Bupropion Hydrochloride

HCID 62884CAS 234447-17-7

Basic information

Standard SMILES
CC(NC(C)(C)C)C(=O)c1cccc(Cl)c1.Cl
InChIKey
HEYVINCGKDONRU-UHFFFAOYSA-N
Molecular formula
C13H19Cl2NO
Average molar mass
276.2 g/mol
Monoisotopic mass
275.08436959

Overview

Bupropion hydrochloride is an aromatic ketone.

Names & identifiers

Preferred name
Bupropion Hydrochloride
IUPAC
2-(tert-butylamino)-1-(3-chlorophenyl)propan-1-one;hydrochloride

Names & synonyms

Bupropion hydrochloride31677-93-7Bupropion HclAmfebutamone hydrochlorideWellbutrin XLWellbutrin SRForfivo XLMysimbaBudeprion XLBW 323DTXSID6044561ZG7E5POY8O
Show more names
NSC-315851BW323BW-323DTXCID4024561NSC315851CONTRAVE COMPONENT BUPROPION HYDROCHLORIDEAppbutamoneForfivo

Database identifiers

CAS
234447-17-7、31677-93-7、34841-36-6、34911-55-2
PubChem CID
62884
DTXSID
DTXSID6044561
ChEMBL
CHEMBL1698
ChEBI
CHEBI:3220
UNII
ZG7E5POY8O
EC Number
250-759-9、252-243-9

Properties

Computed structural properties

Topological polar surface area
29.1 Ų
Hydrogen bond donors
2
Hydrogen bond acceptors
2
Rotatable bonds
4
Heavy atoms
17

Experimental & physicochemical properties

Human Drugs · 4 items

Breast Feeding; Lactation; Milk, Human; Antidepressive Agents; Antidepressive Agents, Second-Generation; Dopamine Uptake Inhibitors; Smoking Cessation Agents

FDA approved drugs -> Active ingredient

EMA approved medicines: Human medicine

FDA approved drugs -> Active ingredient

Safety & regulation

GHS classification

GHS Classification · 5 items

This chemical does not meet GHS hazard criteria for 48.1% (52 of 108) of reports.

Warning

H302 (51.9%): Harmful if swallowed [Warning Acute toxicity, oral]

P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 108 reports by companies from 10 notifications to the ECHA C&L Inventory.

Hazard information

Hazard Classes and CategoriesAcute Tox. 4 (51.9%)

Toxicology

Treatment · 1 item

Ensure an adequate airway, oxygenation, and ventilation. Monitor cardiac rhythm and vital signs. EEG monitoring is also recommended for the first 48 hours post-ingestion. General supportive and symptomatic measures are also recommended. Induction of emesis is not recommended. Activated charcoal should be administered. There is no experience with the use of forced diuresis, dialysis, hemoperfusion, or exchange transfusion in the management of bupropion overdoses. No specific antidotes for bupropion are known. Due to the dose-related risk of seizures with Bupropion, hospitalization following suspected overdose should be considered. Based on studies in animals, it is recommended that seizures be treated with intravenous benzodiazepine administration and other supportive measures, as appropriate. (L1712)

Exposure RoutesFor sustained release, peak plasma concentrations are achieved within 3 hours.
Toxicity Summary · 1 item

Bupropion selectively inhibits the neuronal reuptake of dopamine, norepinephrine, and serotonin; actions on dopaminergic systems are more significant than imipramine or amitriptyline whereas the blockade of norepinephrine and serotonin reuptake at the neuronal membrane is weaker for bupropion than for tricyclic antidepressants. The increase in norepinephrine may attenuate nicotine withdrawal symptoms and the increase in dopamine at neuronal sites may reduce nicotine cravings and the urge to smoke. Bupropion exhibits moderate anticholinergic effects.

Signs and SymptomsSymptoms of overdose include seizures, hallucinations, loss of consciousness, tachycardia, and cardiac arrest.
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Drug Induced Liver Injury · 6 items

Drug Induced Liver Injury Rank (DILIrank 2.0)

Bupropion hydrochloride

vLess-DILI-concern

5

Adverse reactions

DOI:10.1016/j.drudis.2016.02.015

Chemistry & industry

Pharmacology

Metabolism/Metabolites · 1 item

Reduction of the carbonyl groupand/or hydroxylation of the tert-butyl group of bupropion. Route of Elimination: Bupropion is extensively metabolized in humans. Oxidation of the bupropion side chain results in the formation of a glycine conjugate of metachlorobenzoic acid, which is then excreted as the major urinary metabolite. Following oral administration of 200 mg of 14C-bupropion in humans, 87% and 10% of the radioactive dose were recovered in the urine and feces, respectively. However, the fraction of the oral dose of bupropion excreted unchanged was only 0.5%, a finding consistent with the extensive metabolism of bupropion. Half Life: 24 hours

FDA Pharmacological Classification · 6 items

BUPROPION HCL

Increased Norepinephrine Activity [PE]; Increased Dopamine Activity [PE]; Norepinephrine Uptake Inhibitors [MoA]; Dopamine Uptake Inhibitors [MoA]; Aminoketone [EPC]

BUPROPION HYDROCHLORIDE

Dopamine Uptake Inhibitors [MoA]; Aminoketone [EPC]; Increased Norepinephrine Activity [PE]; Increased Dopamine Activity [PE]; Norepinephrine Uptake Inhibitors [MoA]

BUPROPION HYDROCHLORIDE SR

Dopamine Uptake Inhibitors [MoA]; Aminoketone [EPC]; Increased Norepinephrine Activity [PE]; Norepinephrine Uptake Inhibitors [MoA]; Increased Dopamine Activity [PE]

MeSH Pharmacological Classification · 5 items

Substances that facilitate the cessation of tobacco smoking.

A structurally and mechanistically diverse group of drugs that are not tricyclics or monoamine oxidase inhibitors. The most clinically important appear to act selectively on serotonergic systems, especially by inhibiting serotonin reuptake.

Drugs that block the transport of DOPAMINE into axon terminals or into storage vesicles within terminals. Most of the ADRENERGIC UPTAKE INHIBITORS also inhibit dopamine uptake.

Agents that increase energy expenditure and weight loss by neural and metabolic regulation.

Drugs and compounds which inhibit or antagonize the biosynthesis or actions of CYTOCHROME P-450 CYP2D6.

Uses & manufacturing

UsesFor the treatment of depression and as aid to smoking cessation.

Related reactions

41 records

Linked notes

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