desvenlafaxine Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
4380 93413-62-8

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • desvenlafaxine
  • desvenlafaxine succinate
  • pristiq
  • DVS-233
  • desvenlafaxine fumarate
The exact mechanism of the antidepressant action of desvenlafaxine is unknown, but is thought to be related to the potentiation of serotonin and norepinephrine in the central nervous system, through inhibition of their reuptake. Non-clinical studies have shown that desvenlafaxine is a potent and selective serotonin and norepinephrine reuptake inhibitor (SNRI).
  • Molecular weight: 263.38
  • Formula: C16H25NO2
  • CLOGP: 2.68
  • LIPINSKI: 0
  • HAC: 3
  • HDO: 2
  • TPSA: 43.70
  • ALOGS: -2.27
  • ROTB: 4

  • Status: OFP

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

Drug dosage:

DoseUnitRoute
50 mg O

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 3 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 572 mg/mL Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 45 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 5.42 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
Vd (Volume of distribution) 3.50 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 4.90 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.70 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 8.40 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
Feb. 29, 2008 FDA WYETH PHARMS INC

FDA Adverse Event Reporting System (Female)

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
Product residue present 726.26 16.05 195 20904 3687 46661276
Drug withdrawal syndrome 585.58 16.05 273 20826 27111 46637852
Suicidal ideation 327.08 16.05 241 20858 56141 46608822
Anxiety 270.67 16.05 370 20729 181587 46483376
Feeling abnormal 267.14 16.05 305 20794 124755 46540208
Crying 264.82 16.05 147 20952 20994 46643969
Withdrawal syndrome 254.62 16.05 136 20963 17998 46646965
Insomnia 216.38 16.05 316 20783 164608 46500355
Depression 206.08 16.05 314 20785 169790 46495173
Irritability 168.26 16.05 124 20975 28822 46636141
Dizziness 151.30 16.05 414 20685 340000 46324963
Anger 141.79 16.05 80 21019 11772 46653191
Nausea 113.72 16.05 609 20490 686845 45978118
Hyperhidrosis 109.48 16.05 166 20933 89142 46575821
Condition aggravated 106.57 16.05 296 20803 244756 46420207
Headache 105.73 16.05 461 20638 477891 46187072
Panic attack 89.95 16.05 74 21025 20168 46644795
Nervousness 84.70 16.05 83 21016 28392 46636571
Emotional disorder 83.54 16.05 58 21041 12266 46652697
Intentional product misuse 80.79 16.05 103 20996 47025 46617938
Agitation 79.49 16.05 111 20988 55304 46609659
Abnormal dreams 78.30 16.05 52 21047 10227 46654736
Tremor 77.26 16.05 165 20934 115474 46549489
Feeling jittery 75.06 16.05 52 21047 10956 46654007
Drug ineffective 61.52 16.05 518 20581 677320 45987643
Thinking abnormal 59.15 16.05 43 21056 9771 46655192
Nightmare 56.23 16.05 52 21047 16546 46648417
Death 49.85 16.05 47 21052 335501 46329462
Suicide attempt 49.43 16.05 89 21010 54947 46610016
Serotonin syndrome 48.05 16.05 57 21042 24163 46640800
Completed suicide 47.08 16.05 159 20940 145761 46519202
Acute kidney injury 46.97 16.05 24 21075 235831 46429132
Middle insomnia 46.96 16.05 37 21062 9478 46655485
Anaemia 45.30 16.05 30 21069 255749 46409214
Depressed mood 45.18 16.05 65 21034 33254 46631709
Neutropenia 44.53 16.05 6 21093 143198 46521765
Disturbance in attention 43.42 16.05 62 21037 31498 46633465
Overdose 42.99 16.05 122 20977 101857 46563106
Rheumatoid arthritis 42.77 16.05 28 21071 240187 46424776
Pyrexia 41.88 16.05 58 21041 348744 46316219
Paraesthesia 41.49 16.05 132 20967 117305 46547658
Weight increased 41.10 16.05 165 20934 164308 46500655
Migraine 40.07 16.05 94 21005 69932 46595031
Mydriasis 39.55 16.05 35 21064 10518 46654445
Mania 38.73 16.05 35 21064 10811 46654152
Vision blurred 38.22 16.05 100 20999 79608 46585355
Energy increased 38.11 16.05 19 21080 2175 46662788
Anorgasmia 37.63 16.05 13 21086 585 46664378
Tinnitus 36.08 16.05 53 21046 27620 46637343
Drug screen positive 35.35 16.05 22 21077 3869 46661094
Coma scale abnormal 34.95 16.05 24 21075 4982 46659981
Impaired driving ability 33.70 16.05 22 21077 4202 46660761
Thrombocytopenia 33.53 16.05 8 21091 126573 46538390
Seizure 32.78 16.05 126 20973 122928 46542035
Drug screen false positive 32.78 16.05 13 21086 864 46664099
Product substitution issue 32.53 16.05 37 21062 14994 46649969
Pneumonia 32.26 16.05 77 21022 376243 46288720
Mood altered 31.57 16.05 34 21065 12973 46651990
Blood pressure increased 30.77 16.05 126 20973 126540 46538423
Aggression 30.29 16.05 44 21055 22700 46642263
Prescribed overdose 30.21 16.05 30 21069 10419 46654544
Sepsis 29.92 16.05 12 21087 136002 46528961
Mood swings 28.59 16.05 36 21063 16216 46648747
Drug hypersensitivity 28.41 16.05 198 20901 243627 46421336
Hostility 27.27 16.05 13 21086 1349 46663614
Bruxism 27.26 16.05 17 21082 3000 46661963
Restlessness 26.47 16.05 44 21055 25480 46639483
Somnolence 26.43 16.05 140 20959 156381 46508582
Nonspecific reaction 26.29 16.05 14 21085 1836 46663127
Amnesia 25.03 16.05 57 21042 41574 46623389
Paranoia 24.50 16.05 27 21072 10570 46654393
Libido decreased 24.35 16.05 15 21084 2590 46662373
Maternal exposure during pregnancy 24.33 16.05 8 21091 102541 46562422
Panic reaction 24.15 16.05 17 21082 3672 46661291
Therapeutic response unexpected 23.45 16.05 32 21067 15584 46649379
Palpitations 23.31 16.05 95 21004 95164 46569799
Pre-existing condition improved 22.94 16.05 21 21078 6591 46658372
Abnormal behaviour 22.78 16.05 37 21062 21021 46643942
Dyspnoea 22.41 16.05 139 20960 515409 46149554
Mental disorder 22.38 16.05 38 21061 22387 46642576
Hypersensitivity vasculitis 22.10 16.05 17 21082 4204 46660759
Euphoric mood 21.92 16.05 17 21082 4255 46660708
Tachyphrenia 21.87 16.05 11 21088 1283 46663680
Loss of libido 21.43 16.05 11 21088 1338 46663625
Febrile neutropenia 21.38 16.05 8 21091 94619 46570344
General physical health deterioration 21.26 16.05 13 21086 115756 46549207
Apathy 21.25 16.05 21 21078 7247 46657716
Post-traumatic stress disorder 20.53 16.05 16 21083 4032 46660931
Muscle twitching 20.43 16.05 29 21070 14643 46650320
Haemoglobin decreased 20.37 16.05 17 21082 128932 46536031
Unevaluable event 20.18 16.05 56 21043 46119 46618844
Bradycardia 20.08 16.05 3 21096 66295 46598668
Drug effective for unapproved indication 20.05 16.05 11 21088 1531 46663432
Negative thoughts 20.03 16.05 9 21090 816 46664147
Urinary tract infection 18.89 16.05 45 21054 220221 46444742
Stomatitis 18.71 16.05 4 21095 68293 46596670
Intestinal pseudo-obstruction 18.53 16.05 8 21091 659 46664304
Peripheral swelling 18.21 16.05 27 21072 158044 46506919
Dissociation 18.04 16.05 11 21088 1866 46663097
Blood cholesterol increased 17.95 16.05 49 21050 39964 46624999
Treatment failure 17.73 16.05 10 21089 93077 46571886
Suicidal behaviour 17.72 16.05 12 21087 2436 46662527
Change in seizure presentation 17.45 16.05 6 21093 266 46664697
Renal impairment 17.29 16.05 6 21093 74366 46590597
Food craving 16.92 16.05 9 21090 1178 46663785
Respiratory failure 16.92 16.05 11 21088 94805 46570158
Coma 16.86 16.05 3 21096 58346 46606617
Joint swelling 16.69 16.05 31 21068 166042 46498921
Septic shock 16.68 16.05 3 21096 57890 46607073
Hallucination 16.58 16.05 55 21044 49896 46615067
Brain injury 16.57 16.05 17 21082 6133 46658830
Stress 16.44 16.05 56 21043 51495 46613468
Wrong technique in product usage process 16.38 16.05 58 21041 54364 46610599
Impaired work ability 16.18 16.05 24 21075 12612 46652351
Impatience 16.13 16.05 6 21093 335 46664628
Affect lability 16.11 16.05 19 21080 8001 46656962

FDA Adverse Event Reporting System (Male)

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
Product residue present 227.03 23.59 60 5630 2618 29944170
Drug withdrawal syndrome 162.71 23.59 78 5612 19731 29927057
Serotonin syndrome 136.50 23.59 67 5623 17824 29928964
Suicidal ideation 111.65 23.59 75 5615 36039 29910749
Anxiety 96.24 23.59 101 5589 89770 29857018
Depression 76.70 23.59 90 5600 90347 29856441
Overdose 63.42 23.59 79 5611 84258 29862530
Suicide attempt 61.67 23.59 53 5637 36644 29910144
Sexual dysfunction 56.50 23.59 26 5664 5975 29940813
Hyperhidrosis 52.26 23.59 64 5626 67026 29879762
Insomnia 51.19 23.59 75 5615 93261 29853527
Drug ineffective 50.43 23.59 160 5530 340227 29606561
Anger 49.14 23.59 29 5661 11091 29935697
Withdrawal syndrome 48.83 23.59 29 5661 11221 29935567
Feeling abnormal 42.34 23.59 53 5637 56703 29890085
Thinking abnormal 40.78 23.59 20 5670 5291 29941497
Completed suicide 38.18 23.59 68 5622 99424 29847364
Mania 33.09 23.59 21 5669 9133 29937655
Coma scale abnormal 32.94 23.59 15 5675 3361 29943427
Dry mouth 32.39 23.59 30 5660 22820 29923968
Nervousness 30.54 23.59 22 5668 11766 29935022
Libido decreased 28.64 23.59 15 5675 4551 29942237
Drug screen positive 26.29 23.59 14 5676 4393 29942395
Headache 26.18 23.59 85 5605 182221 29764567
Erectile dysfunction 26.11 23.59 24 5666 18078 29928710
Abnormal behaviour 25.90 23.59 28 5662 25595 29921193
Bipolar disorder 25.39 23.59 13 5677 3763 29943025
Paralysis 25.05 23.59 15 5675 5886 29940902
Irritability 24.74 23.59 26 5664 23024 29923764
Paraesthesia 24.59 23.59 40 5650 54287 29892501
Drug screen false positive 24.49 23.59 8 5682 731 29946057
Tremor 24.49 23.59 48 5642 75315 29871473
Emotional disorder 24.39 23.59 14 5676 5080 29941708
Condition aggravated 24.19 23.59 69 5621 137797 29808991
Acute kidney injury 24.08 23.59 11 5679 273831 29672957
Vasoplegia syndrome 23.81 23.59 9 5681 1262 29945526
Intentional product misuse 23.66 23.59 31 5659 34636 29912152

Pharmacologic Action:

SourceCodeDescription
ATC N06AX23 NERVOUS SYSTEM
PSYCHOANALEPTICS
ANTIDEPRESSANTS
Other antidepressants
FDA MoA N0000000102 Norepinephrine Uptake Inhibitors
FDA MoA N0000000109 Serotonin Uptake Inhibitors
FDA EPC N0000175749 Serotonin and Norepinephrine Reuptake Inhibitor
MeSH PA D000928 Antidepressive Agents
MeSH PA D002491 Central Nervous System Agents
MeSH PA D049990 Membrane Transport Modulators
MeSH PA D018377 Neurotransmitter Agents
MeSH PA D014179 Neurotransmitter Uptake Inhibitors
MeSH PA D011619 Psychotropic Drugs
MeSH PA D000068760 Serotonin and Noradrenaline Reuptake Inhibitors
FDA MoA N0000182137 Cytochrome P450 2D6 Inhibitors
CHEBI has role CHEBI:35469 thymoanaleptics
CHEBI has role CHEBI:49103 drug metabolites
CHEBI has role CHEBI:83399 marine xenobiotic metabolites

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Major depressive disorder indication 370143000
Generalized anxiety disorder off-label use 21897009 DOID:14320
Social phobia off-label use 25501002 DOID:11257
Menopausal flushing off-label use 198436008
Neuropathic pain off-label use 247398009
Panic disorder off-label use 371631005 DOID:594
Ocular hypertension contraindication 4210003 DOID:9282
Suicidal thoughts contraindication 6471006
Hypercholesterolemia contraindication 13644009
Bipolar disorder contraindication 13746004 DOID:3312
Neuroleptic malignant syndrome contraindication 15244003 DOID:14464
Hypertensive disorder contraindication 38341003 DOID:10763
Disorder of cardiovascular system contraindication 49601007 DOID:1287
Syndrome of inappropriate vasopressin secretion contraindication 55004003 DOID:3401
Cerebrovascular disease contraindication 62914000 DOID:6713
Blood coagulation disorder contraindication 64779008 DOID:1247
Hyponatremia contraindication 89627008
Seizure disorder contraindication 128613002
Bleeding contraindication 131148009
Impaired renal function disorder contraindication 197663003
Mania contraindication 231494001
Hypomania contraindication 231496004
Interstitial lung disease contraindication 233703007 DOID:3082
Disease of liver contraindication 235856003 DOID:409
Hypertriglyceridemia contraindication 302870006
Serotonin syndrome contraindication 371089000
Angle-closure glaucoma contraindication 392291006 DOID:13550
Myocardial infarction in recovery phase contraindication 418044006
Hypertensive urgency contraindication 443482000

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 10.79 acidic
pKa2 9.33 Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRouteExclusivity dateDescription
EQ 100MG BASE PRISTIQ PF PRISM CV N021992 Feb. 29, 2008 RX TABLET, EXTENDED RELEASE ORAL Feb. 6, 2021 ADDITION OF DATA BASED ON THE ASSESSMENT OF SAFETY AND EFFICACY IN PEDIATRIC PATIENTS WITH MAJOR DEPRESSIVE DISORDER TO FULFILL POSTMARKETING STUDY REQUIREMENT 1229-1
EQ 25MG BASE PRISTIQ PF PRISM CV N021992 Aug. 20, 2014 RX TABLET, EXTENDED RELEASE ORAL Feb. 6, 2021 ADDITION OF DATA BASED ON THE ASSESSMENT OF SAFETY AND EFFICACY IN PEDIATRIC PATIENTS WITH MAJOR DEPRESSIVE DISORDER TO FULFILL POSTMARKETING STUDY REQUIREMENT 1229-1
EQ 50MG BASE PRISTIQ PF PRISM CV N021992 Feb. 29, 2008 RX TABLET, EXTENDED RELEASE ORAL Feb. 6, 2021 ADDITION OF DATA BASED ON THE ASSESSMENT OF SAFETY AND EFFICACY IN PEDIATRIC PATIENTS WITH MAJOR DEPRESSIVE DISORDER TO FULFILL POSTMARKETING STUDY REQUIREMENT 1229-1

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Sodium-dependent noradrenaline transporter Transporter INHIBITOR Ki 6.27 WOMBAT-PK CHEMBL
Sodium-dependent serotonin transporter Transporter INHIBITOR Ki 7.33 WOMBAT-PK CHEMBL
Alpha-1A adrenergic receptor GPCR IC50 7.22 CHEMBL

External reference:

IDSource
D07793 KEGG_DRUG
4027338 VUID
N0000176142 NUI
93414-04-1 SECONDARY_CAS_RN
4027338 VANDF
C1880288 UMLSCUI
CHEBI:83527 CHEBI
CHEMBL1118 ChEMBL_ID
CHEMBL3989861 ChEMBL_ID
CHEMBL1201728 ChEMBL_ID
DB06700 DRUGBANK_ID
D000069468 MESH_DESCRIPTOR_UI
125017 PUBCHEM_CID
7158 IUPHAR_LIGAND_ID
8361 INN_ID
NG99554ANW UNII
683693 RXNORM
132507 MMSL
200628 MMSL
25184 MMSL
339716 MMSL
38906 MMSL
d07113 MMSL
012574 NDDF
012575 NDDF
015249 NDDF
430267008 SNOMEDCT_US
430271006 SNOMEDCT_US
433292007 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Pristiq Extended-Release HUMAN PRESCRIPTION DRUG LABEL 1 0008-1210 TABLET, EXTENDED RELEASE 25 mg ORAL NDA 31 sections
Pristiq Extended-Release HUMAN PRESCRIPTION DRUG LABEL 1 0008-1211 TABLET, EXTENDED RELEASE 50 mg ORAL NDA 31 sections
Pristiq Extended-Release HUMAN PRESCRIPTION DRUG LABEL 1 0008-1222 TABLET, EXTENDED RELEASE 100 mg ORAL NDA 31 sections
Desvenlafaxine HUMAN PRESCRIPTION DRUG LABEL 1 0054-0400 TABLET, FILM COATED, EXTENDED RELEASE 50 mg ORAL ANDA 30 sections
Desvenlafaxine HUMAN PRESCRIPTION DRUG LABEL 1 0054-0401 TABLET, FILM COATED, EXTENDED RELEASE 100 mg ORAL ANDA 30 sections
Desvenlafaxine HUMAN PRESCRIPTION DRUG LABEL 1 0054-0603 TABLET, FILM COATED, EXTENDED RELEASE 25 mg ORAL ANDA 30 sections
Desvenlafaxine HUMAN PRESCRIPTION DRUG LABEL 1 0591-3659 TABLET, EXTENDED RELEASE 50 mg ORAL ANDA 30 sections
Desvenlafaxine HUMAN PRESCRIPTION DRUG LABEL 1 0591-3660 TABLET, EXTENDED RELEASE 100 mg ORAL ANDA 30 sections
Desvenlafaxine HUMAN PRESCRIPTION DRUG LABEL 1 0591-4060 TABLET, EXTENDED RELEASE 25 mg ORAL ANDA 30 sections
Desvenlafaxine Human Prescription Drug Label 1 35208-009 TABLET, EXTENDED RELEASE 50 mg ORAL ANDA 30 sections
Desvenlafaxine Human Prescription Drug Label 1 35208-010 TABLET, EXTENDED RELEASE 100 mg ORAL ANDA 30 sections
PristiqExtended-Release HUMAN PRESCRIPTION DRUG LABEL 1 43063-262 TABLET, EXTENDED RELEASE 50 mg ORAL NDA 31 sections
Desvenlafaxine Human Prescription Drug Label 1 46708-152 TABLET, EXTENDED RELEASE 50 mg ORAL NDA 30 sections
Desvenlafaxine Human Prescription Drug Label 1 46708-153 TABLET, EXTENDED RELEASE 100 mg ORAL NDA 30 sections
Desvenlafaxine Human Prescription Drug Label 1 46708-540 TABLET, EXTENDED RELEASE 50 mg ORAL ANDA 30 sections
Desvenlafaxine Human Prescription Drug Label 1 46708-541 TABLET, EXTENDED RELEASE 100 mg ORAL ANDA 30 sections
Desvenlafaxine Human Prescription Drug Label 1 46708-542 TABLET, EXTENDED RELEASE 25 mg ORAL ANDA 30 sections
Desvenlafaxine Succinate HUMAN PRESCRIPTION DRUG LABEL 1 50090-4069 TABLET, EXTENDED RELEASE 50 mg ORAL NDA AUTHORIZED GENERIC 30 sections
Desvenlafaxine HUMAN PRESCRIPTION DRUG LABEL 1 50090-4388 TABLET, EXTENDED RELEASE 25 mg ORAL ANDA 30 sections
Desvenlafaxine HUMAN PRESCRIPTION DRUG LABEL 1 50090-4806 TABLET, FILM COATED, EXTENDED RELEASE 50 mg ORAL ANDA 30 sections
Desvenlafaxine Human Prescription Drug Label 1 50090-5274 TABLET, EXTENDED RELEASE 25 mg ORAL ANDA 30 sections
Desvenlafaxine Human Prescription Drug Label 1 50090-5293 TABLET, EXTENDED RELEASE 50 mg ORAL ANDA 30 sections
Desvenlafaxine HUMAN PRESCRIPTION DRUG LABEL 1 51407-021 TABLET, EXTENDED RELEASE 25 mg ORAL ANDA 30 sections
Desvenlafaxine HUMAN PRESCRIPTION DRUG LABEL 1 51407-022 TABLET, EXTENDED RELEASE 50 mg ORAL ANDA 30 sections
Desvenlafaxine HUMAN PRESCRIPTION DRUG LABEL 1 51407-023 TABLET, EXTENDED RELEASE 100 mg ORAL ANDA 30 sections
Desvenlafaxine Human Prescription Drug Label 1 51991-006 TABLET, EXTENDED RELEASE 25 mg ORAL ANDA 30 sections
Desvenlafaxine Human Prescription Drug Label 1 51991-311 TABLET, EXTENDED RELEASE 50 mg ORAL ANDA 30 sections
Desvenlafaxine Human Prescription Drug Label 1 51991-312 TABLET, EXTENDED RELEASE 100 mg ORAL ANDA 30 sections
PristiqExtended-Release HUMAN PRESCRIPTION DRUG LABEL 1 54868-2932 TABLET, EXTENDED RELEASE 50 mg ORAL NDA 33 sections
Desvenlafaxine Succinate HUMAN PRESCRIPTION DRUG LABEL 1 59762-1210 TABLET, EXTENDED RELEASE 25 mg ORAL NDA AUTHORIZED GENERIC 31 sections