APREPITANT

Search structure
Trade Names:
Synonyms:
Status: Approved (2003)
Entry Type: Small molecule
Molecule Category: UNKNOWN
ATC: A04AD12
UNII: 1NF15YR6UY

Structure
InChI Key ATALOFNDEOCMKK-OITMNORJSA-N
Smile C[C@@H](O[C@H]1OCCN(Cc2n[nH]c(=O)[nH]2)[C@H]1c1ccc(F)cc1)c1cc(C(F)(F)F)cc(C(F)(F)F)c1
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

Physicochemical Descriptors

Property Name Value
Molecular Formula C23H21F7N4O3
Molecular Weight 534.43
AlogP 4.95
Hydrogen Bond Acceptor 5.0
Hydrogen Bond Donor 2.0
Number of Rotational Bond 6.0
Polar Surface Area 83.24
Molecular species NEUTRAL
Aromatic Rings 3.0
Heavy Atoms 37.0

Pharmacology

Action Mechanism of Action Reference
ANTAGONIST Neurokinin 1 receptor antagonist DailyMed
Primary Target
NK1 receptor
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Cytochrome P450 Cytochrome P450 family 3 Cytochrome P450 family 3A Cytochrome P450 3A4
- 46 - - -
Membrane receptor Family A G protein-coupled receptor Peptide receptor (family A GPCR) Short peptide receptor (family A GPCR) Neurokinin receptor
- 0-0 8 0-3 -

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Nausea 4 D009325 ClinicalTrials
Postoperative Nausea and Vomiting 4 D020250 ClinicalTrials
Carcinoma, Non-Small-Cell Lung 3 D002289 ClinicalTrials
Multiple Myeloma 3 D009101 ClinicalTrials
Depressive Disorder, Major 3 D003865 ClinicalTrials
Neoplasms, Germ Cell and Embryonal 3 D009373 ClinicalTrials
Vomiting 3 D014839 ClinicalTrials
Severe Acute Respiratory Syndrome 2 D045169 ClinicalTrials
Leukemia, Myeloid, Acute 2 D015470 ClinicalTrials
Pruritus 2 D011537 ClinicalTrials
Gastroparesis 2 D018589 ClinicalTrials
Cocaine-Related Disorders 2 D019970 ClinicalTrials
Alcoholism 2 D000437 ClinicalTrials
Pain 2 D010146 ClinicalTrials
Marijuana Abuse 2 D002189 ClinicalTrials
HIV Infections 1 D015658 ClinicalTrials
Heroin Dependence 1 D006556 ClinicalTrials
Glioblastoma 1 D005909 ClinicalTrials
Opioid-Related Disorders 1 D009293 ClinicalTrials

Related Entries

MCS

Scaffolds

Side Effects from Label

Side effects Relative Frequency (%) Labels
Skin and subcutaneous tissue disorders Alopecia 24.0
Skin and subcutaneous tissue disorders Alopecia 22.2
General disorders and administration site conditions Asthenia 21.9
General disorders and administration site conditions Fatigue 21.9
General disorders and administration site conditions Asthenia 21.5
General disorders and administration site conditions Fatigue 21.5
Gastrointestinal disorders Constipation 18.0
Nervous system disorders Headache 16.4
Gastrointestinal disorders Nausea 12.7
Skin and subcutaneous tissue disorders Alopecia 12.4
Gastrointestinal disorders Constipation 12.3
Skin and subcutaneous tissue disorders Alopecia 11.9
Gastrointestinal disorders Nausea 11.8
Gastrointestinal disorders Hiccups 10.8
Investigations Body temperature increased 10.6
Gastrointestinal disorders Diarrhoea 10.3
General disorders and administration site conditions Decreased appetite 10.1
General disorders and administration site conditions Decreased appetite 9.5
Blood and lymphatic system disorders Neutropenia 8.9
Nervous system disorders Headache 8.7
Gastrointestinal disorders Nausea 8.6
Gastrointestinal disorders Constipation 8.5
Nervous system disorders Headache 8.5
Gastrointestinal disorders Nausea 8.5
Gastrointestinal disorders Dyspepsia 8.4
Blood and lymphatic system disorders Neutropenia 8.4
Skin and subcutaneous tissue disorders Pruritus 8.4
Gastrointestinal disorders Constipation 7.6
Skin and subcutaneous tissue disorders Pruritus 7.6
Gastrointestinal disorders Diarrhoea 7.5
Gastrointestinal disorders Nausea 7.5
General disorders and administration site conditions Decreased appetite 7.2
Gastrointestinal disorders Nausea 7.1
Nervous system disorders Headache 6.5
Gastrointestinal disorders Diarrhoea 6.3
General disorders and administration site conditions Decreased appetite 6.2
Investigations Body temperature increased 5.9
General disorders and administration site conditions Decreased appetite 5.8
Gastrointestinal disorders Flatulence 5.8
Blood and lymphatic system disorders Neutropenia 5.8
Vascular disorders Hypotension 5.7
Gastrointestinal disorders Hiccups 5.6
Nervous system disorders Insomnia 5.6
Blood and lymphatic system disorders Neutropenia 5.6
Gastrointestinal disorders Diarrhoea 5.5
Gastrointestinal disorders Dyspepsia 5.3
Gastrointestinal disorders Stomatitis 5.3
Nervous system disorders Headache 5.0
Gastrointestinal disorders Dyspepsia 4.9
Gastrointestinal disorders Hiccups 4.6
Vascular disorders Hypotension 4.6
Respiratory, thoracic and mediastinal disorders Mediastinal disorder 4.6
Cardiac disorders Bradycardia 4.4
Gastrointestinal disorders Stomatitis 4.4
Blood and lymphatic system disorders Anaemia 4.3
General disorders and administration site conditions Decreased appetite 4.3
Cardiac disorders Dizziness 4.2
Gastrointestinal disorders Gastritis 4.2
Gastrointestinal disorders Flatulence 4.1
Nervous system disorders Insomnia 4.1
Gastrointestinal disorders Epigastric discomfort 4.0
Cardiac disorders Bradycardia 3.9
Gastrointestinal disorders Vomiting 3.9
Ear and labyrinth disorders Tinnitus 3.8
General disorders and administration site conditions Asthenia 3.7
Nervous system disorders Insomnia 3.7
Ear and labyrinth disorders Tinnitus 3.7
General disorders and administration site conditions Mucosal inflammation 3.5
General disorders and administration site conditions Asthenia 3.4
Cardiac disorders Dizziness 3.4
Nervous system disorders Insomnia 3.3
Vascular disorders Hypertension 3.2
Infections and infestations Urinary tract infection 3.2
Gastrointestinal disorders Epigastric discomfort 3.1
Gastrointestinal disorders Gastritis 3.1
Nervous system disorders Insomnia 3.1
Blood and lymphatic system disorders Neutropenia 3.1
Blood and lymphatic system disorders Anaemia 3.0
General disorders and administration site conditions Hot flush 3.0
Respiratory, thoracic and mediastinal disorders Laryngeal pain 3.0
Reproductive system and breast disorders Menopausal symptoms 3.0
General disorders and administration site conditions Asthenia 2.9
General disorders and administration site conditions Fatigue 2.9
Gastrointestinal disorders Hiccups 2.9
Nervous system disorders Insomnia 2.9
Respiratory, thoracic and mediastinal disorders Mediastinal disorder 2.9
Blood and lymphatic system disorders Neutropenia 2.9
Investigations Alanine aminotransferase increased 2.8
Nervous system disorders Insomnia 2.6
General disorders and administration site conditions Mucosal inflammation 2.5
Gastrointestinal disorders Vomiting 2.5
Respiratory, thoracic and mediastinal disorders Laryngeal pain 2.3
Infections and infestations Urinary tract infection 2.3
Gastrointestinal disorders Constipation 2.2
Nervous system disorders Headache 2.2
Vascular disorders Hypertension 2.1
Nervous system disorders Insomnia 2.1
Gastrointestinal disorders Constipation 2.0
General disorders and administration site conditions Decreased appetite 2.0
Nervous system disorders Headache 1.8
General disorders and administration site conditions Asthenia 1.6
General disorders and administration site conditions Fatigue 1.6
Investigations Alanine aminotransferase increased 1.5
General disorders and administration site conditions Asthenia 1.5
Gastrointestinal disorders Dyspepsia 1.5
General disorders and administration site conditions Asthenia 1.4
General disorders and administration site conditions Fatigue 1.4
General disorders and administration site conditions Hot flush 1.4
Reproductive system and breast disorders Menopausal symptoms 1.4
Investigations Alanine aminotransferase increased 1.1
Investigations Aspartate aminotransferase increased 1.1
Gastrointestinal disorders Diarrhoea 1.1
Gastrointestinal disorders Eructation 1.0
Investigations Aspartate aminotransferase increased 0.9
General disorders and administration site conditions Asthenia 0.9
Gastrointestinal disorders Diarrhoea 0.9
General disorders and administration site conditions Fatigue 0.9
Gastrointestinal disorders Dyspepsia 0.8
Gastrointestinal disorders Dyspepsia 0.7
Blood and lymphatic system disorders Anaemia 0.6
Psychiatric disorders Anxiety 0.5
General disorders and administration site conditions Decreased appetite 0.5
Gastrointestinal disorders Hiccups 0.5
Gastrointestinal disorders Dyspepsia 0.4
General disorders and administration site conditions Asthenia 0.2
Gastrointestinal disorders Hiccups 0.2
Gastrointestinal disorders Eructation 0.1

Adverse Reactions

SOC By Demographic Distribution
System Organ Classification (SOC)
Relative Frequency (%)
General disorders and administration site conditions
15.83
Gastrointestinal disorders
11.81
Investigations
9.53
Nervous system disorders
7.91
Respiratory, thoracic and mediastinal disorders
7.59
Blood and lymphatic system disorders
5.54
Skin and subcutaneous tissue disorders
5.34
Vascular disorders
4.9
Metabolism and nutrition disorders
4.53
Injury, poisoning and procedural complications
4.3
Cardiac disorders
3.81
Musculoskeletal and connective tissue disorders
2.85
Infections and infestations
2.23
Immune system disorders
2.17
Neoplasms benign, malignant and unspecified (incl cysts and polyps)
2.17
Psychiatric disorders
2.11

Cross References

Resources Reference
CAS NUMBER 170729-80-3
ChEBI 499361
ChEMBL CHEMBL1471
DrugBank DB00673
DrugCentral 230
EPA CompTox DTXSID3049047
FDA SRS 1NF15YR6UY
Human Metabolome Database HMDB0014811
Guide to Pharmacology 3490
KEGG D02968
PDB GBQ
PubChem 135413536
SureChEMBL SCHEMBL264924
ZINC ZINC000027428713
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