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

Stem definitionDrug idCAS RN
1752 60-99-1

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • methotrimeprazine
  • hirnamin
  • levomeprazine
  • levomepromazin
  • levopromazine
  • levoprome
  • levopromethazine
  • levotomin
  • mepromazine
  • levomepromazine
  • levomepromazine maleate
  • methotrimeprazine hydrochloride
  • nozinan
A phenothiazine with pharmacological activity similar to that of both CHLORPROMAZINE and PROMETHAZINE. It has the histamine-antagonist properties of the antihistamines together with CENTRAL NERVOUS SYSTEM effects resembling those of chlorpromazine. (From Martindale, The Extra Pharmacopoeia, 30th ed, p604)
  • Molecular weight: 328.47
  • Formula: C19H24N2OS
  • CLOGP: 5.03
  • LIPINSKI: 1
  • HAC: 3
  • HDO: 0
  • TPSA: 15.71
  • ALOGS: -4.80
  • ROTB: 5

  • Status: OFM

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

Drug dosage:

DoseUnitRoute
0.30 g O
0.10 g P

ADMET properties:

PropertyValueReference
BA (Bioavailability) 50 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution) 12 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 9.90 mL/min/kg Lombardo F, Berellini G, Obach RS
t_half (Half-life) 30 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
None FDA IMMUNEX

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
Intentional overdose 226.32 20.06 141 8038 64803 46613080
Intentional self-injury 145.12 20.06 75 8104 24091 46653792
Drug interaction 137.35 20.06 173 8006 202921 46474962
Somnolence 119.75 20.06 142 8037 156379 46521504
Neuroleptic malignant syndrome 107.88 20.06 48 8131 11074 46666809
Extrapyramidal disorder 100.93 20.06 46 8133 11222 46666661
Toxicity to various agents 100.28 20.06 152 8027 211614 46466269
Suicide attempt 99.22 20.06 80 8099 54956 46622927
Urinary retention 69.61 20.06 48 8131 26013 46651870
Aggression 65.76 20.06 44 8135 22700 46655183
Overdose 61.07 20.06 82 8097 101897 46575986
Altered state of consciousness 60.00 20.06 42 8137 23306 46654577
Sopor 56.46 20.06 38 8141 19790 46658093
Electrocardiogram QT prolonged 55.55 20.06 56 8123 51269 46626614
Hypothermia 51.47 20.06 30 8149 12153 46665730
Coma 51.31 20.06 57 8122 58292 46619591
Hallucination, auditory 49.49 20.06 28 8151 10728 46667155
Depressed level of consciousness 48.03 20.06 50 8129 47519 46630364
Drug abuse 47.45 20.06 57 8122 63351 46614532
Excessive eye blinking 45.07 20.06 12 8167 583 46677300
Psychiatric symptom 42.28 20.06 19 8160 4478 46673405
Agitation 40.13 20.06 49 8130 55366 46622517
Disturbance in attention 38.92 20.06 37 8142 31523 46646360
Ileus paralytic 36.66 20.06 17 8162 4306 46673577
Asphyxia 36.23 20.06 18 8161 5308 46672575
Disinhibition 35.73 20.06 11 8168 900 46676983
Akathisia 35.26 20.06 20 8159 7694 46670189
Illusion 34.13 20.06 11 8168 1045 46676838
Hyperprolactinaemia 32.80 20.06 14 8165 2918 46674965
Galactorrhoea 32.41 20.06 15 8164 3782 46674101
Blood prolactin increased 32.37 20.06 14 8165 3013 46674870
Perforation 30.75 20.06 10 8169 977 46676906
Schizophrenia 30.75 20.06 19 8160 8549 46669334
Vascular pain 30.21 20.06 9 8170 659 46677224
Drug hypersensitivity 29.34 20.06 4 8175 243821 46434062
Mental disorder 29.01 20.06 27 8152 22398 46655485
Bradykinesia 28.75 20.06 14 8165 3952 46673931
Psychomotor hyperactivity 28.74 20.06 19 8160 9594 46668289
Sudden death 26.53 20.06 18 8161 9486 46668397
Tension 26.49 20.06 12 8167 2880 46675003
Ovarian germ cell cancer stage II 25.75 20.06 5 8174 56 46677827
Psychomotor retardation 25.22 20.06 12 8167 3221 46674662
Persecutory delusion 24.67 20.06 11 8168 2544 46675339
Diabetic hyperosmolar coma 24.49 20.06 7 8172 443 46677440
Flat affect 24.34 20.06 9 8170 1289 46676594
Behaviour disorder 24.06 20.06 10 8169 1951 46675932
Delusion 23.89 20.06 18 8161 11170 46666713
Dyskinesia 23.27 20.06 27 8152 28898 46648985
Salivary hypersecretion 22.39 20.06 14 8165 6431 46671452
Partial seizures with secondary generalisation 21.95 20.06 6 8173 322 46677561
Asthenia 21.57 20.06 14 8165 311061 46366822
Blood creatine phosphokinase increased 20.84 20.06 25 8154 27699 46650184
Circulatory collapse 20.51 20.06 22 8157 21602 46656281

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
Neuroleptic malignant syndrome 226.81 19.09 106 8771 16189 29927412
Intentional self-injury 114.72 19.09 63 8814 13469 29930132
Extrapyramidal disorder 102.43 19.09 54 8823 10639 29932962
Drug abuse 91.59 19.09 117 8760 81955 29861646
Blood creatine phosphokinase increased 86.04 19.09 84 8793 43764 29899837
Sopor 84.50 19.09 48 8829 10943 29932658
Suicide attempt 62.25 19.09 65 8812 36632 29906969
Restlessness 61.39 19.09 52 8825 22547 29921054
Toxicity to various agents 60.49 19.09 150 8727 177033 29766568
Somnolence 57.69 19.09 103 8774 96660 29846941
Aggression 56.65 19.09 62 8815 36845 29906756
Acute pulmonary oedema 52.90 19.09 31 8846 7484 29936117
Miosis 51.92 19.09 31 8846 7745 29935856
Delusion 50.98 19.09 36 8841 11953 29931648
Altered state of consciousness 50.37 19.09 44 8833 19875 29923726
Intentional overdose 49.14 19.09 61 8816 41420 29902181
Respiratory depression 47.66 19.09 34 8843 11469 29932132
Dystonic tremor 46.27 19.09 10 8867 112 29943489
Rhabdomyolysis 46.24 19.09 74 8803 63506 29880095
Parkinsonism 46.01 19.09 28 8849 7241 29936360
Muscle rigidity 44.06 19.09 31 8846 10230 29933371
Psychotic disorder 43.62 19.09 42 8835 21473 29922128
Depressed level of consciousness 43.34 19.09 55 8822 38167 29905434
Overdose 43.01 19.09 84 8793 84253 29859348
Mania 42.46 19.09 29 8848 9125 29934476
Wrong patient received product 42.24 19.09 17 8860 1800 29941801
Dystonia 40.87 19.09 29 8848 9698 29933903
Agitation 40.78 19.09 64 8813 54009 29889592
Schizophrenia 40.40 19.09 28 8849 9020 29934581
Gastrointestinal hypermotility 40.13 19.09 9 8868 121 29943480
Electrocardiogram QT prolonged 38.17 19.09 50 8827 35785 29907816
Drug interaction 37.57 19.09 137 8740 199431 29744170
Hypothermia 36.72 19.09 27 8850 9540 29934061
Blood glucose fluctuation 36.50 19.09 19 8858 3642 29939959
Intestinal haemorrhage 35.94 19.09 18 8859 3183 29940418
Victim of chemical submission 35.59 19.09 7 8870 47 29943554
Hyperprolactinaemia 34.15 19.09 13 8864 1187 29942414
Coma 33.48 19.09 50 8827 40399 29903202
Electrocardiogram QT shortened 32.78 19.09 8 8869 158 29943443
Abnormal behaviour 32.46 19.09 39 8838 25584 29918017
Dyskinesia 32.30 19.09 36 8841 21798 29921803
Psychiatric symptom 32.16 19.09 17 8860 3362 29940239
Pneumonia aspiration 31.69 19.09 47 8830 37733 29905868
Ileus paralytic 31.30 19.09 20 8857 5628 29937973
Sudden death 30.94 19.09 30 8847 15462 29928139
Wrong schedule 29.96 19.09 7 8870 114 29943487
Dyspnoea 29.84 19.09 33 8844 333262 29610339
Intentional product misuse 28.89 19.09 43 8834 34624 29908977
Drug screen false positive 28.44 19.09 10 8867 729 29942872
Blood glucose abnormal 27.61 19.09 18 8859 5241 29938360
Hallucination, auditory 27.54 19.09 23 8854 9766 29933835
Diarrhoea 25.81 19.09 37 8840 334066 29609535
Product administration error 25.31 19.09 26 8851 14351 29929250
Mumps 25.22 19.09 6 8871 106 29943495
Arthralgia 24.89 19.09 5 8872 135786 29807815
Asphyxia 24.71 19.09 17 8860 5408 29938193
Anxiety 24.38 19.09 70 8807 89801 29853800
Sedation 24.22 19.09 27 8850 16346 29927255
Hyperhidrosis 24.06 19.09 58 8819 67032 29876569
Water intoxication 24.03 19.09 8 8869 494 29943107
Salivary hypersecretion 23.86 19.09 19 8858 7547 29936054
Mydriasis 22.81 19.09 17 8860 6126 29937475
Insomnia 22.75 19.09 70 8807 93266 29850335
Cognitive disorder 22.09 19.09 31 8846 23659 29919942
Urinary incontinence 21.80 19.09 26 8851 16914 29926687
Substance abuse 20.76 19.09 17 8860 7023 29936578
Polydipsia 20.53 19.09 13 8864 3600 29940001
Multiple drug therapy 20.51 19.09 6 8871 241 29943360
Psychomotor hyperactivity 20.44 19.09 18 8859 8206 29935395
Pyrexia 20.41 19.09 153 8724 294336 29649265
Neuroleptic-induced deficit syndrome 20.19 19.09 4 8873 28 29943573
Chemical poisoning 19.52 19.09 5 8872 121 29943480
Colitis ischaemic 19.26 19.09 15 8862 5771 29937830

Pharmacologic Action:

SourceCodeDescription
ATC N05AA02 NERVOUS SYSTEM
PSYCHOLEPTICS
ANTIPSYCHOTICS
Phenothiazines with aliphatic side-chain
MeSH PA D000700 Analgesics
MeSH PA D018712 Analgesics, Non-Narcotic
MeSH PA D014150 Antipsychotic Agents
MeSH PA D002491 Central Nervous System Agents
MeSH PA D002492 Central Nervous System Depressants
MeSH PA D015259 Dopamine Agents
MeSH PA D018492 Dopamine Antagonists
MeSH PA D018377 Neurotransmitter Agents
MeSH PA D018373 Peripheral Nervous System Agents
MeSH PA D011619 Psychotropic Drugs
MeSH PA D018689 Sensory System Agents
MeSH PA D014149 Tranquilizing Agents
CHEBI has role CHEBI:37930 phenothiazine antipsychotics
CHEBI has role CHEBI:48279 serotonin antagonists
CHEBI has role CHEBI:48561 dopamine blocker
CHEBI has role CHEBI:48873 anticholinergika
CHEBI has role CHEBI:76779 prolyl oligopeptidase (ec 3.4.21.26) inhibitor
CHEBI has role CHEBI:149553 anti-coronaviral agents

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Alcoholism contraindication 7200002
Organophosphate poisoning contraindication 8260003
Weight gain finding contraindication 8943002
Neuroleptic malignant syndrome contraindication 15244003 DOID:14464
Senile dementia contraindication 15662003
Chronic disease of respiratory system contraindication 17097001
Myocardial infarction contraindication 22298006 DOID:5844
Glaucoma contraindication 23986001 DOID:1686
Orthostatic hypotension contraindication 28651003
Torsades de pointes contraindication 31722008
Parkinsonism contraindication 32798002
Conduction disorder of the heart contraindication 44808001
Chronic heart failure contraindication 48447003
Bradycardia contraindication 48867003
Extrapyramidal disease contraindication 76349003
Hyperglycemia contraindication 80394007 DOID:4195
Epilepsy contraindication 84757009 DOID:1826
Leukopenia contraindication 84828003 DOID:615
Stupor contraindication 89458003
Tardive dyskinesia contraindication 102449007
Prolonged QT interval contraindication 111975006
Acute disease of cardiovascular system contraindication 128487001
Angina pectoris contraindication 194828000
Disease of liver contraindication 235856003 DOID:409
Metabolic syndrome X contraindication 237602007 DOID:14221
Hyperprolactinemia contraindication 237662005 DOID:12700
Benign prostatic hyperplasia contraindication 266569009
Retention of urine contraindication 267064002
Anemia contraindication 271737000 DOID:2355
Thrombocytopenic disorder contraindication 302215000 DOID:1588
Neutropenic disorder contraindication 303011007 DOID:1227
Coma contraindication 371632003
At risk for aspiration contraindication 371736008
Visual impairment contraindication 397540003
Breastfeeding (mother) contraindication 413712001
Myocardial ischemia contraindication 414795007 DOID:3393
Obesity contraindication 414916001 DOID:9970
Congenital long QT syndrome contraindication 442917000
Carcinoma of female breast contraindication 447782002

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 8.92 Basic
pKa2 4.55 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
Histamine H1 receptor GPCR Ki 9.24 PDSP
Pleiotropic ABC efflux transporter of multiple drugs Transporter IC50 5.02 CHEMBL

External reference:

IDSource
4018915 VUID
N0000147208 NUI
D00403 KEGG_DRUG
7104-38-3 SECONDARY_CAS_RN
4018915 VANDF
C0025678 UMLSCUI
CHEBI:6838 CHEBI
CHEMBL1764 ChEMBL_ID
CHEMBL1725730 ChEMBL_ID
CHEMBL2104973 ChEMBL_ID
D008728 MESH_DESCRIPTOR_UI
DB01403 DRUGBANK_ID
C017901 MESH_SUPPLEMENTAL_RECORD_UI
7603 IUPHAR_LIGAND_ID
705 INN_ID
9G0LAW7ATQ UNII
3916 PUBCHEM_CID
160372 RXNORM
1834 MMSL
5078 MMSL
d00814 MMSL
001581 NDDF
004134 NDDF
005070 NDDF
387509007 SNOMEDCT_US
395790003 SNOMEDCT_US
57911003 SNOMEDCT_US
89029005 SNOMEDCT_US

Pharmaceutical products:

None