- 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 Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- 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 Minaprine is combined with 1,2-Benzodiazepine. Abaloparatide Minaprine may increase the orthostatic hypotensive activities of Abaloparatide. Abatacept The metabolism of Minaprine can be increased when combined with Abatacept. Abciximab The risk or severity of bleeding and hemorrhage can be increased when Minaprine is combined with Abciximab. Abiraterone The metabolism of Minaprine can be decreased when combined with Abiraterone. - Food Interactions
- Not Available
Products
- Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.
- Product Ingredients
Ingredient UNII CAS InChI Key Minaprine dihydrochloride 82Y7NT6DFT 25953-17-7 GNUCGROXDZMCJI-UHFFFAOYSA-N - International/Other Brands
- Cantor (Sanofi-Aventis)
Categories
- ATC Codes
- N06AX07 — Minaprine
- Drug Categories
- Agents that produce hypertension
- Agents that reduce seizure threshold
- Antidepressive Agents
- Central Nervous System Agents
- Central Nervous System Depressants
- Central Nervous System Stimulants
- Cholinesterase Inhibitors
- Cytochrome P-450 CYP2D6 Substrates
- Cytochrome P-450 Substrates
- Monoamine Oxidase A Inhibitors for interaction with Monoamine Oxidase A substrates
- Monoamine Oxidase Inhibitors
- Nervous System
- Psychoanaleptics
- Psychotropic Drugs
- Serotonergic Drugs Shown to Increase Risk of Serotonin Syndrome
- Serotonin 5-HT2 Receptor Antagonists
- Serotonin 5-HT2A Receptor Antagonists
- Serotonin 5-HT2C Receptor Antagonists
- Serotonin Agents
- Serotonin Receptor Antagonists
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as phenylpyridazines. These are organic compounds containing a pyridazine ring substituted by a phenyl group.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Diazines
- Sub Class
- Pyridazines and derivatives
- Direct Parent
- Phenylpyridazines
- Alternative Parents
- Morpholines / Imidolactams / Benzene and substituted derivatives / Heteroaromatic compounds / Trialkylamines / Oxacyclic compounds / Dialkyl ethers / Azacyclic compounds / Organopnictogen compounds / Hydrocarbon derivatives
- Substituents
- Amine / Aromatic heteromonocyclic compound / Azacycle / Benzenoid / Dialkyl ether / Ether / Heteroaromatic compound / Hydrocarbon derivative / Imidolactam / Monocyclic benzene moiety
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- secondary amine, pyridazines, morpholines (CHEBI:51038)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 00U7GX0NLM
- CAS number
- 25905-77-5
- InChI Key
- LDMWSLGGVTVJPG-UHFFFAOYSA-N
- InChI
- InChI=1S/C17H22N4O/c1-14-13-16(15-5-3-2-4-6-15)19-20-17(14)18-7-8-21-9-11-22-12-10-21/h2-6,13H,7-12H2,1H3,(H,18,20)
- IUPAC Name
- 4-methyl-N-[2-(morpholin-4-yl)ethyl]-6-phenylpyridazin-3-amine
- SMILES
- CC1=CC(=NN=C1NCCN1CCOCC1)C1=CC=CC=C1
References
- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0014943
- KEGG Drug
- D05039
- PubChem Compound
- 4199
- PubChem Substance
- 46505380
- ChemSpider
- 4054
- BindingDB
- 50074289
- 30031
- ChEBI
- 51038
- ChEMBL
- CHEMBL278819
- ZINC
- ZINC000019796082
- Therapeutic Targets Database
- DAP000475
- PharmGKB
- PA164748351
- Wikipedia
- Minaprine
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 122 °C PhysProp water solubility 2360 mg/L Not Available logP 2.03 HANSCH,C ET AL. (1995) - Predicted Properties
Property Value Source Water Solubility 0.0701 mg/mL ALOGPS logP 2.15 ALOGPS logP 2.19 Chemaxon logS -3.6 ALOGPS pKa (Strongest Acidic) 19.25 Chemaxon pKa (Strongest Basic) 6.28 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 5 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 50.28 Å2 Chemaxon Rotatable Bond Count 5 Chemaxon Refractivity 91.17 m3·mol-1 Chemaxon Polarizability 33.82 Å3 Chemaxon Number of Rings 3 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 + 1.0 Blood Brain Barrier + 0.9843 Caco-2 permeable + 0.5161 P-glycoprotein substrate Substrate 0.7122 P-glycoprotein inhibitor I Inhibitor 0.5884 P-glycoprotein inhibitor II Non-inhibitor 0.6707 Renal organic cation transporter Non-inhibitor 0.5938 CYP450 2C9 substrate Non-substrate 0.8053 CYP450 2D6 substrate Substrate 0.8918 CYP450 3A4 substrate Non-substrate 0.5794 CYP450 1A2 substrate Inhibitor 0.9106 CYP450 2C9 inhibitor Non-inhibitor 0.9071 CYP450 2D6 inhibitor Inhibitor 0.576 CYP450 2C19 inhibitor Non-inhibitor 0.9025 CYP450 3A4 inhibitor Inhibitor 0.7959 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.5741 Ames test Non AMES toxic 0.7642 Carcinogenicity Non-carcinogens 0.7084 Biodegradation Not ready biodegradable 0.9972 Rat acute toxicity 2.4667 LD50, mol/kg Not applicable hERG inhibition (predictor I) Strong inhibitor 0.7911 hERG inhibition (predictor II) Inhibitor 0.6866
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-0uds-7950000000-d5d6a90ec878b84d8656 Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-0002-0090000000-8e8f591e1f9da5d5ca57 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0002-0290000000-c3c7ebe246de636ef053 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-001i-0390000000-06eb14d2a218d59ca5c8 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-02cb-1890000000-0e34c7b528359e61fc65 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-03l0-6960000000-d1c60667be1203e8a5fe Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-00mo-3950000000-abb1b71d41b24cd88406 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]- 181.3421384 predictedDarkChem Lite v0.1.0 [M-H]- 166.6946 predictedDeepCCS 1.0 (2019) [M+H]+ 181.8582384 predictedDarkChem Lite v0.1.0 [M+H]+ 169.0526 predictedDeepCCS 1.0 (2019) [M+Na]+ 181.5856384 predictedDarkChem Lite v0.1.0 [M+Na]+ 175.14575 predictedDeepCCS 1.0 (2019)
Targets
![](https://go.drugbank.com/assets/locked/DrugTargets2-682eb846d210ae4bf33ca03febccfb57bb1c61318e699b729e5df4dfab2c5b67.png)
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Serotonin binding
- Specific Function
- Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral...
- Gene Name
- MAOA
- Uniprot ID
- P21397
- Uniprot Name
- Amine oxidase [flavin-containing] A
- Molecular Weight
- 59681.27 Da
References
- Kan JP, Mouget-Goniot C, Worms P, Biziere K: Effect of the antidepressant minaprine on both forms of monoamine oxidase in the rat. Biochem Pharmacol. 1986 Mar 15;35(6):973-8. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Antagonist
- General Function
- Serotonin receptor activity
- Specific Function
- G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various ergot alkaloid derivatives and psychoactive substances. Ligand binding causes a conformation...
- Gene Name
- HTR2B
- Uniprot ID
- P41595
- Uniprot Name
- 5-hydroxytryptamine receptor 2B
- Molecular Weight
- 54297.41 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
- Kodama K, Shibata S, Ueki S: Protective effect of minaprine against the abnormal changes of 2-deoxyglucose uptake by rat hippocampal slices induced by hypoxia/hypoglycemia. Jpn J Pharmacol. 1992 Sep;60(1):33-8. [Article]
- Muramatsu M, Tamaki-Ohashi J, Usuki C, Araki H, Chaki S, Aihara H: 5-HT2 antagonists and minaprine block the 5-HT-induced inhibition of dopamine release from rat brain striatal slices. Eur J Pharmacol. 1988 Aug 9;153(1):89-95. [Article]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Antagonist
- General Function
- Virus receptor activity
- Specific Function
- G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various drugs and psychoactive substances, including mescaline, psilocybin, 1-(2,5-dimethoxy-4-iodop...
- Gene Name
- HTR2A
- Uniprot ID
- P28223
- Uniprot Name
- 5-hydroxytryptamine receptor 2A
- Molecular Weight
- 52602.58 Da
References
- Kodama K, Shibata S, Ueki S: Protective effect of minaprine against the abnormal changes of 2-deoxyglucose uptake by rat hippocampal slices induced by hypoxia/hypoglycemia. Jpn J Pharmacol. 1992 Sep;60(1):33-8. [Article]
- Nabeshima T, Kawashima K, Kameyama T: Effect of minaprine on cycloheximide-induced amnesia in mice. Eur J Pharmacol. 1989 Oct 10;169(2-3):249-57. [Article]
- Muramatsu M, Tamaki-Ohashi J, Usuki C, Araki H, Chaki S, Aihara H: 5-HT2 antagonists and minaprine block the 5-HT-induced inhibition of dopamine release from rat brain striatal slices. Eur J Pharmacol. 1988 Aug 9;153(1):89-95. [Article]
- Biziere K, Worms P, Kan JP, Mandel P, Garattini S, Roncucci R: Minaprine, a new drug with antidepressant properties. Drugs Exp Clin Res. 1985;11(12):831-40. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Antagonist
- General Function
- Serotonin receptor activity
- Specific Function
- G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various drugs and psychoactive substances, including ergot alkaloid derivatives, 1-2,5,-dimethoxy-4-...
- Gene Name
- HTR2C
- Uniprot ID
- P28335
- Uniprot Name
- 5-hydroxytryptamine receptor 2C
- Molecular Weight
- 51820.705 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
- Kodama K, Shibata S, Ueki S: Protective effect of minaprine against the abnormal changes of 2-deoxyglucose uptake by rat hippocampal slices induced by hypoxia/hypoglycemia. Jpn J Pharmacol. 1992 Sep;60(1):33-8. [Article]
- Muramatsu M, Tamaki-Ohashi J, Usuki C, Araki H, Chaki S, Aihara H: 5-HT2 antagonists and minaprine block the 5-HT-induced inhibition of dopamine release from rat brain striatal slices. Eur J Pharmacol. 1988 Aug 9;153(1):89-95. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- 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
- Duarte CD, Barreiro EJ, Fraga CA: Privileged structures: a useful concept for the rational design of new lead drug candidates. Mini Rev Med Chem. 2007 Nov;7(11):1108-19. [Article]
- Contreras JM, Rival YM, Chayer S, Bourguignon JJ, Wermuth CG: Aminopyridazines as acetylcholinesterase inhibitors. J Med Chem. 1999 Feb 25;42(4):730-41. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- Curator comments
- As an anti-depressant with mechanisms influencing serotonin levels, there is strong potential that Minaprine interacts with this target.
- General Function
- Serotonin:sodium symporter activity
- Specific Function
- Serotonin transporter whose primary function in the central nervous system involves the regulation of serotonergic signaling via transport of serotonin molecules from the synaptic cleft back into t...
- Gene Name
- SLC6A4
- Uniprot ID
- P31645
- Uniprot Name
- Sodium-dependent serotonin transporter
- Molecular Weight
- 70324.165 Da
References
- Schloss P, Williams DC: The serotonin transporter: a primary target for antidepressant drugs. J Psychopharmacol. 1998;12(2):115-21. doi: 10.1177/026988119801200201. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Agonist
- General Function
- G-protein coupled amine receptor activity
- Specific Function
- Dopamine receptor whose activity is mediated by G proteins which activate adenylyl cyclase.
- Gene Name
- DRD1
- Uniprot ID
- P21728
- Uniprot Name
- D(1A) dopamine receptor
- Molecular Weight
- 49292.765 Da
References
- Puglisi-Allegra S, Cabib S, Cestari V, Castellano C: Post-training minaprine enhances memory storage in mice: involvement of D1 and D2 dopamine receptors. Psychopharmacology (Berl). 1994 Jan;113(3-4):476-80. doi: 10.1007/BF02245226. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Agonist
- General Function
- Potassium channel regulator activity
- Specific Function
- Dopamine receptor whose activity is mediated by G proteins which inhibit adenylyl cyclase.
- Gene Name
- DRD2
- Uniprot ID
- P14416
- Uniprot Name
- D(2) dopamine receptor
- Molecular Weight
- 50618.91 Da
References
- Puglisi-Allegra S, Cabib S, Cestari V, Castellano C: Post-training minaprine enhances memory storage in mice: involvement of D1 and D2 dopamine receptors. Psychopharmacology (Berl). 1994 Jan;113(3-4):476-80. doi: 10.1007/BF02245226. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Agonist
- General Function
- Phosphatidylinositol phospholipase c activity
- Specific Function
- The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the...
- Gene Name
- CHRM1
- Uniprot ID
- P11229
- Uniprot Name
- Muscarinic acetylcholine receptor M1
- Molecular Weight
- 51420.375 Da
References
- Duarte CD, Barreiro EJ, Fraga CA: Privileged structures: a useful concept for the rational design of new lead drug candidates. Mini Rev Med Chem. 2007 Nov;7(11):1108-19. [Article]
- Worms P, Kan JP, Steinberg R, Terranova JP, Perio A, Biziere K: Cholinomimetic activities of minaprine. Naunyn Schmiedebergs Arch Pharmacol. 1989 Oct;340(4):411-8. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Steroid hydroxylase activity
- Specific Function
- Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
- Gene Name
- CYP2D6
- Uniprot ID
- P10635
- Uniprot Name
- Cytochrome P450 2D6
- Molecular Weight
- 55768.94 Da
References
- Chico LK, Behanna HA, Hu W, Zhong G, Roy SM, Watterson DM: Molecular properties and CYP2D6 substrates: central nervous system therapeutics case study and pattern analysis of a substrate database. Drug Metab Dispos. 2009 Nov;37(11):2204-11. doi: 10.1124/dmd.109.028134. Epub 2009 Aug 6. [Article]
- Puangpetch A, Vanwong N, Nuntamool N, Hongkaew Y, Chamnanphon M, Sukasem C: CYP2D6 polymorphisms and their influence on risperidone treatment. Pharmgenomics Pers Med. 2016 Dec 1;9:131-147. doi: 10.2147/PGPM.S107772. eCollection 2016. [Article]
- Flockhart Table of Drug Interactions [Link]
Drug created at June 13, 2005 13:24 / Updated at February 02, 2024 22:44