You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on DrugBank.
Identification
NameAprepitant
Accession NumberDB00673  (APRD00100)
TypeSmall Molecule
GroupsApproved, Investigational
Description

Aprepitant, an antiemetic, is a substance P/neurokinin 1 (NK1) receptor antagonist which, in combination with other antiemetic agents, is indicated for the prevention of acute and delayed nausea and vomiting associated with initial and repeat courses of highly emetogenic cancer chemotherapy. Aprepitant is a selective high-affinity antagonist of human substance P/neurokinin 1 (NK1) receptors. Aprepitant has little or no affinity for serotonin (5-HT3), dopamine, and corticosteroid receptors, the targets of existing therapies for chemotherapy-induced nausea and vomiting (CI NV).

Structure
Thumb
Synonyms
3-(((2R,3S)-3-(P-Fluorophenyl)-2-(((alphar)-alpha-methyl-3,5-bis(trifluoromethyl)benzyl)oxy)morpholino)methyl)-delta(2)-1,2,4-triazolin-5-one
Aprepitant
Aprépitant
Aprepitantum
External Identifiers
  • L 754030
  • L-754939
  • MK-0517
  • MK-869
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Emendcapsule80 mgoralMerck Canada Inc2007-09-24Not applicableCanada
Emendcapsule80 mg/1oralMerck Sharp & Dohme Corp.2003-03-26Not applicableUs
Emendpowder, for suspension125 mg/1oralMerck Sharp & Dohme Corp.2015-12-17Not applicableUs
EmendkitPhysicians Total Care, Inc.2005-06-24Not applicableUs
Emendcapsule80 mg/1oralPhysicians Total Care, Inc.2005-06-29Not applicableUs
Emendcapsule40 mg/1oralRebel Distributors Corp2003-03-26Not applicableUs
EmendkitMerck Sharp & Dohme Corp.2003-03-26Not applicableUs
Emendcapsule40 mg/1oralMerck Sharp & Dohme Corp.2003-03-26Not applicableUs
Emendcapsule125 mgoralMerck Canada Inc2007-09-24Not applicableCanada
Emendcapsule125 mg/1oralMerck Sharp & Dohme Corp.2003-03-26Not applicableUs
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
AprecapGlenmark
Brand mixtures
NameLabellerIngredients
Emend Tri-packMerck Canada Inc
SaltsNot Available
Categories
UNII1NF15YR6UY
CAS number170729-80-3
WeightAverage: 534.4267
Monoisotopic: 534.150187993
Chemical FormulaC23H21F7N4O3
InChI KeyInChIKey=ATALOFNDEOCMKK-OITMNORJSA-N
InChI
InChI=1S/C23H21F7N4O3/c1-12(14-8-15(22(25,26)27)10-16(9-14)23(28,29)30)37-20-19(13-2-4-17(24)5-3-13)34(6-7-36-20)11-18-31-21(35)33-32-18/h2-5,8-10,12,19-20H,6-7,11H2,1H3,(H2,31,32,33,35)/t12-,19+,20-/m1/s1
IUPAC Name
3-{[(2R,3S)-2-[(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethoxy]-3-(4-fluorophenyl)morpholin-4-yl]methyl}-4,5-dihydro-1H-1,2,4-triazol-5-one
SMILES
C[C@@H](O[[email protected]]1OCCN(CC2=NNC(=O)N2)[[email protected]]1C1=CC=C(F)C=C1)C1=CC(=CC(=C1)C(F)(F)F)C(F)(F)F
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as phenylmorpholines. These are aromatic compounds containing a morpholine ring and a benzene ring linked to each other through a CC or a CN bond.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassOxazinanes
Sub ClassMorpholines
Direct ParentPhenylmorpholines
Alternative Parents
Substituents
  • Phenylmorpholine
  • Aralkylamine
  • Halobenzene
  • Fluorobenzene
  • Benzenoid
  • Monocyclic benzene moiety
  • Aryl halide
  • Aryl fluoride
  • Heteroaromatic compound
  • 1,2,4-triazole
  • Azole
  • Tertiary aliphatic amine
  • Tertiary amine
  • Oxacycle
  • Azacycle
  • Acetal
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organofluoride
  • Organohalogen compound
  • Amine
  • Alkyl halide
  • Alkyl fluoride
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Pharmacology
IndicationFor the prevention of nausea and vomiting associated with highly emetogenic cancer chemotherapy, including high-dose cisplatin (in combination with other antiemetic agents).
PharmacodynamicsAprepitant, an antiemetic, is a substance P/neurokinin 1 (NK1) receptor antagonist which, in combination with other antiemetic agents, is indicated for the prevention of acute and delayed nausea and vomiting associated with initial and repeat courses of highly emetogenic cancer chemotherapy. Aprepitant is a selective high-affinity antagonist of human substance P/neurokinin 1 (NK1) receptors. Aprepitant has little or no affinity for serotonin (5-HT3), dopamine, and corticosteroid receptors, the targets of existing therapies for chemotherapy-induced nausea and vomiting (CI NV).
Mechanism of actionAprepitant has been shown in animal models to inhibit emesis induced by cytotoxic chemotherapeutic agents, such as cisplatin, via central actions. Animal and human Positron Emission Tomography (PET) studies with Aprepitant have shown that it crosses the blood brain barrier and occupies brain NK1 receptors. Animal and human studies show that Aprepitant augments the antiemetic activity of the 5-HT3-receptor antagonist ondansetron and the corticosteroid ethasone and inhibits both the acute and delayed phases of cisplatin induced emesis.
Related Articles
AbsorptionThe mean absolute oral bioavailability of aprepitant is approximately 60 to 65%.
Volume of distribution
  • 70 L
Protein binding>95%
Metabolism

Aprepitant is metabolized primarily by CYP3A4 with minor metabolism by CYP1A2 and CYP2C19. Seven metabolites of aprepitant, which are only weakly active, have been identified in human plasma.

SubstrateEnzymesProduct
Aprepitant
(2S,3R)-2-[(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethoxy]-3-(4-fluorophenyl)morpholineDetails
Aprepitant
5-({[(1R)-1-(4-fluorophenyl)-2-hydroxyethyl]amino}methyl)-2,3-dihydro-1H-1,2,4-triazol-3-oneDetails
Aprepitant
(2R)-2-(4-fluorophenyl)-2-{[(5-oxo-2,5-dihydro-1H-1,2,4-triazol-3-yl)methyl]amino}acetic acidDetails
Route of eliminationAprepitant is eliminated primarily by metabolism; aprepitant is not renally excreted. Aprepitant is excreted in the milk of rats. It is not known whether this drug is excreted in human milk.
Half life9-13 hours
Clearance
  • Apparent plasma cl=62-90 mL/min
ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9952
Blood Brain Barrier+0.5588
Caco-2 permeable-0.6237
P-glycoprotein substrateSubstrate0.8106
P-glycoprotein inhibitor IInhibitor0.5243
P-glycoprotein inhibitor IINon-inhibitor0.9564
Renal organic cation transporterNon-inhibitor0.7444
CYP450 2C9 substrateNon-substrate0.788
CYP450 2D6 substrateNon-substrate0.9115
CYP450 3A4 substrateSubstrate0.6461
CYP450 1A2 substrateNon-inhibitor0.6012
CYP450 2C9 inhibitorNon-inhibitor0.535
CYP450 2D6 inhibitorNon-inhibitor0.84
CYP450 2C19 inhibitorNon-inhibitor0.5862
CYP450 3A4 inhibitorInhibitor0.5
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.8396
Ames testNon AMES toxic0.5758
CarcinogenicityNon-carcinogens0.8152
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.6055 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.6598
hERG inhibition (predictor II)Inhibitor0.8163
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Merck and co inc
Packagers
Dosage forms
FormRouteStrength
Capsuleoral125 mg
Capsuleoral125 mg/1
Capsuleoral40 mg/1
Capsuleoral80 mg/1
Capsuleoral80 mg
Kit
Powder, for suspensionoral125 mg/1
Kit; capsuleoral
Prices
Unit descriptionCostUnit
Emend 6 125 mg capsule Box1046.01USD box
Emend 6 80 mg capsule Box678.62USD box
Emend 5 80 mg capsule Box553.13USD box
Emend 3 80 & 125 mg capsule Disp Pack415.76USD disp
Emend 115 mg Solution 1 Vial = 10ml242.13USD vial
Emend 115 mg vial232.82USD vial
Emend 2 80 mg capsule Disp Pack226.21USD disp
Emend 125 mg capsule161.34USD capsule
Emend 80 mg capsule108.76USD capsule
Emend 40 mg capsule Box58.17USD box
Emend 40 mg capsule55.89USD capsule
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
CA2469315 No2008-12-022022-12-19Canada
US5145684 No1994-01-252011-01-25Us
US6096742 No1998-07-012018-07-01Us
US8258132 No2007-09-262027-09-26Us
Properties
StateSolid
Experimental Properties
PropertyValueSource
water solubilityPractically insolubleNot Available
logP4.5Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0194 mg/mLALOGPS
logP2.44ALOGPS
logP5.22ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)9.65ChemAxon
pKa (Strongest Basic)3.51ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area75.19 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity116.93 m3·mol-1ChemAxon
Polarizability45.56 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis Reference

Mangesh Shivram Sawant, Girish Dixit, Nitin Sharad Chandra Pradhan, Mubeen Ahmad Khan, Sukumar Sinha, “Amorphous and Crystalline Forms of Aprepitant and Processes for the Preparation Thereof.” U.S. Patent US20090192161, issued July 30, 2009.

US20090192161
General ReferencesNot Available
External Links
ATC CodesA04AD12
AHFS Codes
  • 56:22.92
PDB EntriesNot Available
FDA labelDownload (293 KB)
MSDSNot Available
Interactions
Drug Interactions
Drug
Ado-trastuzumab emtansineThe serum concentration of ado-trastuzumab emtansine can be increased when it is combined with Aprepitant.
AlfentanilThe serum concentration of Alfentanil can be increased when it is combined with Aprepitant.
AlfuzosinThe serum concentration of Alfuzosin can be increased when it is combined with Aprepitant.
AlitretinoinThe serum concentration of Alitretinoin can be increased when it is combined with Aprepitant.
AlprazolamThe serum concentration of Alprazolam can be increased when it is combined with Aprepitant.
AminophyllineThe serum concentration of Aminophylline can be increased when it is combined with Aprepitant.
AmiodaroneThe serum concentration of Amiodarone can be increased when it is combined with Aprepitant.
AmlodipineThe serum concentration of Amlodipine can be increased when it is combined with Aprepitant.
ApixabanThe serum concentration of Apixaban can be increased when it is combined with Aprepitant.
AripiprazoleThe serum concentration of Aripiprazole can be increased when it is combined with Aprepitant.
ArmodafinilThe serum concentration of Armodafinil can be increased when it is combined with Aprepitant.
AtorvastatinThe serum concentration of Atorvastatin can be increased when it is combined with Aprepitant.
AvanafilThe serum concentration of Avanafil can be increased when it is combined with Aprepitant.
AxitinibThe serum concentration of Axitinib can be increased when it is combined with Aprepitant.
BenzphetamineThe serum concentration of Benzphetamine can be increased when it is combined with Aprepitant.
BetamethasoneThe serum concentration of Betamethasone can be increased when it is combined with Aprepitant.
BexaroteneThe serum concentration of Aprepitant can be decreased when it is combined with Bexarotene.
BisoprololThe serum concentration of Bisoprolol can be increased when it is combined with Aprepitant.
BosentanThe serum concentration of Aprepitant can be decreased when it is combined with Bosentan.
BosutinibThe serum concentration of Bosutinib can be increased when it is combined with Aprepitant.
BrexpiprazoleThe serum concentration of Brexpiprazole can be increased when it is combined with Aprepitant.
BromocriptineThe serum concentration of Bromocriptine can be increased when it is combined with Aprepitant.
BudesonideThe serum concentration of Budesonide can be increased when it is combined with Aprepitant.
BuprenorphineThe serum concentration of Buprenorphine can be increased when it is combined with Aprepitant.
BuspironeThe serum concentration of Buspirone can be increased when it is combined with Aprepitant.
CabazitaxelThe serum concentration of Cabazitaxel can be increased when it is combined with Aprepitant.
CabozantinibThe serum concentration of Cabozantinib can be increased when it is combined with Aprepitant.
CalcitriolThe serum concentration of Calcitriol can be increased when it is combined with Aprepitant.
ChlordiazepoxideThe serum concentration of Chlordiazepoxide can be increased when it is combined with Aprepitant.
ChloroquineThe serum concentration of Chloroquine can be increased when it is combined with Aprepitant.
ChlorotrianiseneThe serum concentration of Chlorotrianisene can be decreased when it is combined with Aprepitant.
CilostazolThe serum concentration of Cilostazol can be increased when it is combined with Aprepitant.
CinacalcetThe serum concentration of Cinacalcet can be increased when it is combined with Aprepitant.
CisaprideThe serum concentration of Cisapride can be increased when it is combined with Aprepitant.
CitalopramThe serum concentration of Citalopram can be increased when it is combined with Aprepitant.
ClonazepamThe serum concentration of Clonazepam can be increased when it is combined with Aprepitant.
ClorazepateThe serum concentration of Clorazepate can be increased when it is combined with Aprepitant.
CocaineThe serum concentration of Cocaine can be increased when it is combined with Aprepitant.
ColchicineThe serum concentration of Colchicine can be increased when it is combined with Aprepitant.
ConivaptanThe serum concentration of Aprepitant can be increased when it is combined with Conivaptan.
CorticotropinThe serum concentration of Corticotropin can be increased when it is combined with Aprepitant.
Cortisone acetateThe serum concentration of Cortisone acetate can be increased when it is combined with Aprepitant.
CrizotinibThe serum concentration of Crizotinib can be increased when it is combined with Aprepitant.
CyclosporineThe serum concentration of Cyclosporine can be increased when it is combined with Aprepitant.
Cyproterone acetateThe serum concentration of Cyproterone acetate can be increased when it is combined with Aprepitant.
DabrafenibThe serum concentration of Aprepitant can be decreased when it is combined with Dabrafenib.
DaclatasvirThe serum concentration of Daclatasvir can be increased when it is combined with Aprepitant.
DantroleneThe serum concentration of Dantrolene can be increased when it is combined with Aprepitant.
DapoxetineThe serum concentration of Dapoxetine can be increased when it is combined with Aprepitant.
DarifenacinThe serum concentration of Darifenacin can be increased when it is combined with Aprepitant.
DasatinibThe serum concentration of Aprepitant can be increased when it is combined with Dasatinib.
DeferasiroxThe serum concentration of Aprepitant can be decreased when it is combined with Deferasirox.
DexamethasoneThe serum concentration of Dexamethasone can be increased when it is combined with Aprepitant.
DiazepamThe serum concentration of Diazepam can be increased when it is combined with Aprepitant.
DiclofenacThe serum concentration of Diclofenac can be decreased when it is combined with Aprepitant.
DienogestThe serum concentration of Dienogest can be decreased when it is combined with Aprepitant.
DihydroergotamineThe serum concentration of Dihydroergotamine can be increased when it is combined with Aprepitant.
DiltiazemThe serum concentration of Diltiazem can be increased when it is combined with Aprepitant.
DisopyramideThe serum concentration of Disopyramide can be increased when it is combined with Aprepitant.
DofetilideThe serum concentration of Dofetilide can be increased when it is combined with Aprepitant.
DomperidoneThe serum concentration of Domperidone can be increased when it is combined with Aprepitant.
DoxazosinThe serum concentration of Doxazosin can be increased when it is combined with Aprepitant.
DoxorubicinThe serum concentration of Doxorubicin can be increased when it is combined with Aprepitant.
DronabinolThe serum concentration of Dronabinol can be increased when it is combined with Aprepitant.
DronedaroneThe serum concentration of Dronedarone can be increased when it is combined with Aprepitant.
EletriptanThe serum concentration of Eletriptan can be increased when it is combined with Aprepitant.
EliglustatThe serum concentration of Eliglustat can be increased when it is combined with Aprepitant.
EplerenoneThe serum concentration of Eplerenone can be increased when it is combined with Aprepitant.
Ergoloid mesylateThe serum concentration of Ergoloid mesylate can be increased when it is combined with Aprepitant.
ErgonovineThe serum concentration of Ergonovine can be increased when it is combined with Aprepitant.
ErgotamineThe serum concentration of Ergotamine can be increased when it is combined with Aprepitant.
ErlotinibThe serum concentration of Erlotinib can be increased when it is combined with Aprepitant.
ErythromycinThe serum concentration of Erythromycin can be increased when it is combined with Aprepitant.
EscitalopramThe serum concentration of Escitalopram can be increased when it is combined with Aprepitant.
EszopicloneThe serum concentration of Eszopiclone can be increased when it is combined with Aprepitant.
EthosuximideThe serum concentration of Ethosuximide can be increased when it is combined with Aprepitant.
EtonogestrelThe serum concentration of Etonogestrel can be decreased when it is combined with Aprepitant.
EtoposideThe serum concentration of Etoposide can be increased when it is combined with Aprepitant.
EverolimusThe serum concentration of Everolimus can be increased when it is combined with Aprepitant.
FelbamateThe serum concentration of Felbamate can be increased when it is combined with Aprepitant.
FelodipineThe serum concentration of Felodipine can be increased when it is combined with Aprepitant.
FentanylThe serum concentration of Fentanyl can be increased when it is combined with Aprepitant.
FesoterodineThe serum concentration of Fesoterodine can be increased when it is combined with Aprepitant.
FlibanserinThe serum concentration of Flibanserin can be increased when it is combined with Aprepitant.
FluconazoleThe metabolism of Aprepitant can be decreased when combined with Fluconazole.
FludrocortisoneThe serum concentration of Fludrocortisone can be increased when it is combined with Aprepitant.
FlunisolideThe serum concentration of Flunisolide can be increased when it is combined with Aprepitant.
FlurazepamThe serum concentration of Flurazepam can be increased when it is combined with Aprepitant.
FlutamideThe serum concentration of Flutamide can be increased when it is combined with Aprepitant.
FosaprepitantThe serum concentration of Aprepitant can be increased when it is combined with Fosaprepitant.
Fusidic AcidThe serum concentration of Aprepitant can be increased when it is combined with Fusidic Acid.
GefitinibThe serum concentration of Gefitinib can be increased when it is combined with Aprepitant.
GuanfacineThe serum concentration of Guanfacine can be increased when it is combined with Aprepitant.
HalofantrineThe serum concentration of Halofantrine can be increased when it is combined with Aprepitant.
HaloperidolThe serum concentration of Haloperidol can be increased when it is combined with Aprepitant.
HydrocodoneThe serum concentration of Hydrocodone can be increased when it is combined with Aprepitant.
HydrocortisoneThe serum concentration of Hydrocortisone can be increased when it is combined with Aprepitant.
Hydroxyprogesterone caproateThe serum concentration of Hydroxyprogesterone caproate can be increased when it is combined with Aprepitant.
IbrutinibThe serum concentration of Ibrutinib can be increased when it is combined with Aprepitant.
IdelalisibThe serum concentration of Aprepitant can be increased when it is combined with Idelalisib.
IfosfamideThe serum concentration of Ifosfamide can be increased when it is combined with Aprepitant.
ImatinibThe serum concentration of Imatinib can be increased when it is combined with Aprepitant.
IrinotecanThe serum concentration of Irinotecan can be increased when it is combined with Aprepitant.
IsavuconazoniumThe serum concentration of Isavuconazonium can be increased when it is combined with Aprepitant.
IsosorbideThe serum concentration of Isosorbide can be increased when it is combined with Aprepitant.
Isosorbide DinitrateThe serum concentration of Isosorbide Dinitrate can be increased when it is combined with Aprepitant.
Isosorbide MononitrateThe serum concentration of Isosorbide Mononitrate can be increased when it is combined with Aprepitant.
IsradipineThe serum concentration of Isradipine can be increased when it is combined with Aprepitant.
IvabradineThe serum concentration of Ivabradine can be increased when it is combined with Aprepitant.
IvacaftorThe serum concentration of Ivacaftor can be increased when it is combined with Aprepitant.
IxabepiloneThe serum concentration of Ixabepilone can be increased when it is combined with Aprepitant.
LapatinibThe serum concentration of Lapatinib can be increased when it is combined with Aprepitant.
LevomilnacipranThe serum concentration of Levomilnacipran can be increased when it is combined with Aprepitant.
LevonorgestrelThe serum concentration of Levonorgestrel can be decreased when it is combined with Aprepitant.
LidocaineThe serum concentration of Lidocaine can be increased when it is combined with Aprepitant.
LomitapideThe serum concentration of Lomitapide can be increased when it is combined with Aprepitant.
LovastatinThe serum concentration of Lovastatin can be increased when it is combined with Aprepitant.
LuliconazoleThe serum concentration of Aprepitant can be increased when it is combined with Luliconazole.
LurasidoneThe serum concentration of Lurasidone can be increased when it is combined with Aprepitant.
MacitentanThe serum concentration of MACITENTAN can be increased when it is combined with Aprepitant.
MaravirocThe serum concentration of Maraviroc can be increased when it is combined with Aprepitant.
Medroxyprogesterone AcetateThe serum concentration of Medroxyprogesterone Acetate can be decreased when it is combined with Aprepitant.
MefloquineThe serum concentration of Mefloquine can be increased when it is combined with Aprepitant.
MethadoneThe serum concentration of Methadone can be increased when it is combined with Aprepitant.
MethylprednisoloneThe serum concentration of Methylprednisolone can be increased when it is combined with Aprepitant.
MidazolamThe serum concentration of Midazolam can be increased when it is combined with Aprepitant.
MifepristoneThe serum concentration of Aprepitant can be increased when it is combined with Mifepristone.
MirtazapineThe serum concentration of Mirtazapine can be increased when it is combined with Aprepitant.
MitotaneThe serum concentration of Aprepitant can be decreased when it is combined with Mitotane.
ModafinilThe serum concentration of Modafinil can be increased when it is combined with Aprepitant.
NaloxegolThe serum concentration of Naloxegol can be increased when it is combined with Aprepitant.
NelfinavirThe metabolism of Aprepitant can be decreased when combined with Nelfinavir.
NetupitantThe serum concentration of Aprepitant can be increased when it is combined with Netupitant.
NicardipineThe serum concentration of Nicardipine can be increased when it is combined with Aprepitant.
NifedipineThe serum concentration of Nifedipine can be increased when it is combined with Aprepitant.
NilotinibThe serum concentration of Nilotinib can be increased when it is combined with Aprepitant.
NimodipineThe serum concentration of Nimodipine can be increased when it is combined with Aprepitant.
NisoldipineThe serum concentration of Nisoldipine can be increased when it is combined with Aprepitant.
NorethisteroneThe serum concentration of Norethindrone can be decreased when it is combined with Aprepitant.
OlaparibThe serum concentration of Olaparib can be increased when it is combined with Aprepitant.
OxycodoneThe risk or severity of adverse effects can be increased when Aprepitant is combined with Oxycodone.
PaclitaxelThe serum concentration of Paclitaxel can be increased when it is combined with Aprepitant.
PalbociclibThe serum concentration of Aprepitant can be increased when it is combined with Palbociclib.
PanobinostatThe serum concentration of Panobinostat can be increased when it is combined with Aprepitant.
ParoxetineThe serum concentration of Aprepitant can be decreased when it is combined with Paroxetine.
PazopanibThe serum concentration of Pazopanib can be increased when it is combined with Aprepitant.
PhenytoinThe metabolism of Aprepitant can be increased when combined with Phenytoin.
PimecrolimusThe metabolism of Pimecrolimus can be decreased when combined with Aprepitant.
PimozideThe serum concentration of Pimozide can be increased when it is combined with Aprepitant.
PipotiazineThe serum concentration of Pipotiazine can be increased when it is combined with Aprepitant.
PraziquantelThe serum concentration of Praziquantel can be increased when it is combined with Aprepitant.
PrednisoloneThe serum concentration of Prednisolone can be increased when it is combined with Aprepitant.
PrednisoneThe serum concentration of Prednisone can be increased when it is combined with Aprepitant.
PropafenoneThe serum concentration of Propafenone can be increased when it is combined with Aprepitant.
QuetiapineThe serum concentration of Quetiapine can be increased when it is combined with Aprepitant.
QuinidineThe serum concentration of Quinidine can be increased when it is combined with Aprepitant.
QuinineThe serum concentration of Quinine can be increased when it is combined with Aprepitant.
RanolazineThe serum concentration of Ranolazine can be increased when it is combined with Aprepitant.
RegorafenibThe serum concentration of Regorafenib can be increased when it is combined with Aprepitant.
Repository corticotropinThe serum concentration of Repository corticotropin can be increased when it is combined with Aprepitant.
RifampicinThe serum concentration of Aprepitant can be decreased when it is combined with Rifampicin.
RuxolitinibThe serum concentration of Ruxolitinib can be increased when it is combined with Aprepitant.
SalmeterolThe serum concentration of Salmeterol can be increased when it is combined with Aprepitant.
SaxagliptinThe serum concentration of Saxagliptin can be increased when it is combined with Aprepitant.
SildenafilThe serum concentration of Sildenafil can be increased when it is combined with Aprepitant.
SilodosinThe serum concentration of Silodosin can be increased when it is combined with Aprepitant.
SiltuximabThe serum concentration of Aprepitant can be decreased when it is combined with Siltuximab.
SimeprevirThe serum concentration of Simeprevir can be increased when it is combined with Aprepitant.
SimvastatinThe serum concentration of Simvastatin can be increased when it is combined with Aprepitant.
SirolimusThe serum concentration of Sirolimus can be increased when it is combined with Aprepitant.
SolifenacinThe serum concentration of Solifenacin can be increased when it is combined with Aprepitant.
SonidegibThe serum concentration of Sonidegib can be increased when it is combined with Aprepitant.
SpiramycinThe serum concentration of Spiramycin can be increased when it is combined with Aprepitant.
St. John's WortThe serum concentration of Aprepitant can be decreased when it is combined with St. John's Wort.
StiripentolThe serum concentration of Aprepitant can be increased when it is combined with Stiripentol.
SufentanilThe serum concentration of Sufentanil can be increased when it is combined with Aprepitant.
SunitinibThe serum concentration of Sunitinib can be increased when it is combined with Aprepitant.
SuvorexantThe serum concentration of Suvorexant can be increased when it is combined with Aprepitant.
TacrolimusThe serum concentration of Tacrolimus can be increased when it is combined with Aprepitant.
TadalafilThe serum concentration of Tadalafil can be increased when it is combined with Aprepitant.
TamsulosinThe serum concentration of Tamsulosin can be increased when it is combined with Aprepitant.
TemsirolimusThe serum concentration of Temsirolimus can be increased when it is combined with Aprepitant.
TeniposideThe serum concentration of Teniposide can be increased when it is combined with Aprepitant.
TheophyllineThe serum concentration of Theophylline can be increased when it is combined with Aprepitant.
TiagabineThe serum concentration of Tiagabine can be increased when it is combined with Aprepitant.
TocilizumabThe serum concentration of Aprepitant can be decreased when it is combined with Tocilizumab.
TofacitinibThe serum concentration of Tofacitinib can be increased when it is combined with Aprepitant.
TolbutamideThe serum concentration of Tolbutamide can be decreased when it is combined with Aprepitant.
TolterodineThe serum concentration of Tolterodine can be increased when it is combined with Aprepitant.
TolvaptanThe serum concentration of Tolvaptan can be increased when it is combined with Aprepitant.
TrabectedinThe serum concentration of Trabectedin can be increased when it is combined with Aprepitant.
TrazodoneThe serum concentration of Trazodone can be increased when it is combined with Aprepitant.
TriamcinoloneThe serum concentration of Triamcinolone can be increased when it is combined with Aprepitant.
TriazolamThe serum concentration of Triazolam can be increased when it is combined with Aprepitant.
TrimipramineThe serum concentration of Trimipramine can be increased when it is combined with Aprepitant.
UlipristalThe serum concentration of Ulipristal can be increased when it is combined with Aprepitant.
VardenafilThe serum concentration of Vardenafil can be increased when it is combined with Aprepitant.
VemurafenibThe serum concentration of Vemurafenib can be increased when it is combined with Aprepitant.
VenlafaxineThe serum concentration of Venlafaxine can be increased when it is combined with Aprepitant.
VerapamilThe serum concentration of Verapamil can be increased when it is combined with Aprepitant.
VilazodoneThe serum concentration of Vilazodone can be increased when it is combined with Aprepitant.
VinblastineThe serum concentration of Vinblastine can be increased when it is combined with Aprepitant.
VincristineThe serum concentration of Vincristine can be increased when it is combined with Aprepitant.
VindesineThe serum concentration of Vindesine can be increased when it is combined with Aprepitant.
VinorelbineThe serum concentration of Vinorelbine can be increased when it is combined with Aprepitant.
WarfarinThe serum concentration of Warfarin can be decreased when it is combined with Aprepitant.
ZolpidemThe serum concentration of Zolpidem can be increased when it is combined with Aprepitant.
ZonisamideThe serum concentration of Zonisamide can be increased when it is combined with Aprepitant.
ZopicloneThe serum concentration of Zopiclone can be increased when it is combined with Aprepitant.
ZuclopenthixolThe serum concentration of Zuclopenthixol can be increased when it is combined with Aprepitant.
Food Interactions
  • Take without regard to meals.

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
antagonist
General Function:
Tachykinin receptor activity
Specific Function:
This is a receptor for the tachykinin neuropeptide substance P. It is probably associated with G proteins that activate a phosphatidylinositol-calcium second messenger system. The rank order of affinity of this receptor to tachykinins is: substance P > substance K > neuromedin-K.
Gene Name:
TACR1
Uniprot ID:
P25103
Molecular Weight:
46250.5 Da
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
  2. Brands KM, Payack JF, Rosen JD, Nelson TD, Candelario A, Huffman MA, Zhao MM, Li J, Craig B, Song ZJ, Tschaen DM, Hansen K, Devine PN, Pye PJ, Rossen K, Dormer PG, Reamer RA, Welch CJ, Mathre DJ, Tsou NN, McNamara JM, Reider PJ: Efficient synthesis of NK(1) receptor antagonist aprepitant using a crystallization-induced diastereoselective transformation. J Am Chem Soc. 2003 Feb 26;125(8):2129-35. [PubMed:12590540 ]
  3. Rodgers J, Bradley B, Kennedy PG: Combination chemotherapy with a substance P receptor antagonist (aprepitant) and melarsoprol in a mouse model of human African trypanosomiasis. Parasitol Int. 2007 Dec;56(4):321-4. Epub 2007 Jun 29. [PubMed:17643344 ]
  4. Poli-Bigelli S, Rodrigues-Pereira J, Carides AD, Julie Ma G, Eldridge K, Hipple A, Evans JK, Horgan KJ, Lawson F: Addition of the neurokinin 1 receptor antagonist aprepitant to standard antiemetic therapy improves control of chemotherapy-induced nausea and vomiting. Results from a randomized, double-blind, placebo-controlled trial in Latin America. Cancer. 2003 Jun 15;97(12):3090-8. [PubMed:12784346 ]
  5. Zhao MM, McNamara JM, Ho GJ, Emerson KM, Song ZJ, Tschaen DM, Brands KM, Dolling UH, Grabowski EJ, Reider PJ, Cottrell IF, Ashwood MS, Bishop BC: Practical asymmetric synthesis of aprepitant, a potent human NK-1 receptor antagonist, via a stereoselective Lewis acid-catalyzed trans acetalization reaction. J Org Chem. 2002 Sep 20;67(19):6743-7. [PubMed:12227806 ]
  6. Bergstrom M, Hargreaves RJ, Burns HD, Goldberg MR, Sciberras D, Reines SA, Petty KJ, Ogren M, Antoni G, Langstrom B, Eskola O, Scheinin M, Solin O, Majumdar AK, Constanzer ML, Battisti WP, Bradstreet TE, Gargano C, Hietala J: Human positron emission tomography studies of brain neurokinin 1 receptor occupancy by aprepitant. Biol Psychiatry. 2004 May 15;55(10):1007-12. [PubMed:15121485 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrateinhibitor
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 reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiot...
Gene Name:
CYP3A4
Uniprot ID:
P08684
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 ]
  2. Sanchez RI, Wang RW, Newton DJ, Bakhtiar R, Lu P, Chiu SH, Evans DC, Huskey SE: Cytochrome P450 3A4 is the major enzyme involved in the metabolism of the substance P receptor antagonist aprepitant. Drug Metab Dispos. 2004 Nov;32(11):1287-92. Epub 2004 Aug 10. [PubMed:15304427 ]
  3. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrateinhibitor
General Function:
Oxygen binding
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 unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP3A5
Uniprot ID:
P20815
Molecular Weight:
57108.065 Da
References
  1. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrateinhibitor
General Function:
Oxygen binding
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 unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP3A7
Uniprot ID:
P24462
Molecular Weight:
57525.03 Da
References
  1. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
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 unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N...
Gene Name:
CYP1A2
Uniprot ID:
P05177
Molecular Weight:
58293.76 Da
References
  1. Sanchez RI, Wang RW, Newton DJ, Bakhtiar R, Lu P, Chiu SH, Evans DC, Huskey SE: Cytochrome P450 3A4 is the major enzyme involved in the metabolism of the substance P receptor antagonist aprepitant. Drug Metab Dispos. 2004 Nov;32(11):1287-92. Epub 2004 Aug 10. [PubMed:15304427 ]
  2. 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
substrateinhibitor
General Function:
Steroid hydroxylase activity
Specific Function:
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:
CYP2C19
Uniprot ID:
P33261
Molecular Weight:
55930.545 Da
References
  1. Sanchez RI, Wang RW, Newton DJ, Bakhtiar R, Lu P, Chiu SH, Evans DC, Huskey SE: Cytochrome P450 3A4 is the major enzyme involved in the metabolism of the substance P receptor antagonist aprepitant. Drug Metab Dispos. 2004 Nov;32(11):1287-92. Epub 2004 Aug 10. [PubMed:15304427 ]
  2. 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
inhibitorinducer
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 unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenyto...
Gene Name:
CYP2C9
Uniprot ID:
P11712
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 ]
Comments
comments powered by Disqus
Drug created on June 13, 2005 07:24 / Updated on May 27, 2016 02:17