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dextromethorphan 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definition	Drug id	CAS RN
opioid receptor antagonists/agonists, morphinan derivates	842	125-71-3

Description:

Molecule	Description
Molfile Inchi Smiles Synonyms: dextromethorphan HBr dextromethorphan hydrochloride dextromethorphan hydrobromide hydrate dextromethorphan (+)-Dextromethorphan d-Methorphan dextromethorphan hydrobromide dextromethorphan hydriodide dextromethorphan hydrobromide monohydrate dextromethorphan polistirex	Methyl analog of DEXTRORPHAN that 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. Molecular weight: 271.40 Formula: C18H25NO CLOGP: 3.94 LIPINSKI: 0 HAC: 2 HDO: 0 TPSA: 12.47 ALOGS: -4.50 ROTB: 1 Status: OFP Legend: OFP - off patent OFM - off market ONP - on patent

Molecule

Description

Molfile Inchi Smiles

Synonyms:

dextromethorphan HBr
dextromethorphan hydrochloride
dextromethorphan hydrobromide hydrate
dextromethorphan
(+)-Dextromethorphan
d-Methorphan
dextromethorphan hydrobromide
dextromethorphan hydriodide
dextromethorphan hydrobromide monohydrate
dextromethorphan polistirex

Methyl analog of DEXTRORPHAN that 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.

Molecular weight: 271.40
Formula: C18H25NO
CLOGP: 3.94
LIPINSKI: 0
HAC: 2
HDO: 0
TPSA: 12.47
ALOGS: -4.50
ROTB: 1

Status: OFP

Legend:
OFP - off patent
OFM - off market
ONP - on patent

Drug dosage:

Dose	Unit	Route
40	mg	O
90	mg	O

ADMET properties:

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Property	Value	Reference
MRTD (Maximum Recommended Therapeutic Daily Dose)	4.88 µM/kg/day	Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
S (Water solubility)	15 mg/mL	Benet LZ, Broccatelli F, Oprea TI
BA (Bioavailability)	11 %	Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
BDDCS (Biopharmaceutical Drug Disposition Classification System)	1	Benet LZ, Broccatelli F, Oprea TI
fu (Fraction unbound in plasma)	0.24 %	Kawashima H, Watanabe R, Esaki T, Kuroda M, Nagao C, Natsume-Kitatani Y, Ohashi R, Komura H, Mizuguchi K
EoM (Fraction excreted unchanged in urine)	0.19 %	Benet LZ, Broccatelli F, Oprea TI

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Approvals:

Date	Agency	Company	Orphan
Dec. 3, 1957	FDA	ANI PHARMS

FDA Adverse Event Reporting System (Female)

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MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Toxicity to various agents	2354.78	10.23	5663	492864	241587	62748908
Completed suicide	2266.17	10.23	4084	494443	141589	62848906
Infusion related reaction	862.75	10.23	4015	494512	241506	62748989
Exposure to toxic agent	862.21	10.23	541	497986	5046	62985449
Sinusitis	686.21	10.23	3553	494974	223100	62767395
Muscle injury	560.97	10.23	1441	497086	63904	62926591
Folliculitis	547.17	10.23	1495	497032	68822	62921673
Acute hepatic failure	501.64	10.23	668	497859	17659	62972836
Irritable bowel syndrome	485.57	10.23	1588	496939	80824	62909671
Lower respiratory tract infection	466.32	10.23	2167	496360	130140	62860355

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FDA Adverse Event Reporting System (Male)

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MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Toxicity to various agents	1333.18	10.35	3240	192174	197122	34564395
Completed suicide	1204.96	10.35	2049	193365	96119	34665398
Exposure to toxic agent	503.76	10.35	292	195122	3383	34758134
Infusion related reaction	474.76	10.35	968	194446	52089	34709428
Blood pressure fluctuation	433.37	10.35	616	194798	24633	34736884
Overdose	386.14	10.35	1253	194161	89806	34671711
Intentional product misuse	346.71	10.35	779	194635	44832	34716685
Intentional overdose	301.24	10.35	718	194696	42956	34718561
Acute hepatic failure	283.27	10.35	371	195043	13703	34747814
Drug ineffective	274.71	10.35	1470	193944	455281	34306236

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FDA Adverse Event Reporting System (Geriatric)

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MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Completed suicide	3621.87	9.99	6402	567362	239365	78931259
Toxicity to various agents	3451.70	9.99	8627	565137	412913	78757711
Exposure to toxic agent	1336.59	9.99	829	572935	8329	79162295
Infusion related reaction	1127.93	9.99	3932	569832	226305	78944319
Blood pressure fluctuation	820.70	9.99	1617	572147	65528	79105096
Intentional overdose	796.84	9.99	2105	571659	103855	79066769
Intentional product misuse	749.85	9.99	1924	571840	93241	79077383
Acute hepatic failure	737.44	9.99	994	572770	29119	79141505
Overdose	699.08	9.99	2901	570863	181305	78989319
Rheumatoid arthritis	394.84	9.99	2711	571053	205759	78964865

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FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

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Source	Code	Description
ATC	N07XX59	NERVOUS SYSTEM OTHER NERVOUS SYSTEM DRUGS OTHER NERVOUS SYSTEM DRUGS Other nervous system drugs
ATC	R05DA09	RESPIRATORY SYSTEM COUGH AND COLD PREPARATIONS COUGH SUPPRESSANTS, EXCL. COMBINATIONS WITH EXPECTORANTS Opium alkaloids and derivatives
CHEBI has role	CHEBI:35703	Xenobiotic
CHEBI has role	CHEBI:50266	Prodrugs
CHEBI has role	CHEBI:50910	agente neurotoxico
CHEBI has role	CHEBI:51177	anti-tussive
CHEBI has role	CHEBI:60643	N-methyl-D-aspartate receptor antagonists
CHEBI has role	CHEBI:78298	environmental contaminants
CHEBI has role	CHEBI:146270	oneirogens
FDA EPC	N0000181821	Uncompetitive N-methyl-D-aspartate Receptor Antagonist

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Drug Use | Suggest Off label Use Form| |View source of the data|

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Disease	Relation	SNOMED_ID	DOID
Vasomotor rhinitis	indication	8229003	DOID:4730
Cough	indication	49727002
Allergic rhinitis	indication	61582004
Nasal discharge	indication	64531003
Nasal congestion	indication	68235000
Rhinitis	indication	70076002	DOID:4483
Sneezing	indication	76067001
Common cold	indication	82272006	DOID:10459
Headache disorder	indication	230461009
Sore throat symptom	indication	267102003

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🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation level	Dissociation constant	Type (acidic/basic)
pKa1	9.55	Basic

Orange Book patent data (new drug applications)

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Formulation strength	Trade name	Applicant	Application number	Approval date	Type	Dose form	Route	Patent number	Patent expiration date	Patent use
105MG;45MG	AUVELITY	AXSOME	N215430	Aug. 18, 2022	RX	TABLET, EXTENDED RELEASE	ORAL	8569328	Oct. 29, 2033	DEXTROMETHORPHAN AND BUPROPION IN COMBINATION TO TREAT MAJOR DEPRESSIVE DISORDER
105MG;45MG	AUVELITY	AXSOME	N215430	Aug. 18, 2022	RX	TABLET, EXTENDED RELEASE	ORAL	10058518	Nov. 5, 2034	DEXTROMETHORPHAN AND BUPROPION IN COMBINATION TO TREAT MAJOR DEPRESSIVE DISORDER
105MG;45MG	AUVELITY	AXSOME	N215430	Aug. 18, 2022	RX	TABLET, EXTENDED RELEASE	ORAL	10064857	Nov. 5, 2034	DEXTROMETHORPHAN AND BUPROPION IN COMBINATION TO TREAT MAJOR DEPRESSIVE DISORDER
105MG;45MG	AUVELITY	AXSOME	N215430	Aug. 18, 2022	RX	TABLET, EXTENDED RELEASE	ORAL	10080727	Nov. 5, 2034	DEXTROMETHORPHAN AND BUPROPION IN COMBINATION TO TREAT MAJOR DEPRESSIVE DISORDER
105MG;45MG	AUVELITY	AXSOME	N215430	Aug. 18, 2022	RX	TABLET, EXTENDED RELEASE	ORAL	10092560	Nov. 5, 2034	DEXTROMETHORPHAN AND BUPROPION IN COMBINATION TO TREAT MAJOR DEPRESSIVE DISORDER
105MG;45MG	AUVELITY	AXSOME	N215430	Aug. 18, 2022	RX	TABLET, EXTENDED RELEASE	ORAL	10092561	Nov. 5, 2034	DEXTROMETHORPHAN AND BUPROPION IN COMBINATION TO TREAT MAJOR DEPRESSIVE DISORDER
105MG;45MG	AUVELITY	AXSOME	N215430	Aug. 18, 2022	RX	TABLET, EXTENDED RELEASE	ORAL	10105327	Nov. 5, 2034	DEXTROMETHORPHAN AND BUPROPION IN COMBINATION TO TREAT MAJOR DEPRESSIVE DISORDER
105MG;45MG	AUVELITY	AXSOME	N215430	Aug. 18, 2022	RX	TABLET, EXTENDED RELEASE	ORAL	10105361	Nov. 5, 2034	DEXTROMETHORPHAN AND BUPROPION IN COMBINATION TO TREAT MAJOR DEPRESSIVE DISORDER
105MG;45MG	AUVELITY	AXSOME	N215430	Aug. 18, 2022	RX	TABLET, EXTENDED RELEASE	ORAL	10251879	Nov. 5, 2034	DEXTROMETHORPHAN AND BUPROPION IN COMBINATION TO TREAT MAJOR DEPRESSIVE DISORDER
105MG;45MG	AUVELITY	AXSOME	N215430	Aug. 18, 2022	RX	TABLET, EXTENDED RELEASE	ORAL	10463634	Nov. 5, 2034	DEXTROMETHORPHAN AND BUPROPION IN COMBINATION TO TREAT MAJOR DEPRESSIVE DISORDER

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Orange Book exclusivity data (new drug applications)

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Formulation strength	Trade name	Applicant	Application number	Approval date	Type	Dose form	Route	Exclusivity date	Description
105MG;45MG	AUVELITY	AXSOME	N215430	Aug. 18, 2022	RX	TABLET, EXTENDED RELEASE	ORAL	Aug. 18, 2025	NEW PRODUCT

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Bioactivity Summary:

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Target	Class	Pharos	UniProt	Action	Type	Activity value (-log[M])	Bioact source
Sigma non-opioid intracellular receptor 1	Membrane receptor	Q99720	SGMR1_HUMAN	AGONIST	D2	6.46	WOMBAT-PK
Sodium-dependent serotonin transporter	Transporter	P31645	SC6A4_HUMAN		Ki	8.84	DRUG MATRIX
Cytochrome P450 2D6	Enzyme	P10635	CP2D6_HUMAN		Ks	4.48	WOMBAT-PK
Glutamate receptor ionotropic, NMDA 3A	Ion channel	Q8TCU5	NMD3A_HUMAN	ANTAGONIST	IC50	5.70	WOMBAT-PK
Glutamate receptor ionotropic, NMDA 2C	Ion channel	Q14957	NMDE3_HUMAN	BLOCKER	IC50	6.33	IUPHAR
Solute carrier family 22 member 1	Transporter	O15245	S22A1_HUMAN		IC50	4.98	CHEMBL
Taste receptor type 2 member 46	GPCR	P59540	T2R46_HUMAN		EC50	4.51	CHEMBL
Sigma non-opioid intracellular receptor 1	Membrane receptor		SGMR1_RAT		Ki	5.29	CHEMBL
Sigma non-opioid intracellular receptor 1	Membrane other		SGMR1_CAVPO		IC50	7.82	CHEMBL
Glutamate NMDA receptor	Ion channel		NMDZ1_RAT NMDE1_RAT NMDE2_RAT NMDE3_RAT NMDE4_RAT NMD3B_RAT NMD3A_RAT		Ki	5.65	CHEMBL

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External reference:

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ID	Source
001653	NDDF
004427	NDDF
005215	NDDF
102490	RXNORM
166	INN_ID
18609-21-7	SECONDARY_CAS_RN
18766	MMSL
2016004	SNOMEDCT_US
387114001	SNOMEDCT_US
387237004	SNOMEDCT_US

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Pharmaceutical products:

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Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
CHILDRENS DIMETAPP COLD AND COUGH	HUMAN OTC DRUG LABEL	3	0031-2234	LIQUID	5 mg	ORAL	OTC monograph final	16 sections
Childrens Robitussin 12 Hour Cough Relief	HUMAN OTC DRUG LABEL	1	0031-8725	SUSPENSION, EXTENDED RELEASE	30 mg	ORAL	ANDA	15 sections
Childrens Robitussin 12 Hour Cough Relief	HUMAN OTC DRUG LABEL	1	0031-8725	SUSPENSION, EXTENDED RELEASE	30 mg	ORAL	ANDA	15 sections
Childrens Robitussin 12 Hour Cough Relief	HUMAN OTC DRUG LABEL	1	0031-8726	SUSPENSION, EXTENDED RELEASE	30 mg	ORAL	ANDA	15 sections
Childrens Robitussin 12 Hour Cough Relief	HUMAN OTC DRUG LABEL	1	0031-8726	SUSPENSION, EXTENDED RELEASE	30 mg	ORAL	ANDA	15 sections
Childrens Robitussin Cough and Chest Congestion DM	HUMAN OTC DRUG LABEL	2	0031-8702	LIQUID	20 mg	ORAL	OTC MONOGRAPH FINAL	15 sections
Childrens Robitussin Cough and Chest Congestion DM	HUMAN OTC DRUG LABEL	2	0031-8702	LIQUID	20 mg	ORAL	OTC MONOGRAPH FINAL	15 sections
Childrens Robitussin Cough and Chest Congestion DM	HUMAN OTC DRUG LABEL	2	0031-8715	LIQUID	5 mg	ORAL	OTC monograph final	15 sections
Childrens Robitussin Cough and Chest Congestion DM	HUMAN OTC DRUG LABEL	2	0031-8715	LIQUID	5 mg	ORAL	OTC monograph final	15 sections
Childrens Robitussin Cough and Cold CF	HUMAN OTC DRUG LABEL	3	0031-8716	LIQUID	5 mg	ORAL	OTC monograph final	17 sections

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