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

Stem definitionDrug idCAS RN
diphenylmethyl piperazine derivatives 749 82-92-8

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • cyclizine
  • marezine
  • nautazine
  • cyclizine hydrochloride
  • cyclizine lactate
  • cyclizine HCl
A histamine H1 antagonist given by mouth or parenterally for the control of postoperative and drug-induced vomiting and in motion sickness. (From Martindale, The Extra Pharmacopoeia, 30th ed, p935)
  • Molecular weight: 266.39
  • Formula: C18H22N2
  • CLOGP: 3.80
  • LIPINSKI: 0
  • HAC: 2
  • HDO: 0
  • TPSA: 6.48
  • ALOGS: -3.55
  • ROTB: 3

Drug dosage:

DoseUnitRoute
0.10 g O
0.10 g P
0.30 g R

Approvals:

DateAgencyCompanyOrphan
None FDA GLAXOSMITHKLINE

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
Skull malformation 173.21 81.20 21 165 241 3385432
Spina bifida 165.85 81.20 21 165 351 3385322
Cerebral ventricle dilatation 163.50 81.20 21 165 395 3385278
Foetal exposure during pregnancy 142.20 81.20 31 155 15520 3370153
Exposure during pregnancy 114.41 81.20 29 157 27534 3358139

Pharmacologic Action:

SourceCodeDescription
ATC R06AE03 RESPIRATORY SYSTEM
ANTIHISTAMINES FOR SYSTEMIC USE
ANTIHISTAMINES FOR SYSTEMIC USE
Piperazine derivatives
ATC R06AE53 RESPIRATORY SYSTEM
ANTIHISTAMINES FOR SYSTEMIC USE
ANTIHISTAMINES FOR SYSTEMIC USE
Piperazine derivatives
CHEBI has role CHEBI:50919 antiemetic
CHEBI has role CHEBI:48873 cholinergic antagonist
CHEBI has role CHEBI:35488 central nervous system depressant
CHEBI has role CHEBI:36333 local anaesthetic
CHEBI has role CHEBI:37955 H1-receptor antagonist
MeSH PA D000932 Antiemetics
MeSH PA D001337 Autonomic Agents
MeSH PA D002491 Central Nervous System Agents
MeSH PA D005765 Gastrointestinal Agents
MeSH PA D018494 Histamine Agents
MeSH PA D006633 Histamine Antagonists
MeSH PA D006634 Histamine H1 Antagonists
MeSH PA D018377 Neurotransmitter Agents
MeSH PA D018373 Peripheral Nervous System Agents

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Vasomotor rhinitis indication 8229003 DOID:4730
Motion sickness indication 37031009 DOID:2951
Cough indication 49727002
Allergic rhinitis indication 61582004
Nasal discharge indication 64531003
Nasal congestion indication 68235000
Sneezing indication 76067001
Common cold indication 82272006 DOID:10459
Seasonal allergic rhinitis indication 367498001
Allergic conjunctivitis indication 473460002 DOID:11204
Ocular hypertension contraindication 4210003 DOID:9282
Dependent drug abuse contraindication 6525002
Peptic ulcer contraindication 13200003 DOID:750
Chronic disease of respiratory system contraindication 17097001
Mood swings contraindication 18963009
Myocardial infarction contraindication 22298006 DOID:5844
Inflammatory bowel disease contraindication 24526004 DOID:0050589
Ventricular tachycardia contraindication 25569003
Hyperthyroidism contraindication 34486009 DOID:7998
Acute hepatitis contraindication 37871000
Hypertensive disorder contraindication 38341003 DOID:10763
Disorder of gallbladder contraindication 39621005 DOID:0060262
Hypothyroidism contraindication 40930008 DOID:1459
Conduction disorder of the heart contraindication 44808001
Low blood pressure contraindication 45007003
Chronic heart failure contraindication 48447003
Bradycardia contraindication 48867003
Acidosis contraindication 51387008
Coronary arteriosclerosis contraindication 53741008 DOID:3393
Arterial thrombosis contraindication 65198009
Drug AND/OR toxin-induced diarrhea contraindication 65979008
Substance abuse contraindication 66214007
Benign intracranial hypertension contraindication 68267002 DOID:11459
Arteriosclerotic vascular disease contraindication 72092001 DOID:2349
Diabetes mellitus contraindication 73211009 DOID:9351
Urethral stricture contraindication 76618002
Decreased respiratory function contraindication 80954004
Injury of head contraindication 82271004
Chronic idiopathic constipation contraindication 82934008
Epilepsy contraindication 84757009 DOID:1826
Kidney disease contraindication 90708001 DOID:2527
Acute abdominal pain contraindication 116290004
Procedure on urinary system contraindication 118677009
Partial atrioventricular block contraindication 195039008
Acute pancreatitis contraindication 197456007 DOID:2913
Disease of liver contraindication 235856003 DOID:409
Bladder outflow obstruction contraindication 236645006
Telangiectasia disorder contraindication 247479008 DOID:1272
Benign prostatic hyperplasia contraindication 266569009 DOID:2883
Retention of urine contraindication 267064002
Lesion of brain contraindication 301766008
Primary adrenocortical insufficiency contraindication 373662000 DOID:13774
Adrenal cortical hypofunction contraindication 386584007 DOID:10493
Operation on gastrointestinal tract contraindication 386621005
Hypoxia contraindication 389086002
Angle-closure glaucoma contraindication 392291006 DOID:13550
Pseudomembranous enterocolitis contraindication 397683000 DOID:0060185
Atrophoderma contraindication 399979006 DOID:2733
Peripheral vascular disease contraindication 400047006
Disorder of coronary artery contraindication 414024009
Central nervous system depression contraindication 418072004
Ultrarapid metabolizer due to cytochrome p450 CYP2D6 variant contraindication 422681000
Dysfunction of sphincter of Oddi contraindication 430887001
Hypertensive urgency contraindication 443482000
Acute exacerbation of asthma contraindication 708038006

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 8.19 Basic
pKa2 3.88 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 ANTAGONIST Ki 8.35 DRUG MATRIX CHEMBL
5-hydroxytryptamine receptor 2A GPCR Ki 7.19 DRUG MATRIX
5-hydroxytryptamine receptor 2B GPCR Ki 6.62 DRUG MATRIX
5-hydroxytryptamine receptor 2C GPCR Ki 6.27 DRUG MATRIX
D(3) dopamine receptor GPCR Ki 5.99 DRUG MATRIX
Muscarinic acetylcholine receptor M1 GPCR Ki 6.79 DRUG MATRIX
Muscarinic acetylcholine receptor M2 GPCR Ki 6.39 DRUG MATRIX
Muscarinic acetylcholine receptor M3 GPCR Ki 6.80 DRUG MATRIX
Muscarinic acetylcholine receptor M4 GPCR Ki 6.92 DRUG MATRIX
Muscarinic acetylcholine receptor M5 GPCR Ki 6.34 DRUG MATRIX
Sodium-dependent dopamine transporter Transporter Ki 6.22 DRUG MATRIX
Cytochrome P450 2D6 Enzyme IC50 5.21 DRUG MATRIX
Alpha-1D adrenergic receptor GPCR Ki 6.22 DRUG MATRIX
Alpha-2A adrenergic receptor GPCR Ki 6.24 DRUG MATRIX
Amine oxidase [flavin-containing] B Enzyme WOMBAT-PK
Alpha-1B adrenergic receptor GPCR Ki 5.86 DRUG MATRIX

External reference:

IDSource
4019698 VUID
N0000147790 NUI
C0010547 UMLSCUI
7151 IUPHAR_LIGAND_ID
D02090 KEGG_DRUG
CHEMBL648 ChEMBL_ID
6726 PUBCHEM_CID
4019698 VANDF
N0000147790 NDFRT
N0000005884 NDFRT
003395 NDDF
2977 RXNORM
387491004 SNOMEDCT_US
85354008 SNOMEDCT_US
d00858 MMSL
861R00J986 UNII
5897-19-8 SECONDARY_CAS_RN
CHEBI:3994 CHEBI
CHEMBL1200497 ChEMBL_ID
CHEMBL1324714 ChEMBL_ID
D003501 MESH_DESCRIPTOR_UI
DB01176 DRUGBANK_ID
176 INN_ID

Pharmaceutical products:

None