Identification

Name
Alosetron
Accession Number
DB00969  (APRD00580)
Type
Small Molecule
Groups
Approved, Withdrawn
Description

Alosetron is a 5-HT3 antagonist used only for the management of severe diarrhoea-predominant irritable bowel syndrome (IBS) in women. Alosetron has an antagonist action on the 5-HT3 receptors and thus may modulate serotonin-sensitive gastrointestinal (GI) processes. Alosetron was voluntarily withdrawn from the US market in November 2000 by the manufacturer due to numerous reports of severe adverse effects including ischemic colitis, severely obstructed or ruptured bowel, and death. In June 2002, the FDA approved a supplemental new drug application allowing the remarketing of the drug under restricted conditions of use.

Structure
Thumb
Synonyms
  • 2,3,4,5-Tetrahydro-5-methyl-2-((5-methyl-1H-imidazol-4-yl)methyl)-1H-pyrido(4,3-b)indol-1-one
External IDs
A03AE01
Product Ingredients
IngredientUNIICASInChI Key
Alosetron Hydrochloride2F5R1A46YW122852-69-1FNYQZOVOVDSGJH-UHFFFAOYSA-N
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Alosetron HydrochlorideTablet1 mg/1OralActavis Pharma Company2015-05-26Not applicableUs
Alosetron HydrochlorideTablet.5 mg/1OralActavis Pharma Company2015-05-26Not applicableUs
LotronexTablet1 mg/1OralPrometheus Laboratories2009-02-09Not applicableUs
LotronexTablet.5 mg/1OralSebela Pharmaceuticals Inc.2016-07-11Not applicableUs
LotronexTablet.5 mg/1OralPrometheus Laboratories2009-02-09Not applicableUs
LotronexTablet1 mg/1OralSebela Pharmaceuticals Inc.2016-07-11Not applicableUs
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Alosetron HydrochlorideTablet, film coated1 mg/1OralAmneal Pharmaceuticals2017-01-02Not applicableUs
Alosetron HydrochlorideTablet, film coated.5 mg/1OralAmneal Pharmaceuticals2017-01-02Not applicableUs
Alosetron HydrochlorideTablet1 mg/1OralWest Ward Pharmaceutical2013-07-15Not applicableUs
Alosetron HydrochlorideTablet.5 mg/1OralPar Pharmaceutical2018-02-16Not applicableUs
Alosetron HydrochlorideTablet.5 mg/1OralWest Ward Pharmaceutical2013-07-15Not applicableUs
Alosetron HydrochlorideTablet, film coated1 mg/1OralAv Kare, Inc.2017-02-23Not applicableUs
Alosetron HydrochlorideTablet, film coated.5 mg/1OralAv Kare, Inc.2017-02-23Not applicableUs
Alosetron HydrochlorideTablet1 mg/1OralPar Pharmaceutical2018-02-16Not applicableUs
Categories
UNII
13Z9HTH115
CAS number
122852-42-0
Weight
Average: 294.351
Monoisotopic: 294.148061218
Chemical Formula
C17H18N4O
InChI Key
JSWZEAMFRNKZNL-UHFFFAOYSA-N
InChI
InChI=1S/C17H18N4O/c1-11-13(19-10-18-11)9-21-8-7-15-16(17(21)22)12-5-3-4-6-14(12)20(15)2/h3-6,10H,7-9H2,1-2H3,(H,18,19)
IUPAC Name
5-methyl-2-[(5-methyl-1H-imidazol-4-yl)methyl]-1H,2H,3H,4H,5H-pyrido[4,3-b]indol-1-one
SMILES
CN1C2=C(C3=CC=CC=C13)C(=O)N(CC1=C(C)NC=N1)CC2

Pharmacology

Indication

Only for the treatment of symptoms of severe diarrhea-predominant irritable bowel syndrome (IBS) in women with chronic symptoms (generally lasting greater than 6 months) who does not present with anatomic or biochemical GI abnormalities and have not responded to conventional therapy.

Associated Conditions
Pharmacodynamics

Alosetron is a potent and selective antagonist of the serotonin 5-HT3 receptor type. Activation of these receptors and the resulting neuronal depolarization affects the regulation of visceral pain, colonic transit, and GI secretions processes that are related to IBS. By blocking these receptors, alosetron is able to effectively control IBS.

Mechanism of action

Alosetron is a potent and selective 5-HT3 receptor antagonist. 5-HT3 receptors are nonselective cation channels that are extensively distributed on enteric neurons in the human gastrointestinal tract, as well as other peripheral and central locations. Activation of these channels and the resulting neuronal depolarization affect the regulation of visceral pain, colonic transit and gastrointestinal secretions, processes that relate to the pathophysiology of irritable bowel syndrome (IBS). 5-HT3 receptor antagonists such as alosetron inhibit activation of non-selective cation channels which results in the modulation of serotonin-sensitive GI motor and sensory processes.

TargetActionsOrganism
A5-hydroxytryptamine receptor 3A
antagonist
Human
Absorption

50-60 %

Volume of distribution
  • 65 to 95 L
Protein binding

82%

Metabolism

Hepatic, via microsomal cytochrome P450 (CYP)

Route of elimination

Renal elimination of unchanged alosetron accounts for only 6% of the dose. Alosetron is extensively metabolized in humans.

Half life

1.5 hours

Clearance
  • 600 mL/min
Toxicity
Not Available
Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
AbirateroneThe serum concentration of Alosetron can be increased when it is combined with Abiraterone.Approved
AcetaminophenThe metabolism of Acetaminophen can be decreased when combined with Alosetron.Approved
Acetyl sulfisoxazoleThe metabolism of Alosetron can be decreased when combined with Acetyl sulfisoxazole.Approved, Vet Approved
AlmotriptanAlosetron may increase the serotonergic activities of Almotriptan.Approved, Investigational
AmikacinThe risk or severity of adverse effects can be increased when Amikacin is combined with Alosetron.Approved, Investigational, Vet Approved
AmiodaroneThe metabolism of Alosetron can be decreased when combined with Amiodarone.Approved, Investigational
AmitriptylineAlosetron may increase the serotonergic activities of Amitriptyline.Approved
AmoxapineAlosetron may increase the serotonergic activities of Amoxapine.Approved
ApalutamideThe serum concentration of Alosetron can be decreased when it is combined with Apalutamide.Approved, Investigational
ApomorphineAlosetron may increase the hypotensive activities of Apomorphine.Approved, Investigational
AprepitantThe serum concentration of Alosetron can be increased when it is combined with Aprepitant.Approved, Investigational
AtazanavirThe serum concentration of Alosetron can be increased when it is combined with Atazanavir.Approved, Investigational
AtomoxetineThe metabolism of Alosetron can be decreased when combined with Atomoxetine.Approved
AzithromycinThe metabolism of Alosetron can be decreased when combined with Azithromycin.Approved
BenzphetamineThe risk or severity of adverse effects can be increased when Benzphetamine is combined with Alosetron.Approved, Illicit
Benzyl alcoholThe risk or severity of adverse effects can be increased when Benzyl alcohol is combined with Alosetron.Approved
BoceprevirThe serum concentration of Alosetron can be increased when it is combined with Boceprevir.Approved, Withdrawn
BortezomibThe metabolism of Alosetron can be decreased when combined with Bortezomib.Approved, Investigational
BosentanThe serum concentration of Alosetron can be decreased when it is combined with Bosentan.Approved, Investigational
BromocriptineAlosetron may increase the serotonergic activities of Bromocriptine.Approved, Investigational
BupropionThe risk or severity of adverse effects can be increased when Bupropion is combined with Alosetron.Approved
BuspironeAlosetron may increase the serotonergic activities of Buspirone.Approved, Investigational
CabergolineAlosetron may increase the serotonergic activities of Cabergoline.Approved
CaffeineThe metabolism of Alosetron can be decreased when combined with Caffeine.Approved
CapecitabineThe metabolism of Alosetron can be decreased when combined with Capecitabine.Approved, Investigational
CarbamazepineThe metabolism of Alosetron can be increased when combined with Carbamazepine.Approved, Investigational
CarvedilolThe metabolism of Carvedilol can be decreased when combined with Alosetron.Approved, Investigational
CeritinibThe serum concentration of Alosetron can be increased when it is combined with Ceritinib.Approved
CetirizineThe risk or severity of adverse effects can be increased when Cetirizine is combined with Alosetron.Approved
CholecalciferolThe metabolism of Alosetron can be decreased when combined with Cholecalciferol.Approved, Nutraceutical
CinnarizineThe metabolism of Cinnarizine can be decreased when combined with Alosetron.Approved, Investigational
CiprofloxacinThe metabolism of Alosetron can be decreased when combined with Ciprofloxacin.Approved, Investigational
CitalopramThe metabolism of Alosetron can be decreased when combined with Citalopram.Approved
ClarithromycinThe serum concentration of Alosetron can be increased when it is combined with Clarithromycin.Approved
ClemastineThe risk or severity of adverse effects can be increased when Clemastine is combined with Alosetron.Approved, Investigational
ClindamycinThe risk or severity of adverse effects can be increased when Clindamycin is combined with Alosetron.Approved, Vet Approved
ClomipramineAlosetron may increase the serotonergic activities of Clomipramine.Approved, Investigational, Vet Approved
ClotrimazoleThe serum concentration of Alosetron can be increased when it is combined with Clotrimazole.Approved, Vet Approved
CobicistatThe serum concentration of Alosetron can be increased when it is combined with Cobicistat.Approved
CodeineThe risk or severity of adverse effects can be increased when Codeine is combined with Alosetron.Approved, Illicit
ConivaptanThe serum concentration of Conivaptan can be increased when it is combined with Alosetron.Approved, Investigational
CrisaboroleThe metabolism of Alosetron can be decreased when combined with Crisaborole.Approved, Investigational
CrizotinibThe metabolism of Alosetron can be decreased when combined with Crizotinib.Approved
CurcuminThe serum concentration of Alosetron can be increased when it is combined with Curcumin.Approved, Investigational
CyclobenzaprineThe risk or severity of adverse effects can be increased when Cyclobenzaprine is combined with Alosetron.Approved
CyclosporineThe metabolism of Alosetron can be decreased when combined with Cyclosporine.Approved, Investigational, Vet Approved
Cyproterone acetateThe serum concentration of Alosetron can be decreased when it is combined with Cyproterone acetate.Approved, Investigational
DabrafenibThe serum concentration of Alosetron can be decreased when it is combined with Dabrafenib.Approved, Investigational
DarunavirThe serum concentration of Alosetron can be increased when it is combined with Darunavir.Approved
DasatinibThe serum concentration of Alosetron can be increased when it is combined with Dasatinib.Approved, Investigational
DeferasiroxThe serum concentration of Alosetron can be decreased when it is combined with Deferasirox.Approved, Investigational
DelavirdineThe metabolism of Alosetron can be decreased when combined with Delavirdine.Approved
DesipramineAlosetron may increase the serotonergic activities of Desipramine.Approved, Investigational
DesvenlafaxineAlosetron may increase the serotonergic activities of Desvenlafaxine.Approved, Investigational
DexamethasoneThe serum concentration of Alosetron can be decreased when it is combined with Dexamethasone.Approved, Investigational, Vet Approved
DexbrompheniramineThe risk or severity of adverse effects can be increased when Dexbrompheniramine is combined with Alosetron.Approved
DextromethorphanAlosetron may increase the serotonergic activities of Dextromethorphan.Approved
DiclofenacThe metabolism of Diclofenac can be decreased when combined with Alosetron.Approved, Vet Approved
DihydroergotamineThe metabolism of Alosetron can be decreased when combined with Dihydroergotamine.Approved, Investigational
DiltiazemThe serum concentration of Alosetron can be increased when it is combined with Diltiazem.Approved, Investigational
DimenhydrinateThe risk or severity of adverse effects can be increased when Dimenhydrinate is combined with Alosetron.Approved
DosulepinThe metabolism of Alosetron can be decreased when combined with Dosulepin.Approved
DotarizineThe risk or severity of adverse effects can be increased when Alosetron is combined with Dotarizine.Investigational
DoxepinAlosetron may increase the serotonergic activities of Doxepin.Approved, Investigational
DoxycyclineThe metabolism of Alosetron can be decreased when combined with Doxycycline.Approved, Investigational, Vet Approved
DoxylamineDoxylamine may increase the central nervous system depressant (CNS depressant) activities of Alosetron.Approved, Vet Approved
DronedaroneThe metabolism of Alosetron can be decreased when combined with Dronedarone.Approved
DuloxetineAlosetron may increase the serotonergic activities of Duloxetine.Approved
EfavirenzThe metabolism of Alosetron can be decreased when combined with Efavirenz.Approved, Investigational
EletriptanAlosetron may increase the serotonergic activities of Eletriptan.Approved, Investigational
EluxadolineAlosetron may increase the constipating activities of Eluxadoline.Approved, Investigational
EnzalutamideThe serum concentration of Alosetron can be decreased when it is combined with Enzalutamide.Approved
EperisoneThe risk or severity of adverse effects can be increased when Eperisone is combined with Alosetron.Approved, Investigational
Ergoloid mesylateAlosetron may increase the serotonergic activities of Ergoloid mesylate.Approved
ErgonovineAlosetron may increase the serotonergic activities of Ergonovine.Approved
ErgotamineAlosetron may increase the serotonergic activities of Ergotamine.Approved
ErythromycinThe metabolism of Alosetron can be decreased when combined with Erythromycin.Approved, Investigational, Vet Approved
EscitalopramAlosetron may increase the serotonergic activities of Escitalopram.Approved, Investigational
EstradiolThe metabolism of Estradiol can be decreased when combined with Alosetron.Approved, Investigational, Vet Approved
EthanolAlosetron may increase the central nervous system depressant (CNS depressant) activities of Ethanol.Approved
EthosuximideThe risk or severity of adverse effects can be increased when Ethosuximide is combined with Alosetron.Approved
EtomidateThe risk or severity of adverse effects can be increased when Etomidate is combined with Alosetron.Approved
EtravirineThe metabolism of Alosetron can be decreased when combined with Etravirine.Approved
FentanylThe risk or severity of adverse effects can be increased when Fentanyl is combined with Alosetron.Approved, Illicit, Investigational, Vet Approved
FloxuridineThe metabolism of Alosetron can be decreased when combined with Floxuridine.Approved
FluconazoleThe metabolism of Alosetron can be decreased when combined with Fluconazole.Approved, Investigational
FlunarizineThe risk or severity of adverse effects can be increased when Flunarizine is combined with Alosetron.Approved
FluorouracilThe metabolism of Alosetron can be decreased when combined with Fluorouracil.Approved
FluoxetineAlosetron may increase the serotonergic activities of Fluoxetine.Approved, Vet Approved
FluspirileneThe risk or severity of adverse effects can be increased when Fluspirilene is combined with Alosetron.Approved, Investigational
Fluticasone propionateThe risk or severity of adverse effects can be increased when Fluticasone propionate is combined with Alosetron.Approved
FluvoxamineThe metabolism of Alosetron can be decreased when combined with Fluvoxamine.Approved, Investigational
FosamprenavirThe metabolism of Alosetron can be decreased when combined with Fosamprenavir.Approved
FosaprepitantThe serum concentration of Alosetron can be increased when it is combined with Fosaprepitant.Approved
FosphenytoinThe metabolism of Alosetron can be increased when combined with Fosphenytoin.Approved, Investigational
FrovatriptanAlosetron may increase the serotonergic activities of Frovatriptan.Approved, Investigational
Fusidic AcidThe serum concentration of Alosetron can be increased when it is combined with Fusidic Acid.Approved, Investigational
GabapentinThe risk or severity of adverse effects can be increased when Gabapentin is combined with Alosetron.Approved, Investigational
GemfibrozilThe metabolism of Alosetron can be decreased when combined with Gemfibrozil.Approved
GuanfacineThe risk or severity of adverse effects can be increased when Guanfacine is combined with Alosetron.Approved, Investigational
HydrocodoneAlosetron may increase the central nervous system depressant (CNS depressant) activities of Hydrocodone.Approved, Illicit
HydroxyzineHydroxyzine may increase the central nervous system depressant (CNS depressant) activities of Alosetron.Approved
IdelalisibThe serum concentration of Alosetron can be increased when it is combined with Idelalisib.Approved
ImatinibThe metabolism of Alosetron can be decreased when combined with Imatinib.Approved
ImipramineAlosetron may increase the serotonergic activities of Imipramine.Approved
IndinavirThe serum concentration of Alosetron can be increased when it is combined with Indinavir.Approved
IrbesartanThe metabolism of Alosetron can be decreased when combined with Irbesartan.Approved, Investigational
IsavuconazoleThe serum concentration of Alosetron can be increased when it is combined with Isavuconazole.Approved, Investigational
IsavuconazoniumThe metabolism of Alosetron can be decreased when combined with Isavuconazonium.Approved, Investigational
IsocarboxazidAlosetron may increase the serotonergic activities of Isocarboxazid.Approved
ItraconazoleThe serum concentration of Alosetron can be increased when it is combined with Itraconazole.Approved, Investigational
IvacaftorThe serum concentration of Alosetron can be increased when it is combined with Ivacaftor.Approved
KetoconazoleThe serum concentration of Alosetron can be increased when it is combined with Ketoconazole.Approved, Investigational
LamotrigineThe risk or severity of adverse effects can be increased when Lamotrigine is combined with Alosetron.Approved, Investigational
LeflunomideThe metabolism of Alosetron can be decreased when combined with Leflunomide.Approved, Investigational
LevetiracetamThe risk or severity of adverse effects can be increased when Levetiracetam is combined with Alosetron.Approved, Investigational
LevomilnacipranAlosetron may increase the serotonergic activities of Levomilnacipran.Approved, Investigational
LidocaineThe metabolism of Alosetron can be decreased when combined with Lidocaine.Approved, Vet Approved
LinezolidAlosetron may increase the serotonergic activities of Linezolid.Approved, Investigational
Lithium cationAlosetron may increase the serotonergic activities of Lithium.Experimental
LobeglitazoneThe metabolism of Alosetron can be decreased when combined with Lobeglitazone.Approved, Investigational
LopinavirThe serum concentration of Alosetron can be increased when it is combined with Lopinavir.Approved
LoratadineThe risk or severity of adverse effects can be increased when Loratadine is combined with Alosetron.Approved, Investigational
LorcaserinAlosetron may increase the serotonergic activities of Lorcaserin.Approved
LorpiprazoleThe serum concentration of Alosetron can be increased when it is combined with Lorpiprazole.Approved
LovastatinThe metabolism of Alosetron can be decreased when combined with Lovastatin.Approved, Investigational
LuliconazoleThe serum concentration of Alosetron can be increased when it is combined with Luliconazole.Approved
LumacaftorThe serum concentration of Alosetron can be decreased when it is combined with Lumacaftor.Approved
Magnesium carbonateThe risk or severity of adverse effects can be increased when Magnesium carbonate is combined with Alosetron.Approved, Investigational
Magnesium citrateThe risk or severity of adverse effects can be increased when Magnesium citrate is combined with Alosetron.Approved
Magnesium sulfateThe therapeutic efficacy of Alosetron can be increased when used in combination with Magnesium sulfate.Approved, Investigational, Vet Approved
Magnesium TrisilicateThe risk or severity of adverse effects can be increased when Magnesium Trisilicate is combined with Alosetron.Approved
MaprotilineAlosetron may increase the serotonergic activities of Maprotiline.Approved, Investigational
MeclizineThe risk or severity of adverse effects can be increased when Meclizine is combined with Alosetron.Approved
MethadoneAlosetron may increase the serotonergic activities of Methadone.Approved
MethsuximideThe risk or severity of adverse effects can be increased when Methsuximide is combined with Alosetron.Approved
MexiletineThe metabolism of Alosetron can be decreased when combined with Mexiletine.Approved, Investigational
MibefradilThe serum concentration of Alosetron can be increased when it is combined with Mibefradil.Investigational, Withdrawn
MiconazoleThe metabolism of Alosetron can be decreased when combined with Miconazole.Approved, Investigational, Vet Approved
MidostaurinThe metabolism of Alosetron can be decreased when combined with Midostaurin.Approved, Investigational
MifepristoneThe serum concentration of Alosetron can be increased when it is combined with Mifepristone.Approved, Investigational
MilnacipranAlosetron may increase the serotonergic activities of Milnacipran.Approved, Investigational
MirtazapineAlosetron may increase the serotonergic activities of Mirtazapine.Approved
MitotaneThe serum concentration of Alosetron can be decreased when it is combined with Mitotane.Approved
MoclobemideAlosetron may increase the serotonergic activities of Moclobemide.Approved, Investigational
NabiloneThe metabolism of Alosetron can be decreased when combined with Nabilone.Approved, Investigational
NaproxenThe metabolism of Naproxen can be decreased when combined with Alosetron.Approved, Vet Approved
NaratriptanAlosetron may increase the serotonergic activities of Naratriptan.Approved, Investigational
NefazodoneThe serum concentration of Alosetron can be increased when it is combined with Nefazodone.Approved, Withdrawn
NelfinavirThe serum concentration of Alosetron can be increased when it is combined with Nelfinavir.Approved
NetupitantThe serum concentration of Alosetron can be increased when it is combined with Netupitant.Approved, Investigational
NevirapineThe metabolism of Alosetron can be increased when combined with Nevirapine.Approved
NicardipineThe metabolism of Alosetron can be decreased when combined with Nicardipine.Approved, Investigational
NicotineThe metabolism of Nicotine can be decreased when combined with Alosetron.Approved
NilotinibThe metabolism of Alosetron can be decreased when combined with Nilotinib.Approved, Investigational
NortriptylineAlosetron may increase the serotonergic activities of Nortriptyline.Approved
OlaparibThe metabolism of Alosetron can be decreased when combined with Olaparib.Approved
OmeprazoleThe metabolism of Omeprazole can be decreased when combined with Alosetron.Approved, Investigational, Vet Approved
OndansetronThe risk or severity of adverse effects can be increased when Ondansetron is combined with Alosetron.Approved
OsimertinibThe serum concentration of Alosetron can be increased when it is combined with Osimertinib.Approved
OxycodoneThe risk or severity of adverse effects can be increased when Oxycodone is combined with Alosetron.Approved, Illicit, Investigational
OxymorphoneThe risk or severity of adverse effects can be increased when Oxymorphone is combined with Alosetron.Approved, Investigational, Vet Approved
PalbociclibThe serum concentration of Alosetron can be increased when it is combined with Palbociclib.Approved, Investigational
ParomomycinThe risk or severity of adverse effects can be increased when Paromomycin is combined with Alosetron.Approved, Investigational
ParoxetineThe risk or severity of adverse effects can be increased when Alosetron is combined with Paroxetine.Approved, Investigational
Peginterferon alfa-2bThe serum concentration of Alosetron can be increased when it is combined with Peginterferon alfa-2b.Approved
PenfluridolThe risk or severity of adverse effects can be increased when Penfluridol is combined with Alosetron.Experimental
PentobarbitalThe metabolism of Alosetron can be increased when combined with Pentobarbital.Approved, Investigational, Vet Approved
PethidineAlosetron may increase the serotonergic activities of Pethidine.Approved
PhenelzineAlosetron may increase the serotonergic activities of Phenelzine.Approved
PhenobarbitalThe metabolism of Alosetron can be increased when combined with Phenobarbital.Approved, Investigational
PhenytoinThe metabolism of Alosetron can be increased when combined with Phenytoin.Approved, Vet Approved
PitolisantThe serum concentration of Alosetron can be decreased when it is combined with Pitolisant.Approved, Investigational
PosaconazoleThe serum concentration of Alosetron can be increased when it is combined with Posaconazole.Approved, Investigational, Vet Approved
PramipexoleAlosetron may increase the sedative activities of Pramipexole.Approved, Investigational
PregabalinThe therapeutic efficacy of Alosetron can be increased when used in combination with Pregabalin.Approved, Illicit, Investigational
PrimidoneThe metabolism of Alosetron can be increased when combined with Primidone.Approved, Vet Approved
ProcarbazineAlosetron may increase the serotonergic activities of Procarbazine.Approved, Investigational
ProchlorperazineThe risk or severity of adverse effects can be increased when Prochlorperazine is combined with Alosetron.Approved, Vet Approved
PromethazineThe risk or severity of adverse effects can be increased when Promethazine is combined with Alosetron.Approved, Investigational
PropafenoneThe metabolism of Propafenone can be decreased when combined with Alosetron.Approved
PropranololThe metabolism of Propranolol can be decreased when combined with Alosetron.Approved, Investigational
ProtriptylineAlosetron may increase the serotonergic activities of Protriptyline.Approved
PseudoephedrineThe risk or severity of adverse effects can be increased when Alosetron is combined with Pseudoephedrine.Approved
PyrantelThe risk or severity of adverse effects can be increased when Pyrantel is combined with Alosetron.Approved, Vet Approved
PyrimethamineThe metabolism of Alosetron can be decreased when combined with Pyrimethamine.Approved, Investigational, Vet Approved
QuetiapineThe risk or severity of adverse effects can be increased when Quetiapine is combined with Alosetron.Approved
QuinineThe metabolism of Alosetron can be decreased when combined with Quinine.Approved
RanitidineThe metabolism of Ranitidine can be decreased when combined with Alosetron.Approved
RanolazineThe metabolism of Alosetron can be decreased when combined with Ranolazine.Approved, Investigational
RasagilineAlosetron may increase the serotonergic activities of Rasagiline.Approved
RifabutinThe metabolism of Alosetron can be increased when combined with Rifabutin.Approved, Investigational
RifampicinThe metabolism of Alosetron can be increased when combined with Rifampicin.Approved
RifapentineThe metabolism of Alosetron can be increased when combined with Rifapentine.Approved, Investigational
RizatriptanThe risk or severity of adverse effects can be increased when Rizatriptan is combined with Alosetron.Approved
RopiniroleThe metabolism of Alosetron can be decreased when combined with Ropinirole.Approved, Investigational
RucaparibThe metabolism of Alosetron can be decreased when combined with Rucaparib.Approved, Investigational
SaquinavirThe serum concentration of Alosetron can be increased when it is combined with Saquinavir.Approved, Investigational
SarilumabThe therapeutic efficacy of Alosetron can be decreased when used in combination with Sarilumab.Approved, Investigational
ScopolamineThe risk or severity of adverse effects can be increased when Scopolamine is combined with Alosetron.Approved, Investigational
SecobarbitalThe metabolism of Alosetron can be increased when combined with Secobarbital.Approved, Vet Approved
SelegilineAlosetron may increase the serotonergic activities of Selegiline.Approved, Investigational, Vet Approved
SertralineAlosetron may increase the serotonergic activities of Sertraline.Approved
SildenafilThe metabolism of Alosetron can be decreased when combined with Sildenafil.Approved, Investigational
SiltuximabThe serum concentration of Alosetron can be decreased when it is combined with Siltuximab.Approved, Investigational
SimeprevirThe serum concentration of Alosetron can be increased when it is combined with Simeprevir.Approved
SorafenibThe metabolism of Alosetron can be decreased when combined with Sorafenib.Approved, Investigational
St. John's WortThe serum concentration of Alosetron can be decreased when it is combined with St. John's Wort.Approved, Investigational, Nutraceutical
StiripentolThe serum concentration of Alosetron can be increased when it is combined with Stiripentol.Approved
SulfadiazineThe metabolism of Alosetron can be decreased when combined with Sulfadiazine.Approved, Investigational, Vet Approved
SulfamethoxazoleThe metabolism of Alosetron can be decreased when combined with Sulfamethoxazole.Approved
SulfisoxazoleThe metabolism of Alosetron can be decreased when combined with Sulfisoxazole.Approved, Vet Approved
SumatriptanThe risk or severity of adverse effects can be increased when Sumatriptan is combined with Alosetron.Approved, Investigational
TapentadolAlosetron may decrease the analgesic activities of Tapentadol.Approved
Tedizolid phosphateAlosetron may increase the serotonergic activities of Tedizolid Phosphate.Approved
TelaprevirThe serum concentration of Alosetron can be increased when it is combined with Telaprevir.Approved, Withdrawn
TelithromycinThe serum concentration of Alosetron can be increased when it is combined with Telithromycin.Approved
Tenofovir disoproxilThe metabolism of Alosetron can be decreased when combined with Tenofovir disoproxil.Approved, Investigational
TerbinafineThe metabolism of Terbinafine can be decreased when combined with Alosetron.Approved, Investigational, Vet Approved
TeriflunomideThe serum concentration of Alosetron can be decreased when it is combined with Teriflunomide.Approved
TetracyclineThe risk or severity of adverse effects can be increased when Tetracycline is combined with Alosetron.Approved, Vet Approved
TetrahydropalmatineThe risk or severity of adverse effects can be increased when Tetrahydropalmatine is combined with Alosetron.Investigational
TheophyllineThe metabolism of Alosetron can be decreased when combined with Theophylline.Approved
TicagrelorThe metabolism of Alosetron can be decreased when combined with Ticagrelor.Approved
TiclopidineThe metabolism of Alosetron can be decreased when combined with Ticlopidine.Approved
TocilizumabThe serum concentration of Alosetron can be decreased when it is combined with Tocilizumab.Approved
TolbutamideThe metabolism of Alosetron can be decreased when combined with Tolbutamide.Approved, Investigational
TopiramateThe risk or severity of adverse effects can be increased when Topiramate is combined with Alosetron.Approved
TopiroxostatThe metabolism of Alosetron can be decreased when combined with Topiroxostat.Approved, Investigational
TramadolThe therapeutic efficacy of Tramadol can be decreased when used in combination with Alosetron.Approved, Investigational
TranylcypromineAlosetron may increase the serotonergic activities of Tranylcypromine.Approved, Investigational
TrazodoneAlosetron may increase the serotonergic activities of Trazodone.Approved, Investigational
TrimethadioneThe risk or severity of adverse effects can be increased when Trimethadione is combined with Alosetron.Approved
TrimethoprimThe metabolism of Alosetron can be decreased when combined with Trimethoprim.Approved, Vet Approved
TrimipramineAlosetron may increase the serotonergic activities of Trimipramine.Approved
ValsartanThe metabolism of Alosetron can be decreased when combined with Valsartan.Approved, Investigational
VancomycinThe risk or severity of adverse effects can be increased when Vancomycin is combined with Alosetron.Approved
VecuroniumThe risk or severity of adverse effects can be increased when Vecuronium is combined with Alosetron.Approved
VemurafenibThe risk or severity of QTc prolongation can be increased when Vemurafenib is combined with Alosetron.Approved
VenlafaxineAlosetron may increase the serotonergic activities of Venlafaxine.Approved
VerapamilThe metabolism of Alosetron can be decreased when combined with Verapamil.Approved
VilazodoneAlosetron may increase the serotonergic activities of Vilazodone.Approved
VinpocetineThe risk or severity of adverse effects can be increased when Vinpocetine is combined with Alosetron.Investigational
VoriconazoleThe serum concentration of Alosetron can be increased when it is combined with Voriconazole.Approved, Investigational
VortioxetineAlosetron may increase the serotonergic activities of Vortioxetine.Approved, Investigational
ZafirlukastThe metabolism of Alosetron can be decreased when combined with Zafirlukast.Approved, Investigational
ZiconotideThe risk or severity of adverse effects can be increased when Ziconotide is combined with Alosetron.Approved
ZiprasidoneThe metabolism of Alosetron can be decreased when combined with Ziprasidone.Approved
ZolmitriptanThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Alosetron.Approved, Investigational
ZolpidemThe metabolism of Zolpidem can be decreased when combined with Alosetron.Approved
ZonisamideThe risk or severity of adverse effects can be increased when Zonisamide is combined with Alosetron.Approved, Investigational
ZucapsaicinThe metabolism of Alosetron can be decreased when combined with Zucapsaicin.Approved, Investigational
Food Interactions
  • Absorption is decreased by about 25% when taken with meals.
  • Take without regard to meals.

References

Synthesis Reference

Buchi Reddy REGURI, Sampathkumar UPPARAPALLI, Nilam SAHU, Karunakara Rao JAVVAJI, Brahma Reddy GADE, "PROCESS FOR THE PREPARATION OF ALOSETRON." U.S. Patent US20120178937, issued July 12, 2012.

US20120178937
General References
  1. Andresen V, Hollerbach S: Reassessing the benefits and risks of alosetron: what is its place in the treatment of irritable bowel syndrome? Drug Saf. 2004;27(5):283-92. [PubMed:15061683]
  2. Camilleri M: Pharmacology and clinical experience with alosetron. Expert Opin Investig Drugs. 2000 Jan;9(1):147-59. [PubMed:11060667]
  3. Mayer EA, Bradesi S: Alosetron and irritable bowel syndrome. Expert Opin Pharmacother. 2003 Nov;4(11):2089-98. [PubMed:14596662]
  4. Rahimi R, Nikfar S, Abdollahi M: Efficacy and tolerability of alosetron for the treatment of irritable bowel syndrome in women and men: a meta-analysis of eight randomized, placebo-controlled, 12-week trials. Clin Ther. 2008 May;30(5):884-901. doi: 10.1016/j.clinthera.2008.05.002. [PubMed:18555935]
  5. Lewis JH: Alosetron for severe diarrhea-predominant irritable bowel syndrome: safety and efficacy in perspective. Expert Rev Gastroenterol Hepatol. 2010 Feb;4(1):13-29. doi: 10.1586/egh.09.72. [PubMed:20136586]
External Links
Human Metabolome Database
HMDB0015104
PubChem Compound
2099
PubChem Substance
46506274
ChemSpider
2015
BindingDB
50014558
ChEBI
253342
ChEMBL
CHEMBL1110
Therapeutic Targets Database
DAP000369
PharmGKB
PA164745502
IUPHAR
2296
Guide to Pharmacology
GtP Drug Page
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Alosetron
ATC Codes
A03AE01 — Alosetron
FDA label
Download (208 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2CompletedTreatmentIrritable Bowel Syndrome (IBS)1
3CompletedTreatmentIrritable Bowel Syndrome (IBS)2
4CompletedTreatmentIrritable Bowel Syndrome (IBS)1

Pharmacoeconomics

Manufacturers
  • Prometheus laboratories inc
Packagers
  • GlaxoSmithKline Inc.
  • Prometheus Laboratories Inc.
Dosage forms
FormRouteStrength
TabletOral.5 mg/1
Tablet, film coatedOral.5 mg/1
Tablet, film coatedOral1 mg/1
TabletOral1 mg/1
Prices
Unit descriptionCostUnit
Lotronex 1 mg tablet19.47USD tablet
Lotronex 0.5 mg tablet14.3USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US5360800No1993-01-132013-01-13Us
US6284770No1998-10-052018-10-05Us

Properties

State
Solid
Experimental Properties
PropertyValueSource
logP2Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.438 mg/mLALOGPS
logP1.85ALOGPS
logP1.21ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)13.32ChemAxon
pKa (Strongest Basic)6.81ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area53.92 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity86.41 m3·mol-1ChemAxon
Polarizability32.52 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9745
Blood Brain Barrier+0.9139
Caco-2 permeable+0.6511
P-glycoprotein substrateSubstrate0.8033
P-glycoprotein inhibitor IInhibitor0.7435
P-glycoprotein inhibitor IINon-inhibitor0.5707
Renal organic cation transporterInhibitor0.7795
CYP450 2C9 substrateNon-substrate0.7501
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateSubstrate0.7672
CYP450 1A2 substrateNon-inhibitor0.5781
CYP450 2C9 inhibitorNon-inhibitor0.8878
CYP450 2D6 inhibitorInhibitor0.6507
CYP450 2C19 inhibitorNon-inhibitor0.9239
CYP450 3A4 inhibitorNon-inhibitor0.8274
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6424
Ames testNon AMES toxic0.6156
CarcinogenicityNon-carcinogens0.967
BiodegradationNot ready biodegradable0.981
Rat acute toxicity2.7709 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8334
hERG inhibition (predictor II)Inhibitor0.8554
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0udi-0390000000-3b813a9458d2bce7516f

Taxonomy

Description
This compound belongs to the class of organic compounds known as n-alkylindoles. These are compounds containing an indole moiety that carries an alkyl chain at the 1-position.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Indoles and derivatives
Sub Class
N-alkylindoles
Direct Parent
N-alkylindoles
Alternative Parents
Indoles / N-methylpyrroles / Benzenoids / Vinylogous amides / Tertiary carboxylic acid amides / Imidazoles / Heteroaromatic compounds / Lactams / Azacyclic compounds / Organopnictogen compounds
show 4 more
Substituents
N-alkylindole / Indole / N-methylpyrrole / Substituted pyrrole / Benzenoid / Imidazole / Heteroaromatic compound / Pyrrole / Vinylogous amide / Azole
show 13 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
imidazoles, pyridoindole (CHEBI:253342)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Antagonist
General Function
Voltage-gated potassium channel activity
Specific Function
This is one of the several different receptors for 5-hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. This receptor is a ligand-gate...
Gene Name
HTR3A
Uniprot ID
P46098
Uniprot Name
5-hydroxytryptamine receptor 3A
Molecular Weight
55279.835 Da
References
  1. Clayton NM, Sargent R, Butler A, Gale J, Maxwell MP, Hunt AA, Barrett VJ, Cambridge D, Bountra C, Humphrey PP: The pharmacological properties of the novel selective 5-HT3 receptor antagonist, alosetron, and its effects on normal and perturbed small intestinal transit in the fasted rat. Neurogastroenterol Motil. 1999 Jun;11(3):207-17. [PubMed:10354345]
  2. Mayer EA, Bradesi S: Alosetron and irritable bowel syndrome. Expert Opin Pharmacother. 2003 Nov;4(11):2089-98. [PubMed:14596662]
  3. Coldwell JR, Phillis BD, Sutherland K, Howarth GS, Blackshaw LA: Increased responsiveness of rat colonic splanchnic afferents to 5-HT after inflammation and recovery. J Physiol. 2007 Feb 15;579(Pt 1):203-13. Epub 2006 Nov 30. [PubMed:17138606]
  4. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
  5. Houghton LA, Foster JM, Whorwell PJ: Alosetron, a 5-HT3 receptor antagonist, delays colonic transit in patients with irritable bowel syndrome and healthy volunteers. Aliment Pharmacol Ther. 2000 Jun;14(6):775-82. [PubMed:10848662]
  6. Gunput MD: Review article: clinical pharmacology of alosetron. Aliment Pharmacol Ther. 1999 May;13 Suppl 2:70-6. [PubMed:10429744]
  7. Balfour JA, Goa KL, Perry CM: Alosetron. Drugs. 2000 Mar;59(3):511-8; discussion 519-20. [PubMed:10776833]
  8. Camilleri M: Pharmacology and clinical experience with alosetron. Expert Opin Investig Drugs. 2000 Jan;9(1):147-59. [PubMed:11060667]
  9. Rahimi R, Nikfar S, Abdollahi M: Efficacy and tolerability of alosetron for the treatment of irritable bowel syndrome in women and men: a meta-analysis of eight randomized, placebo-controlled, 12-week trials. Clin Ther. 2008 May;30(5):884-901. doi: 10.1016/j.clinthera.2008.05.002. [PubMed:18555935]
  10. Lewis JH: Alosetron for severe diarrhea-predominant irritable bowel syndrome: safety and efficacy in perspective. Expert Rev Gastroenterol Hepatol. 2010 Feb;4(1):13-29. doi: 10.1586/egh.09.72. [PubMed:20136586]
  11. Andresen V, Hollerbach S: Reassessing the benefits and risks of alosetron: what is its place in the treatment of irritable bowel syndrome? Drug Saf. 2004;27(5):283-92. [PubMed:15061683]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C9
Uniprot ID
P11712
Uniprot Name
Cytochrome P450 2C9
Molecular Weight
55627.365 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
Details
2. Cytochrome P450 3A4
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP1A2
Uniprot ID
P05177
Uniprot Name
Cytochrome P450 1A2
Molecular Weight
58293.76 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  2. Wang B, Zhou SF: Synthetic and natural compounds that interact with human cytochrome P450 1A2 and implications in drug development. Curr Med Chem. 2009;16(31):4066-218. [PubMed:19754423]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic ...
Gene Name
CYP2E1
Uniprot ID
P05181
Uniprot Name
Cytochrome P450 2E1
Molecular Weight
56848.42 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]

Drug created on June 13, 2005 07:24 / Updated on August 02, 2018 07:39