Page last updated: 2024-12-04

bw 306u

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

hydroxybupropion: active metabolite of bupropion; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID Source	ID
PubMed CID	446
CHEMBL ID	3544616
CHEBI ID	166487
SCHEMBL ID	1226857
MeSH ID	M0140048

Synonyms (28)

Synonym
82793-84-8
CHEBI:166487
92264-81-8
1-(3-chlorophenyl)-2-[(1-hydroxy-2-methylpropan-2-yl)amino]propan-1-one
hydroxybupropion
AKOAEVOSDHIVFX-UHFFFAOYSA-N
2-(1-hydroxy-2-methylpropan-2-ylamino)-1-(3-chlorophenyl)propan-1-one
SCHEMBL1226857
hydroxybupropione
unii-v94f513635
v94f513635 ,
6-hydroxybupropion
bw-306u
hydroxybupropion, (+/-)-
1-propanone, 1-(3-chlorophenyl)-2-((2-hydroxy-1,1-dimethylethyl)amino)-
CHEMBL3544616
1-(3-chlorophenyl)-2-[(2-hydroxy-1,1-dimethylethyl)amino]-1-propanone
bdbm224811
us9333197, hydroxybupropion
1-(3-chlorophenyl)-2-(1-hydroxy-2-methylpropan-2-ylamino)propan-1-one
HY-100637
CS-0019871
Q18206601
(+/-)-hydroxybupropion
DTXSID101002894
B0094-467887
AKOS040733401
hydroxybupropion, 1mg/ml in acetonitrile

Research Excerpts

Pharmacokinetics

Excerpt	Reference	Relevance
" Recently, the chirality of bupropion has received significant attention in the delineation of stereoselective pharmacokinetic (PK) and disposition data."	( Chirality and neuropsychiatric drugs: an update on stereoselective disposition and clinical pharmacokinetics of bupropion. Dash, RP; Rais, R; Srinivas, NR, 2018)	0.48
" The concentration-time curve (AUC(0→96)), maximum plasma concentration (Cmax), and terminal half-life (t1/2) values of BUP in CYP2B61/4 were lower than those of CYP2B61/1."	( Effects of Genetic Polymorphisms of CYP2B6 on the Pharmacokinetics of Bupropion and Hydroxybupropion in Healthy Chinese Subjects. Dang, H; Ma, H; Ma, Y; Wei, S; Yang, X; Zhang, H; Zhang, W; Zhang, Y, 2018)	0.48

Dosage Studied

Excerpt	Relevance	Reference
" Alternatively, a curvilinear dose-response relationship may exist for bupropion metabolites."	( Bupropion in depression. II. The role of metabolites in clinical outcome. De Vane, CL; Golden, RN; Laizure, SC; Potter, WZ; Rudorfer, MV; Sherer, MA, 1988)	0.27
" However, therapeutic efficacy and treatment success is often variable, requiring changes in dosing regimens or drug selection."	( The development and validation of a turbulent flow-liquid chromatography-tandem mass spectrometric method for the simultaneous quantification of citalopram, sertraline, bupropion and hydroxybupropion in serum. Clarke, W; Jannetto, PJ; Johnson-Davis, KL; Langman, LJ; Marzinke, MA; Moskowitz, J; Petrides, AK, 2014)	0.4
" Human subjects were dosed with a single oral dose of 75 mg of an immediate release bupropion HCl tablet."	( Identification of non-reported bupropion metabolites in human plasma. Babiskin, A; Connarn, JN; Ellingrod, VL; Harrington, G; Kamali, M; Kelly, M; Luo, R; McInnis, M; Sun, D; Windak, J; Zhang, X, 2016)	0.43
" The findings of this study suggest opportunities to further study precision dosing strategies for bupropion therapy based on CYP2B6 genotype."	( Association of CYP2B6 genetic polymorphisms with bupropion and hydroxybupropion exposure: A systematic review and meta-analysis. Bishop, JR; Eum, S; Lee, AM; Sayre, F; Stingl, JC, 2022)	0.72

[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

Class	Description
aromatic ketone	A ketone in which the carbonyl group is attached to an aromatic ring.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Research

Studies (32)

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	1 (3.13)	18.7374
1990's	0 (0.00)	18.2507
2000's	0 (0.00)	29.6817
2010's	26 (81.25)	24.3611
2020's	5 (15.63)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 10.74

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

Metric	This Compound (vs All)
Research Demand Index	10.74 (24.57)
Research Supply Index	3.64 (2.92)
Research Growth Index	4.38 (4.65)
Search Engine Demand Index	0.00 (26.88)
Search Engine Supply Index	0.00 (0.95)

This Compound (10.74)

All Compounds (24.57)

Study Types

Publication Type	This drug (%)	All Drugs (%)
Trials	5 (15.63%)	5.53%
Reviews	3 (9.38%)	6.00%
Case Studies	3 (9.38%)	4.05%
Observational	0 (0.00%)	0.25%
Other	21 (65.63%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Trials	Classes	Roles
bupropion Bupropion: A propiophenone-derived antidepressant and antismoking agent that inhibits the uptake of DOPAMINE.. bupropion : An aromatic ketone that is propiophenone carrying a tert-butylamino group at position 2 and a chloro substituent at position 3 on the phenyl ring.	10.56	32	5	aromatic ketone; monochlorobenzenes; secondary amino compound	antidepressant; environmental contaminant; xenobiotic
citalopram Citalopram: A furancarbonitrile that is one of the serotonin uptake inhibitors used as an antidepressant. The drug is also effective in reducing ethanol uptake in alcoholics and is used in depressed patients who also suffer from TARDIVE DYSKINESIA in preference to tricyclic antidepressants, which aggravate dyskinesia.. citalopram : A racemate comprising equimolar amounts of (R)-citalopram and its enantiomer, escitalopram. It is used as an antidepressant, although only escitalopram is active.. 1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-2-benzofuran-5-carbonitrile : A nitrile that is 1,3-dihydro-2-benzofuran-5-carbonitrile in which one of the hydrogens at position 1 is replaced by a p-fluorophenyl group, while the other is replaced by a 3-(dimethylamino)propyl group.	2.1	1	0	2-benzofurans; cyclic ether; nitrile; organofluorine compound; tertiary amino compound
diclofenac Diclofenac: A non-steroidal anti-inflammatory agent (NSAID) with antipyretic and analgesic actions. It is primarily available as the sodium salt.. diclofenac : A monocarboxylic acid consisting of phenylacetic acid having a (2,6-dichlorophenyl)amino group at the 2-position.	2.1	1	0	amino acid; aromatic amine; dichlorobenzene; monocarboxylic acid; secondary amino compound	antipyretic; drug allergen; EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; environmental contaminant; non-narcotic analgesic; non-steroidal anti-inflammatory drug; xenobiotic
deuterium Deuterium: The stable isotope of hydrogen. It has one neutron and one proton in the nucleus.	2.59	2	0	dihydrogen
sertraline Sertraline: A selective serotonin uptake inhibitor that is used in the treatment of depression.. sertraline : A member of the class of tetralins that is tetralin which is substituted at positions 1 and 4 by a methylamino and a 3,4-dichlorophenyl group, respectively (the S,S diastereoisomer). A selective serotonin-reuptake inhibitor (SSRI), it is administered orally as the hydrochloride salt as an antidepressant for the treatment of depression, obsessive-compulsive disorder, panic disorder and post-traumatic stress disorder.	2.1	1	0	dichlorobenzene; secondary amino compound; tetralins	antidepressant; serotonin uptake inhibitor
nicotine (S)-nicotine : A 3-(1-methylpyrrolidin-2-yl)pyridine in which the chiral centre has S-configuration. The naturally occurring and most active enantiomer of nicotine, isolated from Nicotiana tabacum.	2.49	2	0	3-(1-methylpyrrolidin-2-yl)pyridine	anxiolytic drug; biomarker; immunomodulator; mitogen; neurotoxin; nicotinic acetylcholine receptor agonist; peripheral nervous system drug; phytogenic insecticide; plant metabolite; psychotropic drug; teratogenic agent; xenobiotic
4'-hydroxydiclofenac 4'-hydroxydiclofenac: metabolite of diclofenac; structure in first source. 4'-hydroxydiclofenac : A monocarboxylic acid that is the 4'-hydroxylated metabolite of diclofenac.	2.1	1	0	dichlorobenzene; monocarboxylic acid; phenols; secondary amino compound	allergen; drug metabolite
5-hydroxymethylomeprazole 5-hydroxymethylomeprazole: metabolite of omeprazole. 5'-hydroxyomeprazole : A sulfoxide that is omeprazole in which one of the methyl hydrogens at position 5 on the pyridine ring is substituted by a hydroxy group.	2.1	1	0	aromatic ether; benzimidazoles; pyridines; sulfoxide	drug metabolite
tartaric acid tartaric acid: RN given refers to cpd with unspecified isomeric designation. D-tartaric acid : The D-enantiomer of tartaric acid.	2.15	1	0	tartaric acid	Escherichia coli metabolite
ferulic acid ferulate : A monocarboxylic acid anion obtained by the deprotonation of the carboxy group of ferulic acid.	3.47	1	1	ferulic acids	anti-inflammatory agent; antioxidant; apoptosis inhibitor; cardioprotective agent; MALDI matrix material; plant metabolite
digoxin Digoxin: A cardiotonic glycoside obtained mainly from Digitalis lanata; it consists of three sugars and the aglycone DIGOXIGENIN. Digoxin has positive inotropic and negative chronotropic activity. It is used to control ventricular rate in ATRIAL FIBRILLATION and in the management of congestive heart failure with atrial fibrillation. Its use in congestive heart failure and sinus rhythm is less certain. The margin between toxic and therapeutic doses is small. (From Martindale, The Extra Pharmacopoeia, 30th ed, p666). digoxin : A cardenolide glycoside that is digitoxin beta-hydroxylated at C-12. A cardiac glycoside extracted from the foxglove plant, Digitalis lanata, it is used to control ventricular rate in atrial fibrillation and in the management of congestive heart failure with atrial fibrillation, but the margin between toxic and therapeutic doses is small.	2.1	1	0	cardenolide glycoside; steroid saponin	anti-arrhythmia drug; cardiotonic drug; EC 3.6.3.9 (Na(+)/K(+)-transporting ATPase) inhibitor; epitope
granisetron Granisetron: A serotonin receptor (5HT-3 selective) antagonist that has been used as an antiemetic for cancer chemotherapy patients.. granisetron : A monocarboxylic acid amide resulting from the formal condensation of the carboxy group of 1-methyl-1H-indazole-3-carboxylic acid with the primary amino group of (3-endo)-9-methyl-9-azabicyclo[3.3.1]nonan-3-amine. A selective 5-HT3 receptor antagonist, it is used (generally as the monohydrochloride salt) to manage nausea and vomiting caused by cancer chemotherapy and radiotherapy, and to prevent and treat postoperative nausea and vomiting.	2.15	1	0	aromatic amide; indazoles
isoborneol isoborneol: RN given refers to cpd without isomeric designation; structure	2.15	1	0	borneol

Condition	Relationship Strength	Studies	Trials
Smoking Cessation Discontinuing the habit of SMOKING.	5.53	5	1
Depression, Involutional Form of depression in those MIDDLE AGE with feelings of ANXIETY.	2.25	1	0
Depressive Disorder, Major Disorder in which five (or more) of the following symptoms have been present during the same 2-week period and represent a change from previous functioning; at least one of the symptoms is either (1) depressed mood or (2) loss of interest or pleasure. Symptoms include: depressed mood most of the day, nearly every daily; markedly diminished interest or pleasure in activities most of the day, nearly every day; significant weight loss when not dieting or weight gain; Insomnia or hypersomnia nearly every day; psychomotor agitation or retardation nearly every day; fatigue or loss of energy nearly every day; feelings of worthlessness or excessive or inappropriate guilt; diminished ability to think or concentrate, or indecisiveness, nearly every day; or recurrent thoughts of death, recurrent suicidal ideation without a specific plan, or a suicide attempt. (DSM-5)	2.25	1	0
Adipocere [description not available]	2.15	1	0
Bezoars Concretions of swallowed hair, fruit or vegetable fibers, or similar substances found in the alimentary canal.	2.15	1	0
Drug Overdose Accidental or deliberate use of a medication or street drug in excess of normal dosage.	2.52	2	0
Cardiac Diseases [description not available]	2.08	1	0
Absence Seizure [description not available]	2.08	1	0
Absence Status [description not available]	2.08	1	0
Heart Diseases Pathological conditions involving the HEART including its structural and functional abnormalities.	2.08	1	0
Seizures Clinical or subclinical disturbances of cortical function due to a sudden, abnormal, excessive, and disorganized discharge of brain cells. Clinical manifestations include abnormal motor, sensory and psychic phenomena. Recurrent seizures are usually referred to as EPILEPSY or seizure disorder.	2.08	1	0
Status Epilepticus A prolonged seizure or seizures repeated frequently enough to prevent recovery between episodes occurring over a period of 20-30 minutes. The most common subtype is generalized tonic-clonic status epilepticus, a potentially fatal condition associated with neuronal injury and respiratory and metabolic dysfunction. Nonconvulsive forms include petit mal status and complex partial status, which may manifest as behavioral disturbances. Simple partial status epilepticus consists of persistent motor, sensory, or autonomic seizures that do not impair cognition (see also EPILEPSIA PARTIALIS CONTINUA). Subclinical status epilepticus generally refers to seizures occurring in an unresponsive or comatose individual in the absence of overt signs of seizure activity. (From N Engl J Med 1998 Apr 2;338(14):970-6; Neurologia 1997 Dec;12 Suppl 6:25-30)	2.08	1	0
Depression, Endogenous [description not available]	3.8	2	1
Depressive Disorder An affective disorder manifested by either a dysphoric mood or loss of interest or pleasure in usual activities. The mood disturbance is prominent and relatively persistent.	3.8	2	1
Central Nervous System Disease [description not available]	3.01	1	0
Central Nervous System Diseases Diseases of any component of the brain (including the cerebral hemispheres, diencephalon, brain stem, and cerebellum) or the spinal cord.	3.01	1	0
Sensitivity and Specificity Binary classification measures to assess test results. Sensitivity or recall rate is the proportion of true positives. Specificity is the probability of correctly determining the absence of a condition. (From Last, Dictionary of Epidemiology, 2d ed)	2.1	1	0
Nicotine Addiction [description not available]	2.11	1	0
Tobacco Use Disorder Tobacco used to the detriment of a person's health or social functioning. Tobacco dependence is included.	2.11	1	0
Aging The gradual irreversible changes in structure and function of an organism that occur as a result of the passage of time.	2.13	1	0
Complications, Pregnancy [description not available]	2.13	1	0
Depression Depressive states usually of moderate intensity in contrast with MAJOR DEPRESSIVE DISORDER present in neurotic and psychotic disorders.	2.13	1	0
Pregnancy The status during which female mammals carry their developing young (EMBRYOS or FETUSES) in utero before birth, beginning from FERTILIZATION to BIRTH.	2.53	2	0

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