duloxetine indications/contra

Stem definitionDrug idCAS RN
serotonin and/or norepinephrine reuptake inhibitors, fluoxetine derivatives 972 116539-59-4

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • yentreve
  • cymbalta
  • duloxetine
  • (S)-Duloxetine
  • duloxetine hydrochloride
  • duloxetine HCl
A thiophene derivative and selective NEUROTRANSMITTER UPTAKE INHIBITOR for SEROTONIN and NORADRENALINE (SNRI). It is an ANTIDEPRESSIVE AGENT and ANXIOLYTIC, and is also used for the treatment of pain in patients with DIABETES MELLITUS and FIBROMYALGIA.
  • Molecular weight: 297.42
  • Formula: C18H19NOS
  • CLOGP: 4.26
  • LIPINSKI: 0
  • HAC: 2
  • HDO: 1
  • TPSA: 21.26
  • ALOGS: -5
  • ROTB: 6

Drug dosage:

DoseUnitRoute
60 mg O

Approvals:

DateAgencyCompanyOrphan
Aug. 3, 2004 FDA LILLY

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
Drug withdrawal syndrome 14870.70 36.28 3038 14676 8747 3359398
Dysphoria 10913.86 36.28 1852 15862 696 3367449
Affect lability 10678.19 36.28 1883 15831 1356 3366789
Irritability 9722.63 36.28 2131 15583 9085 3359060
Paraesthesia 9719.80 36.28 2525 15189 25023 3343122
Agitation 8796.38 36.28 2184 15530 17522 3350623
Insomnia 8769.20 36.28 2463 15251 33435 3334710
Dizziness 8523.70 36.28 2865 14849 73647 3294498
Anxiety 8136.14 36.28 2376 15338 37253 3330892
Suicidal ideation 7635.88 36.28 1912 15802 15793 3352352
Vertigo 7327.27 36.28 1707 16007 9925 3358220
Nausea 6837.55 36.28 2805 14909 126840 3241305
Hyperhidrosis 6574.75 36.28 1803 15911 21807 3346338
Confusional state 5989.33 36.28 1865 15849 36133 3332012
Headache 5935.35 36.28 2311 15403 89669 3278476
Sensory disturbance 5922.79 36.28 1175 16539 2545 3365600
Fatigue 5625.58 36.28 2321 15393 104919 3263226
Lethargy 4267.57 36.28 1153 16561 12862 3355283
Tinnitus 3674.90 36.28 897 16817 6368 3361777
Tremor 3429.74 36.28 1142 16572 27002 3341143
Vomiting 2971.96 36.28 1417 16297 88114 3280031
Nightmare 2951.90 36.28 718 16996 4984 3363161
Diarrhoea 2602.40 36.28 1361 16353 102987 3265158
Hypomania 2465.98 36.28 481 17233 888 3367257
Mood swings 2338.26 36.28 577 17137 4265 3363880
Completed suicide 1804.17 36.28 733 16981 30381 3337764
Sleep disorder 1800.80 36.28 526 17188 7787 3360358
Suicide attempt 1623.77 36.28 567 17147 15280 3352865
Depression 1566.94 36.28 713 17001 39057 3329088
Alanine aminotransferase increased 1461.93 36.28 584 17130 23056 3345089

Pharmacologic Action:

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SourceCodeDescription
ATC N06AX21 NERVOUS SYSTEM
PSYCHOANALEPTICS
ANTIDEPRESSANTS
Other antidepressants
FDA MoA N0000000102 Norepinephrine Uptake Inhibitors
FDA EPC N0000175749 Serotonin and Norepinephrine Reuptake Inhibitor
FDA MoA N0000000109 Serotonin Uptake Inhibitors
MeSH PA D000700 Analgesics
CHEBI has role CHEBI:35469 antidepressant
MeSH PA D000928 Antidepressive Agents
MeSH PA D002491 Central Nervous System Agents
MeSH PA D015259 Dopamine Agents
MeSH PA D049990 Membrane Transport Modulators
MeSH PA D018377 Neurotransmitter Agents
MeSH PA D014179 Neurotransmitter Uptake Inhibitors
MeSH PA D018373 Peripheral Nervous System Agents
MeSH PA D011619 Psychotropic Drugs
MeSH PA D018689 Sensory System Agents
MeSH PA D000068760 Serotonin and Noradrenaline Reuptake Inhibitors

Drug Use (View source of the data)

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DiseaseRelationSNOMED_IDDOID
Generalized anxiety disorder indication 21897009 DOID:14320
Female stress incontinence indication 60241006 DOID:724
Fibromyalgia indication 203082005 DOID:631
Major depressive disorder indication 370143000
Diabetic peripheral neuropathy indication 424736006
Chronic Musculoskeletal Pain indication
Suicidal thoughts contraindication 6471006
Alcoholism contraindication 7200002
Bipolar disorder contraindication 13746004 DOID:3312
Neuroleptic malignant syndrome contraindication 15244003 DOID:14464
Jaundice contraindication 18165001
Cirrhosis of liver contraindication 19943007 DOID:5082
Orthostatic hypotension contraindication 28651003
Hypertensive disorder contraindication 38341003 DOID:10763
Alcoholic liver damage contraindication 41309000
Syndrome of inappropriate vasopressin secretion contraindication 55004003 DOID:3401
Acute nephropathy contraindication 58574008
Blood coagulation disorder contraindication 64779008 DOID:1247
Chronic hepatitis contraindication 76783007 DOID:2237
Hyperglycemia contraindication 80394007 DOID:4195
Epilepsy contraindication 84757009 DOID:1826
Hyponatremia contraindication 89627008
Inflammatory disease of liver contraindication 128241005
Liver function tests abnormal contraindication 166603001
Mania contraindication 231494001
Hypomania contraindication 231496004
Disease of liver contraindication 235856003 DOID:409
Retention of urine contraindication 267064002
Serotonin syndrome contraindication 371089000
Angle-closure glaucoma contraindication 392291006 DOID:13550
Gastrointestinal hypomotility contraindication 421807004

Acid dissociation constants calculated using MoKa v3.0.0

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Dissociation levelDissociation constantType (acidic/basic)
pKa1 8.7 Basic

Orange Book patent data (new drug applications)

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Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRoutePatent numberPatent expiration datePatent use
EQ 20MG BASE CYMBALTA LILLY N021427 Aug. 3, 2004 RX CAPSULE, DELAYED REL PELLETS ORAL 6596756 Sept. 10, 2019 MANAGEMENT OF FIBROMYALGIA (FM)
EQ 30MG BASE CYMBALTA LILLY N021427 Aug. 3, 2004 RX CAPSULE, DELAYED REL PELLETS ORAL 6596756 Sept. 10, 2019 MANAGEMENT OF FIBROMYALGIA (FM)
EQ 60MG BASE CYMBALTA LILLY N021427 Aug. 3, 2004 RX CAPSULE, DELAYED REL PELLETS ORAL 6596756 Sept. 10, 2019 MANAGEMENT OF FIBROMYALGIA (FM)

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 8.22 CHEMBL CHEMBL
Sodium-dependent serotonin transporter Transporter INHIBITOR Ki 9.62 CHEMBL CHEMBL
5-hydroxytryptamine receptor 2C GPCR ANTAGONIST Ki 6 IUPHAR
Sodium-dependent dopamine transporter Transporter Ki 6.62 CHEMBL
5-hydroxytryptamine receptor 2B GPCR Ki 5.68 PDSP
5-hydroxytryptamine receptor 7 GPCR Ki 5.65 PDSP
Histamine H1 receptor GPCR Ki 5.64 PDSP
5-hydroxytryptamine receptor 1D GPCR Ki 5.52 PDSP
5-hydroxytryptamine receptor 1E GPCR Ki 5.43 PDSP
5-hydroxytryptamine receptor 1B GPCR Ki 5.40 PDSP
5-hydroxytryptamine receptor 1F GPCR Ki 5.35 PDSP
5-hydroxytryptamine receptor 6 GPCR ANTAGONIST Ki 6.40 IUPHAR
5-hydroxytryptamine receptor 1A GPCR Ki 5.30 PDSP
5-hydroxytryptamine receptor 2A GPCR ANTAGONIST Ki 6.30 IUPHAR
Sodium-dependent dopamine transporter Transporter IC50 6.43 CHEMBL
Sodium-dependent serotonin transporter Transporter Ki 10.09 CHEMBL
Transporter Transporter Ki 8.52 CHEMBL

External reference:

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IDSource
DB00476 DRUGBANK_ID
202 IUPHAR_LIGAND_ID
C1505021 UMLSCUI
D01179 KEGG_DRUG
60835 PUBCHEM_CID
72625 RXNORM
4021477 VANDF
N0000148860 NDFRT
d05355 MMSL
407032004 SNOMEDCT_US
407033009 SNOMEDCT_US
008705 NDDF
9044SC542W UNII
136434-34-9 SECONDARY_CAS_RN
CHEMBL1175 ChEMBL_ID
CHEBI:31526 CHEBI
CHEMBL1200328 ChEMBL_ID
7012 INN_ID
D000068736 MESH_DESCRIPTOR_UI
29E PDB_CHEM_ID

Pharmaceutical products:

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ProductCategoryIngredientsNDCFormQuantityRoute MarketingLabel
Cymbalta HUMAN PRESCRIPTION DRUG LABEL 1 0002-3235 CAPSULE, DELAYED RELEASE 20 mg ORAL NDA 20 sections
Cymbalta HUMAN PRESCRIPTION DRUG LABEL 1 0002-3240 CAPSULE, DELAYED RELEASE 30 mg ORAL NDA 20 sections
Cymbalta HUMAN PRESCRIPTION DRUG LABEL 1 0002-3270 CAPSULE, DELAYED RELEASE 60 mg ORAL NDA 20 sections
Duloxetine HUMAN PRESCRIPTION DRUG LABEL 1 0093-7542 CAPSULE, DELAYED RELEASE PELLETS 20 mg ORAL ANDA 20 sections
Duloxetine HUMAN PRESCRIPTION DRUG LABEL 1 0093-7543 CAPSULE, DELAYED RELEASE PELLETS 30 mg ORAL ANDA 20 sections
Duloxetine HUMAN PRESCRIPTION DRUG LABEL 1 0093-7544 CAPSULE, DELAYED RELEASE PELLETS 60 mg ORAL ANDA 20 sections
Duloxetine HUMAN PRESCRIPTION DRUG LABEL 1 0179-0144 CAPSULE, DELAYED RELEASE 20 mg ORAL ANDA 20 sections
Duloxetine HUMAN PRESCRIPTION DRUG LABEL 1 0228-2890 CAPSULE, DELAYED RELEASE PELLETS 20 mg ORAL ANDA 19 sections
Duloxetine HUMAN PRESCRIPTION DRUG LABEL 1 0228-2891 CAPSULE, DELAYED RELEASE PELLETS 30 mg ORAL ANDA 19 sections
Duloxetine HUMAN PRESCRIPTION DRUG LABEL 1 0228-2892 CAPSULE, DELAYED RELEASE PELLETS 60 mg ORAL ANDA 19 sections
Duloxetine hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0615-7894 CAPSULE, DELAYED RELEASE 30 mg ORAL ANDA 20 sections
Duloxetine hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0615-7895 CAPSULE, DELAYED RELEASE 60 mg ORAL ANDA 20 sections
Duloxetine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0615-8034 CAPSULE, DELAYED RELEASE 30 mg ORAL ANDA 20 sections
Duloxetine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0615-8035 CAPSULE, DELAYED RELEASE 60 mg ORAL ANDA 20 sections
Duloxetine hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0904-6366 CAPSULE, DELAYED RELEASE 20 mg ORAL ANDA 19 sections
Duloxetine hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0904-6367 CAPSULE, DELAYED RELEASE 30 mg ORAL ANDA 19 sections
Duloxetine hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0904-6368 CAPSULE, DELAYED RELEASE 60 mg ORAL ANDA 19 sections
Duloxetine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0904-6452 CAPSULE, DELAYED RELEASE 20 mg ORAL ANDA 20 sections
Duloxetine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0904-6453 CAPSULE, DELAYED RELEASE 30 mg ORAL ANDA 20 sections
Duloxetine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0904-6454 CAPSULE, DELAYED RELEASE 60 mg ORAL ANDA 20 sections
Duloxetine hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 13668-111 CAPSULE, DELAYED RELEASE 60 mg ORAL ANDA 20 sections
Cymbalta HUMAN PRESCRIPTION DRUG LABEL 1 21695-145 CAPSULE, DELAYED RELEASE 30 mg ORAL NDA 20 sections
Cymbalta HUMAN PRESCRIPTION DRUG LABEL 1 21695-146 CAPSULE, DELAYED RELEASE 60 mg ORAL NDA 20 sections
Cymbalta HUMAN PRESCRIPTION DRUG LABEL 1 21695-657 CAPSULE, DELAYED RELEASE 20 mg ORAL NDA 21 sections
Duloxetine HUMAN PRESCRIPTION DRUG LABEL 1 27241-097 CAPSULE, DELAYED RELEASE 20 mg ORAL ANDA 20 sections
Duloxetine HUMAN PRESCRIPTION DRUG LABEL 1 27241-098 CAPSULE, DELAYED RELEASE 30 mg ORAL ANDA 20 sections
Duloxetine HUMAN PRESCRIPTION DRUG LABEL 1 27241-099 CAPSULE, DELAYED RELEASE 60 mg ORAL ANDA 20 sections
Irenka HUMAN PRESCRIPTION DRUG LABEL 1 27437-298 CAPSULE, DELAYED RELEASE 40 mg ORAL ANDA 20 sections
Duloxetine HUMAN PRESCRIPTION DRUG LABEL 1 31722-581 CAPSULE, DELAYED RELEASE 20 mg ORAL ANDA 20 sections
Duloxetine HUMAN PRESCRIPTION DRUG LABEL 1 31722-582 CAPSULE, DELAYED RELEASE 30 mg ORAL ANDA 20 sections