NAV

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
3D
Similar Structures
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
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Pharmacology

Indication

For the treatment of depression

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Contraindications & Blackbox Warnings
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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.

TargetActionsOrganism
AAmine oxidase [flavin-containing] A
inhibitor
Humans
A5-hydroxytryptamine receptor 2B
antagonist
Humans
A5-hydroxytryptamine receptor 2A
antagonist
Humans
A5-hydroxytryptamine receptor 2C
antagonist
Humans
AAcetylcholinesterase
inhibitor
Humans
USodium-dependent serotonin transporter
inhibitor
Humans
UDopamine D1 receptor
agonist
Humans
UDopamine D2 receptor
agonist
Humans
UMuscarinic acetylcholine receptor M1
agonist
Humans
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
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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.
DrugInteraction
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1,2-BenzodiazepineThe risk or severity of CNS depression can be increased when Minaprine is combined with 1,2-Benzodiazepine.
AbaloparatideMinaprine may increase the orthostatic hypotensive activities of Abaloparatide.
AbataceptThe metabolism of Minaprine can be increased when combined with Abatacept.
AbciximabThe risk or severity of bleeding and hemorrhage can be increased when Minaprine is combined with Abciximab.
AbirateroneThe metabolism of Minaprine can be decreased when combined with Abiraterone.
Food Interactions
Not Available

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Product Ingredients
IngredientUNIICASInChI Key
Minaprine dihydrochloride82Y7NT6DFT25953-17-7GNUCGROXDZMCJI-UHFFFAOYSA-N
International/Other Brands
Cantor (Sanofi-Aventis)

Categories

ATC Codes
N06AX07 — Minaprine
Drug Categories
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
Human Metabolome Database
HMDB0014943
KEGG Drug
D05039
PubChem Compound
4199
PubChem Substance
46505380
ChemSpider
4054
BindingDB
50074289
RxNav
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);">
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

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

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)122 °CPhysProp
water solubility2360 mg/LNot Available
logP2.03HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility0.0701 mg/mLALOGPS
logP2.15ALOGPS
logP2.19Chemaxon
logS-3.6ALOGPS
pKa (Strongest Acidic)19.25Chemaxon
pKa (Strongest Basic)6.28Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area50.28 Å2Chemaxon
Rotatable Bond Count5Chemaxon
Refractivity91.17 m3·mol-1Chemaxon
Polarizability33.82 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9843
Caco-2 permeable+0.5161
P-glycoprotein substrateSubstrate0.7122
P-glycoprotein inhibitor IInhibitor0.5884
P-glycoprotein inhibitor IINon-inhibitor0.6707
Renal organic cation transporterNon-inhibitor0.5938
CYP450 2C9 substrateNon-substrate0.8053
CYP450 2D6 substrateSubstrate0.8918
CYP450 3A4 substrateNon-substrate0.5794
CYP450 1A2 substrateInhibitor0.9106
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorInhibitor0.576
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorInhibitor0.7959
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.5741
Ames testNon AMES toxic0.7642
CarcinogenicityNon-carcinogens0.7084
BiodegradationNot ready biodegradable0.9972
Rat acute toxicity2.4667 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Strong inhibitor0.7911
hERG inhibition (predictor II)Inhibitor0.6866
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 GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0uds-7950000000-d5d6a90ec878b84d8656
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0002-0090000000-8e8f591e1f9da5d5ca57
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0002-0290000000-c3c7ebe246de636ef053
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-001i-0390000000-06eb14d2a218d59ca5c8
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-02cb-1890000000-0e34c7b528359e61fc65
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-03l0-6960000000-d1c60667be1203e8a5fe
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-00mo-3950000000-abb1b71d41b24cd88406
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-181.3421384
predicted
DarkChem Lite v0.1.0
[M-H]-166.6946
predicted
DeepCCS 1.0 (2019)
[M+H]+181.8582384
predicted
DarkChem Lite v0.1.0
[M+H]+169.0526
predicted
DeepCCS 1.0 (2019)
[M+Na]+181.5856384
predicted
DarkChem Lite v0.1.0
[M+Na]+175.14575
predicted
DeepCCS 1.0 (2019)

Targets

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insights and accelerate drug research.
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Details1. Amine oxidase [flavin-containing] A
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
  1. 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]
Details2. 5-hydroxytryptamine receptor 2B
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
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. 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]
  3. 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]
  4. 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]
  5. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
Details3. 5-hydroxytryptamine receptor 2A
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
  1. 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]
  2. 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]
  3. 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]
  4. 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]
Details4. 5-hydroxytryptamine receptor 2C
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
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. 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]
  3. 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]
  4. 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]
Details5. Acetylcholinesterase
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
  1. 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]
  2. 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]
Details6. Sodium-dependent serotonin transporter
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
  1. 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]
Details7. Dopamine D1 receptor
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
  1. 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]
Details8. Dopamine D2 receptor
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
  1. 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]
Details9. Muscarinic acetylcholine receptor M1
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
  1. 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]
  2. 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

Details1. Cytochrome P450 2D6
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
  1. 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]
  2. 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]
  3. Flockhart Table of Drug Interactions [Link]

Drug created at June 13, 2005 13:24 / Updated at February 02, 2024 22:44