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93413-62-8

93413-62-8 | Desvenlafaxine

CAS No: 93413-62-8 Catalog No: AG006FY3 MDL No:MFCD00871934

Product Description

Catalog Number:
AG006FY3
Chemical Name:
Desvenlafaxine
CAS Number:
93413-62-8
Molecular Formula:
C16H25NO2
Molecular Weight:
263.3752
MDL Number:
MFCD00871934
IUPAC Name:
4-[2-(dimethylamino)-1-(1-hydroxycyclohexyl)ethyl]phenol
InChI:
InChI=1S/C16H25NO2/c1-17(2)12-15(13-6-8-14(18)9-7-13)16(19)10-4-3-5-11-16/h6-9,15,18-19H,3-5,10-12H2,1-2H3
InChI Key:
KYYIDSXMWOZKMP-UHFFFAOYSA-N
SMILES:
CN(CC(C1(O)CCCCC1)c1ccc(cc1)O)C
EC Number:
700-516-2

Properties

Complexity:
266  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
263.189g/mol
Formal Charge:
0
Heavy Atom Count:
19  
Hydrogen Bond Acceptor Count:
3  
Hydrogen Bond Donor Count:
2  
Isotope Atom Count:
0
Molecular Weight:
263.381g/mol
Monoisotopic Mass:
263.189g/mol
Rotatable Bond Count:
4  
Topological Polar Surface Area:
43.7A^2
Undefined Atom Stereocenter Count:
1  
Undefined Bond Stereocenter Count:
0
XLogP3:
2.6  

Literature

Title Journal
Systems pharmacological analysis of drugs inducing stevens-johnson syndrome and toxic epidermal necrolysis. Chemical research in toxicology 20150518
Syndrome of inappropriate antidiuretic hormone secretion associated with desvenlafaxine. International journal of clinical pharmacy 20140401
Discovery of a potent, dual serotonin and norepinephrine reuptake inhibitor. ACS medicinal chemistry letters 20130613
The effect of age, sex, smoking and co-medication on serum levels of venlafaxine and O-desmethylvenlafaxine under naturalistic conditions. Pharmacopsychiatry 20120901
Metabolites: novel therapeutics or 'me-too' drugs? Using desvenlafaxine as an example. CNS spectrums 20120901
High-dose desvenlafaxine in outpatients with major depressive disorder. CNS spectrums 20120901
An indirect comparison of the efficacy and safety of desvenlafaxine and venlafaxine using placebo as the common comparator. CNS spectrums 20120901
Field and laboratory studies of the fate and enantiomeric enrichment of venlafaxine and O-desmethylvenlafaxine under aerobic and anaerobic conditions. Chemosphere 20120601
A short-term double-blind randomized controlled pilot trial with active or placebo pindolol in patients treated with venlafaxine for major depression. Nordic journal of psychiatry 20120601
Lack of a pharmacokinetic drug-drug interaction with venlafaxine extended-release/indinavir and desvenlafaxine extended-release/indinavir. European journal of clinical pharmacology 20120501
Effective and clinically meaningful non-hormonal hot flash therapies. Maturitas 20120501
Impact of wastewater treatment plant discharge of lidocaine, tramadol, venlafaxine and their metabolites on the quality of surface waters and groundwater. Journal of environmental monitoring : JEM 20120501
Occurrence of Tako-Tsubo cardiomyopathy in association with ingestion of serotonin/noradrenaline reuptake inhibitors. Heart, lung & circulation 20120401
Occurrence and removal of lidocaine, tramadol, venlafaxine, and their metabolites in German wastewater treatment plants. Environmental science and pollution research international 20120301
Species comparison of in vivo P-glycoprotein-mediated brain efflux using mdr1a-deficient rats and mice. Drug metabolism and disposition: the biological fate of chemicals 20120301
The effect of dose titration and dose tapering on the tolerability of desvenlafaxine in women with vasomotor symptoms associated with menopause. Journal of women's health (2002) 20120201
Randomized placebo- and active-controlled study of desvenlafaxine for menopausal vasomotor symptoms. Climacteric : the journal of the International Menopause Society 20120201
Influence of CYP2D6 genotype on the disposition of the enantiomers of venlafaxine and its major metabolites in postmortem femoral blood. Forensic science international 20120110
Assessing the relationship between functional impairment/recovery and depression severity: a pooled analysis. International clinical psychopharmacology 20120101
Duloxetine versus other anti-depressive agents for depression. The Cochrane database of systematic reviews 20120101
Desvenlafaxine in the treatment of major depressive disorder. Expert opinion on pharmacotherapy 20111201
Translating clinical findings into knowledge in drug safety evaluation--drug induced liver injury prediction system (DILIps). PLoS computational biology 20111201
Preclinical pharmacology of TP1, a novel potent triple reuptake inhibitor with antidepressant properties. Neuroscience 20111124
Severe acute cardiomyopathy associated with venlafaxine overdose and possible role of CYP2D6 and CYP2C19 polymorphisms. Clinical toxicology (Philadelphia, Pa.) 20111101
Inhibitory effects of desvenlafaxine on gastric slow waves, antral contractions, and gastric accommodation mediated via the sympathetic mechanism in dogs. American journal of physiology. Gastrointestinal and liver physiology 20111001
Symptomatic and functional improvement in employed depressed patients: a double-blind clinical trial of desvenlafaxine versus placebo. Journal of clinical psychopharmacology 20111001
Clinical outcomes following switch from venlafaxine ER to desvenlafaxine in nonresponders and responders. Current medical research and opinion 20110901
A simple HPLC method for the simultaneous determination of venlafaxine and its major metabolite O-desmethylvenlafaxine in human serum. Bioanalysis 20110801
Fatal venlafaxine poisonings are associated with a high prevalence of drug interactions. International journal of legal medicine 20110501
Induction of drug efflux protein expression by venlafaxine but not desvenlafaxine. Biopharmaceutics & drug disposition 20110501
A rapid, Web-based method for obtaining patient views on effects and side-effects of antidepressants. Journal of affective disorders 20110401
Antidepressant-mediated gastroesophageal reflux disease. The Consultant pharmacist : the journal of the American Society of Consultant Pharmacists 20110401
Tolerance to desvenlafaxine in rapid metabolizing depressed patients. International clinical psychopharmacology 20110301
Open-label treatment with desvenlafaxine in postmenopausal women with major depressive disorder not responding to acute treatment with desvenlafaxine or escitalopram. CNS drugs 20110301
Estimation of desvenlafaxine transfer into milk and infant exposure during its use in lactating women with postnatal depression. Archives of women's mental health 20110201
Quantification of antidepressants and antipsychotics in human serum by precipitation and ultra high pressure liquid chromatography-tandem mass spectrometry. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20110101
The pharmacokinetics and safety of desvenlafaxine in subjects with chronic renal impairment. International journal of clinical pharmacology and therapeutics 20110101
Pharmacokinetics of venlafaxine extended release 75  mg and desvenlafaxine 50  mg in healthy CYP2D6 extensive and poor metabolizers: a randomized, open-label, two-period, parallel-group, crossover study. Clinical drug investigation 20110101
Comments on 'Desvenlafaxine as a possible cause of acquired hemophilia'. General hospital psychiatry 20110101
Assessment of infant dose through milk in a lactating woman taking amisulpride and desvenlafaxine for treatment-resistant depression. Therapeutic drug monitoring 20101201
Desvenlafaxine for major depressive disorder: incremental clinical benefits from a second-generation serotonin-norepinephrine reuptake inhibitor. Expert opinion on drug metabolism & toxicology 20101201
Stereoselective determination of venlafaxine and its three demethylated metabolites in human plasma and whole blood by liquid chromatography with electrospray tandem mass spectrometric detection and solid phase extraction. Journal of pharmaceutical and biomedical analysis 20101102
Cytochrome P450 2D6 phenotype predicts antidepressant efficacy of venlafaxine: a secondary analysis of 4 studies in major depressive disorder. The Journal of clinical psychiatry 20101101
HAM-D17 and HAM-D6 sensitivity to change in relation to desvenlafaxine dose and baseline depression severity in major depressive disorder. Pharmacopsychiatry 20101101
Differential outcomes from metabolic ratios in the identification of CYP2D6 phenotypes--focus on venlafaxine and O-desmethylvenlafaxine. European journal of clinical pharmacology 20100901
Retrospective analysis of suicidality in patients treated with the antidepressant desvenlafaxine. Journal of clinical psychopharmacology 20100801
Pharmacological and clinical profile of newer antidepressants: implications for the treatment of elderly patients. Drugs & aging 20100801
Short-term efficacy and safety of desvenlafaxine in a randomized, placebo-controlled study of perimenopausal and postmenopausal women with major depressive disorder. The Journal of clinical psychiatry 20100801
Antidepressant 'treatment'. Menopause (New York, N.Y.) 20100701
Desvenlafaxine and escitalopram for the treatment of postmenopausal women with major depressive disorder. Menopause (New York, N.Y.) 20100701
Analysis by age and sex of efficacy data from placebo-controlled trials of desvenlafaxine in outpatients with major depressive disorder. Journal of clinical psychopharmacology 20100601
Desvenlafaxine: a therapeutic option for treatment of menopausal hot flashes. Maturitas 20100501
Simultaneous quantification of venlafaxine and O-desmethylvenlafaxine in human plasma by ultra performance liquid chromatography-tandem mass spectrometry and its application in a pharmacokinetic study. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20100301
Analysis of the effect of desvenlafaxine on anxiety symptoms associated with major depressive disorder: pooled data from 9 short-term, double-blind, placebo-controlled trials. CNS spectrums 20100301
Desvenlafaxine for the prevention of relapse in major depressive disorder: results of a randomized trial. Journal of clinical psychopharmacology 20100201
Clinical utility of desvenlafaxine 50 mg/d for treating MDD: a review of two randomized placebo-controlled trials for the practicing physician. Current medical research and opinion 20100101
Understanding outliers on the usual dose-response curve: venlafaxine as a way to phenotype patients in terms of their CYP 2D6 status and why it matters. Journal of psychiatric practice 20100101
Mania possibly induced by desvenlafaxine. Journal of psychiatric practice 20100101
Desvenlafaxine succinate: a newer antidepressant for the treatment of depression and somatic symptoms. Postgraduate medicine 20100101
Correction of venlafaxine- and duloxetine-induced transaminase elevations with desvenlafaxine in a patient with Gilbert's syndrome. CNS spectrums 20100101
Efficacy, safety, and tolerability of Desvenlafaxine 50 mg/d for the treatment of major depressive disorder:a systematic review of clinical trials. Primary care companion to the Journal of clinical psychiatry 20100101
Desvenlafaxine as a possible cause of acquired hemophilia. General hospital psychiatry 20100101
IFN-gamma reduction by tricyclic antidepressants. International journal of psychiatry in medicine 20100101
Rapid high-performance liquid chromatography-tandem mass spectrometry method for simultaneous measurement of venlafaxine and O-desmethylvenlafaxine in human plasma and its application in comparative bioavailability study. Biomedical chromatography : BMC 20091201
Discontinuation symptoms and taper/poststudy-emergent adverse events with desvenlafaxine treatment for major depressive disorder. International clinical psychopharmacology 20091101
Simultaneous determination of venlafaxine and its main active metabolite O-desmethyl venlafaxine in rat plasma by LC-MS/MS. Analytical sciences : the international journal of the Japan Society for Analytical Chemistry 20091001
Desvenlafaxine: application withdrawal. Desvenlafaxine: withdrawal of marketing application for depression also. Prescrire international 20091001
[Non-hormonal treatment for vasomotor symptoms during menopause: role of desvenlafaxine]. Ginecologia y obstetricia de Mexico 20091001
Assessing the efficacy of desvenlafaxine for improving functioning and well-being outcome measures in patients with major depressive disorder: a pooled analysis of 9 double-blind, placebo-controlled, 8-week clinical trials. The Journal of clinical psychiatry 20091001
Venlafaxine in human breast milk and nursing infant plasma: determination of exposure. The Journal of clinical psychiatry 20090901
Venlafaxine metabolism as a marker of cytochrome P450 enzyme 2D6 metabolizer status. Journal of clinical psychopharmacology 20090801
Desvenlafaxine: a new serotonin-norepinephrine reuptake inhibitor for the treatment of adults with major depressive disorder. Clinical therapeutics 20090601
Desvenlafaxine 50 and 100 mg/d in the treatment of major depressive disorder: an 8-week, phase III, multicenter, randomized, double-blind, placebo-controlled, parallel-group trial and a post hoc pooled analysis of three studies. Clinical therapeutics 20090601
Desvenlafaxine: a new antidepressant or just another one? Expert opinion on pharmacotherapy 20090401
New drug update: 2008. The Consultant pharmacist : the journal of the American Society of Consultant Pharmacists 20090401
Desvenlafaxine for the treatment of vasomotor symptoms associated with menopause: a double-blind, randomized, placebo-controlled trial of efficacy and safety. American journal of obstetrics and gynecology 20090301
The effects of desvenlafaxine and paroxetine on the pharmacokinetics of the cytochrome P450 2D6 substrate desipramine in healthy adults. Journal of clinical pharmacology 20090201
A double-blind, randomly assigned, placebo-controlled study of desvenlafaxine efficacy and safety for the treatment of vasomotor symptoms associated with menopause. American journal of obstetrics and gynecology 20090201
Comparison of the pharmacokinetics of venlafaxine extended release and desvenlafaxine in extensive and poor cytochrome P450 2D6 metabolizers. Journal of clinical psychopharmacology 20090201
Drug approvals: '08 in review. Desvenlafaxine (Pristiq). The Nurse practitioner 20090201
Desvenlafaxine, a serotonin-norepinephrine uptake inhibitor for major depressive disorder, neuropathic pain and the vasomotor symptoms associated with menopause. Current opinion in investigational drugs (London, England : 2000) 20090101
A placebo-controlled study evaluating the efficacy and safety of flexible-dose desvenlafaxine treatment in outpatients with major depressive disorder. CNS spectrums 20090101
Desvenlafaxine and venlafaxine exert minimal in vitro inhibition of human cytochrome P450 and P-glycoprotein activities. Psychopharmacology bulletin 20090101
Analysis of depressive symptoms in patients with major depressive disorder treated with desvenlafaxine or placebo. Psychopharmacology bulletin 20090101
An assessment of drug-drug interactions: the effect of desvenlafaxine and duloxetine on the pharmacokinetics of the CYP2D6 probe desipramine in healthy subjects. Drug metabolism and disposition: the biological fate of chemicals 20081201
Desvenlafaxine succinate for major depressive disorder: a critical review of the evidence. Expert review of neurotherapeutics 20081201
Effect of desvenlafaxine on the cytochrome P450 2D6 enzyme system. Journal of psychiatric practice 20081101
Desvenlafaxine: another 'me too' drug? The Annals of pharmacotherapy 20081001
Desvenlafaxine succinate for the treatment of major depressive disorder. Expert opinion on pharmacotherapy 20080801
Liquid chromatography tandem mass spectrometry assay for the simultaneous determination of venlafaxine and O-desmethylvenlafaxine in human plasma and its application to a bioequivalence study. Journal of pharmaceutical and biomedical analysis 20080715
Efficacy, safety, and tolerability of desvenlafaxine 50 mg/day and 100 mg/day in outpatients with major depressive disorder. Current medical research and opinion 20080701
A pooled analysis of two placebo-controlled trials of desvenlafaxine in major depressive disorder. International clinical psychopharmacology 20080701
Flat dose-response curves for efficacy: what do they mean to the clinician? Journal of psychiatric practice 20080701
Desvenlafaxine succinate for major depressive disorder. Drugs of today (Barcelona, Spain : 1998) 20080701
Desvenlafaxine for depression. The Medical letter on drugs and therapeutics 20080519
Serum concentrations of venlafaxine and its metabolites O-desmethylvenlafaxine and N-desmethylvenlafaxine in heterozygous carriers of the CYP2D6*3, *4 or *5 allele. European journal of clinical pharmacology 20080501
Desvenlafaxine succinate monohydrate. Acta crystallographica. Section C, Crystal structure communications 20080501
Effect of terbinafine and voriconazole on the pharmacokinetics of the antidepressant venlafaxine. Clinical pharmacology and therapeutics 20080201
Efficacy and tolerability of desvenlafaxine succinate treatment for menopausal vasomotor symptoms: a randomized controlled trial. Obstetrics and gynecology 20080101
Identifying meaningful differences in vasomotor symptoms among menopausal women. Menopause (New York, N.Y.) 20080101
New drugs: Etravirine, sinecatechins, and desvenlafaxine succinate. Journal of the American Pharmacists Association : JAPhA 20080101
Desvenlafaxine extended release. CNS drugs 20080101
Desvenlafaxine succinate identifies novel antagonist binding determinants in the human norepinephrine transporter. The Journal of pharmacology and experimental therapeutics 20071101
A randomized, double-blind, placebo-controlled trial of desvenlafaxine succinate in the treatment of major depressive disorder. International clinical psychopharmacology 20071101
A randomized, double-blind, placebo-controlled trial of desvenlafaxine succinate in adult outpatients with major depressive disorder. The Journal of clinical psychiatry 20071101
New products and regimens (since 2003). Climacteric : the journal of the International Menopause Society 20071001
Analysis of the second generation antidepressant venlafaxine and its main active metabolite O-desmethylvenlafaxine in human plasma by HPLC with spectrofluorimetric detection. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20070901
Venlafaxine in the treatment of children and adolescents with attention-deficit/hyperactivity disorder. Journal of child and adolescent psychopharmacology 20070801
Simultaneous stereoselective analysis of venlafaxine and O-desmethylvenlafaxine enantiomers in human plasma by HPLC-ESI/MS using a vancomycin chiral column. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20070501
A double-blind, placebo-controlled study of the efficacy and safety of desvenlafaxine succinate in the treatment of major depressive disorder. The Journal of clinical psychiatry 20070501
Alleviation of thermoregulatory dysfunction with the new serotonin and norepinephrine reuptake inhibitor desvenlafaxine succinate in ovariectomized rodent models. Endocrinology 20070301
Employing atmospheric pressure photoionization in liquid chromatography/tandem mass spectrometry to minimize ion suppression and matrix effects for the quantification of venlafaxine and O-desmethylvenlafaxine. Rapid communications in mass spectrometry : RCM 20070101
CYP2D6 polymorphism and clinical effect of the antidepressant venlafaxine. Journal of clinical pharmacy and therapeutics 20061001
Desvenlafaxine succinate: A new serotonin and norepinephrine reuptake inhibitor. The Journal of pharmacology and experimental therapeutics 20060801
Pharmacokinetic and pharmacodynamic profiles of the novel serotonin and norepinephrine reuptake inhibitor desvenlafaxine succinate in ovariectomized Sprague-Dawley rats. Brain research 20060707
CYP2D6 genotype and venlafaxine-XR concentrations in depressed elderly. International journal of geriatric psychiatry 20060601
[Trazodone for the treatment of behavioral and psychological symptoms of dementia (BPSD) in Alzheimer's disease: a retrospective study focused on the aggression and negativism in caregiving situations]. No to shinkei = Brain and nerve 20060601
Anesthesiologist suicide with atracurium. Journal of analytical toxicology 20060301
Liquid chromatography-tandem mass spectrometry (LC-MS-MS) method for simultaneous determination of venlafaxine and its active metabolite O-desmethyl venlafaxine in human plasma. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20051227
Development of a solid phase extraction for 13 'new' generation antidepressants and their active metabolites for gas chromatographic-mass spectrometric analysis. Journal of chromatography. A 20051209
Metabolic ratios of psychotropics as indication of cytochrome P450 2D6/2C19 genotype. Therapeutic drug monitoring 20050801
Efficacy and tolerability of venlafaxine in geriatric outpatients with major depression: a double-blind, randomised 6-month comparative trial with citalopram. International journal of geriatric psychiatry 20041201
Quantification of venlafaxine and O-desmethylvenlafaxine in human serum using HPLC analysis. International journal of clinical pharmacology and therapeutics 20041201
Time course of clinical response to venlafaxine: relevance of plasma level and chirality. European journal of clinical pharmacology 20040201
A double blind comparison of venlafaxine and paroxetine in obsessive-compulsive disorder. Journal of clinical psychopharmacology 20031201
Inhibition of P-glycoprotein by newer antidepressants. The Journal of pharmacology and experimental therapeutics 20030401
Therapeutic drug monitoring of racemic venlafaxine and its main metabolites in an everyday clinical setting. Therapeutic drug monitoring 20020801
Steady-state concentration of venlafaxine enantiomers: model-based analysis of between-patient variability. European journal of clinical pharmacology 20020801
Distribution of venlafaxine and its O-desmethyl metabolite in human milk and their effects in breastfed infants. British journal of clinical pharmacology 20020101
Venlafaxine in neuropathic pain following treatment of breast cancer. European journal of pain (London, England) 20020101
False-positive phencyclidine immunoassay results caused by venlafaxine and O-desmethylvenlafaxine. Clinical chemistry 20020101
Venlafaxine and breast-feeding. The American journal of psychiatry 20011201
Rapid high-performance liquid chromatographic measurement of venlafaxine and O-desmethylvenlafaxine in human plasma. Application to management of acute intoxications. Journal of chromatography. B, Biomedical sciences and applications 20010905
Use of vancomycin silica stationary phase in packed capillary electrochromatography. II. Enantiomer separation of venlafaxine and O-desmethylvenlafaxine in human plasma. Journal of chromatography. A 20010601
Nonaqueous capillary electrophoresis-mass spectrometry for separation of venlafaxine and its phase I metabolites. Electrophoresis 20010201

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