Aprepitant (CED0004664)

Record Information

Version

1.0

Creation Date

2016-05-22 06:57:32 UTC

Update Date

2026-05-14 16:45:42 UTC

SynCED ID

CED0004664

Secondary Accession Numbers

CHEM020257

Identification

Common Name

Aprepitant

Class

Small Molecule

Description

Aprepitant belongs to the trifluoromethylbenzenes, a subclass of benzene and substituted derivatives within the organic compounds. With an average molecular weight of 538.47 g/mol, Aprepitant is a heavy molecule. Its chemical formula is C23H25F7N4O3. In terms of biological activity, it acts as an antagonist of the Substance-P receptor (TACR1). This compound is utilized within healthcare, pharmaceuticals, and veterinary products as an antiemetic and antinauseant. Recorded routes of exposure for Aprepitant include intravenous and oral administration.

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Chemical Formula

C₂₃H₂₅F₇N₄O₃

Average Molecular Mass

538.467 g/mol

Monoisotopic Mass

538.181 g/mol

CAS Registry Number

170729-80-3

IUPAC Name

5-{[(2R,3S)-2-[(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethoxy]-3-(4-fluorocyclohexyl)morpholin-4-yl]methyl}-3H-1,2,4-triazol-3-one

Traditional Name

5-{[(2R,3S)-2-[(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethoxy]-3-(4-fluorocyclohexyl)morpholin-4-yl]methyl}-1,2,4-triazol-3-one

SMILES

[H][C@](C)(O[C@@]1([H])OCCN(CC2=NC(=O)N=N2)[C@@]1([H])C1([H])CCC([H])(F)CC1)C1=CC(=CC(=C1)C(F)(F)F)C(F)(F)F

InChI Identifier

InChI=1S/C23H25F7N4O3/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/h8-10,12-13,17,19-20H,2-7,11H2,1H3/t12-,13?,17?,19+,20-/m1/s1

InChI Key

RRFQFDMDZFLXRY-GTQYJQEFSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as trifluoromethylbenzenes. These are organofluorine compounds that contain a benzene ring substituted with one or more trifluoromethyl groups.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Trifluoromethylbenzenes

Direct Parent

Trifluoromethylbenzenes

Alternative Parents

Substituents

Trifluoromethylbenzene
Cyclohexyl halide
Morpholine
Oxazinane
Triazolone
1,2,4-triazolone
Azo compound
Carbonic acid derivative
Tertiary amine
Tertiary aliphatic amine
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Oxacycle
Azacycle
Organoheterocyclic compound
Acetal
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Organofluoride
Organohalogen compound
Alkyl fluoride
Organic nitrogen compound
Carbonyl group
Alkyl halide
Amine
Organopnictogen compound
Organic oxide
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Organoleptic Effects

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.008 g/L	ALOGPS
logP	4.46	ALOGPS
logP	4.66	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Basic)	3.57	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	75.85 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	116.22 m³·mol⁻¹	ChemAxon
Polarizability	47.07 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-000l-0080190000-ae51ee0ebd9221229019	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4l-0190000000-92619a435145ad241183	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-03di-1930000000-0adb1ed1be05de7ac5db	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-000f-0070930000-eebb8a1ab9883b64554e	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-052f-7090220000-3f32f80edf4acbdf7e0d	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0006-9120000000-97e6bd661da69efafaf4	Not Available	View Spectrum

Toxicity Profile

Toxicity Values

Toxicity Value	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Toxicity Rating	Reference
1525.0 Log mg/kg [860:2700]	Rat	LD50	oral	predicted	Not Available	Not Available

Toxicity / Toxin Class

Not Available

Mechanism of Toxicity

Not Available

Carcinogenicity (IARC Classification)

Not Available

Minimum Risk Level

Not Available

Symptoms

Not Available

Treatment

Not Available

Health Effects

Health Effect	Relationship	Direction	Reference

Exposure Sources

Source ID	Source	Sector	Reference
CEDs000249	Antiemetics and antinauseants?Antiemetics and antinauseants are synthetic compounds used to prevent or alleviate nausea and vomiting, often resulting from various medical conditions, treatments, or medications.	Healthcare, pharmaceuticals & veterinary products	Not Available

Pathways

1 pathwayPathway Source: PathBank

Aprepitant Drug Metabolism Action Pathway

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Substance-P receptor	P25103	Humans	Predicted (SEA)	Prediction Confidence Score 0.301 Applicability Domain 0.47 Statistical Significance 0.0316 Supporting Reference Compounds 122 E-value 246.315
Click to view 3D structure	Cytochrome P450 3A4	P08684	Humans	Predicted (SEA)	Prediction Confidence Score 0.265 Applicability Domain 0.47 Statistical Significance 0.4003 Supporting Reference Compounds 1538 E-value 3116.54
Click to view 3D structure	Neuromedin-K receptor	P29371	Humans	Predicted (SEA)	Prediction Confidence Score 0.252 Applicability Domain 0.47 Statistical Significance 0.0579 Supporting Reference Compounds 57 E-value 450.436
Click to view 3D structure	Substance-P receptor	Q5DUB1	Meriones unguiculatus	Predicted (SEA)	Prediction Confidence Score 0.249 Applicability Domain 0.47 Statistical Significance 7.50e-04 Supporting Reference Compounds 4 E-value 5.83869
Click to view 3D structure	G-protein coupled receptor 35	Q9HC97	Humans	Predicted (SEA)	Prediction Confidence Score 0.232 Applicability Domain 0.47 Statistical Significance 0.0767 Supporting Reference Compounds 115 E-value 597.259
Click to view 3D structure	G-protein coupled receptor 183	P32249	Humans	Predicted (SEA)	Prediction Confidence Score 0.232 Applicability Domain 0.47 Statistical Significance 0.0451 Supporting Reference Compounds 63 E-value 351.256
Click to view 3D structure	Sodium- and chloride-dependent glycine transporter 1	Q28039	Bos taurus	Predicted (SEA)	Prediction Confidence Score 0.229 Applicability Domain 0.229 Low confidence Statistical Significance 0.0045 Supporting Reference Compounds 1 E-value 35.3435
Click to view 3D structure	Voltage-gated inwardly rectifying potassium channel KCNH2	Q12809	Humans	Predicted (SEA)	Prediction Confidence Score 0.227 Applicability Domain 0.239 Low confidence Statistical Significance 0.7911 Supporting Reference Compounds 1498 E-value 6158.89
Click to view 3D structure	Melanin-concentrating hormone receptor 1	B6F061	Macaca fascicularis	Predicted (SEA)	Prediction Confidence Score 0.222 Applicability Domain 0.222 Low confidence Statistical Significance 0.0035 Supporting Reference Compounds 1 E-value 27.1694
Click to view 3D structure	C-C chemokine receptor type 2	P41597	Humans	Predicted (SEA)	Prediction Confidence Score 0.222 Applicability Domain 0.232 Low confidence Statistical Significance 0.106 Supporting Reference Compounds 72 E-value 825.435
Click to view 3D structure	G-protein coupled receptor 65	Q8IYL9	Humans	Predicted (SEA)	Prediction Confidence Score 0.221 Applicability Domain 0.47 Statistical Significance 0.0562 Supporting Reference Compounds 43 E-value 437.902
Click to view 3D structure	3-beta-hydroxysteroid-Delta(8),Delta(7)-isomerase	P70245	Mus musculus	Predicted (SEA)	Prediction Confidence Score 0.221 Applicability Domain 0.247 Low confidence Statistical Significance 0.0037 Supporting Reference Compounds 4 E-value 28.8042
Click to view 3D structure	Cytochrome P450 2D6	P10635	Humans	Predicted (SEA)	Prediction Confidence Score 0.217 Applicability Domain 0.238 Low confidence Statistical Significance 0.8199 Supporting Reference Compounds 1130 E-value 6383.01
Click to view 3D structure	C-C chemokine receptor type 5	P51681	Humans	Predicted (SEA)	Prediction Confidence Score 0.217 Applicability Domain 0.232 Low confidence Statistical Significance 0.1146 Supporting Reference Compounds 71 E-value 891.841
Click to view 3D structure	Ras-related C3 botulinum toxin substrate 3	P60763	Humans	Predicted (SEA)	Prediction Confidence Score 0.212 Applicability Domain 0.212 Low confidence Statistical Significance 0.0051 Supporting Reference Compounds 1 E-value 39.4696
Click to view 3D structure	D(2) dopamine receptor	P61169	Rat	Predicted (SEA)	Prediction Confidence Score 0.211 Applicability Domain 0.233 Low confidence Statistical Significance 0.4808 Supporting Reference Compounds 528 E-value 3742.91
Click to view 3D structure	D(3) dopamine receptor	P35462	Humans	Predicted (SEA)	Prediction Confidence Score 0.209 Applicability Domain 0.233 Low confidence Statistical Significance 0.6952 Supporting Reference Compounds 861 E-value 5411.92
Click to view 3D structure	Nuclear receptor subfamily 1 group I member 2	O75469	Humans	Predicted (SEA)	Prediction Confidence Score 0.207 Applicability Domain 0.287 Low confidence Statistical Significance 0.2699 Supporting Reference Compounds 146 E-value 2101.38
Click to view 3D structure	D(2) dopamine receptor	P14416	Humans	Predicted (SEA)	Prediction Confidence Score 0.206 Applicability Domain 0.233 Low confidence Statistical Significance 0.7647 Supporting Reference Compounds 1103 E-value 5952.82
Click to view 3D structure	Cholesteryl ester transfer protein	P11597	Humans	Predicted (SEA)	Prediction Confidence Score 0.206 Applicability Domain 0.232 Low confidence Statistical Significance 0.0248 Supporting Reference Compounds 18 E-value 193.455
Click to view 3D structure	3-beta-hydroxysteroid-Delta(8),Delta(7)-isomerase	Q15125	Humans	Predicted (SEA)	Prediction Confidence Score 0.206 Applicability Domain 0.247 Low confidence Statistical Significance 0.0701 Supporting Reference Compounds 27 E-value 545.957
Click to view 3D structure	Cytochrome P450 1A2	P05177	Humans	Predicted (SEA)	Prediction Confidence Score 0.206 Applicability Domain 0.232 Low confidence Statistical Significance 0.8508 Supporting Reference Compounds 793 E-value 6623.18
Click to view 3D structure	Cyclin-dependent kinase 2	P24941	Humans	Predicted (SEA)	Prediction Confidence Score 0.205 Applicability Domain 0.248 Low confidence Statistical Significance 0.813 Supporting Reference Compounds 1029 E-value 6329.45
Click to view 3D structure	Sigma non-opioid intracellular receptor 1	Q99720	Humans	Predicted (SEA)	Prediction Confidence Score 0.205 Applicability Domain 0.224 Low confidence Statistical Significance 0.6767 Supporting Reference Compounds 562 E-value 5268.37
Click to view 3D structure	Cytochrome P450 2C9	P11712	Humans	Predicted (SEA)	Prediction Confidence Score 0.202 Applicability Domain 0.213 Low confidence Statistical Significance 0.928 Supporting Reference Compounds 1245 E-value 7224.49