FOSAPREPITANT

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C23H22F7N4O6P
Molecular Weight	614.4066
Optical Activity	UNSPECIFIED
Defined Stereocenters	3 / 3
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C[C@@H](O[C@H]1OCCN(CC2=NN(C(=O)N2)P(O)(O)=O)[C@H]1C3=CC=C(F)C=C3)C4=CC(=CC(=C4)C(F)(F)F)C(F)(F)F

InChI

InChIKey=BARDROPHSZEBKC-OITMNORJSA-N

InChI=1S/C23H22F7N4O6P/c1-12(14-8-15(22(25,26)27)10-16(9-14)23(28,29)30)40-20-19(13-2-4-17(24)5-3-13)33(6-7-39-20)11-18-31-21(35)34(32-18)41(36,37)38/h2-5,8-10,12,19-20H,6-7,11H2,1H3,(H,31,32,35)(H2,36,37,38)/t12-,19+,20-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C23H22F7N4O6P
Molecular Weight	614.4066
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	3 / 3
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: http://www.drugbank.ca/drugs/DB06717http://www.accessdata.fda.gov/drugsatfda_docs/label/2014/021549s024lbl.pdf
Curator's Comment: Description was created based on several sources, including http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/021549s025lbl.pdf

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.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Neurokinin 1 receptor 35 Target ID: CHEMBL249 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/021549s025lbl.pdf	Antagonist 2849
Neurokinin 1 receptor 35 Target ID: CHEMBL249 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12590540	Antagonist 2849

Conditions

Condition	Modality	Highest Phase	Product
Postoperative nausea and vomiting 31 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2014/021549s024lbl.pdf	Preventing	Approved 8583	EMEND Approved Use 1.1 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 Date 2006
Chemotherapy induced nausea and vomiting 10 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2014/021549s024lbl.pdf	Preventing	Approved 8583	EMEND Approved Use 1.1 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 Date 2006
Chemotherapy induced nausea and vomiting 10 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/021549s025lbl.pdf	Secondary	Approved 8583	EMEND Approved Use EMEND® is a substance P/neurokinin 1 (NK1) receptor antagonist, indicated: • in combination with other antiemetic agents in patients 12 years of age and older and patients less than 12 years of age who weight at least 30 kg for prevention of: • acute and delayed nausea and vomiting associated with initial and repeat courses of highly emetogenic cancer chemotherapy (HEC) including high-dose cisplatin (1.1) • nausea and vomiting associated with initial and repeat courses of moderately emetogenic cancer chemotherapy (MEC) (1.1) • for prevention of postoperative nausea and vomiting (PONV) in adults (1.2) Launch Date 2008
Postoperative nausea and vomiting 31 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/021549s025lbl.pdf	Preventing	Approved 8583	EMEND Approved Use EMEND® is a substance P/neurokinin 1 (NK1) receptor antagonist, indicated: • in combination with other antiemetic agents in patients 12 years of age and older and patients less than 12 years of age who weight at least 30 kg for prevention of: • acute and delayed nausea and vomiting associated with initial and repeat courses of highly emetogenic cancer chemotherapy (HEC) including high-dose cisplatin (1.1) • nausea and vomiting associated with initial and repeat courses of moderately emetogenic cancer chemotherapy (MEC) (1.1) • for prevention of postoperative nausea and vomiting (PONV) in adults (1.2) Launch Date 2008

C_max

Value	Dose	Analyte	Population
6.1 μg/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/209296s000lbl.pdf	130 mg single, intravenous dose: 130 mg route of administration: Intravenous experiment type: SINGLE co-administered:	APREPITANT plasma	Homo sapiens population: HEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN
4.3 μg/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/209296s000lbl.pdf	100 mg single, intravenous dose: 100 mg route of administration: Intravenous experiment type: SINGLE co-administered:	APREPITANT plasma	Homo sapiens population: HEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN
1354 ng/mL REVIEW https://www.ncbi.nlm.nih.gov/pubmed/21042544	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

AUC

Value	Dose	Analyte	Population
43.9 μg × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/209296s000lbl.pdf	130 mg single, intravenous dose: 130 mg route of administration: Intravenous experiment type: SINGLE co-administered:	APREPITANT plasma	Homo sapiens population: HEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN
27.8 μg × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/209296s000lbl.pdf	100 mg single, intravenous dose: 100 mg route of administration: Intravenous experiment type: SINGLE co-administered:	APREPITANT plasma	Homo sapiens population: HEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN
27759 ng × h/mL REVIEW https://www.ncbi.nlm.nih.gov/pubmed/21042544	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
44578 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17525168/	100 mg single, intravenous dose: 100 mg route of administration: Intravenous experiment type: SINGLE co-administered:	FOSAPREPITANT plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
14 h REVIEW https://www.ncbi.nlm.nih.gov/pubmed/21042544	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
2.2 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17525168/	100 mg single, intravenous dose: 100 mg route of administration: Intravenous experiment type: SINGLE co-administered:		FOSAPREPITANT plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

F_unbound

Value	Dose	Co-administered	Analyte	Population
5% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17525168/	100 mg single, intravenous dose: 100 mg route of administration: Intravenous experiment type: SINGLE co-administered:		FOSAPREPITANT plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

Doses

Dose	Population	Adverse events
150 mg single, intravenous Recommended Dose: 150 mg Route: intravenous Route: single Dose: 150 mg Sources: https://pubmed.ncbi.nlm.nih.gov/29873529	healthy, 33 Health Status: healthy Age Group: 33 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/29873529	Disc. AE: Dyspnea... AEs leading to discontinuation/dose reduction: Dyspnea (2%) Sources: https://pubmed.ncbi.nlm.nih.gov/29873529
150 mg single, intravenous Recommended Dose: 150 mg Route: intravenous Route: single Dose: 150 mg Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/022023s017lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/022023s017lbl.pdf	Disc. AE: Hypersensitivity reaction, Anaphylaxis... AEs leading to discontinuation/dose reduction: Hypersensitivity reaction Anaphylaxis Anaphylactic shock Infusion site reactions Thrombophlebitis Necrosis Vasculitis Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/022023s017lbl.pdf

AEs

AE	Significance	Dose	Population
Dyspnea	2% Disc. AE	150 mg single, intravenous Recommended Dose: 150 mg Route: intravenous Route: single Dose: 150 mg Sources: https://pubmed.ncbi.nlm.nih.gov/29873529	healthy, 33 Health Status: healthy Age Group: 33 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/29873529
Anaphylactic shock	Disc. AE	150 mg single, intravenous Recommended Dose: 150 mg Route: intravenous Route: single Dose: 150 mg Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/022023s017lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/022023s017lbl.pdf
Anaphylaxis	Disc. AE	150 mg single, intravenous Recommended Dose: 150 mg Route: intravenous Route: single Dose: 150 mg Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/022023s017lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/022023s017lbl.pdf
Hypersensitivity reaction	Disc. AE	150 mg single, intravenous Recommended Dose: 150 mg Route: intravenous Route: single Dose: 150 mg Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/022023s017lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/022023s017lbl.pdf
Infusion site reactions	Disc. AE	150 mg single, intravenous Recommended Dose: 150 mg Route: intravenous Route: single Dose: 150 mg Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/022023s017lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/022023s017lbl.pdf
Necrosis	Disc. AE	150 mg single, intravenous Recommended Dose: 150 mg Route: intravenous Route: single Dose: 150 mg Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/022023s017lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/022023s017lbl.pdf
Thrombophlebitis	Disc. AE	150 mg single, intravenous Recommended Dose: 150 mg Route: intravenous Route: single Dose: 150 mg Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/022023s017lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/022023s017lbl.pdf
Vasculitis	Disc. AE	150 mg single, intravenous Recommended Dose: 150 mg Route: intravenous Route: single Dose: 150 mg Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/022023s017lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/022023s017lbl.pdf

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1946 inhibitor 2252 inducer 1087	substrate 1193 inducer 440 inhibitor 2438	substrate 1388 inhibitor 2507

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP2C19 2057 CYP1A2 2153 CYP2E1 1060 CYP2B6 926 CYP2C8 1057 CYP 110 P-gp 1741	CYP1A2 1197 CYP2E1 729 P-gp 2052 CYP2C19 1119	P-gp 301

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
CYP3A4 2633	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2003/21549_Emend_lbl.pdf#page=7 Page: 7.0	moderate		yes (co-administration study) Comment: 2.3 to 3.3 fold increase in mean AUC of orally coadministered midazolam; Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2003/21549_Emend_lbl.pdf#page=7 Page: 7.0
CYP3A4 2633	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/022023s017lbl.pdf Page: 15.0	no
CYP 150	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/NDA/2008/022023s000_ClinPharmR.pdf Page: 29, 34	unlikely
P-gp 1932	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2003/21549_Emend_lbl.pdf#page=7 Page: 7.0	unlikely
P-gp 1932	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2003/21549_Emend_lbl.pdf#page=7 Page: 7.0	unlikely
CYP2B6 1160	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/NDA/2008/022023s000_PharmR_P2.pdf Page: 9.0	weak [IC50 44.7 uM]	aprepitant 3
CYP1A2 2333	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/NDA/2008/022023s000_PharmR_P2.pdf Page: 8.0	weak [IC50 >100 uM]	aprepitant 3
CYP2C8 1117	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/NDA/2008/022023s000_PharmR_P2.pdf Page: 9.0	weak [IC50 >100 uM]	aprepitant 3
CYP2D6 2546	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/NDA/2008/022023s000_PharmR_P2.pdf Page: 8.0	weak [IC50 >100 uM]	aprepitant 3
CYP2E1 1146	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/NDA/2008/022023s000_PharmR_P2.pdf Page: 8.0	weak [IC50 >100 uM]	aprepitant 3
CYP2C9 2497	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/NDA/2008/022023s000_PharmR_P2.pdf Page: 8.0	weak [Ki 108 uM]	aprepitant 3
CYP2C19 2141	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/NDA/2008/022023s000_PharmR_P2.pdf Page: 8.0	weak [Ki 66 uM]	aprepitant 3
CYP3A4 2633	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/022023s017lbl.pdf Page: 15, 16	weak		yes (co-administration study) Comment: fosaprepitant increased the AUC of midazolam by 1.8-fold; fosaprepitant increased diltiazem AUC by 1.4-fold Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/022023s017lbl.pdf Page: 15, 16
CYP3A4 2633	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2003/21549_Emend_lbl.pdf#page=7 Page: 7.0	yes
CYP3A4 2633	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/022023s017lbl.pdf Page: 15.0	yes	aprepitant 3
CYP2C9 2497	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2003/21549_Emend_lbl.pdf#page=7 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); Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2003/21549_Emend_lbl.pdf#page=7 Page: 7.0
CYP2C9 2497	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/022023s017lbl.pdf Page: 9, 15	yes	aprepitant 3	yes (co-administration study) Comment: oral aprepitant decreased the AUC of tolbutamide by 23% on Day 4; fosaprepitant/aprepitant decreased warfarin exposure and prolongation of prothrombin time Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/022023s017lbl.pdf Page: 9, 15
CYP3A4 2633	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/NDA/2008/022023s000_PharmR_P2.pdf Page: 8.0	yes	aprepitant 3	yes (co-administration study) Comment: fosaprepitant/aprepitant increased pimozide exposure; fosaprepitant/aprepitant increased midazolam exposure; fosaprepitant/aprepitant increased dexamethazone exposure; ifosaprepitant/aprepitant increased methylprednisolone exposure Sources: https://www.accessdata.fda.gov/drugsatfda_docs/NDA/2008/022023s000_PharmR_P2.pdf Page: 8.0

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
CYP3A4 1946	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2003/21549_Emend_lbl.pdf#page=2 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; Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2003/21549_Emend_lbl.pdf#page=2 Page: 2.0
CYP3A4 1946	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/NDA/2008/022023s000_PharmR_P2.pdf Page: 8, 12	major	aprepitant 3	yes (co-administration study) Comment: ketoconazole completely inhibited metabolism of MK-0869 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/NDA/2008/022023s000_PharmR_P2.pdf Page: 8, 12
CYP1A2 1197	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2003/21549_Emend_lbl.pdf#page=2 Page: 2.0	minor
CYP1A2 1197	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/NDA/2008/022023s000_PharmR_P1.pdf Page: 52.0	minor	aprepitant 3
CYP2C19 1119	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2003/21549_Emend_lbl.pdf#page=2 Page: 2.0	minor
CYP2C9 1193	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2003/21549_Emend_lbl.pdf#page=2 Page: 2.0	no
CYP2C9 1193	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/NDA/2008/022023s000_PharmR_P2.pdf Page: 8.0	no	aprepitant 3
CYP2D6 1388	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2003/21549_Emend_lbl.pdf#page=2 Page: 2.0	no
CYP2D6 1388	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/NDA/2008/022023s000_PharmR_P2.pdf Page: 8.0	no	aprepitant 3
CYP2E1 729	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2003/21549_Emend_lbl.pdf#page=2 Page: 2.0	no
CYP2E1 729	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/NDA/2008/022023s000_PharmR_P2.pdf Page: 8.0	no	aprepitant 3
P-gp 2052	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/NDA/2008/022023s000_PharmR_P1.pdf Page: 72.0	weak	aprepitant 3	no (co-administration study) Comment: lack of interaction between aprepitant with digoxin in clinical drug interaction study Sources: https://www.accessdata.fda.gov/drugsatfda_docs/NDA/2008/022023s000_PharmR_P1.pdf Page: 72.0

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:64321	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:64321
ChemicalBook	CB11515191	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB11515191
eMolecules	36758241	https://www.emolecules.com/cgi-bin/more?vid=36758241
ZINC	ZINC000003939013	http://zinc15.docking.org/substances/ZINC000003939013
ChEBI	CHEBI:499361	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:499361
ChemicalBook	CB32557888	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB32557888
ChemicalBook	CB7500857	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB7500857
eMolecules	30153720	https://www.emolecules.com/cgi-bin/more?vid=30153720
eMolecules	8763262	https://www.emolecules.com/cgi-bin/more?vid=8763262
MolPort	MolPort-006-392-367	https://www.molport.com/shop/molecule-link/MolPort-006-392-367
MolPort	MolPort-009-679-399	https://www.molport.com/shop/molecule-link/MolPort-009-679-399
Selleck Chemicals	Aprepitant	http://www.selleckchem.com/products/Aprepitant.html
ZINC	ZINC000027428713	http://zinc15.docking.org/substances/ZINC000027428713

PubMed

Title	Date	PubMed
Utilization of human nuclear receptors as an early counter screen for off-target activity: a case study with a compendium of 615 known drugs.	2015-06	25752796
Systems pharmacological analysis of drugs inducing stevens-johnson syndrome and toxic epidermal necrolysis.	2015-05-18	25811541
Use of high-dose cisplatin with aprepitant in an outpatient setting.	2012-07	21883567
[The efficacy of aprepitant and palonosetron on cisplatin doublet in lung cancer].	2011-10	21996961
Differential time course of action of 5-HT3 and NK1 receptor antagonists when used with highly and moderately emetogenic chemotherapy (HEC and MEC).	2011-09	20623144
Palonosetron plus 3-day aprepitant and dexamethasone to prevent nausea and vomiting in patients receiving highly emetogenic chemotherapy.	2011-08	20552375
Pemirolast reduces cisplatin-induced kaolin intake in rats.	2011-07-01	21539837
[Retrospective analysis of antiemetic effect in patients receiving cisplatin].	2011-07	21772101
The involvement of TRPA1 channel activation in the inflammatory response evoked by topical application of cinnamaldehyde to mice.	2011-06-20	21466812
Single-dose fosaprepitant for the prevention of chemotherapy-induced nausea and vomiting associated with cisplatin therapy: randomized, double-blind study protocol--EASE.	2011-04-10	21383291
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.	2011-02-24	21229983
Multicenter, phase II, placebo-controlled, double-blind, randomized study of aprepitant in Japanese patients receiving high-dose cisplatin.	2010-11	20718754
Fosaprepitant and aprepitant: an update of the evidence for their place in the prevention of chemotherapy-induced nausea and vomiting.	2010-10-21	21042544
Pharmacokinetic evaluation of fosaprepitant dimeglumine.	2010-10	20795794
Recent trends in the impurity profile of pharmaceuticals.	2010-07	22247862
Case report: delirium due to a diltiazem-fentanyl CYP3A4 drug interaction.	2010-04-23	21112467
Lack of effect of aprepitant or its prodrug fosaprepitant on QTc intervals in healthy subjects.	2009-08	19608812
Fosaprepitant dimeglumine (MK-0517 or L-785,298), an intravenous neurokinin-1 antagonist for the prevention of chemotherapy induced nausea and vomiting.	2008-12	19040346
Fosaprepitant: a neurokinin-1 receptor antagonist for the prevention of chemotherapy-induced nausea and vomiting.	2008-11	18983233
Characterization of the occurrence of ifosfamide-induced neurotoxicity with concomitant aprepitant.	2008-09	18719071
Metalloelastase in lungs and alveolar macrophages is modulated by extracellular substance P in mice.	2008-07	18441096
Prevention of chemotherapy-induced nausea and vomiting: focus on fosaprepitant.	2008-04	18728837
Fosaprepitant (MK-0517): a neurokinin-1 receptor antagonist for the prevention of chemotherapy-induced nausea and vomiting.	2007-12	18042005
Tolerability of fosaprepitant and bioequivalency to aprepitant in healthy subjects.	2007-07	17525168
Antiemetic neurokinin-1 antagonist aprepitant and ifosfamide-induced encephalopathy.	2007-04	17389531
Central neurocircuitry associated with emesis.	2001-12-03	11749934
Phosphorylated morpholine acetal human neurokinin-1 receptor antagonists as water-soluble prodrugs.	2000-03-23	10737756
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.	1998-11-05	9804700

Patents

Sample Use Guides

In Vivo Use Guide

Prevention of Chemotherapy Induced Nausea and Vomiting (CINV) • Recommended dosage of EMEND in adults and pediatric patients 12 years of age and older and patients less than 12 years of age who weigh at least 30 kg, and who can swallow oral capsules, is 125 mg on Day 1 and 80 mg on Days 2 and 3. • Administer EMEND orally 1 hour prior to chemotherapy on Days 1, 2, and 3. If no chemotherapy is given on Days 2 and 3, administer EMEND in morning. PONV • Recommended oral EMEND dosage in adults is 40 mg within 3 hours prior to induction of anesthesia.

Route of Administration: Oral

In Vitro Use Guide

Aprepitant (active moiety of Fosaprepitant) showed robust human osteosarcoma cell line MG-63 growth inhibition, with 50.78% inhibition at 30 uM and 97.25% at 60 uM.

Substance Class	Chemical Created by `admin` on `Wed Apr 02 07:50:12 GMT 2025` Edited by `admin` on `Wed Apr 02 07:50:12 GMT 2025`
Record UNII	6L8OF9XRDC
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

L-758298

Preferred Name

English

FOSAPREPITANT

Official Name

English

PHOSPHONIC ACID, (3-(((2R,3S)-2-((1R)-1-(3,5-BIS(TRIFLUOROMETHYL)PHENYL)ETHOXY)-3-(4-FLUOROPHENYL)-4-MORPHOLINYL)METHYL)-4,5-DIHYDRO-5-OXO-1H-1,2,4-TRIAZOL-1-YL)-

Common Name

English

FOSAPREPITANT [MART.]

Common Name

English

FOSAPREPITANT [MI]

Common Name

English

fosaprepitant [INN]

Common Name

English

FOSAPREPITANT [EMA EPAR]

Common Name

English

Fosaprepitant [WHO-DD]

Common Name

English

FOSAPREPITANT [VANDF]

Common Name

English

(3-(((2R,3S)-2-((1R)-1-(3,5-BIS(TRIFLUOROMETHYL)PHENYL)ETHOXY)-3-(4-FLUOROPHENYL)MORPHOLIN-4-YL)METHYL)-5-OXO-4,5-DIHYDRO-1H-1,2,4-TRIAZOL-1-YL)PHOSPHONIC ACID

Systematic Name

English

Classification Tree Code System Code

NDF-RT

N0000175786