aprepitant 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definition	Drug id	CAS RN
neurokinin NK1 (substance P) receptor antagonist	230	170729-80-3

Description:

Molecule	Description
Molfile Inchi Smiles Synonyms: emend aprepitant L-754030	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 (CINV). Aprepitant has been shown in animal models to inhibit emesis induced by cytotoxic chemotherapeutic agents, such as cisplatin, via central actions. Molecular weight: 534.44 Formula: C23H21F7N4O3 CLOGP: 4.40 LIPINSKI: 1 HAC: 7 HDO: 2 TPSA: 75.19 ALOGS: -4.44 ROTB: 8 Status: OFP Legend: OFP - off patent OFM - off market ONP - on patent

Molecule

Description

Molfile Inchi Smiles

Synonyms:

emend
aprepitant
L-754030

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 (CINV). Aprepitant has been shown in animal models to inhibit emesis induced by cytotoxic chemotherapeutic agents, such as cisplatin, via central actions.

Molecular weight: 534.44
Formula: C23H21F7N4O3
CLOGP: 4.40
LIPINSKI: 1
HAC: 7
HDO: 2
TPSA: 75.19
ALOGS: -4.44
ROTB: 8

Status: OFP

Legend:
OFP - off patent
OFM - off market
ONP - on patent

Drug dosage:

Dose	Unit	Route
165	mg	O
150	mg	P

ADMET properties:

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Property	Value	Reference
BA (Bioavailability)	62.50 %	Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
MRTD (Maximum Recommended Therapeutic Daily Dose)	3.34 µM/kg/day	Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BDDCS (Biopharmaceutical Drug Disposition Classification System)	2	Benet LZ, Broccatelli F, Oprea TI
t_half (Half-life)	13 hours	Lombardo F, Berellini G, Obach RS
CL (Clearance)	1 mL/min/kg	Lombardo F, Berellini G, Obach RS
Vd (Volume of distribution)	0.94 L/kg	Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma)	0.05 %	Lombardo F, Berellini G, Obach RS
S (Water solubility)	0.02 mg/mL	Bocci G, Oprea TI, Benet LZ
EoM (Fraction excreted unchanged in urine)	0 %	Benet LZ, Broccatelli F, Oprea TI

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Approvals:

Date	Agency	Company	Orphan
March 27, 2003	FDA	MERCK

FDA Adverse Event Reporting System (Female)

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MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Febrile neutropenia	496.24	16.75	439	31779	118010	63338794
Mucosal inflammation	168.89	16.75	160	32058	46768	63410036
Computerised tomogram thorax abnormal	156.13	16.75	51	32167	1712	63455092
Neutropenia	139.07	16.75	287	31931	174718	63282086
Gastrointestinal disorder	138.62	16.75	243	31975	130996	63325808
Pyrexia	133.54	16.75	531	31687	469947	62986857
Drug ineffective	133.01	16.75	204	32014	1044561	62412243
Atelectasis	132.65	16.75	100	32118	21383	63435421
Nausea	130.74	16.75	808	31410	853663	62603141
Febrile bone marrow aplasia	113.44	16.75	61	32157	7264	63449540

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FDA Adverse Event Reporting System (Male)

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MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Febrile neutropenia	249.18	18.86	288	13560	136561	34806522
Hiccups	112.14	18.86	62	13786	10020	34933063
Neutropenia	109.97	18.86	211	13637	156567	34786516
Erythema	98.87	18.86	147	13701	88633	34854450
Hypersensitivity	96.75	18.86	120	13728	60915	34882168
Neutrophil count decreased	95.03	18.86	109	13739	50995	34892088
Drug ineffective	84.38	18.86	38	13810	456713	34486370
Stomatitis	71.24	18.86	86	13762	42428	34900655
Nausea	70.37	18.86	293	13555	339615	34603468
Thrombocytopenia	70.29	18.86	176	13672	156071	34787012

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FDA Adverse Event Reporting System (Geriatric)

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MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Febrile neutropenia	637.71	15.76	688	40714	230311	79472675
Neutropenia	187.92	15.76	442	40960	287268	79415718
Erythema	187.91	15.76	380	41022	222910	79480076
Nausea	173.02	15.76	962	40440	956234	78746752
Stomatitis	155.92	15.76	276	41126	146481	79556505
Drug ineffective	151.30	15.76	205	41197	1080708	78622278
Mucosal inflammation	147.63	15.76	189	41213	75391	79627595
Neutrophil count decreased	144.18	15.76	209	41193	93750	79609236
Febrile bone marrow aplasia	139.56	15.76	86	41316	12934	79690052
Computerised tomogram thorax abnormal	139.19	15.76	51	41351	2368	79700618

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FDA Adverse Event Reporting System (Pediatric)

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MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Small for dates baby	12.13	12.06	5	3	2804	86980

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Pharmacologic Action:

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Source	Code	Description
ATC	A04AD12	ALIMENTARY TRACT AND METABOLISM ANTIEMETICS AND ANTINAUSEANTS ANTIEMETICS AND ANTINAUSEANTS Other antiemetics
CHEBI has role	CHEBI:35469	antidepressants
CHEBI has role	CHEBI:49110	peripheral nervous system drugs
CHEBI has role	CHEBI:50919	antiemetico
CHEBI has role	CHEBI:55350	neurokinin-1 receptor antagonists
CHEBI has role	CHEBI:55351	substance P receptor antagonists
FDA EPC	N0000175786	Substance P/Neurokinin-1 Receptor Antagonist
FDA MoA	N0000010262	Neurokinin 1 Antagonists
FDA MoA	N0000182141	Cytochrome P450 3A4 Inhibitors
FDA MoA	N0000185506	Cytochrome P450 3A4 Inducers

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Drug Use | Suggest Off label Use Form| |View source of the data|

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Disease	Relation	SNOMED_ID
Chemotherapy-induced nausea and vomiting	indication	236084000
Prevention of Post-Operative Nausea and Vomiting	indication
Hepatic failure	contraindication	59927004

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🐶 Veterinary Drug Use

None

🐶 Veterinary products

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Acid dissociation constants calculated using MoKa v3.0.0

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Dissociation level	Dissociation constant	Type (acidic/basic)
pKa1	8.8	acidic
pKa2	13.0	acidic
pKa3	3.22	Basic
pKa4	2.56	Basic

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Orange Book patent data (new drug applications)

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Formulation strength	Trade name	Applicant	Application number	Approval date	Type	Dose form	Route	Patent number	Patent expiration date	Patent use
125MG	EMEND	MERCK	N021549	March 26, 2003	RX	CAPSULE	ORAL	8258132	Sept. 26, 2027	FOR THE PREVENTION OF NAUSEA AND VOMITING ASSOCIATED WITH CHEMOTHERAPY
125MG	EMEND	MERCK	N021549	March 26, 2003	RX	CAPSULE	ORAL	8258132	Sept. 26, 2027	PREVENTION OF POSTOPERATIVE NAUSEA AND VOMITING
125MG/KIT	EMEND	MSD MERCK CO	N207865	Dec. 17, 2015	RX	FOR SUSPENSION	ORAL	8258132	Sept. 26, 2027	PREVENTION OF NAUSEA AND VOMITING ASSOCIATED WITH CHEMOTHERAPY (CINV)
130MG/18ML (7.2MG/ML)	CINVANTI	HERON THERAPS INC	N209296	Nov. 9, 2017	RX	EMULSION	INTRAVENOUS	10624850	Sept. 18, 2035	TREATMENT OF NAUSEA AND VOMITING, INCLUDING THE PREVENTION OF ACUTE AND DELAYED NAUSEA AND VOMITING ASSOCIATED WITH INITIAL AND REPEAT COURSES OF HIGHLY OR MODERATELY EMETOGENIC CANCER CHEMOTHERAPY
130MG/18ML (7.2MG/ML)	CINVANTI	HERON THERAPS INC	N209296	Nov. 9, 2017	RX	EMULSION	INTRAVENOUS	10953018	Sept. 18, 2035	TREATMENT OF NAUSEA AND VOMITING, INCLUDING THE PREVENTION OF ACUTE AND DELAYED NAUSEA AND VOMITING ASSOCIATED WITH INITIAL AND REPEAT COURSES OF HIGHLY OR MODERATELY EMETOGENIC CANCER CHEMOTHERAPY
130MG/18ML (7.2MG/ML)	CINVANTI	HERON THERAPS INC	N209296	Nov. 9, 2017	RX	EMULSION	INTRAVENOUS	9561229	Sept. 18, 2035	TREATMENT OF NAUSEA AND VOMITING, INCLUDING THE PREVENTION OF ACUTE AND DELAYED NAUSEA AND VOMITING ASSOCIATED WITH INITIAL AND REPEAT COURSES OF HIGHLY OR MODERATELY EMETOGENIC CANCER CHEMOTHERAPY
130MG/18ML (7.2MG/ML)	CINVANTI	HERON THERAPS INC	N209296	Nov. 9, 2017	RX	EMULSION	INTRAVENOUS	9808465	Sept. 18, 2035	TREATMENT OF NAUSEA AND VOMITING, INCLUDING THE PREVENTION OF ACUTE AND DELAYED NAUSEA AND VOMITING ASSOCIATED WITH INITIAL AND REPEAT COURSES OF HIGHLY OR MODERATELY EMETOGENIC CANCER CHEMOTHERAPY
130MG/18ML (7.2MG/ML)	CINVANTI	HERON THERAPS INC	N209296	Nov. 9, 2017	RX	EMULSION	INTRAVENOUS	9974794	Sept. 18, 2035	TREATMENT OF NAUSEA AND VOMITING, INCLUDING THE PREVENTION OF ACUTE AND DELAYED NAUSEA AND VOMITING ASSOCIATED WITH INITIAL AND REPEAT COURSES OF HIGHLY OR MODERATELY EMETOGENIC CANCER CHEMOTHERAPY
32MG/4.4ML (7.2MG/ML)	APONVIE	HERON THERAPS INC	N216457	Sept. 16, 2022	RX	EMULSION	INTRAVENOUS	10624850	Sept. 18, 2035	A METHOD OF ADMINISTERING APREPITANT FOR PREVENTION OF POST-OPERATIVE NAUSEA AND VOMITING
32MG/4.4ML (7.2MG/ML)	APONVIE	HERON THERAPS INC	N216457	Sept. 16, 2022	RX	EMULSION	INTRAVENOUS	10953018	Sept. 18, 2035	A METHOD OF ADMINISTERING APREPITANT FOR PREVENTION OF POST-OPERATIVE NAUSEA AND VOMITING

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Orange Book exclusivity data (new drug applications)

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Bioactivity Summary:

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Target	Class	Pharos	UniProt	Action	Type	Activity value (-log[M])	Bioact source	MoA source
Substance-P receptor	GPCR	P25103	NK1R_HUMAN	ANTAGONIST	Ki	10.70	CHEMBL	CHEMBL
Cytochrome P450 3A4	Enzyme	P08684	CP3A4_HUMAN				WOMBAT-PK
Neuromedin-K receptor	GPCR	P29371	NK3R_HUMAN		Ki	6.34	CHEMBL
Substance-P receptor	GPCR		NK1R_MERUN		IC50	10.05	CHEMBL

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External reference:

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ID	Source
009926	NDDF
135413536	PUBCHEM_CID
17180	MMSL
1NF15YR6UY	UNII
247683	MMSL
3490	IUPHAR_LIGAND_ID
357280	RXNORM
398690007	SNOMEDCT_US
4021391	VANDF
409205009	SNOMEDCT_US

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Pharmaceutical products:

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Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
APONVIE	HUMAN PRESCRIPTION DRUG LABEL	1	47426-401	EMULSION	32 mg	INTRAVENOUS	NDA	29 sections
Aprepitant	HUMAN PRESCRIPTION DRUG LABEL	1	0781-2321	CAPSULE	40 mg	ORAL	ANDA	26 sections
Aprepitant	HUMAN PRESCRIPTION DRUG LABEL	1	0781-2321	CAPSULE	40 mg	ORAL	ANDA	26 sections
Aprepitant	HUMAN PRESCRIPTION DRUG LABEL	1	0781-2322	CAPSULE	80 mg	ORAL	ANDA	26 sections
Aprepitant	HUMAN PRESCRIPTION DRUG LABEL	1	0781-2322	CAPSULE	80 mg	ORAL	ANDA	26 sections
Aprepitant	HUMAN PRESCRIPTION DRUG LABEL	1	0781-2323	CAPSULE	125 mg	ORAL	ANDA	26 sections
Aprepitant	HUMAN PRESCRIPTION DRUG LABEL	1	0781-2323	CAPSULE	125 mg	ORAL	ANDA	26 sections
APREPITANT	HUMAN PRESCRIPTION DRUG LABEL	1	13668-591	CAPSULE	40 mg	ORAL	ANDA	25 sections
APREPITANT	HUMAN PRESCRIPTION DRUG LABEL	1	13668-591	CAPSULE	40 mg	ORAL	ANDA	25 sections
APREPITANT	HUMAN PRESCRIPTION DRUG LABEL	1	13668-592	CAPSULE	80 mg	ORAL	ANDA	25 sections

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