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

Stem definitionDrug idCAS RN
sulpiride derivatives 660 81098-60-4

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • R51619
  • R-51619
  • R 51619
  • cisapride monohydrate
  • cisapride
  • acenalin
  • alimix
  • cipril
  • coordinax
  • prepulsid
  • propulsid
  • risamal
A substituted benzamide used for its prokinetic properties. It is used in the management of gastroesophageal reflux disease, functional dyspepsia, and other disorders associated with impaired gastrointestinal motility. (Martindale The Extra Pharmacopoeia, 31st ed)
  • Molecular weight: 465.95
  • Formula: C23H29ClFN3O4
  • CLOGP: 3.81
  • LIPINSKI: 0
  • HAC: 7
  • HDO: 2
  • TPSA: 86.05
  • ALOGS: -4.59
  • ROTB: 9

  • Status: OFM

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

Drug dosage:

DoseUnitRoute
30 mg O
30 mg R

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 2 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 0.00 mg/mL Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 2.85 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 40 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution) 1.20 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 1.50 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.02 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 11.70 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
July 29, 1993 FDA

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
Electrocardiogram QT prolonged 1004.61 52.67 163 199 7651 2350072
Oesophagogastric fundoplasty 57.77 52.67 7 355 25 2357698

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
Electrocardiogram QT prolonged 523.34 94.64 88 116 5457 1741120

Pharmacologic Action:

SourceCodeDescription
ATC A03FA02 ALIMENTARY TRACT AND METABOLISM
DRUGS FOR FUNCTIONAL GASTROINTESTINAL DISORDERS
PROPULSIVES
Propulsives
MeSH PA D000897 Anti-Ulcer Agents
MeSH PA D005765 Gastrointestinal Agents
MeSH PA D018377 Neurotransmitter Agents
MeSH PA D018490 Serotonin Agents
MeSH PA D017366 Serotonin Receptor Agonists
CHEBI has role CHEBI:35941 serotonergic agonist
CHEBI has role CHEBI:49201 anti-ulcer drug
CHEBI has role CHEBI:55324 gastrointestinal drug

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Gastroesophageal reflux disease indication 235595009 DOID:8534
Gastroparesis off-label use 235675006
Hypophosphatemia contraindication 4996001
Hypocalcemia contraindication 5291005
Hypokalemia contraindication 43339004
Ventricular arrhythmia contraindication 44103008
Mechanical ileus contraindication 46420000
Chronic heart failure contraindication 48447003
Bradycardia contraindication 48867003
Gastrointestinal hemorrhage contraindication 74474003
Epilepsy contraindication 84757009 DOID:1826
Kidney disease contraindication 90708001 DOID:557
Prolonged QT interval contraindication 111975006
Hypomagnesemia contraindication 190855004
Angina pectoris contraindication 194828000
Disease of liver contraindication 235856003 DOID:409
Disorder of electrolytes contraindication 237840007
Respiratory insufficiency contraindication 409623005
Myocardial ischemia contraindication 414795007 DOID:3393
Congenital long QT syndrome contraindication 442917000
Severe dehydration contraindication 450316000

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 10.79 acidic
pKa2 7.8 Basic
pKa3 1.0 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 4 GPCR AGONIST Ki 7.54 CHEMBL CHEMBL
Alpha-2A adrenergic receptor GPCR Ki 6.18 DRUG MATRIX
Sigma non-opioid intracellular receptor 1 Membrane receptor Ki 6.38 DRUG MATRIX
Cytochrome P450 3A4 Enzyme IC50 6.52 DRUG MATRIX
Sodium-dependent serotonin transporter Transporter Ki 6.69 DRUG MATRIX
5-hydroxytryptamine receptor 2C GPCR Ki 6.40 DRUG MATRIX
Alpha-2B adrenergic receptor GPCR Ki 6.28 DRUG MATRIX
D(3) dopamine receptor GPCR Ki 7.31 DRUG MATRIX
Alpha-2C adrenergic receptor GPCR Ki 6.95 DRUG MATRIX
Cytochrome P450 2D6 Enzyme IC50 7.15 DRUG MATRIX
Alpha-1D adrenergic receptor GPCR Ki 7.31 DRUG MATRIX
3-hydroxy-3-methylglutaryl-coenzyme A reductase Enzyme IC50 5.47 DRUG MATRIX
5-hydroxytryptamine receptor 7 GPCR EC50 5.70 WOMBAT-PK
D(2) dopamine receptor GPCR IC50 6.64 CHEMBL
D(1A) dopamine receptor GPCR IC50 5.77 CHEMBL
Potassium voltage-gated channel subfamily H member 2 Ion channel IC50 8.19 CHEMBL
Serotonin 3 (5-HT3) receptor Ion channel Ki 6.82 CHEMBL
5-hydroxytryptamine receptor 2A GPCR Ki 8.96 CHEMBL
5-hydroxytryptamine receptor 2B GPCR Ki 7.15 CHEMBL
Alpha-1B adrenergic receptor GPCR Ki 8.06 DRUG MATRIX
Membrane-associated progesterone receptor component 1 Membrane receptor Ki 6.96 DRUG MATRIX
5-hydroxytryptamine receptor 4 GPCR Ki 7.84 CHEMBL
Serotonin 2 (5-HT2) receptor GPCR Ki 8.21 CHEMBL
Adrenergic receptor alpha-2 GPCR Ki 5.35 CHEMBL
Serotonin 3 (5-HT3) receptor Ion channel Ki 7.02 CHEMBL
D(1A) dopamine receptor GPCR Ki 5.77 CHEMBL
Alpha-2A adrenergic receptor GPCR Ki 7.52 CHEMBL
5-hydroxytryptamine receptor 2A GPCR Ki 8.14 CHEMBL
Alpha-1A adrenergic receptor GPCR Ki 7.52 CHEMBL
Serotonin 1 (5-HT1) receptor GPCR IC50 5.35 CHEMBL
D(2) dopamine receptor GPCR Ki 6.64 CHEMBL
5-hydroxytryptamine receptor 7 GPCR AGONIST Ki 5.80 IUPHAR
5-hydroxytryptamine receptor 4 GPCR AGONIST Ki 8 IUPHAR
5-hydroxytryptamine receptor 4 Unclassified AGONIST Ki 7.50 IUPHAR

External reference:

IDSource
C0724554 UMLSCUI
D00274 KEGG_DRUG
30317002 SNOMEDCT_US
4020825 VANDF
35255 RXNORM
387164008 SNOMEDCT_US
4453 MMSL
d03166 MMSL
003705 NDDF
DB00604 DRUGBANK_ID
CHEMBL1729 ChEMBL_ID
CHEMBL1200788 ChEMBL_ID
UVL329170W UNII
5338 INN_ID
260779-88-2 SECONDARY_CAS_RN
CHEBI:3720 CHEBI
240 IUPHAR_LIGAND_ID
D020117 MESH_DESCRIPTOR_UI
2769 PUBCHEM_CID

Pharmaceutical products:

None