clomipramine Indications/Contra | FAERs | Orange Book | BioActivity |

Stem definitionDrug idCAS RN
substances of the imipramine group 701 303-49-1

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • clomipramine
  • chlorimipramine
  • clomipramine hydrochloride
  • clomipramine HCl
A tricyclic antidepressant similar to IMIPRAMINE that selectively inhibits the uptake of serotonin in the brain. It is readily absorbed from the gastrointestinal tract and demethylated in the liver to form its primary active metabolite, desmethylclomipramine.
  • Molecular weight: 314.86
  • Formula: C19H23ClN2
  • CLOGP: 5.92
  • LIPINSKI: 1
  • HAC: 2
  • HDO: 0
  • TPSA: 6.48
  • ALOGS: -4.34
  • ROTB: 4

Drug dosage:

DoseUnitRoute
0.10 g O
0.10 g P

Approvals:

DateAgencyCompanyOrphan
Dec. 29, 1989 FDA MALLINCKRODT LLC

FDA Adverse Event Reporting System

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
Toxicity to various agents 525.27 46.24 187 1652 71853 4565300
Coma 435.35 46.24 117 1722 17402 4619751
Suicide attempt 401.55 46.24 114 1725 20728 4616425
Overdose 388.79 46.24 132 1707 43427 4593726
Serotonin syndrome 374.82 46.24 87 1752 7065 4630088
Intentional overdose 312.95 46.24 95 1744 21671 4615482
Agitation 229.32 46.24 77 1762 24123 4613030
Drug interaction 218.71 46.24 97 1742 64411 4572742
Drug ineffective 217.99 46.24 137 1702 185924 4451229
Akathisia 216.85 46.24 49 1790 3494 4633659
Obsessive-compulsive disorder 204.69 46.24 41 1798 1634 4635519
Electrocardiogram QT prolonged 186.60 46.24 59 1780 15236 4621917
Completed suicide 183.74 46.24 76 1763 42369 4594784
Poisoning deliberate 175.42 46.24 38 1801 2224 4634929
Neuroleptic malignant syndrome 173.65 46.24 45 1794 5702 4631451
Hypotension 170.99 46.24 83 1756 67317 4569836
Somnolence 155.11 46.24 68 1771 43592 4593561
Foetal exposure during pregnancy 155.11 46.24 57 1782 23112 4614041
Tachycardia 152.53 46.24 61 1778 31084 4606069
Confusional state 150.96 46.24 69 1770 48765 4588388
Antipsychotic drug level below therapeutic 148.41 46.24 24 1815 272 4636881
Therapeutic product effect variable 144.46 46.24 24 1815 325 4636828
Tremor 143.56 46.24 61 1778 36198 4600955
Disinhibition 128.86 46.24 24 1815 645 4636508
Hyponatraemia 119.44 46.24 48 1791 24682 4612471
Euphoric mood 118.61 46.24 27 1812 1978 4635175
Product use in unapproved indication 118.43 46.24 48 1791 25225 4611928
Intentional self-injury 117.58 46.24 35 1804 7348 4629805
Drug abuse 113.76 46.24 48 1791 27899 4609254
Sopor 112.95 46.24 33 1806 6493 4630660
Anxiety 112.10 46.24 56 1783 47955 4589198
Drug withdrawal syndrome neonatal 111.25 46.24 25 1814 1727 4635426
Increased appetite 110.89 46.24 27 1812 2646 4634507
Acute kidney injury 107.79 46.24 62 1777 70369 4566784
Fall 107.08 46.24 64 1775 77982 4559171
Cardio-respiratory arrest 104.48 46.24 41 1798 19781 4617372
Myoclonus 97.41 46.24 28 1811 5196 4631957
Depressed level of consciousness 96.54 46.24 36 1803 15118 4622035
Depression 94.93 46.24 50 1789 47683 4589470
Hyperhidrosis 94.50 46.24 43 1796 29874 4607279
Bezoar 94.25 46.24 17 1822 380 4636773
Therapeutic product effect incomplete 92.09 46.24 36 1803 17172 4619981
Suicidal ideation 87.52 46.24 37 1802 21546 4615607
Leukopenia 87.27 46.24 37 1802 21699 4615454
Polyuria 85.79 46.24 22 1817 2658 4634495
Psychomotor hyperactivity 85.05 46.24 24 1815 4165 4632988
Seizure 84.21 46.24 47 1792 50190 4586963
Weight increased 83.30 46.24 42 1797 36539 4600614
Coma scale abnormal 81.33 46.24 19 1820 1557 4635596
Rhabdomyolysis 80.86 46.24 34 1805 19524 4617629
Drug intolerance 77.39 46.24 34 1805 21712 4615441
Foetal arrhythmia 77.19 46.24 12 1827 103 4637050
Mania 76.25 46.24 23 1816 5035 4632118
Cerebellar syndrome 75.28 46.24 17 1822 1198 4635955
Insomnia 74.81 46.24 42 1797 45303 4591850
Hallucination, auditory 74.21 46.24 22 1817 4539 4632614
Neutrophil count increased 72.85 46.24 22 1817 4833 4632320
Bronchial hyperreactivity 72.80 46.24 14 1825 447 4636706
Exposure during pregnancy 72.54 46.24 37 1802 32934 4604219
Sinus tachycardia 71.51 46.24 23 1816 6211 4630942
Atrial septal defect 70.86 46.24 20 1819 3469 4633684
Hyperchloraemia 70.55 46.24 12 1827 188 4636965
Obesity 70.43 46.24 19 1820 2789 4634364
International normalised ratio abnormal 70.28 46.24 17 1822 1616 4635537
Off label use 69.62 46.24 60 1779 129053 4508100
Speech disorder 68.26 46.24 26 1813 11536 4625617
Constipation 66.69 46.24 38 1801 42116 4595037
Electrocardiogram QRS complex prolonged 66.56 46.24 17 1822 2019 4635134
Psychomotor retardation 65.90 46.24 15 1824 1095 4636058
Hypotonia 65.52 46.24 19 1820 3627 4633526
Hepatitis 63.36 46.24 25 1814 12180 4624973
Circulatory collapse 62.64 46.24 22 1817 7763 4629390
Loss of consciousness 61.40 46.24 34 1805 35648 4601505
Hypernatraemia 61.37 46.24 16 1823 2059 4635094
White blood cell count increased 61.26 46.24 26 1813 15241 4621912
Breast disorder 60.60 46.24 12 1827 447 4636706
Intentional product misuse 59.63 46.24 27 1812 18466 4618687
Muscle rigidity 59.52 46.24 18 1821 3969 4633184
Hypokalaemia 59.26 46.24 27 1812 18733 4618420
Hypovolaemic shock 58.19 46.24 15 1824 1847 4635306
Tremor neonatal 57.91 46.24 10 1829 172 4636981
Hyperthermia 57.80 46.24 17 1822 3407 4633746
Antipsychotic drug level increased 57.57 46.24 14 1825 1360 4635793
Generalised tonic-clonic seizure 57.04 46.24 22 1817 10088 4627065
Drug level increased 55.34 46.24 19 1820 6267 4630886
Premature baby 53.61 46.24 21 1818 10030 4627123
Inappropriate antidiuretic hormone secretion 53.17 46.24 17 1822 4497 4632656
Shock 52.43 46.24 20 1819 8896 4628257
Cardiac arrest 51.99 46.24 30 1809 33977 4603176
Extrapyramidal disorder 50.47 46.24 17 1822 5289 4631864
Pyrexia 50.09 46.24 46 1793 107098 4530055
Parkinsonism 49.99 46.24 15 1824 3218 4633935
Disorientation 49.25 46.24 21 1818 12438 4624715
Malaise 48.67 46.24 42 1797 90115 4547038
Differential white blood cell count abnormal 48.21 46.24 11 1828 811 4636342
Restlessness 47.75 46.24 19 1820 9450 4627703
Mydriasis 47.65 46.24 15 1824 3773 4633380
Aggression 47.04 46.24 21 1818 13878 4623275
Pulmonary congestion 46.97 46.24 15 1824 3951 4633202

Pharmacologic Action:

SourceCodeDescription
ATC N06AA04 NERVOUS SYSTEM
PSYCHOANALEPTICS
ANTIDEPRESSANTS
Non-selective monoamine reuptake inhibitors
CHEBI has role CHEBI:50949 serotonin uptake inhibitor
CHEBI has role CHEBI:35469 antidepressant
CHEBI has role CHEBI:48279 serotonergic antagonist
CHEBI has role CHEBI:48278 serotonergic drug
MeSH PA D000928 Antidepressive Agents
MeSH PA D000929 Antidepressive Agents, Tricyclic
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 D018490 Serotonin Agents
MeSH PA D017367 Serotonin Uptake Inhibitors
FDA EPC N0000175752 Tricyclic Antidepressant

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Obsessive-compulsive disorder indication 191736004 DOID:10933
Depressive disorder off-label use 35489007
Cataplexy off-label use 46263000
Anxiety off-label use 48694002
Panic disorder off-label use 371631005 DOID:594
Suicidal thoughts contraindication 6471006
Alcoholism contraindication 7200002
Glaucoma contraindication 23986001 DOID:1686
Hyperthyroidism contraindication 34486009 DOID:7998
Acute nephropathy contraindication 58574008
Epilepsy contraindication 84757009 DOID:1826
Bipolar affective disorder, current episode manic contraindication 191618007
Disease of liver contraindication 235856003 DOID:409
Retention of urine contraindication 267064002
Pheochromocytoma contraindication 302835009
Malignant hyperthermia contraindication 405501007
Myocardial infarction in recovery phase contraindication 418044006
Neuroblastoma contraindication 432328008 DOID:769
Atrioventricular Conduction Defect contraindication

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 9.04 Basic
pKa2 6.19 Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Sodium-dependent serotonin transporter Transporter INHIBITOR Ki 9.70 PDSP CHEMBL
Sodium-dependent noradrenaline transporter Transporter INHIBITOR Kd 7.42 WOMBAT-PK IUPHAR
5-hydroxytryptamine receptor 2A GPCR Ki 7.45 PDSP
D(1A) dopamine receptor GPCR Ki 6.66 PDSP
D(2) dopamine receptor GPCR Ki 6.95 PDSP
Alpha-2A adrenergic receptor GPCR Ki 6.28 PDSP
Sigma non-opioid intracellular receptor 1 Membrane receptor Ki 6.24 DRUG MATRIX
5-hydroxytryptamine receptor 2B GPCR Ki 6.82 DRUG MATRIX
Alpha-2B adrenergic receptor GPCR Ki 7.34 DRUG MATRIX
Histamine H1 receptor GPCR Ki 8.01 DRUG MATRIX
Histamine H2 receptor GPCR Ki 5.70 DRUG MATRIX
Muscarinic acetylcholine receptor M1 GPCR Ki 7.66 DRUG MATRIX
Muscarinic acetylcholine receptor M2 GPCR Ki 7.07 DRUG MATRIX
Muscarinic acetylcholine receptor M3 GPCR Ki 7.44 DRUG MATRIX
Muscarinic acetylcholine receptor M4 GPCR Ki 7.89 DRUG MATRIX
Muscarinic acetylcholine receptor M5 GPCR Ki 7.42 DRUG MATRIX
Alpha-2C adrenergic receptor GPCR Ki 6.69 DRUG MATRIX
Alpha-1D adrenergic receptor GPCR Ki 7.40 DRUG MATRIX
Solute carrier family 22 member 1 Transporter IC50 4.71 CHEMBL
5-hydroxytryptamine receptor 6 GPCR Ki 6.95 CHEMBL
Sodium-dependent dopamine transporter Transporter IC50 5.56 CHEMBL
Glutathione S-transferase P Enzyme WOMBAT-PK
Cytochrome P450 2D6 Enzyme Ki 5.66 WOMBAT-PK
Aldehyde oxidase Enzyme IC50 6.32 WOMBAT-PK
Alpha-1A adrenergic receptor GPCR Ki 8.49 WOMBAT-PK
D(3) dopamine receptor GPCR Ki 7.41 PDSP
5-hydroxytryptamine receptor 2C GPCR Ki 7.19 PDSP
Alpha-1B adrenergic receptor GPCR Ki 7.14 DRUG MATRIX
Membrane-associated progesterone receptor component 1 Membrane receptor Ki 5.94 DRUG MATRIX
Trypanothione reductase Enzyme Ki 5.19 CHEMBL
Serotonin 2 (5-HT2) receptor GPCR Ki 8.08 CHEMBL
Adrenergic receptor alpha-2 GPCR Ki 7.29 CHEMBL
Alpha-1A adrenergic receptor GPCR IC50 10.40 CHEMBL
Serotonin 1 (5-HT1) receptor GPCR Ki 5.30 CHEMBL
Histamine H1 receptor GPCR IC50 9.70 CHEMBL
Serotonin (5-HT) receptor GPCR IC50 8.30 CHEMBL
Sodium-dependent noradrenaline transporter Transporter IC50 6.05 CHEMBL
D(2) dopamine receptor GPCR Ki 7.25 CHEMBL
Sodium-dependent serotonin transporter Transporter IC50 7.15 CHEMBL
Trypanothione reductase Unclassified IC50 5.47 CHEMBL
G protein-activated inward rectifier potassium channel 2 Ion channel BLOCKER IC50 4.40 IUPHAR

External reference:

IDSource
D002997 MESH_DESCRIPTOR_UI
4019687 VUID
N0000147779 NUI
C0009010 UMLSCUI
D00811 KEGG_DRUG
2LXW0L6GWJ UNII
17321-77-6 SECONDARY_CAS_RN
96209002 SNOMEDCT_US
4019687 VANDF
2597 RXNORM
004614 NDDF
372903001 SNOMEDCT_US
d00876 MMSL
CHEMBL415 ChEMBL_ID
CHEMBL1200710 ChEMBL_ID
2238 INN_ID
DB01242 DRUGBANK_ID
CHEBI:47780 CHEBI
2398 IUPHAR_LIGAND_ID
2801 PUBCHEM_CID

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Clomipramine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0378-3025 CAPSULE 25 mg ORAL ANDA 15 sections
Clomipramine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0378-3050 CAPSULE 50 mg ORAL ANDA 15 sections
Clomipramine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0378-3075 CAPSULE 75 mg ORAL ANDA 15 sections
CLOMIPRAMINE HYDROCHLORIDE HUMAN PRESCRIPTION DRUG LABEL 1 0406-8806 CAPSULE 25 mg ORAL NDA 15 sections
CLOMIPRAMINE HYDROCHLORIDE HUMAN PRESCRIPTION DRUG LABEL 1 0406-8807 CAPSULE 50 mg ORAL NDA 15 sections
CLOMIPRAMINE HYDROCHLORIDE HUMAN PRESCRIPTION DRUG LABEL 1 0406-8808 CAPSULE 75 mg ORAL NDA 15 sections
ANAFRANIL HUMAN PRESCRIPTION DRUG LABEL 1 0406-9906 CAPSULE 25 mg ORAL NDA 15 sections
ANAFRANIL HUMAN PRESCRIPTION DRUG LABEL 1 0406-9907 CAPSULE 50 mg ORAL NDA 15 sections
ANAFRANIL HUMAN PRESCRIPTION DRUG LABEL 1 0406-9908 CAPSULE 75 mg ORAL NDA 15 sections
Clomipramine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0781-2027 CAPSULE 25 mg ORAL ANDA 15 sections
Clomipramine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0781-2037 CAPSULE 50 mg ORAL ANDA 15 sections
Clomipramine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0832-0630 CAPSULE 25 mg ORAL ANDA 15 sections
Clomipramine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0832-0631 CAPSULE 50 mg ORAL ANDA 15 sections
Clomipramine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0832-0632 CAPSULE 75 mg ORAL ANDA 15 sections
Clomipramine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 16714-849 CAPSULE 25 mg ORAL ANDA 15 sections
Clomipramine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 16714-850 CAPSULE 50 mg ORAL ANDA 15 sections
Clomipramine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 16714-851 CAPSULE 75 mg ORAL ANDA 15 sections
Clomipramine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 43063-257 CAPSULE 25 mg ORAL ANDA 15 sections
CLOMIPRAMINE HYDROCHLORIDE HUMAN PRESCRIPTION DRUG LABEL 1 51672-4011 CAPSULE 25 mg ORAL ANDA 16 sections
CLOMIPRAMINE HYDROCHLORIDE HUMAN PRESCRIPTION DRUG LABEL 1 51672-4012 CAPSULE 50 mg ORAL ANDA 16 sections
CLOMIPRAMINE HYDROCHLORIDE HUMAN PRESCRIPTION DRUG LABEL 1 51672-4013 CAPSULE 75 mg ORAL ANDA 16 sections
CLOMIPRAMINE HYDROCHLORIDE HUMAN PRESCRIPTION DRUG LABEL 1 54868-4023 CAPSULE 50 mg ORAL ANDA 16 sections
Clomipramine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 59746-710 CAPSULE 25 mg ORAL ANDA 16 sections
Clomipramine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 59746-711 CAPSULE 50 mg ORAL ANDA 16 sections
Clomipramine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 59746-712 CAPSULE 75 mg ORAL ANDA 16 sections
CLOMIPRAMINE HYDROCHLORIDE HUMAN PRESCRIPTION DRUG LABEL 1 60429-287 CAPSULE 25 mg ORAL ANDA 16 sections
CLOMIPRAMINE HYDROCHLORIDE HUMAN PRESCRIPTION DRUG LABEL 1 60429-288 CAPSULE 75 mg ORAL ANDA 16 sections
CLOMIPRAMINE HYDROCHLORIDE HUMAN PRESCRIPTION DRUG LABEL 1 60429-289 CAPSULE 50 mg ORAL ANDA 16 sections
CLOMIPRAMINE HYDROCHLORIDE HUMAN PRESCRIPTION DRUG LABEL 1 68084-790 CAPSULE 25 mg ORAL ANDA 16 sections
CLOMIPRAMINE HYDROCHLORIDE HUMAN PRESCRIPTION DRUG LABEL 1 68084-818 CAPSULE 50 mg ORAL ANDA 16 sections