DEXTROMETHORPHAN

Search structure
Synonyms:
Status: Approved (1982)
Entry Type: Small molecule
Molecule Category: Parent
ATC: R05DA09
UNII: 7355X3ROTS

Structure
InChI Key MKXZASYAUGDDCJ-NJAFHUGGSA-N
Smile COc1ccc2c(c1)[C@]13CCCC[C@@H]1[C@H](C2)N(C)CC3
InChI
InChI=1S/C18H25NO/c1-19-10-9-18-8-4-3-5-15(18)17(19)11-13-6-7-14(20-2)12-16(13)18/h6-7,12,15,17H,3-5,8-11H2,1-2H3/t15-,17+,18+/m1/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C18H25NO
Molecular Weight 271.4
AlogP 3.38
Hydrogen Bond Acceptor 2.0
Hydrogen Bond Donor 0.0
Number of Rotational Bond 1.0
Polar Surface Area 12.47
Molecular species BASE
Aromatic Rings 1.0
Heavy Atoms 20.0

Pharmacology

Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Cytochrome P450 Cytochrome P450 family 2 Cytochrome P450 family 2D Cytochrome P450 2D2
- 5600 - - -
Enzyme Cytochrome P450 Cytochrome P450 family 2 Cytochrome P450 family 2D Cytochrome P450 2D3
- 18600 - - -
Enzyme Cytochrome P450 Cytochrome P450 family 2 Cytochrome P450 family 2D Cytochrome P450 2D6
- 1800-3400 - - 94
Ion channel Ligand-gated ion channel Ionotropic glutamate receptor NMDA receptor
- 1320 - 2246-4540 2
Ion channel Ligand-gated ion channel Nicotinic acetylcholine receptor Nicotinic acetylcholine receptor alpha subunit
- 11050 - - -
Ion channel Ligand-gated ion channel Nicotinic acetylcholine receptor Nicotinic acetylcholine receptor beta subunit
- 11050 - - -
Ion channel Voltage-gated ion channel Voltage-gated sodium channel
- 1300 - - 5
Membrane receptor
- - - 348 -
Other membrane protein
- 15-232 - 10-63 -
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - 16
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC22 family of organic cation and anion transporters
- 10450-15000 - - -

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Cough 4 D003371 ClinicalTrials
Multiple Sclerosis, Relapsing-Remitting 3 D020529 ClinicalTrials
Amyotrophic Lateral Sclerosis 3 D000690 ClinicalTrials
Bipolar Disorder 3 D001714 ClinicalTrials
Rett Syndrome 3 D015518 ClinicalTrials
Opioid-Related Disorders 3 D009293 ClinicalTrials
Proteinuria 3 D011507 ClinicalTrials
Multiple Sclerosis 3 D009103 ClinicalTrials
Autistic Disorder 2 D001321 ClinicalTrials
Diabetic Neuropathies 2 D003929 ClinicalTrials
Substance-Related Disorders 2 D019966 ClinicalTrials
Diabetes Mellitus, Type 2 2 D003924 ClinicalTrials
Irritable Bowel Syndrome 2 D043183 ClinicalTrials
Peripheral Nervous System Diseases 2 D010523 ClinicalTrials
Neuralgia 2 D009437 ClinicalTrials
Hypertrophy 2 D006984 ClinicalTrials
Schizophrenia 2 D012559 ClinicalTrials
Fibromyalgia 2 D005356 ClinicalTrials
Neuralgia 2 D009437 ClinicalTrials
Parkinson Disease 2 D010300 ClinicalTrials
Depressive Disorder, Major 2 D003865 ClinicalTrials
Mitochondrial Diseases 1 D028361 ClinicalTrials
Cognitive Dysfunction 1 D060825 ClinicalTrials
Alzheimer Disease 1 D000544 ClinicalTrials
Crohn Disease 1 D003424 ClinicalTrials
Neoplasms 1 D009369 ClinicalTrials
Psoriasis 1 D011565 ClinicalTrials
HIV Infections 1 D015658 ClinicalTrials
Cytomegalovirus Infections 1 D003586 ClinicalTrials
Melanoma 1 D008545 ClinicalTrials
Voice Disorders 1 D014832 ClinicalTrials
Prostatic Neoplasms, Castration-Resistant 1 D064129 ClinicalTrials
Colitis, Ulcerative 1 D003093 ClinicalTrials

Related Entries

Scaffolds

Cross References

Resources Reference
ChEBI 4470
ChEMBL CHEMBL52440
DrugBank DB00514
DrugCentral 842
EPA CompTox DTXSID3022908
FDA SRS 7355X3ROTS
Guide to Pharmacology 6953
PharmGKB PA449273
SureChEMBL SCHEMBL29949
ZINC ZINC000003201907
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