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

Stem definitionDrug idCAS RN
gastrointestinal lipase inhibitors 1996 96829-58-2

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • orlistat
  • tetrahydrolipstatin
  • xenical
  • alli
  • tetrahydrolipastatin
isolated from Streptomyces toxytricini; inhibits 3C protease, viral
  • Molecular weight: 495.75
  • Formula: C29H53NO5
  • CLOGP: 8.61
  • LIPINSKI: 1
  • HAC: 6
  • HDO: 1
  • TPSA: 81.70
  • ALOGS: -6.73
  • ROTB: 23

Drug dosage:

DoseUnitRoute
0.36 g O

Approvals:

DateAgencyCompanyOrphan
April 23, 1999 FDA HOFFMANN LA ROCHE

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
Steatorrhoea 229.42 32.53 32 1203 137 3384487
Abdominal pain 170.70 32.53 71 1164 46154 3338470
Diarrhoea 164.61 32.53 89 1146 104259 3280365
Rectal haemorrhage 158.05 32.53 45 1190 9313 3375311
Nephropathy 149.12 32.53 30 1205 1400 3383224
Abdominal pain upper 136.43 32.53 51 1184 24865 3359759
Haematochezia 123.06 32.53 35 1200 7186 3377438
Cholelithiasis 119.05 32.53 35 1200 8073 3376551
Drug interaction 105.41 32.53 51 1184 46761 3337863
Nausea 94.75 32.53 68 1167 129577 3255047
Flatulence 84.23 32.53 25 1210 5934 3378690
Constipation 82.85 32.53 38 1197 30774 3353850
Rectal discharge 82.77 32.53 13 1222 139 3384485
Diverticulitis 79.01 32.53 23 1212 5102 3379522
Abdominal distension 78.53 32.53 29 1206 13547 3371077
Acute kidney injury 76.60 32.53 42 1193 49641 3334983
Acute hepatic failure 74.75 32.53 21 1214 4102 3380522
Malaise 73.64 32.53 45 1190 65132 3319492
Pancreatitis 69.95 32.53 27 1208 14218 3370406
Hepatic enzyme increased 67.52 32.53 26 1209 13599 3371025
Vomiting 67.50 32.53 48 1187 89483 3295141
Alanine aminotransferase increased 62.99 32.53 29 1206 23611 3361013
Pancreatitis acute 56.62 32.53 19 1216 6689 3377935
Exposure during pregnancy 55.77 32.53 28 1207 27535 3357089
Abortion spontaneous 54.91 32.53 21 1214 10764 3373860
Dizziness 52.96 32.53 39 1196 76473 3308151
Aspartate aminotransferase increased 50.33 32.53 24 1211 21089 3363535
Product quality issue 47.81 32.53 25 1210 26710 3357914
Ill-defined disorder 46.87 32.53 14 1221 3380 3381244
Hepatitis 46.34 32.53 18 1217 9607 3375017
Hepatic steatosis 45.76 32.53 15 1220 4905 3379719
Faeces discoloured 44.70 32.53 14 1221 3958 3380666
Hepatic failure 44.57 32.53 18 1217 10634 3373990
Chromaturia 42.69 32.53 14 1221 4584 3380040
Jaundice 42.01 32.53 17 1218 10090 3374534
Transaminases increased 40.96 32.53 15 1220 6809 3377815
Nephrolithiasis 40.93 32.53 15 1220 6821 3377803
Palpitations 40.37 32.53 20 1215 19063 3365561
Hyperoxaluria 40.10 32.53 6 1229 45 3384579
Faeces pale 38.27 32.53 8 1227 448 3384176
Renal failure 37.70 32.53 23 1212 32917 3351707
Abdominal discomfort 37.61 32.53 19 1216 18865 3365759
Dyspnoea 37.00 32.53 36 1199 102898 3281726
Liver function test abnormal 34.84 32.53 16 1219 12885 3371739
Weight increased 34.03 32.53 20 1215 26720 3357904
Fatigue 33.92 32.53 35 1200 107205 3277419
Gallbladder disorder 33.65 32.53 11 1224 3561 3381063
Asthenia 33.49 32.53 28 1207 65637 3318987
Drug ineffective 33.37 32.53 36 1199 116054 3268570

Pharmacologic Action:

SourceCodeDescription
ATC A08AB01 ALIMENTARY TRACT AND METABOLISM
ANTIOBESITY PREPARATIONS, EXCL. DIET PRODUCTS
ANTIOBESITY PREPARATIONS, EXCL. DIET PRODUCTS
Peripherally acting antiobesity products
MeSH PA D019440 Anti-Obesity Agents
MeSH PA D002491 Central Nervous System Agents
MeSH PA D004791 Enzyme Inhibitors
FDA EPC N0000175591 Intestinal Lipase Inhibitor
FDA MoA N0000009916 Lipase Inhibitors

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Obesity indication 414916001 DOID:9970
Primary hyperoxaluria contraindication 17901006 DOID:2977
Obstruction of bile duct contraindication 30144000 DOID:13580
Anorexia nervosa contraindication 56882008 DOID:8689
Hepatic failure contraindication 59927004
Bulimia nervosa contraindication 78004001 DOID:12129
Vitamin deficiency contraindication 85670002
Hepatic necrosis contraindication 87248009
Liver function tests abnormal contraindication 166603001
Drug-induced hepatitis contraindication 235876009
Malabsorption States contraindication
Calcium Oxalate Renal Calculi contraindication

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 13.77 acidic

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
Pancreatic triacylglycerol lipase Enzyme INHIBITOR IC50 8.90 IUPHAR DRUG LABEL
Gastric triacylglycerol lipase Enzyme INHIBITOR CHEMBL DRUG LABEL
Monoacylglycerol lipase ABHD12 Enzyme IC50 7.10 CHEMBL
Monoacylglycerol lipase ABHD6 Enzyme IC50 7.32 CHEMBL
Sn1-specific diacylglycerol lipase alpha Enzyme IC50 8 CHEMBL
Abhydrolase domain-containing protein 16A Enzyme IC50 7.52 CHEMBL
Platelet-activating factor acetylhydrolase Enzyme IC50 7.30 CHEMBL
Sn1-specific diacylglycerol lipase beta Enzyme IC50 7.22 CHEMBL
Cannabinoid receptor 1 GPCR Ki 5.60 CHEMBL
Fatty-acid amide hydrolase 1 Enzyme IC50 8 CHEMBL
Pancreatic triacylglycerol lipase Enzyme IC50 6.66 CHEMBL

External reference:

IDSource
5277 IUPHAR_LIGAND_ID
4021159 VUID
N0000148610 NUI
C0076275 UMLSCUI
D04028 KEGG_DRUG
DB01083 DRUGBANK_ID
4021159 VANDF
N0000007160 NDFRT
N0000148610 NDFRT
007654 NDDF
d04429 MMSL
8088 MMSL
37925 RXNORM
116093009 SNOMEDCT_US
387007000 SNOMEDCT_US
95M8R751W8 UNII
6318 INN_ID
CHEMBL175247 ChEMBL_ID
3034010 PUBCHEM_CID
C055122 MESH_SUPPLEMENTAL_RECORD_UI
CHEBI:94686 CHEBI

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Xenical HUMAN PRESCRIPTION DRUG LABEL 1 0004-0257 CAPSULE 120 mg ORAL NDA 20 sections
ALLI HUMAN OTC DRUG LABEL 1 0135-0461 CAPSULE 60 mg ORAL NDA 9 sections
Xenical HUMAN PRESCRIPTION DRUG LABEL 1 61269-460 CAPSULE 120 mg ORAL NDA 20 sections