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ChEMBL Statistics
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Compound Report Card

Compound Name and Classification

Compound ID CHEMBL52440
CHEMBL52440
Compound Name DEXTROMETHORPHAN
ChEMBL Synonyms BENYLIN DM | PEDIACARE 1 | TUXIUM | St | BRONTYL | DEXTROMETHORPHAN HYDROBROMIDE | DEXTROMETHORPHAN HYDROBROMIDE OROS TABLETS | Dextromethorphan Hydrobromide Monohydrate | CTP-786 | d6-DM hydrobromide | d6-DM | DELSYM | TUSSABRON | Dextromethorphan | DEUDEXTROMETHORPHAN | DEUDEXTROMETHORPHAN HYDROBROMIDE | BEECHAM COUGHCAPS | CONTAC COUGHCAPS | FRANOLYN DRY | FRANOLYN SED | Dimetane-DX | DRIXORAL COUGH | DEXTROMETHORPHAN POLISTIREX | C100003 | ROMILAR
Max Phase 4 (Approved)
Trade Names St | TUXIUM | DEXTROMETHORPHAN POLISTIREX | PEDIACARE 1 | DRIXORAL COUGH | ROMILAR | BEECHAM COUGHCAPS | CONTAC COUGHCAPS | FRANOLYN DRY | FRANOLYN SED | TUSSABRON | DELSYM | BENYLIN DM | BRONTYL | DEXTROMETHORPHAN HYDROBROMIDE OROS TABLETS
Molecular Formula C18H25NO

Additional synonyms for CHEMBL52440 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES COc1ccc2C[C@H]3[C@H]4CCCC[C@@]4(CCN3C)c2c1
Standard InChI InChI=1S/C18H25NO/c1-19-10-9-18-8-4-3-5-15(18)17(19)11-13-6- ...
Download InChI
Standard InChI Key MKXZASYAUGDDCJ-NJAFHUGGSA-N

Sources

  • 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


CHEMBL52440

Molecule Features

CHEMBL52440 compound icon
Drug Type:Synthetic Small Molecule Rule of Five:Y First In Class:N Chirality:Single Stereoisomer Prodrug:N Oral:Y Parenteral:N Topical:N Black Box:N Availability Type:Over-The-Counter

Mechanism of Action

Mechanism of Action ChEMBL Target References
Glutamate [NMDA] receptor subunit epsilon 1 antagonist Glutamate [NMDA] receptor subunit epsilon 1 PubMed
Sigma opioid receptor agonist Sigma opioid receptor PubMed

Indications

MESH Heading MESH ID EFO ID EFO Term Max phase for indication References
Depressive DisorderD003866EFO:0003761unipolar depression2ClinicalTrials
ClinicalTrials
Irritable Bowel SyndromeD043183EFO:0000555irritable bowel syndrome2ClinicalTrials
Parkinson DiseaseD010300EFO:0002508Parkinson's disease2ClinicalTrials
PsoriasisD011565EFO:0000676psoriasis1ClinicalTrials
Opioid-Related DisordersD009293EFO:0005611opioid dependence3ClinicalTrials
SchizophreniaD012559EFO:0000692schizophrenia2ClinicalTrials
Child Development Disorders, PervasiveD002659EFO:0003756autism spectrum disorder2ClinicalTrials
PainD010146EFO:0003843pain3ClinicalTrials
Alzheimer DiseaseD000544EFO:0000249Alzheimers disease1ClinicalTrials
Multiple Sclerosis, Relapsing-RemittingD020529EFO:0003929relapsing-remitting multiple sclerosis3ClinicalTrials
NeoplasmsD009369EFO:0000616neoplasm1ClinicalTrials
ClinicalTrials
Prostatic NeoplasmsD011471EFO:0001663prostate carcinoma1ClinicalTrials
ClinicalTrials
ProteinuriaD011507HP:0000093Proteinuria3ClinicalTrials
Bipolar DisorderD001714EFO:0000289bipolar disorder3ClinicalTrials
Cognitive DysfunctionD060825HP:0100543cognitive impairment1ClinicalTrials
Diabetes Mellitus, Type 2D003924EFO:0001360type II diabetes mellitus2ClinicalTrials
ClinicalTrials
Migraine DisordersD008881EFO:0003821migraine disorder2ClinicalTrials
HIV InfectionsD015658EFO:0000764HIV infection1ClinicalTrials
NeuralgiaD009437EFO:0005762neuropathic pain2ClinicalTrials
Crohn DiseaseD003424EFO:0000384Crohn's disease1ClinicalTrials
Diabetic NeuropathiesD003929EFO:1000783diabetic neuropathy2ClinicalTrials
Diabetic RetinopathyD003930EFO:0003770diabetic retinopathy1ClinicalTrials
CoughD003371HP:0012735Cough4ATC
Cytomegalovirus InfectionsD003586EFO:0001062cytomegalovirus infection1ClinicalTrials
Peripheral Nervous System DiseasesD010523EFO:0003100peripheral neuropathy2ClinicalTrials
Amyotrophic Lateral SclerosisD000690EFO:0000253amyotrophic lateral sclerosis3ClinicalTrials
Autistic DisorderD001321EFO:0003758autism2ClinicalTrials
Common ColdD003139EFO:0007214common cold1ClinicalTrials
Multiple SclerosisD009103EFO:0003885multiple sclerosis3ClinicalTrials
Rett SyndromeD015518Orphanet:778Rett syndrome3ClinicalTrials

Clinical Data

ClinicalTrials.gov DEXTROMETHORPHAN
The Cochrane Collaboration DEXTROMETHORPHAN

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 CHEMBL52440. 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
CHEMBL236 Delta opioid receptor Homo sapiens 1.000
CHEMBL233 Mu opioid receptor Homo sapiens 1.000
CHEMBL237 Kappa opioid receptor Homo sapiens 1.000
CHEMBL3952 Kappa opioid receptor Cavia porcellus 1.000
CHEMBL4354 Mu opioid receptor Cavia porcellus 1.000
CHEMBL4153 Sigma-1 receptor Cavia porcellus 1.000
CHEMBL3602 Sigma opioid receptor Rattus norvegicus 0.997
CHEMBL4329 Kappa opioid receptor Mus musculus 0.996
CHEMBL2858 Mu opioid receptor Mus musculus 0.996
CHEMBL287 Sigma opioid receptor Homo sapiens 0.979
CHEMBL220 Acetylcholinesterase Homo sapiens 0.966
CHEMBL270 Mu opioid receptor Rattus norvegicus 0.882
CHEMBL289 Cytochrome P450 2D6 Homo sapiens 0.816
CHEMBL1850 Dopamine D5 receptor Homo sapiens 0.627
CHEMBL3222 Delta opioid receptor Mus musculus 0.614
CHEMBL3041 Mu opioid receptor Bos taurus 0.295



10uM


ChEMBL_ID Target Name Organism Score
CHEMBL236 Delta opioid receptor Homo sapiens 1.000
CHEMBL233 Mu opioid receptor Homo sapiens 1.000
CHEMBL237 Kappa opioid receptor Homo sapiens 1.000
CHEMBL3952 Kappa opioid receptor Cavia porcellus 1.000
CHEMBL4354 Mu opioid receptor Cavia porcellus 1.000
CHEMBL4153 Sigma-1 receptor Cavia porcellus 1.000
CHEMBL4329 Kappa opioid receptor Mus musculus 1.000
CHEMBL3602 Sigma opioid receptor Rattus norvegicus 1.000
CHEMBL2858 Mu opioid receptor Mus musculus 1.000
CHEMBL287 Sigma opioid receptor Homo sapiens 0.995
CHEMBL220 Acetylcholinesterase Homo sapiens 0.991
CHEMBL270 Mu opioid receptor Rattus norvegicus 0.987
CHEMBL3222 Delta opioid receptor Mus musculus 0.841
CHEMBL3465 Sigma opioid receptor Mus musculus 0.619
CHEMBL3198 Acetylcholinesterase Mus musculus 0.618
CHEMBL3403 Butyrylcholinesterase Rattus norvegicus 0.501
CHEMBL289 Cytochrome P450 2D6 Homo sapiens 0.455
CHEMBL1850 Dopamine D5 receptor Homo sapiens 0.376
CHEMBL3041 Mu opioid receptor Bos taurus 0.375

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
271.4 271.1936 3.38 1 12.47 BASE


HBA HBD #Ro5 Violations HBA (Lipinski) HBD (Lipinski) #Ro5 Violations (Lipinski)
2 0 0 2 0 0


ACD Acidic pKa ACD Basic pKa ACD LogP ACD LogD pH7.4 Aromatic Rings Heavy Atoms QED Weighted
- 9.13 3.89 2.17 1 20 0.78

Structural Alerts

There are no structural alerts for CHEMBL52440

Compound Cross References

ATC R - RESPIRATORY SYSTEM
R05 - COUGH AND COLD PREPARATIONS
R05D - COUGH SUPPRESSANTS, EXCL. COMBINATIONS WITH EXPECTORANTS
R05DA - Opium alkaloids and derivatives
R05DA09 - dextromethorphan

N - NERVOUS SYSTEM
N07 - OTHER NERVOUS SYSTEM DRUGS
N07X - OTHER NERVOUS SYSTEM DRUGS
N07XX - Other nervous system drugs
N07XX59 - dextromethorphan, combinations

ChemSpider ChemSpider:MKXZASYAUGDDCJ-NJAFHUGGSA-N
DailyMed dextromethorphan hydrobromide dextromethorphan polistirex
PubChem SID: 11111057 SID: 50100218
Wikipedia Dextromethorphan

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL52440



ACToR 125-71-3
BindingDB 50366613
Brenda 24585
ChEBI 92579
DrugBank DB00514
DrugCentral 842
EPA CompTox Dashboard DTXSID3022908
FDA SRS 7355X3ROTS
Guide to Pharmacology 6953
IBM Patent System 9FD4CA38FDFC5FFB28F7596DFB3E5F2C
LINCS LSM-2726
Metabolights MTBLC92579
PharmGKB PA449273
PubChem 5360696
PubChem: Thomson Pharma 14750569 15197408
SureChEMBL SCHEMBL29949
ZINC ZINC000003201907

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