Substance
ID:397
Names and Identifiers
Brand Name
Benylin Pediatric Cough SuppressantCalmylin #1Delsym Cough FormulaDormethanNovahistex DMRobitussin Maximum Strength Cough SuppressantRobitussin Pediatric Cough SuppressantKoffex DMMethorphanMetroratNovahistine DMPertussin DM Extra StrengthRobitussin PediatricBalminil DMBenylin DM 12 HourBenylin DM for Children 12 HourDiabe-Tuss DM SyrupHihustan M.Hold DMDormetanMethorate HydrobromideTrocalTusilanTussadeVicks 44 Cough ReliefAntussanBenylin DMCanfodionCough-XPertussin CS Children's StrengthSucrets 4 Hour Cough SuppressantBenylin Adult Formula Cough SuppressantBenylin DM for ChildrenCosylanCreo-TerpinDelsymMediconRomilarTriaminic DM Long Lasting for ChildrenBalminil DM Children
Synonyms
LevomethorphanLevomethorphane [INN-French]Destrometerfano [Dcit]DemorphanDextromethorphan BromhydrateDextromorphanDelta-MethorphanDextromethorfan [Czech]Dextromethorphan BromideDextrometorphanLevomethorphanum [INN-Latin]DextromethorphanL-MethorphanLevometorfano [INN-Spanish]D-MethorphanD-Methorphan HydrobromideDemorphan HydrobromideDemorphineDextrometorfano [INN-Spanish]DexyromethorphanLevomethorphan [Ban:Dcf:Inn]
IUPAC Traditional name
dextromethorphan
IUPAC name
(1S,9S,10S)-4-methoxy-17-methyl-17-azatetracyclo[7.5.3.0^{1,10}.0^{2,7}]heptadeca-2(7),3,5-triene
Registration numbers
CAS Number
Properties
Physical Property
Hydrophobicity(logP)
3.6
Solubility
74.7 mg/L
Molecule Details
Drug Groups
approved
Description
The d-isomer of the codeine analog of levorphanol. Dextromethorphan shows high affinity binding to several regions of the brain, including the medullary cough center. This compound is an NMDA receptor antagonist (receptors, N-methyl-D-aspartate) and acts as a non-competitive channel blocker. It is one of the widely used antitussives, and is also used to study the involvement of glutamate receptors in neurotoxicity. [PubChem]
Indication
For treatment and relief of dry cough.
Pharmacology
Dextromethorphan suppresses the cough reflex by a direct action on the cough center in the medulla of the brain. Dextromethorphan shows high affinity binding to several regions of the brain, including the medullary cough center. This compound is an NMDA receptor antagonist and acts as a non-competitive channel blocker. It is one of the widely used antitussives, and is also used to study the involvement of glutamate receptors in neurotoxicity.
Affected Organisms
Humans and other mammals
Biotransformation
Hepatic. Rapidly and extensively metabolized to dextrorphan (active metabolite). One well known metabolic catalyst involved is a specific cytochrome P450 enzyme known as 2D6, or CYP2D6.
Absorption
Rapidly absorbed from the gastrointestinal tract.
Half Life
3-6 hours
References
•
Brooks BR, Thisted RA, Appel SH, Bradley WG, Olney RK, Berg JE, Pope LE, Smith RA: Treatment of pseudobulbar affect in ALS with dextromethorphan/quinidine: a randomized trial. Neurology. 2004 Oct 26;63(8):1364-70.
[Pubmed]
•
Olney JW, Labruyere J, Price MT: Pathological changes induced in cerebrocortical neurons by phencyclidine and related drugs. Science. 1989 Jun 16;244(4910):1360-2.
[Pubmed]
•
Hargreaves RJ, Hill RG, Iversen LL: Neuroprotective NMDA antagonists: the controversy over their potential for adverse effects on cortical neuronal morphology. Acta Neurochir Suppl (Wien). 1994;60:15-9.
[Pubmed]
•
Carliss RD, Radovsky A, Chengelis CP, O'Neill TP, Shuey DL: Oral administration of dextromethorphan does not produce neuronal vacuolation in the rat brain. Neurotoxicology. 2007 Jul;28(4):813-8. Epub 2007 Apr 6.
[Pubmed]
•
Hernandez SC, Bertolino M, Xiao Y, Pringle KE, Caruso FS, Kellar KJ: Dextromethorphan and its metabolite dextrorphan block alpha3beta4 neuronal nicotinic receptors. J Pharmacol Exp Ther. 2000 Jun;293(3):962-7.
[Pubmed]
External Links
Molecular Spectra
No Data Available
Click here to submit data
References
• Hargreaves RJ, Hill RG, Iversen LL: Neuroprotective NMDA antagonists: the controversy over their potential for adverse effects on cortical neuronal morphology. Acta Neurochir Suppl (Wien). 1994;60:15-9. Pubmed
• Carliss RD, Radovsky A, Chengelis CP, O'Neill TP, Shuey DL: Oral administration of dextromethorphan does not produce neuronal vacuolation in the rat brain. Neurotoxicology. 2007 Jul;28(4):813-8. Epub 2007 Apr 6. Pubmed
• Hernandez SC, Bertolino M, Xiao Y, Pringle KE, Caruso FS, Kellar KJ: Dextromethorphan and its metabolite dextrorphan block alpha3beta4 neuronal nicotinic receptors. J Pharmacol Exp Ther. 2000 Jun;293(3):962-7. Pubmed
• Olney JW, Labruyere J, Price MT: Pathological changes induced in cerebrocortical neurons by phencyclidine and related drugs. Science. 1989 Jun 16;244(4910):1360-2. Pubmed
• Brooks BR, Thisted RA, Appel SH, Bradley WG, Olney RK, Berg JE, Pope LE, Smith RA: Treatment of pseudobulbar affect in ALS with dextromethorphan/quinidine: a randomized trial. Neurology. 2004 Oct 26;63(8):1364-70. Pubmed