cyamemazine 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | PK/Tox | Related Drugs | BioActivity |

Stem definitionDrug idCAS RN
746 3546-03-0

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • cyamemazine
  • ciamatil
  • cianatil
  • cyamemazin
  • cyamepromazine
  • cyamepromezine
phototoxic neuroleptic effects
  • Molecular weight: 323.46
  • Formula: C19H21N3S
  • CLOGP: 4.87
  • LIPINSKI: 0
  • HAC: 3
  • HDO: 0
  • TPSA: 30.27
  • ALOGS: -4.05
  • ROTB: 4

Drug dosage:

None

ADMET properties:

PropertyValueReference
BA (Bioavailability) 40 %

Predicted pharmacokinetic/toxicological properties (PK-AZ):

PropertyDescriptionValueUnitConfidenceSimilarity
azlogd74 LogD at pH 7.4 2.786 Moderate 0.70
caco2-efflux Caco-2 efflux ratio (BA/AB) 0.364 Moderate 0.70
caco2-intrinsic-papp Caco-2 intrinsic apparent permeability 31.696 10^-6 cm/s Moderate 0.70
dh-clint Dog hepatocyte intrinsic clearance 72.611 uL/min/10^6 cells Moderate 0.70
dppb Dog plasma protein binding (% unbound) 6.890 % Moderate 0.70
fcs-ppb Fetal calf serum protein binding (% unbound) 21.170 % Moderate 0.70
herg hERG pIC50 6.312 pIC50 Moderate 0.70
hh-clint Human hepatocyte intrinsic clearance 12.023 uL/min/10^6 cells Moderate 0.70
hlm-clint Human liver microsomal intrinsic clearance 46.774 uL/min/mg protein Moderate 0.70
hppb Human plasma protein binding (% unbound) 8.770 % Moderate 0.70
kinase-safety-class ACVR2B,AKT2,AKT3,AXL,BRAF,CAMK2B,CAMK2D,CDK5,CDK9,EIF2AK3,EPHB4,ERBB2,GRK2,ITK,MAPK10,MAPK7,MET,NTRK2,PDK1,PDK2,PDK4,PIM2,PRKDC,SIK2,TEK 25
mdck-mdr1-efflux MDCK-MDR1 efflux ratio 0.551 Moderate 0.70
mh-clint Mouse hepatocyte intrinsic clearance 119.124 Moderate 0.70
mppb Mouse plasma protein binding (% unbound) 10.130 Moderate 0.70
nih-mdck-mdr1-efflux NIH MDCK-MDR1 efflux ratio 3.236 Moderate 0.70
pfas-class PFAS structural alert (1 = True, 0 = False) 0
pppb Pig plasma protein binding (% unbound) 21.790 % Moderate 0.70
rh-clint Rat hepatocyte intrinsic clearance 179.061 uL/min/10^6 cells Moderate 0.70
rh-fuinc Rat hepatocyte fraction unbound in incubation 41.340 % Moderate 0.70
rppb Rat plasma protein binding (% unbound) 9.130 % Moderate 0.70
solubility-dd Solubility at pH 7.4 in DMSO 522.396 uM Moderate 0.70

Approvals:

None

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
Coma 1720.98 46.76 519 8504 72113 90547311
Poisoning deliberate 1190.88 46.76 285 8738 16201 90603223
Somnolence 490.80 46.76 287 8736 208797 90410627
Toxicity to various agents 439.68 46.76 301 8722 287545 90331879
Drug abuse 364.25 46.76 173 8850 82174 90537250
Altered state of consciousness 292.14 46.76 112 8911 31420 90588004
Suicide attempt 269.31 46.76 137 8886 75262 90544162
Intentional overdose 235.77 46.76 135 8888 93699 90525725
Drug use disorder 219.46 46.76 65 8958 8278 90611146
Hypotension 196.19 46.76 199 8824 325198 90294226
Rhabdomyolysis 191.28 46.76 96 8927 51160 90568264
Hepatocellular injury 189.07 46.76 80 8943 28878 90590546
Urinary retention 171.81 46.76 81 8942 37663 90581761
Extrapyramidal disorder 158.41 46.76 60 8963 16243 90603181
Poisoning 155.10 46.76 58 8965 15159 90604265
Tachycardia 138.34 46.76 119 8904 157554 90461870
Miosis 137.72 46.76 47 8976 9437 90609987
Wrong patient received product 136.28 46.76 37 8986 3440 90615984
Hepatic cytolysis 133.50 46.76 64 8959 30852 90588572
Drug interaction 129.29 46.76 148 8875 276305 90343119
Electrocardiogram QT prolonged 124.85 46.76 82 8941 72374 90547050
Cardio-respiratory arrest 122.48 46.76 77 8946 63063 90556361
Substance use disorder 110.46 46.76 28 8995 1992 90617432
Pneumonia aspiration 108.31 46.76 61 8962 40879 90578545
Sinus tachycardia 102.18 46.76 52 8971 28461 90590963
Bladder dilatation 101.97 46.76 23 9000 992 90618432
Asphyxia 94.58 46.76 33 8990 7070 90612354
Drug dependence 92.23 46.76 49 8974 29278 90590146
Pyramidal tract syndrome 86.10 46.76 18 9005 541 90618883
Neuroleptic malignant syndrome 83.10 46.76 37 8986 15059 90604365
Respiratory acidosis 82.91 46.76 31 8992 8088 90611336
Serotonin syndrome 80.53 46.76 49 8974 37838 90581586
Pain 79.75 46.76 5 9018 996336 89623088
Victim of crime 72.82 46.76 17 9006 855 90618569
Hypotonia neonatal 69.27 46.76 18 9005 1412 90618012
Drug reaction with eosinophilia and systemic symptoms 67.84 46.76 46 8977 42712 90576712
Mydriasis 67.59 46.76 32 8991 14980 90604444
Arthralgia 65.06 46.76 3 9020 778519 89840905
Agitation 63.57 46.76 53 8970 67045 90552379
Wrong rate 59.95 46.76 11 9012 164 90619260
Drug ineffective 58.27 46.76 33 8990 1384265 89235159
Wrong patient 57.50 46.76 14 9009 843 90618581
Bradycardia 57.16 46.76 55 8968 83792 90535632
Megacolon 57.11 46.76 17 9006 2197 90617227
Overdose 56.61 46.76 74 8949 157635 90461789
Hyperprolactinaemia 56.40 46.76 21 9002 5412 90614012
Hypercapnia 55.68 46.76 22 9001 6655 90612769
Salivary hypersecretion 55.60 46.76 24 8999 9068 90610356
Cholinergic syndrome 55.13 46.76 13 9010 683 90618741
Psychiatric decompensation 54.85 46.76 16 9007 1927 90617497
Faecal vomiting 53.10 46.76 13 9010 801 90618623
Vasoplegia syndrome 53.09 46.76 17 9006 2797 90616627
Suicidal ideation 51.39 46.76 49 8974 73806 90545618
Cerebral microhaemorrhage 49.95 46.76 10 9013 241 90619183
Dysarthria 47.43 46.76 41 8982 54441 90564983
Brain death 47.14 46.76 17 9006 4004 90615420

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
Coma 1792.83 45.75 591 8183 52963 42559598
Poisoning deliberate 1029.71 45.75 266 8508 9868 42602693
Drug abuse 701.61 45.75 367 8407 104404 42508157
Miosis 473.02 45.75 155 8619 13291 42599270
Somnolence 346.42 45.75 262 8512 140843 42471718
Asphyxia 288.64 45.75 95 8679 8231 42604330
Altered state of consciousness 263.97 45.75 126 8648 29133 42583428
Drug use disorder 242.13 45.75 88 8686 10245 42602316
Mydriasis 214.11 45.75 77 8697 8693 42603868
Substance use disorder 205.55 45.75 66 8708 5279 42607282
Hepatic cytolysis 204.37 45.75 103 8671 26741 42585820
Rhabdomyolysis 152.38 45.75 127 8647 77892 42534669
Intentional overdose 149.26 45.75 106 8668 51350 42561211
Poisoning 146.90 45.75 68 8706 14631 42597930
Toxicity to various agents 135.97 45.75 199 8575 228937 42383624
Pneumonia aspiration 131.18 45.75 97 8677 49981 42562580
Extrapyramidal disorder 130.80 45.75 65 8709 16347 42596214
Tachycardia 127.83 45.75 129 8645 100958 42511603
Electrocardiogram QT prolonged 123.63 45.75 92 8682 47853 42564708
Drug dependence 98.57 45.75 66 8708 29028 42583533
Bradypnoea 93.93 45.75 35 8739 4358 42608203
Hepatocellular injury 90.67 45.75 58 8716 23620 42588941
Agitation 84.73 45.75 84 8690 64230 42548331
Suicide attempt 83.62 45.75 72 8702 46028 42566533
Bladder dilatation 82.25 45.75 25 8749 1665 42610896
Wrong patient received product 78.26 45.75 29 8745 3554 42609007
Hyperthermia 77.71 45.75 42 8732 12532 42600029
Diarrhoea 75.62 45.75 5 8769 460844 42151717
Colitis ischaemic 70.82 45.75 33 8741 7193 42605368
Wrong patient 70.69 45.75 18 8756 621 42611940
Respiratory distress 61.39 45.75 58 8716 41762 42570799
Depressed level of consciousness 58.28 45.75 60 8714 47910 42564651
Drug interaction 58.12 45.75 152 8622 266847 42345714
Neuroleptic malignant syndrome 57.06 45.75 42 8732 21430 42591131
Enuresis 55.49 45.75 21 8753 2727 42609834
Respiratory depression 54.91 45.75 39 8735 18829 42593732
Distal intestinal obstruction syndrome 54.70 45.75 14 8760 493 42612068
Death 53.93 45.75 215 8559 470970 42141591
Urinary retention 53.45 45.75 54 8720 42160 42570401
Disturbance in attention 50.81 45.75 45 8729 29821 42582740
Drug ineffective 50.73 45.75 34 8740 630163 41982398
Pneumonia 49.52 45.75 13 8761 422136 42190425
Cholestasis 49.01 45.75 46 8728 32833 42579728
Nausea 48.92 45.75 11 8763 396788 42215773
Dyskinesia 48.75 45.75 41 8733 25349 42587212
Psychomotor skills impaired 48.63 45.75 23 8751 5181 42607380
Rheumatoid nodule 46.77 45.75 19 8755 2976 42609585

FDA Adverse Event Reporting System (Geriatric)

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
Coma 3457.17 42.78 1102 16223 116767 110455207
Poisoning deliberate 2163.74 42.78 552 16773 25779 110546195
Drug abuse 1049.81 42.78 524 16801 176887 110395087
Somnolence 849.13 42.78 545 16780 296904 110275070
Miosis 625.06 42.78 202 17123 21781 110550193
Altered state of consciousness 541.44 42.78 235 17090 57391 110514583
Toxicity to various agents 517.66 42.78 495 16830 480060 110091914
Drug use disorder 460.90 42.78 153 17172 17921 110554053
Intentional overdose 369.61 42.78 240 17085 132261 110439713
Asphyxia 369.06 42.78 122 17203 14093 110557881
Suicide attempt 347.93 42.78 211 17114 103183 110468791
Hepatic cytolysis 325.39 42.78 163 17162 54890 110517084
Rhabdomyolysis 323.30 42.78 213 17112 120188 110451786
Substance use disorder 321.98 42.78 94 17231 7196 110564778
Poisoning 293.86 42.78 125 17200 28980 110542994
Mydriasis 273.96 42.78 110 17215 22047 110549927
Hepatocellular injury 261.71 42.78 137 17188 50505 110521469
Tachycardia 253.42 42.78 239 17086 226406 110345568
Pneumonia aspiration 253.33 42.78 158 17167 81075 110490899
Extrapyramidal disorder 245.90 42.78 110 17215 28757 110543217
Electrocardiogram QT prolonged 240.80 42.78 171 17154 108789 110463185
Urinary retention 213.37 42.78 134 17191 69549 110502425
Hypotension 203.31 42.78 323 17002 523526 110048448
Bladder dilatation 184.45 42.78 48 17277 2391 110569583
Wrong patient received product 184.13 42.78 60 17265 6614 110565360
Drug dependence 178.21 42.78 106 17219 49914 110522060
Drug interaction 175.80 42.78 295 17030 499888 110072086
Agitation 157.31 42.78 135 17190 112916 110459058
Neuroleptic malignant syndrome 139.40 42.78 79 17246 33980 110537994
Bradypnoea 128.24 42.78 49 17276 8600 110563374
Pain 110.45 42.78 11 17314 954944 109617030
Cardio-respiratory arrest 110.24 42.78 112 17213 115724 110456250
Fatigue 107.66 42.78 29 17296 1215929 109356045
Sinus tachycardia 105.56 42.78 73 17252 44420 110527554
Arthralgia 104.87 42.78 4 17321 779628 109792346
Death 103.91 42.78 291 17034 698578 109873396
Victim of crime 103.52 42.78 27 17298 1356 110570618
Respiratory distress 103.47 42.78 86 17239 68788 110503186
Hyperthermia 102.61 42.78 55 17270 21217 110550757
Drug ineffective 102.10 42.78 56 17269 1520484 109051490
Depressed level of consciousness 100.41 42.78 105 17220 112173 110459801
Overdose 98.48 42.78 150 17175 233644 110338330
Wrong patient 96.64 42.78 26 17299 1473 110570501
Disturbance in attention 92.27 42.78 77 17248 61918 110510056
Megacolon 92.21 42.78 32 17293 4273 110567701
Hypothermia 89.14 42.78 54 17271 26248 110545726
Respiratory depression 89.10 42.78 58 17267 31943 110540031
Respiratory acidosis 87.71 42.78 43 17282 13783 110558191
Cholestasis 87.56 42.78 76 17249 64442 110507532
Rash 79.63 42.78 16 17309 820948 109751026
Nausea 79.26 42.78 48 17277 1235642 109336332
Enuresis 78.39 42.78 28 17297 4068 110567906
Colitis ischaemic 77.58 42.78 43 17282 17707 110554267
Diarrhoea 76.28 42.78 42 17283 1139463 109432511
Dizziness 73.39 42.78 11 17314 698182 109873792
Aggression 72.88 42.78 66 17259 59144 110512830
Dysarthria 70.46 42.78 76 17249 84045 110487929
Psychomotor skills impaired 70.15 42.78 30 17295 7028 110564946
Pneumonia 70.12 42.78 25 17300 876689 109695285
Suicidal ideation 68.60 42.78 79 17246 93858 110478116
Hyperprolactinaemia 65.52 42.78 28 17297 6547 110565427
Blood creatine phosphokinase increased 64.69 42.78 68 17257 73009 110498965
Confusional state 64.47 42.78 190 17135 468490 110103484
Serotonin syndrome 63.29 42.78 61 17264 59092 110512882
Dyskinesia 62.63 42.78 57 17268 51389 110520585
Faecaloma 62.12 42.78 35 17290 14873 110557101
Chemical submission 61.69 42.78 15 17310 565 110571409
Drug reaction with eosinophilia and systemic symptoms 61.56 42.78 70 17255 82025 110489949
Headache 61.22 42.78 31 17294 882346 109689628
Pyramidal tract syndrome 60.82 42.78 16 17309 831 110571143
Sudden death 60.15 42.78 41 17284 24354 110547620
Acute respiratory distress syndrome 57.18 42.78 55 17270 53143 110518831
Pain in extremity 55.20 42.78 6 17319 487112 110084862
Bradycardia 54.74 42.78 92 17233 155425 110416549
Pulmonary embolism 54.23 42.78 110 17215 214364 110357610
Cough 54.09 42.78 5 17320 461636 110110338
Sedation 53.23 42.78 60 17265 69623 110502351
Anticholinergic syndrome 52.01 42.78 21 17304 4259 110567715
Hypersensitivity 51.25 42.78 3 17322 403995 110167979
Product administration error 50.80 42.78 44 17281 37173 110534801
Necrotising colitis 49.21 42.78 16 17309 1749 110570225
Dyspnoea 49.04 42.78 61 17264 1106811 109465163
Distal intestinal obstruction syndrome 48.72 42.78 14 17311 1011 110570963
Wrong rate 48.58 42.78 10 17315 173 110571801
Intentional product misuse 47.27 42.78 79 17246 132825 110439149
Agranulocytosis 46.87 42.78 53 17272 61707 110510267
Vasoplegia syndrome 43.98 42.78 20 17305 5419 110566555
Back pain 43.50 42.78 4 17321 370992 110200982

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

SourceCodeDescription
ATC N05AA06 NERVOUS SYSTEM
PSYCHOLEPTICS
ANTIPSYCHOTICS
Phenothiazines with aliphatic side-chain
CHEBI has role CHEBI:35476 antipsychotic agent

Related Drugs by ATC class:

N05AA Phenothiazines with aliphatic side-chain 6 drugs
acepromazinechlorproethazinechlorpromazinelevomepromazinepromazinetriflupromazine

Drug Use | Suggest Off label Use Form| |View source of the data|

None




🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 8.92 Basic
pKa2 2.39 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
5-hydroxytryptamine receptor 3A Ion channel Ki 5.53 PDSP
D(1A) dopamine receptor GPCR Ki 8.42 PDSP
D(2) dopamine receptor GPCR Ki 8.24 PDSP
5-hydroxytryptamine receptor 1A GPCR ANTAGONIST Ki 6.30 IUPHAR
5-hydroxytryptamine receptor 2A GPCR ANTAGONIST Ki 8.80 IUPHAR
5-hydroxytryptamine receptor 2C GPCR ANTAGONIST Ki 7.90 IUPHAR
5-hydroxytryptamine receptor 7 GPCR ANTAGONIST Ki 7.20 IUPHAR
D(3) dopamine receptor GPCR Ki 8.60 PDSP
Muscarinic acetylcholine receptor M1 GPCR Ki 7.89 PDSP
Muscarinic acetylcholine receptor M2 GPCR Ki 7.38 PDSP
Muscarinic acetylcholine receptor M3 GPCR Ki 7.50 PDSP
Muscarinic acetylcholine receptor M4 GPCR Ki 7.92 PDSP
Muscarinic acetylcholine receptor M5 GPCR Ki 7.46 PDSP

External reference:

IDSource
D07307 KEGG_DRUG
21877 RXNORM
C0056643 UMLSCUI
CHEBI:135379 CHEBI
CHEMBL2104153 ChEMBL_ID
DB09000 DRUGBANK_ID
C028457 MESH_SUPPLEMENTAL_RECORD_UI
62865 PUBCHEM_CID
84 IUPHAR_LIGAND_ID
1148 INN_ID
A2JGV5CNU4 UNII
005507 NDDF
A2JGV5CNU4 INXIGHT DRUGS

Pharmaceutical products:

None