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

Stem definition	Drug id	CAS RN
adamantane derivatives	144	768-94-5

Description:

Molecule	Description
Molfile Inchi Smiles Synonyms: amantadine adamantamine adamantanamine adamantylamine amantadine hydrochloride amantidine adamantamine fumarate amantadine HCl amantadine sulfate	An antiviral that is used in the prophylactic or symptomatic treatment of influenza A. It is also used as an antiparkinsonian agent, to treat extrapyramidal reactions, and for postherpetic neuralgia. The mechanisms of its effects in movement disorders are not well understood but probably reflect an increase in synthesis and release of dopamine, with perhaps some inhibition of dopamine uptake. Molecular weight: 151.25 Formula: C10H17N CLOGP: 2 LIPINSKI: 0 HAC: 1 HDO: 1 TPSA: 26.02 ALOGS: -3.25 ROTB: 0 Status: OFP Legend: OFP - off patent OFM - off market ONP - on patent

Molecule

Description

Molfile Inchi Smiles

Synonyms:

amantadine
adamantamine
adamantanamine
adamantylamine
amantadine hydrochloride
amantidine
adamantamine fumarate
amantadine HCl
amantadine sulfate

An antiviral that is used in the prophylactic or symptomatic treatment of influenza A. It is also used as an antiparkinsonian agent, to treat extrapyramidal reactions, and for postherpetic neuralgia. The mechanisms of its effects in movement disorders are not well understood but probably reflect an increase in synthesis and release of dopamine, with perhaps some inhibition of dopamine uptake.

Molecular weight: 151.25
Formula: C10H17N
CLOGP: 2
LIPINSKI: 0
HAC: 1
HDO: 1
TPSA: 26.02
ALOGS: -3.25
ROTB: 0

Status: OFP

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

Drug dosage:

Dose	Unit	Route
0.20	g	O

ADMET properties:

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Property	Value	Reference
BA (Bioavailability)	90 %	Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
EoM (Fraction excreted unchanged in urine)	85 %	Benet LZ, Broccatelli F, Oprea TI
Vd (Volume of distribution)	6.60 L/kg	Lombardo F, Berellini G, Obach RS
S (Water solubility)	50 mg/mL	Benet LZ, Broccatelli F, Oprea TI
CL (Clearance)	4.80 mL/min/kg	Lombardo F, Berellini G, Obach RS
MRTD (Maximum Recommended Therapeutic Daily Dose)	37.78 µM/kg/day	Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BDDCS (Biopharmaceutical Drug Disposition Classification System)	3	Benet LZ, Broccatelli F, Oprea TI
t_half (Half-life)	16 hours	Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma)	0.33 %	Lombardo F, Berellini G, Obach RS

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Approvals:

Date	Agency	Company	Orphan
Feb. 14, 1968	FDA	ENDO 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
Dyskinesia	447.99	14.03	208	18312	31794	63438708
Hallucination	397.76	14.03	229	18291	54588	63415914
Multiple sclerosis relapse	292.78	14.03	180	18340	48298	63422204
Hallucination, visual	228.87	14.03	112	18408	19186	63451316
Fall	218.49	14.03	401	18119	391933	63078569
On and off phenomenon	177.45	14.03	50	18470	1785	63468717
Stoma site discharge	174.98	14.03	48	18472	1550	63468952
Freezing phenomenon	171.34	14.03	45	18475	1227	63469275
Multiple sclerosis	166.44	14.03	98	18422	24274	63446228
Tremor	155.35	14.03	192	18328	132047	63338455

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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
Hallucination	517.38	15.75	300	14166	51198	34891267
Dyskinesia	415.51	15.75	197	14269	22216	34920249
On and off phenomenon	335.84	15.75	95	14371	2402	34940063
Hallucination, visual	256.91	15.75	132	14334	17659	34924806
Dopamine dysregulation syndrome	179.87	15.75	41	14425	415	34942050
Fall	178.04	15.75	308	14158	202577	34739888
Freezing phenomenon	177.76	15.75	52	14414	1484	34940981
Bradykinesia	113.23	15.75	47	14419	3846	34938619
Delusion	111.81	15.75	68	14398	12567	34929898
Muscle rigidity	109.83	15.75	63	14403	10455	34932010

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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
Dyskinesia	716.07	13.40	335	26917	44438	79672698
Hallucination	674.73	13.40	399	26853	85346	79631790
On and off phenomenon	415.65	13.40	114	27138	3126	79714010
Hallucination, visual	414.81	13.40	209	27043	32520	79684616
Fall	318.24	13.40	584	26668	487045	79230091
Freezing phenomenon	257.85	13.40	70	27182	1844	79715292
Multiple sclerosis relapse	256.28	13.40	173	27079	46360	79670776
Dopamine dysregulation syndrome	198.99	13.40	44	27208	473	79716663
Stoma site discharge	190.29	13.40	57	27195	2152	79714984
Tremor	188.38	13.40	260	26992	169823	79547313

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FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

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Source	Code	Description
ATC	N04BB01	NERVOUS SYSTEM ANTI-PARKINSON DRUGS DOPAMINERGIC AGENTS Adamantane derivatives
CHEBI has role	CHEBI:36044	antiviral drugs
CHEBI has role	CHEBI:48407	antiparkinson agent
CHEBI has role	CHEBI:48560	dopaminergic agents
CHEBI has role	CHEBI:60643	N-methyl-D-aspartate receptor antagonists
CHEBI has role	CHEBI:22587	antiviral agents
CHEBI has role	CHEBI:51065	Dopamine receptor agonist
FDA EPC	N0000175543	Influenza A M2 Protein Inhibitor
FDA MoA	N0000175542	M2 Protein Inhibitors
MeSH PA	D000700	Analgesics

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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
Postencephalitic parkinsonism	indication	19972008	DOID:14332
Parkinsonism	indication	32798002
Parkinson's disease	indication	49049000	DOID:14330
Extrapyramidal disease	indication	76349003
Influenza due to Influenza A virus	indication	442438000
Arteriosclerotic Parkinsonism	indication
Influenza A Prevention	indication
Jakob-Creutzfeldt disease	off-label use	792004	DOID:11949
Cognitive impairment following traumatic brain injury	off-label use	127295002
Arousal post traumatic brain injury	off-label use	127295002

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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	10.4	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
EQ 129MG BASE	OSMOLEX ER	ADAMAS OPERATIONS	N209410	Feb. 16, 2018	RX	TABLET, EXTENDED RELEASE	ORAL	8796337	Nov. 23, 2025	TREATMENT OF DRUG-INDUCED EXTRAPYRAMIDAL REACTION IN ADULT PATIENTS
EQ 129MG BASE	OSMOLEX ER	ADAMAS OPERATIONS	N209410	Feb. 16, 2018	RX	TABLET, EXTENDED RELEASE	ORAL	8796337	Nov. 23, 2025	TREATMENT OF DRUG-INDUCED EXTRAPYRAMIDAL REACTIONS IN ADULT PATIENTS WITH PARKINSONS DISEASE
EQ 129MG BASE	OSMOLEX ER	ADAMAS OPERATIONS	N209410	Feb. 16, 2018	RX	TABLET, EXTENDED RELEASE	ORAL	8796337	Nov. 23, 2025	TREATMENT OF PARKINSONS DISEASE
EQ 129MG BASE	OSMOLEX ER	ADAMAS OPERATIONS	N209410	Feb. 16, 2018	RX	TABLET, EXTENDED RELEASE	ORAL	8895615	Nov. 23, 2025	TREATMENT OF DRUG-INDUCED EXTRAPYRAMIDAL REACTIONS IN ADULT PATIENTS WITH PARKINSONS DISEASE
EQ 129MG BASE	OSMOLEX ER	ADAMAS OPERATIONS	N209410	Feb. 16, 2018	RX	TABLET, EXTENDED RELEASE	ORAL	8895615	Nov. 23, 2025	TREATMENT OF PARKINSONS DISEASE
EQ 129MG BASE	OSMOLEX ER	ADAMAS OPERATIONS	N209410	Feb. 16, 2018	RX	TABLET, EXTENDED RELEASE	ORAL	8895616	Nov. 23, 2025	TREATMENT OF DRUG-INDUCED EXTRAPYRAMIDAL REACTIONS IN ADULT PATIENTS WITH PARKINSONS DISEASE
EQ 129MG BASE	OSMOLEX ER	ADAMAS OPERATIONS	N209410	Feb. 16, 2018	RX	TABLET, EXTENDED RELEASE	ORAL	8895616	Nov. 23, 2025	TREATMENT OF PARKINSONS DISEASE
EQ 129MG BASE	OSMOLEX ER	ADAMAS OPERATIONS	N209410	Feb. 16, 2018	RX	TABLET, EXTENDED RELEASE	ORAL	8895617	Nov. 23, 2025	TREATMENT OF DRUG-INDUCED EXTRAPYRAMIDAL REACTIONS IN ADULT PATIENTS WITH PARKINSONS DISEASE
EQ 129MG BASE	OSMOLEX ER	ADAMAS OPERATIONS	N209410	Feb. 16, 2018	RX	TABLET, EXTENDED RELEASE	ORAL	8895617	Nov. 23, 2025	TREATMENT OF PARKINSONS DISEASE
EQ 129MG BASE	OSMOLEX ER	ADAMAS OPERATIONS	N209410	Feb. 16, 2018	RX	TABLET, EXTENDED RELEASE	ORAL	9072697	Nov. 23, 2025	TREATMENT OF DRUG-INDUCED EXTRAPYRAMIDAL REACTIONS IN ADULT PATIENTS WITH PARKINSONS DISEASE

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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
EQ 137MG BASE	GOCOVRI	ADAMAS OPERATIONS	N208944	Aug. 24, 2017	RX	CAPSULE, EXTENDED RELEASE	ORAL	Aug. 24, 2024	TREATMENT OF DYSKINESIA IN PATIENTS WITH PARKINSONS DISEASE RECEIVING LEVODOPA-BASED THERAPY WITH OR WITHOUT CONCOMITANT DOPAMINERGIC MEDICATIONS
EQ 68.5MG BASE	GOCOVRI	ADAMAS OPERATIONS	N208944	Aug. 24, 2017	RX	CAPSULE, EXTENDED RELEASE	ORAL	Aug. 24, 2024	TREATMENT OF DYSKINESIA IN PATIENTS WITH PARKINSONS DISEASE RECEIVING LEVODOPA-BASED THERAPY WITH OR WITHOUT CONCOMITANT DOPAMINERGIC MEDICATIONS

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Bioactivity Summary:

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Target	Class	Pharos	UniProt	Action	Type	Activity value (-log[M])	Bioact source	MoA source
Glutamate [NMDA] receptor	Ion channel	O15399 O60391 Q05586 Q12879 Q13224 Q14957 Q8TCU5	NMDE4_HUMAN NMD3B_HUMAN NMDZ1_HUMAN NMDE1_HUMAN NMDE2_HUMAN NMDE3_HUMAN NMD3A_HUMAN	BLOCKER	Ki	4.98	CHEMBL	CHEMBL
Sigma non-opioid intracellular receptor 1	Membrane receptor	Q99720	SGMR1_HUMAN		Ki	7.69	CHEMBL
Multidrug and toxin extrusion protein 1	Transporter	Q96FL8	S47A1_HUMAN		IC50	4.42	CHEMBL
Matrix protein 2	Ion channel		M2_I72A2	INHIBITOR	IC50	4.80	CHEMBL	CHEMBL
Matrix protein 2	Unclassified		Q20MD5_9INFA		IC50	4.80	CHEMBL
Matrix protein 2	Unclassified		M2_I000F		Kd	6.50	CHEMBL
Matrix protein 2	Unclassified		M2_I72A8		EC50	6.18	CHEMBL
Matrix protein 2	Unclassified		M2_I34A1		Kd	6.50	CHEMBL

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External reference:

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ID	Source
308	PDB_CHEM_ID
001640	NDDF
004663	NDDF
006089	NDDF
1816	INN_ID
2130	PUBCHEM_CID
2543	MMSL
282415	RXNORM
31377-23-8	SECONDARY_CAS_RN
33122	MMSL

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Pharmaceutical products:

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Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
Amantadine HCl	Human Prescription Drug Label	1	10888-5006	CAPSULE, LIQUID FILLED	100 mg	ORAL	ANDA	19 sections
Amantadine HCl	HUMAN PRESCRIPTION DRUG LABEL	1	21695-564	CAPSULE	100 mg	ORAL	ANDA	20 sections
AMANTADINE HYDROCHLORIDE	HUMAN PRESCRIPTION DRUG LABEL	1	0121-0646	SOLUTION	50 mg	ORAL	ANDA	24 sections
AMANTADINE HYDROCHLORIDE	HUMAN PRESCRIPTION DRUG LABEL	1	0121-0646	SOLUTION	50 mg	ORAL	ANDA	24 sections
AMANTADINE HYDROCHLORIDE	HUMAN PRESCRIPTION DRUG LABEL	1	0121-0646	SOLUTION	50 mg	ORAL	ANDA	24 sections
AMANTADINE HYDROCHLORIDE	HUMAN PRESCRIPTION DRUG LABEL	1	0121-0646	SOLUTION	50 mg	ORAL	ANDA	24 sections
Amantadine Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	0527-1704	CAPSULE	100 mg	ORAL	ANDA	22 sections
Amantadine Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	0527-1868	CAPSULE	100 mg	ORAL	ANDA	21 sections
Amantadine Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	0591-4920	TABLET	100 mg	ORAL	ANDA	19 sections
Amantadine Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	0615-8263	CAPSULE	100 mg	ORAL	ANDA	13 sections

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