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

Stem definition	Drug id	CAS RN
anorexics	435	34911-55-2

Description:

Molecule	Description
Molfile Inchi Smiles Synonyms: bupropion (+/-)-Bupropion amfebutamon amfebutamone aplenzin elontril bupropion hydrochloride bupropion hydrobromide bupropion HCl wellbutrin	A propiophenone-derived antidepressant and antismoking agent that inhibits the uptake of DOPAMINE. Molecular weight: 239.74 Formula: C13H18ClNO CLOGP: 3.21 LIPINSKI: 0 HAC: 2 HDO: 1 TPSA: 29.10 ALOGS: -3.54 ROTB: 4 Status: OFP Legend: OFP - off patent OFM - off market ONP - on patent

Molecule

Description

Molfile Inchi Smiles

Synonyms:

bupropion
(+/-)-Bupropion
amfebutamon
amfebutamone
aplenzin
elontril
bupropion hydrochloride
bupropion hydrobromide
bupropion HCl
wellbutrin

A propiophenone-derived antidepressant and antismoking agent that inhibits the uptake of DOPAMINE.

Molecular weight: 239.74
Formula: C13H18ClNO
CLOGP: 3.21
LIPINSKI: 0
HAC: 2
HDO: 1
TPSA: 29.10
ALOGS: -3.54
ROTB: 4

Status: OFP

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

Drug dosage:

Dose	Unit	Route
0.30	g	O

ADMET properties:

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Property	Value	Reference
S (Water solubility)	312 mg/mL	Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose)	31.28 µM/kg/day	Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BDDCS (Biopharmaceutical Drug Disposition Classification System)	1	Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine)	0.50 %	Benet LZ, Broccatelli F, Oprea TI
fu (Fraction unbound in plasma)	0.14 %	Kawashima H, Watanabe R, Esaki T, Kuroda M, Nagao C, Natsume-Kitatani Y, Ohashi R, Komura H, Mizuguchi K

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Approvals:

Date	Agency	Company	Orphan
Dec. 30, 1985	FDA	GLAXOSMITHKLINE

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
Completed suicide	3631.72	9.93	2909	149109	142764	63194240
Toxicity to various agents	849.43	9.93	1845	150173	245405	63091599
Overdose	478.25	9.93	930	151088	114148	63222856
Intentional overdose	444.24	9.93	704	151314	73448	63263556
Seizure	417.57	9.93	957	151061	131677	63205327
Generalised tonic-clonic seizure	410.99	9.93	423	151595	28593	63308411
Depression	410.04	9.93	1215	150803	195277	63141727
Suicidal ideation	402.32	9.93	613	151405	61808	63275196
Suspected suicide	386.88	9.93	224	151794	6344	63330660
Anxiety	386.42	9.93	1272	150746	216269	63120735

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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
Completed suicide	2289.55	11.69	1616	55758	96552	34803005
Depression	1352.99	11.69	1181	56193	95917	34803640
Toxicity to various agents	655.14	11.69	1174	56200	199188	34700369
Drug interaction	629.42	11.69	1236	56138	224710	34674847
Serotonin syndrome	532.22	11.69	358	57016	19575	34879982
Suicidal ideation	450.86	11.69	435	56939	39953	34859604
Intentional overdose	351.73	11.69	395	56979	43279	34856278
Anxiety	335.65	11.69	592	56782	98836	34800721
Psychiatric decompensation	326.53	11.69	137	57237	2800	34896757
Overdose	320.10	11.69	552	56822	90507	34809050

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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	5833.17	10.29	4519	163659	241248	79334962
Toxicity to various agents	1487.71	10.29	2948	165230	418592	79157618
Depression	1023.56	10.29	1722	166456	215068	79361142
Intentional overdose	991.41	10.29	1169	167009	104791	79471419
Overdose	768.34	10.29	1386	166792	182820	79393390
Serotonin syndrome	764.53	10.29	685	167493	44342	79531868
Seizure	673.43	10.29	1329	166849	187505	79388705
Electrocardiogram QRS complex prolonged	642.06	10.29	355	167823	10478	79565732
Cardio-respiratory arrest	573.63	10.29	908	167270	107602	79468608
Suicidal ideation	569.13	10.29	752	167426	75588	79500622

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FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

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Source	Code	Description
ATC	A08AA62	ALIMENTARY TRACT AND METABOLISM ANTIOBESITY PREPARATIONS, EXCL. DIET PRODUCTS ANTIOBESITY PREPARATIONS, EXCL. DIET PRODUCTS Centrally acting antiobesity products
ATC	N06AX12	NERVOUS SYSTEM PSYCHOANALEPTICS ANTIDEPRESSANTS Other antidepressants
CHEBI has role	CHEBI:35469	antidepressants
CHEBI has role	CHEBI:35703	Xenobiotic
CHEBI has role	CHEBI:78298	environmental contaminants
FDA EPC	N0000180855	Aminoketone
FDA MoA	N0000000102	Norepinephrine Uptake Inhibitors
FDA MoA	N0000000114	Dopamine Uptake Inhibitors
FDA PE	N0000009282	Increased Dopamine Activity
FDA PE	N0000009456	Increased Norepinephrine Activity

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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
Depressive disorder	indication	35489007
Nicotine dependence	indication	56294008	DOID:0050742
Seasonal affective disorder	indication	247803002
Major depressive disorder	indication	370143000
Smoking cessation assistance	indication	384742004
Obesity	indication	414916001	DOID:9970
Bipolar affective disorder, current episode depression	off-label use	191627008	DOID:3312
Attention deficit hyperactivity disorder	off-label use	406506008
Suicidal thoughts	contraindication	6471006
Alcoholism	contraindication	7200002

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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	7.87	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	MoA source
Sodium-dependent dopamine transporter	Transporter	Q01959	SC6A3_HUMAN	INHIBITOR	Kd	6.28	WOMBAT-PK	CHEMBL
Sodium-dependent noradrenaline transporter	Transporter	P23975	SC6A2_HUMAN	INHIBITOR	Ki	5.16	CHEMBL	CHEMBL
Cytochrome P450 2D6	Enzyme	P10635	CP2D6_HUMAN				WOMBAT-PK
Neuronal acetylcholine receptor subunit alpha-7	Ion channel	P36544	ACHA7_HUMAN		IC50	4.30	CHEMBL
Cytochrome P450 2C19	Enzyme	P33261	CP2CJ_HUMAN		IC50	5.70	DRUG MATRIX
Neuronal acetylcholine receptor; alpha3/beta4	Ion channel	P30926 P32297	ACHB4_HUMAN ACHA3_HUMAN		IC50	5.74	CHEMBL
Sodium-dependent serotonin transporter	Transporter	P31645	SC6A4_HUMAN		Kd	5.04	WOMBAT-PK
Neuronal acetylcholine receptor; alpha3/beta2	Ion channel	P17787 P32297	ACHB2_HUMAN ACHA3_HUMAN		IC50	6	CHEMBL
Alpha-1A adrenergic receptor	GPCR	P35348	ADA1A_HUMAN		Ki	4.80	PDSP
Membrane-associated progesterone receptor component 1	Membrane receptor		PGRC1_RAT		Ki	5.85	DRUG MATRIX

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External reference:

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ID	Source
001512	NDDF
004611	NDDF
012996	NDDF
01ZG3TPX31	UNII
162122	MMSL
203204	RXNORM
26259	MMSL
31548	MMSL
31677-93-7	SECONDARY_CAS_RN
3562	INN_ID

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Pharmaceutical products:

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Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
Aplenzin	HUMAN PRESCRIPTION DRUG LABEL	1	0187-5810	TABLET, EXTENDED RELEASE	174 mg	ORAL	NDA	29 sections
Aplenzin	HUMAN PRESCRIPTION DRUG LABEL	1	0187-5810	TABLET, EXTENDED RELEASE	174 mg	ORAL	NDA	29 sections
Aplenzin	HUMAN PRESCRIPTION DRUG LABEL	1	0187-5811	TABLET, EXTENDED RELEASE	348 mg	ORAL	NDA	29 sections
Aplenzin	HUMAN PRESCRIPTION DRUG LABEL	1	0187-5811	TABLET, EXTENDED RELEASE	348 mg	ORAL	NDA	29 sections
Bupropion Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	0115-5445	TABLET, FILM COATED, EXTENDED RELEASE	200 mg	ORAL	ANDA	30 sections
Bupropion Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	0115-5445	TABLET, FILM COATED, EXTENDED RELEASE	200 mg	ORAL	ANDA	30 sections
Bupropion Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	0115-6811	TABLET, FILM COATED, EXTENDED RELEASE	150 mg	ORAL	ANDA	30 sections
Bupropion Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	0115-6811	TABLET, FILM COATED, EXTENDED RELEASE	150 mg	ORAL	ANDA	30 sections
Bupropion Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	0185-0410	TABLET, EXTENDED RELEASE	100 mg	ORAL	ANDA	29 sections
Bupropion Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	1	0185-0410	TABLET, EXTENDED RELEASE	100 mg	ORAL	ANDA	29 sections

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