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ChEMBL Statistics
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Compound Report Card

Compound Name and Classification

Compound ID CHEMBL21731
CHEMBL21731
Compound Name MAPROTILINE
ChEMBL Synonyms MAPROTILINE | LUDIOMIL | MAPROTILINE HYDROCHLORIDE | BA-34,276 [AS HYDROCHLORIDE]
Max Phase 4 (Approved)
Trade Names LUDIOMIL | MAPROTILINE HYDROCHLORIDE
Molecular Formula C20H23N

Additional synonyms for CHEMBL21731 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES CNCCCC12CCC(c3ccccc13)c4ccccc24
Standard InChI InChI=1S/C20H23N/c1-21-14-6-12-20-13-11-15(16-7-2-4-9-18(16) ...
Download InChI
Standard InChI Key QSLMDECMDJKHMQ-UHFFFAOYSA-N

Sources

  • AstraZeneca Deposited Data
  • British National Formulary
  • DrugMatrix
  • Orange Book
  • PubChem BioAssays
  • Scientific Literature
  • TP-search Transporter Database
  • USP Dictionary of USAN and International Drug Names
  • WHO Anatomical Therapeutic Chemical Classification

Alternate Forms of Compound in ChEMBL


CHEMBL21731

Molecule Features

CHEMBL21731 compound icon
Drug Type:Synthetic Small Molecule Rule of Five:Y First In Class:N Chirality:Achiral Molecule Prodrug:N Oral:Y Parenteral:N Topical:N Black Box:Y Availability Type:Prescription-only

Mechanism of Action

Mechanism of Action ChEMBL Target References
Norepinephrine transporter inhibitor Norepinephrine transporter DailyMed

Indications

MESH Heading MESH ID EFO ID EFO Term Max phase for indication References
DementiaD003704HP:0000726dementia3ClinicalTrials
SchizophreniaD012559EFO:0000692schizophrenia3ClinicalTrials
Depressive DisorderD003866EFO:0003761unipolar depression4ATC
ClinicalTrials
AnxietyD001007EFO:0005230anxiety3ClinicalTrials

Clinical Data

ClinicalTrials.gov MAPROTILINE
The Cochrane Collaboration MAPROTILINE

Compound Bioactivity Summary

Compound Assay Summary

Compound Target Summary

Target Predictions

The two tables below display ChEMBL single-protein targets which are predicted to interact with CHEMBL21731. A 1uM and 10 uM cut-off have been applied to ChEMBL bioactivity data used to generate the respective models and the yellow coloured rows correspond to genuine predictions, i.e. targets not included in the original training set for this compound.


1uM


ChEMBL_ID Target Name Organism Score
CHEMBL222 Norepinephrine transporter Homo sapiens 1.000
CHEMBL6184 Transporter Rattus norvegicus 0.993
CHEMBL1850 Dopamine D5 receptor Homo sapiens 0.992
CHEMBL1941 Histamine H2 receptor Homo sapiens 0.967
CHEMBL238 Dopamine transporter Homo sapiens 0.866
CHEMBL315 Alpha-1b adrenergic receptor Rattus norvegicus 0.856
CHEMBL289 Cytochrome P450 2D6 Homo sapiens 0.855
CHEMBL228 Serotonin transporter Homo sapiens 0.708
CHEMBL1942 Alpha-2b adrenergic receptor Homo sapiens 0.699
CHEMBL4153 Sigma-1 receptor Cavia porcellus 0.359



10uM


ChEMBL_ID Target Name Organism Score
CHEMBL222 Norepinephrine transporter Homo sapiens 1.000
CHEMBL6184 Transporter Rattus norvegicus 0.997
CHEMBL238 Dopamine transporter Homo sapiens 0.996
CHEMBL1850 Dopamine D5 receptor Homo sapiens 0.978
CHEMBL228 Serotonin transporter Homo sapiens 0.965
CHEMBL315 Alpha-1b adrenergic receptor Rattus norvegicus 0.901
CHEMBL1941 Histamine H2 receptor Homo sapiens 0.679
CHEMBL2370 Norepinephrine transporter Mus musculus 0.462
CHEMBL3251 Nuclear factor NF-kappa-B p105 subunit Homo sapiens 0.407
CHEMBL289 Cytochrome P450 2D6 Homo sapiens 0.333
CHEMBL5038 Melanin-concentrating hormone receptor 2 Homo sapiens 0.289
CHEMBL1916 Alpha-2c adrenergic receptor Homo sapiens 0.287
CHEMBL2034 Glucocorticoid receptor Homo sapiens 0.250

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
277.4 277.183 4.21 4 12.03 BASE


HBA HBD #Ro5 Violations HBA (Lipinski) HBD (Lipinski) #Ro5 Violations (Lipinski)
1 1 0 1 1 0


ACD Acidic pKa ACD Basic pKa ACD LogP ACD LogD pH7.4 Aromatic Rings Heavy Atoms QED Weighted
- 10.62 4.36 1.51 2 21 0.83

Structural Alerts

There are 1 structural alerts for CHEMBL21731. To view alerts please click here.

Compound Cross References

ATC N - NERVOUS SYSTEM
N06 - PSYCHOANALEPTICS
N06A - ANTIDEPRESSANTS
N06AA - Non-selective monoamine reuptake inhibitors
N06AA21 - maprotiline

ChemSpider ChemSpider:QSLMDECMDJKHMQ-UHFFFAOYSA-N
DailyMed maprotiline hydrochloride
PubChem SID: 104171192 SID: 11111502 SID: 11112599 SID: 11113802 SID: 124880790 SID: 124880792 SID: 144203751 SID: 170464778 SID: 26751977 SID: 50085871 SID: 50104649 SID: 90341780
Wikipedia Maprotiline

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL21731



ACToR 10262-69-8
BindingDB 35228 50101973
Brenda 34575
ChEBI 6690
DrugBank DB00934
DrugCentral 1634
eMolecules 902085
EPA CompTox Dashboard DTXSID7045029
FDA SRS 2U1W68TROF
Guide to Pharmacology 2402
Human Metabolome Database HMDB0015069
IBM Patent System B5C393BBBE867061BEF8DD0BCF97699E
KEGG Ligand C07107
LINCS LSM-2043
MolPort MolPort-002-507-847
Nikkaji J9.818C
PharmGKB PA450322
PubChem 4011
PubChem: Thomson Pharma 14775197
SureChEMBL SCHEMBL33993
ZINC ZINC000001530688

UniChem REST Service Call:
https://www.ebi.ac.uk/unichem/rest/verbose_inchikey/QSLMDECMDJKHMQ-UHFFFAOYSA-N spacer
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