Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C23H21F7N4O3 |
Molecular Weight | 534.4275 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 3 / 3 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
C[C@]([H])(c1cc(cc(c1)C(F)(F)F)C(F)(F)F)O[C@]2([H])[C@]([H])(c3ccc(cc3)F)N(CCO2)Cc4nc(n[nH]4)O
InChI
InChIKey=ATALOFNDEOCMKK-OITMNORJSA-N
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
Molecular Formula | C23H21F7N4O3 |
Molecular Weight | 534.4275 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 3 / 3 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
Aprepitant (brand name: Emend (the brand name used in all English-speaking countries 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 has little or no affinity for serotonin (5-HT3), dopamine, and corticosteroid receptors, the targets of existing therapies for chemotherapy-induced nausea and vomiting. Aprepitant has been shown 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.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL249 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12590540 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Preventing | EMEND Approved Use1.1 Prevention of Chemotherapy Induced Nausea and Vomiting (CINV) EMEND, 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 (HEC) including high-dose cisplatin; prevention of nausea and vomiting associated with initial and repeat courses of moderately emetogenic cancer chemotherapy (MEC). Prevention of Postoperative Nausea and Vomiting (PONV): EMEND is indicated for the prevention of postoperative nausea and vomiting Launch Date1.15153922E12 |
|||
Preventing | EMEND Approved Use1.1 Prevention of Chemotherapy Induced Nausea and Vomiting (CINV) EMEND, 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 (HEC) including high-dose cisplatin; prevention of nausea and vomiting associated with initial and repeat courses of moderately emetogenic cancer chemotherapy (MEC). Prevention of Postoperative Nausea and Vomiting (PONV): EMEND is indicated for the prevention of postoperative nausea and vomiting Launch Date1.15162559E12 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1354 ng/mL |
125 mg single, oral dose: 125 mg route of administration: Oral experiment type: SINGLE co-administered: |
APREPITANT plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
|
4.3 μg/mL |
100 mg single, intravenous dose: 100 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
APREPITANT unknown | Homo sapiens population: HEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
|
6.1 μg/mL |
130 mg single, intravenous dose: 130 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
APREPITANT unknown | Homo sapiens population: HEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
27759 ng × h/mL |
125 mg single, oral dose: 125 mg route of administration: Oral experiment type: SINGLE co-administered: |
APREPITANT plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
|
27.8 μg × h/mL |
100 mg single, intravenous dose: 100 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
APREPITANT unknown | Homo sapiens population: HEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
|
43.9 μg × h/mL |
130 mg single, intravenous dose: 130 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
APREPITANT unknown | Homo sapiens population: HEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
14 h |
125 mg single, oral dose: 125 mg route of administration: Oral experiment type: SINGLE co-administered: |
APREPITANT plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
125 mg single, oral |
unhealthy, 53 years (range: 23-73 years) n = 64 Health Status: unhealthy Condition: Cough Age Group: 53 years (range: 23-73 years) Sex: M+F Population Size: 64 Sources: |
|
130 mg single, intravenous Recommended Dose: 130 mg Route: intravenous Route: single Dose: 130 mg Sources: Page: p. 27 |
unhealthy, adult n = 50 Health Status: unhealthy Age Group: adult Population Size: 50 Sources: Page: p. 27 |
Disc. AE: Dyspnea, Nerve injury, peripheral... AEs leading to discontinuation/dose reduction: Dyspnea (2 patients) Sources: Page: p. 27Nerve injury, peripheral (1 patient) Dyspnea (1 patient) Hyperhidrosis (1 patient) |
125 mg 1 times / day steady, oral Dose: 125 mg, 1 times / day Route: oral Route: steady Dose: 125 mg, 1 times / day Sources: |
unhealthy n = 30 Health Status: unhealthy Condition: Post traumatic stress disorder Population Size: 30 Sources: |
Other AEs: Constipation, Diarrhea... Other AEs: Constipation (below serious, 14 patients) Sources: Diarrhea (below serious, 7 patients) Dry mouth (below serious, 7 patients) Abdominal pain (below serious, 13 patients) Weakness (below serious, 18 patients) Nightmares (below serious, 2 patients) Sleepiness (below serious, 2 patients) Sweating (below serious, 8 patients) Pain in extremity (below serious, 5 patients) Dizziness (below serious, 7 patients) Nervousness (below serious, 10 patients) Nightmares (below serious, 2 patients) Depression (below serious, 2 patients) Sexual dysfunction (below serious, 3 patients) |
125 mg 1 times / day steady, oral Dose: 125 mg, 1 times / day Route: oral Route: steady Dose: 125 mg, 1 times / day Sources: |
unhealthy n = 63 Health Status: unhealthy Condition: Chronic Nausea and Vomiting Population Size: 63 Sources: |
Other AEs: Hypoglycemia, Bruising... Other AEs: Hypoglycemia (serious, 1 patient) Sources: Bruising (below serious, 1 patient) Gastrointestinal pain (below serious, 3 patients) Hypokalemia (below serious, 1 patient) Diarrhea (below serious, 1 patient) Musculoskeletal pain (below serious, 1 patient) Fainting (below serious, 1 patient) Renal bleeding (below serious, 1 patient) Fibromyalgia (below serious, 1 patient) Dizziness (below serious, 2 patients) Constipation (below serious, 1 patient) Rhinitis (below serious, 1 patient) Headache (below serious, 2 patients) Malaise (below serious, 1 patient) Pain in limb (below serious, 1 patient) Nosebleed (below serious, 1 patient) |
40 mg single, oral Dose: 40 mg Route: oral Route: single Dose: 40 mg Sources: |
unhealthy n = 34 Health Status: unhealthy Condition: Gynecologic Surgery Population Population Size: 34 Sources: |
Other AEs: Anemia, Clot blood... Other AEs: Anemia (serious, 1 patient) Sources: Clot blood (serious, 1 patient) Hospital acquired pneumonia (serious, 1 patient) Headache (below serious, 2 patients) Hot flashes (below serious, 2 patients) Nausea (below serious, 2 patients) Paresthesia (below serious, 2 patients) Wound dehiscence (below serious, 2 patients) Wound infection (below serious, 6 patients) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Dyspnea | 1 patient Disc. AE |
130 mg single, intravenous Recommended Dose: 130 mg Route: intravenous Route: single Dose: 130 mg Sources: Page: p. 27 |
unhealthy, adult n = 50 Health Status: unhealthy Age Group: adult Population Size: 50 Sources: Page: p. 27 |
Hyperhidrosis | 1 patient Disc. AE |
130 mg single, intravenous Recommended Dose: 130 mg Route: intravenous Route: single Dose: 130 mg Sources: Page: p. 27 |
unhealthy, adult n = 50 Health Status: unhealthy Age Group: adult Population Size: 50 Sources: Page: p. 27 |
Nerve injury, peripheral | 1 patient Disc. AE |
130 mg single, intravenous Recommended Dose: 130 mg Route: intravenous Route: single Dose: 130 mg Sources: Page: p. 27 |
unhealthy, adult n = 50 Health Status: unhealthy Age Group: adult Population Size: 50 Sources: Page: p. 27 |
Dyspnea | 2 patients Disc. AE |
130 mg single, intravenous Recommended Dose: 130 mg Route: intravenous Route: single Dose: 130 mg Sources: Page: p. 27 |
unhealthy, adult n = 50 Health Status: unhealthy Age Group: adult Population Size: 50 Sources: Page: p. 27 |
Nervousness | below serious, 10 patients | 125 mg 1 times / day steady, oral Dose: 125 mg, 1 times / day Route: oral Route: steady Dose: 125 mg, 1 times / day Sources: |
unhealthy n = 30 Health Status: unhealthy Condition: Post traumatic stress disorder Population Size: 30 Sources: |
Abdominal pain | below serious, 13 patients | 125 mg 1 times / day steady, oral Dose: 125 mg, 1 times / day Route: oral Route: steady Dose: 125 mg, 1 times / day Sources: |
unhealthy n = 30 Health Status: unhealthy Condition: Post traumatic stress disorder Population Size: 30 Sources: |
Constipation | below serious, 14 patients | 125 mg 1 times / day steady, oral Dose: 125 mg, 1 times / day Route: oral Route: steady Dose: 125 mg, 1 times / day Sources: |
unhealthy n = 30 Health Status: unhealthy Condition: Post traumatic stress disorder Population Size: 30 Sources: |
Weakness | below serious, 18 patients | 125 mg 1 times / day steady, oral Dose: 125 mg, 1 times / day Route: oral Route: steady Dose: 125 mg, 1 times / day Sources: |
unhealthy n = 30 Health Status: unhealthy Condition: Post traumatic stress disorder Population Size: 30 Sources: |
Depression | below serious, 2 patients | 125 mg 1 times / day steady, oral Dose: 125 mg, 1 times / day Route: oral Route: steady Dose: 125 mg, 1 times / day Sources: |
unhealthy n = 30 Health Status: unhealthy Condition: Post traumatic stress disorder Population Size: 30 Sources: |
Nightmares | below serious, 2 patients | 125 mg 1 times / day steady, oral Dose: 125 mg, 1 times / day Route: oral Route: steady Dose: 125 mg, 1 times / day Sources: |
unhealthy n = 30 Health Status: unhealthy Condition: Post traumatic stress disorder Population Size: 30 Sources: |
Nightmares | below serious, 2 patients | 125 mg 1 times / day steady, oral Dose: 125 mg, 1 times / day Route: oral Route: steady Dose: 125 mg, 1 times / day Sources: |
unhealthy n = 30 Health Status: unhealthy Condition: Post traumatic stress disorder Population Size: 30 Sources: |
Sleepiness | below serious, 2 patients | 125 mg 1 times / day steady, oral Dose: 125 mg, 1 times / day Route: oral Route: steady Dose: 125 mg, 1 times / day Sources: |
unhealthy n = 30 Health Status: unhealthy Condition: Post traumatic stress disorder Population Size: 30 Sources: |
Sexual dysfunction | below serious, 3 patients | 125 mg 1 times / day steady, oral Dose: 125 mg, 1 times / day Route: oral Route: steady Dose: 125 mg, 1 times / day Sources: |
unhealthy n = 30 Health Status: unhealthy Condition: Post traumatic stress disorder Population Size: 30 Sources: |
Pain in extremity | below serious, 5 patients | 125 mg 1 times / day steady, oral Dose: 125 mg, 1 times / day Route: oral Route: steady Dose: 125 mg, 1 times / day Sources: |
unhealthy n = 30 Health Status: unhealthy Condition: Post traumatic stress disorder Population Size: 30 Sources: |
Diarrhea | below serious, 7 patients | 125 mg 1 times / day steady, oral Dose: 125 mg, 1 times / day Route: oral Route: steady Dose: 125 mg, 1 times / day Sources: |
unhealthy n = 30 Health Status: unhealthy Condition: Post traumatic stress disorder Population Size: 30 Sources: |
Dizziness | below serious, 7 patients | 125 mg 1 times / day steady, oral Dose: 125 mg, 1 times / day Route: oral Route: steady Dose: 125 mg, 1 times / day Sources: |
unhealthy n = 30 Health Status: unhealthy Condition: Post traumatic stress disorder Population Size: 30 Sources: |
Dry mouth | below serious, 7 patients | 125 mg 1 times / day steady, oral Dose: 125 mg, 1 times / day Route: oral Route: steady Dose: 125 mg, 1 times / day Sources: |
unhealthy n = 30 Health Status: unhealthy Condition: Post traumatic stress disorder Population Size: 30 Sources: |
Sweating | below serious, 8 patients | 125 mg 1 times / day steady, oral Dose: 125 mg, 1 times / day Route: oral Route: steady Dose: 125 mg, 1 times / day Sources: |
unhealthy n = 30 Health Status: unhealthy Condition: Post traumatic stress disorder Population Size: 30 Sources: |
Bruising | below serious, 1 patient | 125 mg 1 times / day steady, oral Dose: 125 mg, 1 times / day Route: oral Route: steady Dose: 125 mg, 1 times / day Sources: |
unhealthy n = 63 Health Status: unhealthy Condition: Chronic Nausea and Vomiting Population Size: 63 Sources: |
Constipation | below serious, 1 patient | 125 mg 1 times / day steady, oral Dose: 125 mg, 1 times / day Route: oral Route: steady Dose: 125 mg, 1 times / day Sources: |
unhealthy n = 63 Health Status: unhealthy Condition: Chronic Nausea and Vomiting Population Size: 63 Sources: |
Diarrhea | below serious, 1 patient | 125 mg 1 times / day steady, oral Dose: 125 mg, 1 times / day Route: oral Route: steady Dose: 125 mg, 1 times / day Sources: |
unhealthy n = 63 Health Status: unhealthy Condition: Chronic Nausea and Vomiting Population Size: 63 Sources: |
Fainting | below serious, 1 patient | 125 mg 1 times / day steady, oral Dose: 125 mg, 1 times / day Route: oral Route: steady Dose: 125 mg, 1 times / day Sources: |
unhealthy n = 63 Health Status: unhealthy Condition: Chronic Nausea and Vomiting Population Size: 63 Sources: |
Fibromyalgia | below serious, 1 patient | 125 mg 1 times / day steady, oral Dose: 125 mg, 1 times / day Route: oral Route: steady Dose: 125 mg, 1 times / day Sources: |
unhealthy n = 63 Health Status: unhealthy Condition: Chronic Nausea and Vomiting Population Size: 63 Sources: |
Hypokalemia | below serious, 1 patient | 125 mg 1 times / day steady, oral Dose: 125 mg, 1 times / day Route: oral Route: steady Dose: 125 mg, 1 times / day Sources: |
unhealthy n = 63 Health Status: unhealthy Condition: Chronic Nausea and Vomiting Population Size: 63 Sources: |
Malaise | below serious, 1 patient | 125 mg 1 times / day steady, oral Dose: 125 mg, 1 times / day Route: oral Route: steady Dose: 125 mg, 1 times / day Sources: |
unhealthy n = 63 Health Status: unhealthy Condition: Chronic Nausea and Vomiting Population Size: 63 Sources: |
Musculoskeletal pain | below serious, 1 patient | 125 mg 1 times / day steady, oral Dose: 125 mg, 1 times / day Route: oral Route: steady Dose: 125 mg, 1 times / day Sources: |
unhealthy n = 63 Health Status: unhealthy Condition: Chronic Nausea and Vomiting Population Size: 63 Sources: |
Nosebleed | below serious, 1 patient | 125 mg 1 times / day steady, oral Dose: 125 mg, 1 times / day Route: oral Route: steady Dose: 125 mg, 1 times / day Sources: |
unhealthy n = 63 Health Status: unhealthy Condition: Chronic Nausea and Vomiting Population Size: 63 Sources: |
Pain in limb | below serious, 1 patient | 125 mg 1 times / day steady, oral Dose: 125 mg, 1 times / day Route: oral Route: steady Dose: 125 mg, 1 times / day Sources: |
unhealthy n = 63 Health Status: unhealthy Condition: Chronic Nausea and Vomiting Population Size: 63 Sources: |
Renal bleeding | below serious, 1 patient | 125 mg 1 times / day steady, oral Dose: 125 mg, 1 times / day Route: oral Route: steady Dose: 125 mg, 1 times / day Sources: |
unhealthy n = 63 Health Status: unhealthy Condition: Chronic Nausea and Vomiting Population Size: 63 Sources: |
Rhinitis | below serious, 1 patient | 125 mg 1 times / day steady, oral Dose: 125 mg, 1 times / day Route: oral Route: steady Dose: 125 mg, 1 times / day Sources: |
unhealthy n = 63 Health Status: unhealthy Condition: Chronic Nausea and Vomiting Population Size: 63 Sources: |
Dizziness | below serious, 2 patients | 125 mg 1 times / day steady, oral Dose: 125 mg, 1 times / day Route: oral Route: steady Dose: 125 mg, 1 times / day Sources: |
unhealthy n = 63 Health Status: unhealthy Condition: Chronic Nausea and Vomiting Population Size: 63 Sources: |
Headache | below serious, 2 patients | 125 mg 1 times / day steady, oral Dose: 125 mg, 1 times / day Route: oral Route: steady Dose: 125 mg, 1 times / day Sources: |
unhealthy n = 63 Health Status: unhealthy Condition: Chronic Nausea and Vomiting Population Size: 63 Sources: |
Gastrointestinal pain | below serious, 3 patients | 125 mg 1 times / day steady, oral Dose: 125 mg, 1 times / day Route: oral Route: steady Dose: 125 mg, 1 times / day Sources: |
unhealthy n = 63 Health Status: unhealthy Condition: Chronic Nausea and Vomiting Population Size: 63 Sources: |
Hypoglycemia | serious, 1 patient | 125 mg 1 times / day steady, oral Dose: 125 mg, 1 times / day Route: oral Route: steady Dose: 125 mg, 1 times / day Sources: |
unhealthy n = 63 Health Status: unhealthy Condition: Chronic Nausea and Vomiting Population Size: 63 Sources: |
Headache | below serious, 2 patients | 40 mg single, oral Dose: 40 mg Route: oral Route: single Dose: 40 mg Sources: |
unhealthy n = 34 Health Status: unhealthy Condition: Gynecologic Surgery Population Population Size: 34 Sources: |
Hot flashes | below serious, 2 patients | 40 mg single, oral Dose: 40 mg Route: oral Route: single Dose: 40 mg Sources: |
unhealthy n = 34 Health Status: unhealthy Condition: Gynecologic Surgery Population Population Size: 34 Sources: |
Nausea | below serious, 2 patients | 40 mg single, oral Dose: 40 mg Route: oral Route: single Dose: 40 mg Sources: |
unhealthy n = 34 Health Status: unhealthy Condition: Gynecologic Surgery Population Population Size: 34 Sources: |
Paresthesia | below serious, 2 patients | 40 mg single, oral Dose: 40 mg Route: oral Route: single Dose: 40 mg Sources: |
unhealthy n = 34 Health Status: unhealthy Condition: Gynecologic Surgery Population Population Size: 34 Sources: |
Wound dehiscence | below serious, 2 patients | 40 mg single, oral Dose: 40 mg Route: oral Route: single Dose: 40 mg Sources: |
unhealthy n = 34 Health Status: unhealthy Condition: Gynecologic Surgery Population Population Size: 34 Sources: |
Wound infection | below serious, 6 patients | 40 mg single, oral Dose: 40 mg Route: oral Route: single Dose: 40 mg Sources: |
unhealthy n = 34 Health Status: unhealthy Condition: Gynecologic Surgery Population Population Size: 34 Sources: |
Anemia | serious, 1 patient | 40 mg single, oral Dose: 40 mg Route: oral Route: single Dose: 40 mg Sources: |
unhealthy n = 34 Health Status: unhealthy Condition: Gynecologic Surgery Population Population Size: 34 Sources: |
Clot blood | serious, 1 patient | 40 mg single, oral Dose: 40 mg Route: oral Route: single Dose: 40 mg Sources: |
unhealthy n = 34 Health Status: unhealthy Condition: Gynecologic Surgery Population Population Size: 34 Sources: |
Hospital acquired pneumonia | serious, 1 patient | 40 mg single, oral Dose: 40 mg Route: oral Route: single Dose: 40 mg Sources: |
unhealthy n = 34 Health Status: unhealthy Condition: Gynecologic Surgery Population Population Size: 34 Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 7.0 |
moderate | yes (co-administration study) Comment: 2.3 to 3.3 fold increase in mean AUC of orally coadministered midazolam; Page: 7.0 |
||
Page: 7.0 |
unlikely | |||
Page: 7.0 |
unlikely | |||
Page: 7.0 |
yes | |||
Page: 7.0 |
yes | weak (co-administration study) Comment: no effect of drug on the plasma AUC of R(+) and S(-) warfarin; coadministration with tolbutamide (substrate) decreased AUC of tolbutamide by 23% (Day 4), 28% (Day 8), and 15% (Day 15); Page: 7.0 |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 2.0 |
major | yes (co-administration study) Comment: coadministration with ketoconazole (inhibitor) increased AUC of aprepitant by ~5-fold; coadministration with rifampin (inducer) decreased AUC of aprepitant by ~ 11-fold; Page: 2.0 |
||
Page: 2.0 |
minor | |||
Page: 2.0 |
minor | |||
Page: 2.0 |
no | |||
Page: 2.0 |
no | |||
Page: 2.0 |
no |
PubMed
Title | Date | PubMed |
---|---|---|
Structural optimization affording 2-(R)-(1-(R)-3, 5-bis(trifluoromethyl)phenylethoxy)-3-(S)-(4-fluoro)phenyl-4- (3-oxo-1,2,4-triazol-5-yl)methylmorpholine, a potent, orally active, long-acting morpholine acetal human NK-1 receptor antagonist. | 1998 Nov 5 |
|
Phosphorylated morpholine acetal human neurokinin-1 receptor antagonists as water-soluble prodrugs. | 2000 Mar 23 |
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Central neurocircuitry associated with emesis. | 2001 Dec 3 |
|
Antiemetic neurokinin-1 antagonist aprepitant and ifosfamide-induced encephalopathy. | 2007 Apr |
|
Metalloelastase in lungs and alveolar macrophages is modulated by extracellular substance P in mice. | 2008 Jul |
|
Characterization of the occurrence of ifosfamide-induced neurotoxicity with concomitant aprepitant. | 2008 Sep |
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Multicenter, phase II, placebo-controlled, double-blind, randomized study of aprepitant in Japanese patients receiving high-dose cisplatin. | 2010 Nov |
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Case report: delirium due to a diltiazem-fentanyl CYP3A4 drug interaction. | 2010 Nov-Dec |
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Single-dose fosaprepitant for the prevention of chemotherapy-induced nausea and vomiting associated with cisplatin therapy: randomized, double-blind study protocol--EASE. | 2011 Apr 10 |
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Palonosetron plus 3-day aprepitant and dexamethasone to prevent nausea and vomiting in patients receiving highly emetogenic chemotherapy. | 2011 Aug |
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Discovery and biological characterization of (2R,4S)-1'-acetyl-N-{(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethyl}-2-(4-fluoro-2-methylphenyl)-N-methyl-4,4'-bipiperidine-1-carboxamide as a new potent and selective neurokinin 1 (NK1) receptor antagonist clinical candidate. | 2011 Feb 24 |
|
[Retrospective analysis of antiemetic effect in patients receiving cisplatin]. | 2011 Jul |
|
Pemirolast reduces cisplatin-induced kaolin intake in rats. | 2011 Jul 1 |
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The involvement of TRPA1 channel activation in the inflammatory response evoked by topical application of cinnamaldehyde to mice. | 2011 Jun 20 |
|
[The efficacy of aprepitant and palonosetron on cisplatin doublet in lung cancer]. | 2011 Oct |
|
Differential time course of action of 5-HT3 and NK1 receptor antagonists when used with highly and moderately emetogenic chemotherapy (HEC and MEC). | 2011 Sep |
|
Use of high-dose cisplatin with aprepitant in an outpatient setting. | 2012 Jul |
|
Utilization of human nuclear receptors as an early counter screen for off-target activity: a case study with a compendium of 615 known drugs. | 2015 Jun |
|
Systems pharmacological analysis of drugs inducing stevens-johnson syndrome and toxic epidermal necrolysis. | 2015 May 18 |
Patents
Sample Use Guides
Prevention of Chemotherapy Induced Nausea and Vomiting:
125 mg orally 1 hour prior to chemotherapy treatment (Day 1) and 80 mg orally once daily in the morning on Days 2 and 3. The package insert for the co-administered 5-HT3 antagonist must be consulted prior to initiation of treatment with EMEND (aprepitant capsules).
Prevention of Postoperative Nausea and Vomiting:
The recommended oral dosage of EMEND is 40 mg within 3 hours prior to induction of anesthesia EMEND may be taken with or without food.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/18040825
Curator's Comment:: Aprepitant suppressed HIV Bal infection of macrophages. Treatment with aprepitant (10(-6) M) inhibited infection of macrophages with the AZT- resistant viruses (A018, A012) by 0.7 log(10). Aprepitant also suppressed infection of macrophages with RT inhibitor-resistant virus (TC 49 and TC 60) by 0.5 log(10). Furthermore, aprepitant significantly enhanced the anti-HIV activity of antiretrovirals (AZT, Efavirenz, and Indinavir) in HIV Bal-infected macrophages, and aprepitant inhibited CCR5 expression on macrophages, ranging from 50.5 to 29.6%. Donor heterogeneity was observed in antiviral activity and CCR5 receptor expression.
Monocytes isolated from healthy donors were cultured for 7 days and then treated with or without aprepitant (10(-6) M) for 2 h, followed by HIV infection with drug-resistant strains for 2 h.
Substance Class |
Chemical
Created
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admin
on
Edited
Fri Jun 25 21:06:56 UTC 2021
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admin
on
Fri Jun 25 21:06:56 UTC 2021
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Record UNII |
1NF15YR6UY
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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WHO-VATC |
QA04AD12
Created by
admin on Fri Jun 25 21:06:57 UTC 2021 , Edited by admin on Fri Jun 25 21:06:57 UTC 2021
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EMA ASSESSMENT REPORTS |
EMEND (AUTHORIZED: POSTOPERATIVE NAUSEA AND VOMITTING)
Created by
admin on Fri Jun 25 21:06:57 UTC 2021 , Edited by admin on Fri Jun 25 21:06:57 UTC 2021
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NDF-RT |
N0000175786
Created by
admin on Fri Jun 25 21:06:57 UTC 2021 , Edited by admin on Fri Jun 25 21:06:57 UTC 2021
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EMA ASSESSMENT REPORTS |
EMEND (AUTHORIZED: VOMITTING)
Created by
admin on Fri Jun 25 21:06:57 UTC 2021 , Edited by admin on Fri Jun 25 21:06:57 UTC 2021
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LIVERTOX |
61
Created by
admin on Fri Jun 25 21:06:57 UTC 2021 , Edited by admin on Fri Jun 25 21:06:57 UTC 2021
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NDF-RT |
N0000010262
Created by
admin on Fri Jun 25 21:06:57 UTC 2021 , Edited by admin on Fri Jun 25 21:06:57 UTC 2021
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NCI_THESAURUS |
C267
Created by
admin on Fri Jun 25 21:06:57 UTC 2021 , Edited by admin on Fri Jun 25 21:06:57 UTC 2021
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WHO-ATC |
A04AD12
Created by
admin on Fri Jun 25 21:06:56 UTC 2021 , Edited by admin on Fri Jun 25 21:06:56 UTC 2021
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Code System | Code | Type | Description | ||
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N0000185506
Created by
admin on Fri Jun 25 21:06:57 UTC 2021 , Edited by admin on Fri Jun 25 21:06:57 UTC 2021
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PRIMARY | Cytochrome P450 3A4 Inducers [MoA] | ||
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135413536
Created by
admin on Fri Jun 25 21:06:57 UTC 2021 , Edited by admin on Fri Jun 25 21:06:57 UTC 2021
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PRIMARY | |||
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3490
Created by
admin on Fri Jun 25 21:06:57 UTC 2021 , Edited by admin on Fri Jun 25 21:06:57 UTC 2021
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PRIMARY | |||
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N0000182141
Created by
admin on Fri Jun 25 21:06:57 UTC 2021 , Edited by admin on Fri Jun 25 21:06:57 UTC 2021
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PRIMARY | Cytochrome P450 3A4 Inhibitors [MoA] | ||
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APREPITANT
Created by
admin on Fri Jun 25 21:06:57 UTC 2021 , Edited by admin on Fri Jun 25 21:06:57 UTC 2021
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C49173
Created by
admin on Fri Jun 25 21:06:57 UTC 2021 , Edited by admin on Fri Jun 25 21:06:57 UTC 2021
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N0000185507
Created by
admin on Fri Jun 25 21:06:57 UTC 2021 , Edited by admin on Fri Jun 25 21:06:57 UTC 2021
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PRIMARY | Cytochrome P450 2C9 Inducers [MoA] | ||
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230
Created by
admin on Fri Jun 25 21:06:57 UTC 2021 , Edited by admin on Fri Jun 25 21:06:57 UTC 2021
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PRIMARY | |||
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M2011
Created by
admin on Fri Jun 25 21:06:57 UTC 2021 , Edited by admin on Fri Jun 25 21:06:57 UTC 2021
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PRIMARY | Merck Index | ||
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170729-80-3
Created by
admin on Fri Jun 25 21:06:56 UTC 2021 , Edited by admin on Fri Jun 25 21:06:56 UTC 2021
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8050
Created by
admin on Fri Jun 25 21:06:57 UTC 2021 , Edited by admin on Fri Jun 25 21:06:57 UTC 2021
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DB00673
Created by
admin on Fri Jun 25 21:06:57 UTC 2021 , Edited by admin on Fri Jun 25 21:06:57 UTC 2021
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CHEMBL1471
Created by
admin on Fri Jun 25 21:06:57 UTC 2021 , Edited by admin on Fri Jun 25 21:06:57 UTC 2021
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SUB20017
Created by
admin on Fri Jun 25 21:06:56 UTC 2021 , Edited by admin on Fri Jun 25 21:06:56 UTC 2021
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1041904
Created by
admin on Fri Jun 25 21:06:57 UTC 2021 , Edited by admin on Fri Jun 25 21:06:57 UTC 2021
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PRIMARY | USP-RS | ||
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C114556
Created by
admin on Fri Jun 25 21:06:57 UTC 2021 , Edited by admin on Fri Jun 25 21:06:57 UTC 2021
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PRIMARY | |||
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358255
Created by
admin on Fri Jun 25 21:06:57 UTC 2021 , Edited by admin on Fri Jun 25 21:06:57 UTC 2021
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PRIMARY | RxNorm | ||
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170729-80-3
Created by
admin on Fri Jun 25 21:06:57 UTC 2021 , Edited by admin on Fri Jun 25 21:06:57 UTC 2021
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PRIMARY | |||
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1NF15YR6UY
Created by
admin on Fri Jun 25 21:06:57 UTC 2021 , Edited by admin on Fri Jun 25 21:06:57 UTC 2021
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PRIMARY |
Related Record | Type | Details | ||
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EXCRETED UNCHANGED |
Aprepitant is eliminated primarily by metabolism; aprepitant is not renally excreted.
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METABOLIC ENZYME -> SUBSTRATE |
MINOR
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TARGET -> INHIBITOR |
ANTAGONIST
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BINDER->LIGAND |
BINDING
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METABOLIC ENZYME -> SUBSTRATE |
MAJOR
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METABOLIC ENZYME -> SUBSTRATE |
MINOR
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Related Record | Type | Details | ||
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METABOLITE -> PARENT | |||
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METABOLITE -> PARENT |
Related Record | Type | Details | ||
---|---|---|---|---|
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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Related Record | Type | Details | ||
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ACTIVE MOIETY |
Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Volume of Distribution | PHARMACOKINETIC |
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Tmax | PHARMACOKINETIC |
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Biological Half-life | PHARMACOKINETIC |
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