bupropion indications/contra

Stem definitionDrug idCAS RN
anorexics 435 34911-55-2

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • bupropion
  • (+/-)-Bupropion
  • amfebutamon
  • amfebutamone
  • aplenzin
  • elontril
  • bupropion hydrochloride
  • bupropion hydrobromide
  • bupropion HCl
  • wellbutrin
A unicyclic, aminoketone antidepressant. The mechanism of its therapeutic actions is not well understood, but it does appear to block dopamine uptake. The hydrochloride is available as an aid to smoking cessation treatment.
  • Molecular weight: 239.74
  • Formula: C13H18ClNO
  • CLOGP: 3.21
  • LIPINSKI: 0
  • HAC: 2
  • HDO: 1
  • TPSA: 29.10
  • ALOGS: -3.54
  • ROTB: 4

Drug dosage:

DoseUnitRoute
0.30 g O

Approvals:

DateAgencyCompanyOrphan
Dec. 30, 1985 FDA GLAXOSMITHKLINE

FDA Adverse Event Reporting System

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MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Completed suicide 8038.64 34.54 1984 8351 29130 3346394
Toxicity to various agents 2252.70 34.54 828 9507 46226 3329298
Seizure 1893.26 34.54 701 9634 39699 3335825
Overdose 1513.46 34.54 569 9766 33409 3342115
Depression 1391.45 34.54 559 9776 39211 3336313
Poisoning 1307.89 34.54 329 10006 4783 3370741
Cardiac arrest 1275.01 34.54 474 9861 26845 3348679
Generalised tonic-clonic seizure 1242.18 34.54 347 9988 7695 3367829
Drug abuse 1219.20 34.54 414 9921 17916 3357608
Anxiety 1080.89 34.54 467 9868 39162 3336362
Intentional overdose 1051.57 34.54 354 9981 14871 3360653
Product substitution issue 1037.85 34.54 298 10037 7302 3368222
Respiratory arrest 1030.99 34.54 325 10010 11043 3364481
Suicide attempt 1029.82 34.54 352 9983 15495 3360029
Cardio-respiratory arrest 968.21 34.54 334 10001 15106 3360418
Agitation 921.58 34.54 343 9992 19363 3356161
Drug ineffective 832.80 34.54 562 9773 115528 3259996
Nausea 809.05 34.54 576 9759 129069 3246455
Drug hypersensitivity 793.53 34.54 365 9970 35315 3340209
Suicidal ideation 783.03 34.54 296 10039 17409 3358115
Tremor 763.41 34.54 331 10004 27813 3347711
Serotonin syndrome 648.34 34.54 192 10143 5231 3370293
Insomnia 596.52 34.54 301 10034 35597 3339927
Dizziness 571.53 34.54 381 9954 76131 3299393
Feeling abnormal 541.17 34.54 259 10076 27266 3348258
Headache 523.95 34.54 388 9947 91592 3283932
Product quality issue 499.56 34.54 243 10092 26492 3349032
Therapeutic response unexpected 493.56 34.54 154 10181 5014 3370510
Status epilepticus 492.39 34.54 141 10194 3394 3372130
Drug interaction 492.21 34.54 290 10045 46522 3329002

Pharmacologic Action:

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SourceCodeDescription
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
FDA EPC N0000180855 Aminoketone
FDA PE N0000009282 Increased Dopamine Activity
FDA PE N0000009456 Increased Norepinephrine Activity
FDA MoA N0000000102 Norepinephrine Uptake Inhibitors
CHEBI has role CHEBI:35469 antidepressant
MeSH PA D000928 Antidepressive Agents
MeSH PA D018687 Antidepressive Agents, Second-Generation
MeSH PA D002491 Central Nervous System Agents
MeSH PA D065690 Cytochrome P-450 CYP2D6 Inhibitors
MeSH PA D065607 Cytochrome P-450 Enzyme Inhibitors
MeSH PA D015259 Dopamine Agents
MeSH PA D018765 Dopamine Uptake Inhibitors
MeSH PA D004791 Enzyme Inhibitors
MeSH PA D049990 Membrane Transport Modulators
MeSH PA D065606 Metabolic Side Effects of Drugs and Substances
MeSH PA D018377 Neurotransmitter Agents
MeSH PA D014179 Neurotransmitter Uptake Inhibitors
MeSH PA D011619 Psychotropic Drugs

Drug Use (View source of the data)

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DiseaseRelationSNOMED_IDDOID
Depressive disorder indication 35489007 DOID:2848
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
Suicidal thoughts contraindication 6471006
Alcoholism contraindication 7200002
Mood swings contraindication 18963009
Lowered convulsive threshold contraindication 19260006
Cirrhosis of liver contraindication 19943007 DOID:5082
Myocardial infarction contraindication 22298006 DOID:5844
Feeling agitated contraindication 24199005
Hypertensive disorder contraindication 38341003 DOID:10763
Anorexia nervosa contraindication 56882008 DOID:8689
Hepatic failure contraindication 59927004
Psychotic disorder contraindication 69322001
Opioid dependence contraindication 75544000 DOID:2559
Bulimia nervosa contraindication 78004001 DOID:12129
Hostile behavior contraindication 79351003
Injury of head contraindication 82271004
Weight loss contraindication 89362005
Kidney disease contraindication 90708001 DOID:2527
Secondary malignant neoplasm of cerebrum contraindication 94248000
Neoplasm of central nervous system contraindication 126951006 DOID:3620
Seizure disorder contraindication 128613002 DOID:1826
Bipolar affective disorder, current episode manic contraindication 191618007
Disease of liver contraindication 235856003 DOID:409
Diabetic - poor control contraindication 268519009
Alcohol withdrawal-induced convulsion contraindication 308742005
Panic disorder contraindication 371631005 DOID:594
Sedative Drug Dependence contraindication
Seizure due to Abrupt Benzodiazepine Withdrawal contraindication
Stimulant Drug Dependence contraindication
Bipolar affective disorder, current episode depression off-label use 191627008 DOID:3312
Attention deficit hyperactivity disorder off-label use 406506008

Acid dissociation constants calculated using MoKa v3.0.0

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Dissociation levelDissociation constantType (acidic/basic)
pKa1 7.87 Basic

Orange Book patent data (new drug applications)

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Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRoutePatent numberPatent expiration datePatent use
90MG CONTRAVE OREXIGEN N200063 Sept. 10, 2014 RX TABLET, EXTENDED RELEASE ORAL 7462626 July 20, 2024 FOR CHRONIC WEIGHT MANAGEMENT FOR TREATING OVERWEIGHT OR OBESITY
90MG CONTRAVE OREXIGEN N200063 Sept. 10, 2014 RX TABLET, EXTENDED RELEASE ORAL 8815889 July 20, 2024 FOR EFFECT ON BLOOD GLUCOSE PARAMETERS IN PATIENTS WITH INSULIN RESISTANCE
174MG APLENZIN VALEANT PHARMS NORTH N022108 April 23, 2008 RX TABLET, EXTENDED RELEASE ORAL 7569610 June 27, 2026 TREATMENT OF MAJOR DEPRESSIVE DISORDER BY DOSING AT INTERVALS OF 24 HOURS
348MG APLENZIN VALEANT PHARMS NORTH N022108 April 23, 2008 RX TABLET, EXTENDED RELEASE ORAL 7569610 June 27, 2026 TREATMENT OF MAJOR DEPRESSIVE DISORDER BY DOSING AT INTERVALS OF 24 HOURS
522MG APLENZIN VALEANT PHARMS NORTH N022108 April 23, 2008 RX TABLET, EXTENDED RELEASE ORAL 7569610 June 27, 2026 TREATMENT OF MAJOR DEPRESSIVE DISORDER BY DOSING AT INTERVALS OF 24 HOURS
90MG CONTRAVE OREXIGEN N200063 Sept. 10, 2014 RX TABLET, EXTENDED RELEASE ORAL 9107837 June 4, 2027 USE OF NALTREXONE AND BUPROPION IN EXTENDED-RELEASE FORM FOR CHRONIC WEIGHT MANAGEMENT FOR TREATING OVERWEIGHT OR OBESITY
90MG CONTRAVE OREXIGEN N200063 Sept. 10, 2014 RX TABLET, EXTENDED RELEASE ORAL 8318788 Nov. 8, 2027 USE OF NALTREXONE AND BUPROPION IN A LAYERED FORMULATION FOR CHRONIC WEIGHT MANAGEMENT FOR AFFECTING WEIGHT LOSS
90MG CONTRAVE OREXIGEN N200063 Sept. 10, 2014 RX TABLET, EXTENDED RELEASE ORAL 8722085 Nov. 8, 2027 USE OF NALTREXONE AND BUPROPION BASED ON AN ESCALATING DOSE SCHEDULE
90MG CONTRAVE OREXIGEN N200063 Sept. 10, 2014 RX TABLET, EXTENDED RELEASE ORAL 9125868 Nov. 8, 2027 USE OF NALTREXONE AND BUPROPION BASED ON AN ESCALATING DOSE SCHEDULE
90MG CONTRAVE OREXIGEN N200063 Sept. 10, 2014 RX TABLET, EXTENDED RELEASE ORAL 8916195 Feb. 2, 2030 USE OF NALTREXONE AND BUPROPION IN EXTENDED-RELEASE FORM FOR CHRONIC WEIGHT MANAGEMENT FOR TREATING OVERWEIGHT OR OBESITY
90MG CONTRAVE OREXIGEN N200063 Sept. 10, 2014 RX TABLET, EXTENDED RELEASE ORAL 9248123 Jan. 13, 2032 USE OF NALTREXONE AND BUPROPION FOR CHRONIC WEIGHT MANAGEMENT FOR TREATING OVERWEIGHT OR OBESITY IN PATIENTS WITH MAJOR DEPRESSIVE DISORDER

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

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TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Sodium-dependent noradrenaline transporter Transporter INHIBITOR Ki 5.16 CHEMBL CHEMBL
Sodium-dependent dopamine transporter Transporter INHIBITOR Kd 6.28 WOMBAT-PK CHEMBL
Neuronal acetylcholine receptor subunit alpha-7 Ion channel IC50 4.30 CHEMBL
Neuronal acetylcholine receptor; alpha3/beta2 Ion channel IC50 6 CHEMBL
Neuronal acetylcholine receptor; alpha3/beta4 Ion channel IC50 5.74 CHEMBL
Sodium-dependent serotonin transporter Transporter Kd 5.04 WOMBAT-PK
Cytochrome P450 2D6 Enzyme WOMBAT-PK
Alpha-1A adrenergic receptor GPCR Ki 4.80 PDSP
Cytochrome P450 2C19 Enzyme IC50 5.70 DRUG MATRIX
Membrane-associated progesterone receptor component 1 Membrane receptor Ki 5.85 DRUG MATRIX
Sodium-dependent dopamine transporter Transporter IC50 5.91 CHEMBL

External reference:

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IDSource
4019645 VUID
N0000147738 NUI
C0085208 UMLSCUI
7135 IUPHAR_LIGAND_ID
D00817 KEGG_DRUG
01ZG3TPX31 UNII
3562 INN_ID
CHEMBL894 ChEMBL_ID
444 PUBCHEM_CID
4019645 VANDF
N0000006417 NDFRT
N0000147738 NDFRT
42347 RXNORM
004611 NDDF
387564004 SNOMEDCT_US
96199001 SNOMEDCT_US
d00181 MMSL
CHEBI:3219 CHEBI
CHEMBL1698 ChEMBL_ID
CHEMBL1201735 ChEMBL_ID
905818-69-1 SECONDARY_CAS_RN
DB01156 DRUGBANK_ID
D016642 MESH_DESCRIPTOR_UI

Pharmaceutical products:

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ProductCategoryIngredientsNDCFormQuantityRoute MarketingLabel
Aplenzin HUMAN PRESCRIPTION DRUG LABEL 1 0024-5810 TABLET, EXTENDED RELEASE 174 mg ORAL NDA 21 sections
Aplenzin HUMAN PRESCRIPTION DRUG LABEL 1 0024-5811 TABLET, EXTENDED RELEASE 348 mg ORAL NDA 21 sections
Aplenzin HUMAN PRESCRIPTION DRUG LABEL 1 0024-5812 TABLET, EXTENDED RELEASE 522 mg ORAL NDA 21 sections
Naltrexone Hydrochloride and Bupropion Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 2 0051-0629 TABLET, EXTENDED RELEASE 90 mg ORAL Approved Drug Product Manufactured Under Contract 1 sections
Bupropion Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0115-5445 TABLET, FILM COATED, EXTENDED RELEASE 200 mg ORAL ANDA 21 sections
Bupropion Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0115-6811 TABLET, FILM COATED, EXTENDED RELEASE 150 mg ORAL ANDA 21 sections
WELLBUTRIN HUMAN PRESCRIPTION DRUG LABEL 1 0173-0135 TABLET, FILM COATED 150 mg ORAL NDA 20 sections
ZYBAN HUMAN PRESCRIPTION DRUG LABEL 1 0173-0556 TABLET, FILM COATED 150 mg ORAL NDA 20 sections
WELLBUTRIN HUMAN PRESCRIPTION DRUG LABEL 1 0173-0722 TABLET, FILM COATED 200 mg ORAL NDA 20 sections
WELLBUTRIN HUMAN PRESCRIPTION DRUG LABEL 1 0173-0947 TABLET, FILM COATED 100 mg ORAL NDA 20 sections
BuPROPion Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0179-0022 TABLET, EXTENDED RELEASE 100 mg ORAL ANDA 14 sections
Bupropion Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0179-0025 TABLET, FILM COATED 75 mg ORAL ANDA 15 sections
BuPROPion Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0179-0030 TABLET, EXTENDED RELEASE 150 mg ORAL ANDA 14 sections
Bupropion Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0185-0410 TABLET, EXTENDED RELEASE 100 mg ORAL ANDA 20 sections
Bupropion Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0185-0415 TABLET, EXTENDED RELEASE 150 mg ORAL ANDA 20 sections
Bupropion Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0185-1111 TABLET, EXTENDED RELEASE 200 mg ORAL ANDA 20 sections
WELLBUTRIN HUMAN PRESCRIPTION DRUG LABEL 1 0187-0730 TABLET, EXTENDED RELEASE 150 mg ORAL NDA 20 sections
WELLBUTRIN HUMAN PRESCRIPTION DRUG LABEL 1 0187-0731 TABLET, EXTENDED RELEASE 300 mg ORAL NDA 20 sections
Aplenzin HUMAN PRESCRIPTION DRUG LABEL 1 0187-5810 TABLET, EXTENDED RELEASE 174 mg ORAL NDA 20 sections
Aplenzin HUMAN PRESCRIPTION DRUG LABEL 1 0187-5811 TABLET, EXTENDED RELEASE 348 mg ORAL NDA 20 sections
Aplenzin HUMAN PRESCRIPTION DRUG LABEL 1 0187-5812 TABLET, EXTENDED RELEASE 522 mg ORAL NDA 20 sections
Bupropion Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0378-0433 TABLET, FILM COATED 75 mg ORAL ANDA 20 sections
Bupropion Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0378-0435 TABLET, FILM COATED 100 mg ORAL ANDA 20 sections
Bupropion Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0378-2008 TABLET, FILM COATED, EXTENDED RELEASE 150 mg ORAL ANDA 20 sections
Bupropion Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0378-2009 TABLET, FILM COATED, EXTENDED RELEASE 300 mg ORAL ANDA 20 sections
Bupropion hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0378-3411 TABLET, FILM COATED, EXTENDED RELEASE 100 mg ORAL ANDA 20 sections
Bupropion hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0378-3412 TABLET, FILM COATED, EXTENDED RELEASE 150 mg ORAL ANDA 20 sections
Bupropion hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0378-3413 TABLET, FILM COATED, EXTENDED RELEASE 200 mg ORAL ANDA 20 sections
Bupropion Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0378-5521 TABLET, FILM COATED, EXTENDED RELEASE 150 mg ORAL ANDA 20 sections
Bupropion Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0440-7200 TABLET, FILM COATED, EXTENDED RELEASE 150 mg ORAL ANDA 16 sections