Details of the Active Pharmaceutical Ingredient (API)

General Information of API (ID: D00042)
Name
Aprepitant
Synonyms    Click to Show/Hide the Synonyms of This API
170729-80-3; MK-0869; MK-869; L-754030; UNII-1NF15YR6UY; C23H21F7N4O3; 1NF15YR6UY; CHEMBL1471; 5-[[(2R,3S)-2-[(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethoxy]-3-(4-fluorophenyl)morpholin-4-yl]methyl]-1,2-dihydro-1,2,4-triazol-3-one; CHEBI:499361; 5-(((2R,3S)-2-((R)-1-(3,5-bis(trifluoromethyl)phenyl)ethoxy)-3-(4-fluorophenyl)morpholino)methyl)-1H-1,2,4-triazol-3(2H)-one; MK0869; 5-[[(2R,3S)-2-[(1R)-1-[3,5-BIS(Trifluoromethyl)phenyl]ethoxy]-3-(4-fluorophenyl)-4-morpholinyl]methyl]-1,2-dihydro-3H-1,2,4-triazol-3-one; MK 869; 3-(((2R,3S)-2-((R)-1-(3,5-bis(trifluoromethyl)phenyl)ethoxy)-3-(4-fluorophenyl)morpholino)methyl)-1H-1,2,4-triazol-5(4H)-one; 5-[(2R,3S)-2-[(R)-1-(3,5-Bis-trifluoromethyl-phenyl)-ethoxy]-3-(4-fluoro-phenyl)-morpholin-4-ylmethyl]-2,4-dihydro-[1,2,4]triazol-3-one; MK 0869; Emend (TN); Aprepitant (MK-0869); aprepitantum; L 754030; Cinvanti; eMende; Aprepitant [USAN:INN:JAN]; Cinvanti (TN); aprepitant, form I; ONO-7436; aprepitant, form II; Aprepitant(MK-0869); (1R,2R,3R)-Aprepitant; Aprepitant (JAN/USP/INN); Aprepitant Related Compound A; cc-310; MLS006011068; SCHEMBL264924; GTPL3490; L-754,030; DTXSID3049047; AOB6779; EX-A212; HMS2090N12; HMS3714E16; HMS3884G05; 5-[2-[1-(3,5-Bis-trifluoromethyl-phenyl)-ethoxy]-3-(4-fluoro-phenyl)-morpholin-4-ylmethyl]-2,4-dihydro-[1,2,4]triazol-3-one; ONO 7436; ABP000600; BDBM50220136; NSC748825; ZINC27428713; AKOS015895498; AKOS015969344; ACN-037208; BCP9000312; CCG-220747; CCG-264854; CS-0487; DB00673; NSC-748825; SB18892; 3-(((2R,3S)-3-(p-Fluorophenyl)-2-(((alphaR)-alpha-methyl-3,5-bis(trifluoromethyl)benzyl)oxy)morpholino)methyl)-Delta(2)-1,2,4-triazolin-5-one; 3-(((2R,3S)-3-(p-Fluorophenyl)-2-(((alphaR)-alpha-methyl-3,5-bis(trifluoromethyl)benzyl)oxy)morpholino)methyl)-delta(sup 2)-1,2,4-triazolin-5-one; 5-{[(2R,3S)-2-{(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethoxy}-3-(4-fluorophenyl)morpholin-4-yl]methyl}-2,4-dihydro-3H-1,2,4-triazol-3-one; AS-14638; HY-10052; SMR002530053; Aprepitant (MK-0869, L-754030); Aprepitant,MK-0869, L-754030, Emend; C21555; D02968; W-5373; AB01274775-01; AB01274775_02; AB01275535-01; 729A803; SR-05000001531; Q-200647; SR-05000001531-1; BRD-K52827117-001-01-6; Aprepitant, United States Pharmacopeia (USP) Reference Standard; 3-[((2R,5-bis(trifluoromethyl)benzyl]oxy}morpholino)methyl]-.delta.2-1,2,4-triazolin-5-one; 3-[[(2R,3S)-2-[(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethoxy]-3-(4-fluorophenyl)morpholin-4-yl]methyl]-1,4-dihydro-1,2,4-triazol-5-one; 3-[2-{1-[3,5-di(trifluoromethyl)phenyl]ethoxy}-3-(4-fluorophenyl)-1,4-oxazinan-4-ylmethyl]-4,5-dihydro-1H-1,2,4-triazol-5-one; 3-{[(2R,3S)-2-[(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethoxy]-3-(4-fluorophenyl)morpholin-4-yl]methyl}-4,5-dihydro-1H-1,2,4-triazol-5-one; 321125-94-4; 3H-1,2,4-Triazol-3-one, 5-(((2R,3S)-2-((1R)-1-(3,5-bis(trifluoromethyl)phenyl)ethoxy)-3-(4-fluorophenyl)-4-morpholinyl)methyl)-1,2-dihydro-; 3H-1,2,4-Triazol-3-one, 5-((2-(1-(3,5-bis(trifluoromethyl)phenyl)ethoxy)-3-(4-fluorophenyl)-4-morpholinyl)methyl)-1,2-dihydro-, (2R-(2alpha(R*),3alpha))-; 3H-1,2,4-Triazol-3-one, 5-[[(2R,3S)-2-[(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethoxy]-3-(4-fluorophenyl)-4-morpholinyl]methyl]-1,2-dihydro-, rel-; 3H-1,4-Triazol-3-one, 5-[[(2R,3S)-2-[(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethoxy]-3-(4-fluorophenyl)-4-morpholinyl]methyl]-1,2-dihydro-; 5-(((2R,3S)-2-((R)-1-(3,5-bis(trifluoromethyl)phenyl)ethoxy)-3-(4-fluorophenyl)morpholino)methyl)-2H-1,2,4-triazol-3(4H)-one
Clinical Status
Approved
Disease Indication Functional nausea/vomiting ICD-11: DD90 [1]
PubChem CID
135413536
Formula
C23H21F7N4O3
Canonical SMILES
C[C@H](C1=CC(=CC(=C1)C(F)(F)F)C(F)(F)F)O[C@@H]2[C@@H](N(CCO2)CC3=NNC(=O)N3)C4=CC=C(C=C4)F
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
InChIKey
ATALOFNDEOCMKK-OITMNORJSA-N
   Click to Show/Hide the Molecular Data (Structure/Property) of This API
Structure
<iframe style="width: 300px; height: 300px;" frameborder="0" src="https://embed.molview.org/v1/?mode=balls&cid=135413536"></iframe>
3D MOL 2D MOL
Physicochemical Properties Molecular Weight 534.4 Topological Polar Surface Area 75.2
XlogP 4.2 Complexity 810
Heavy Atom Count 37 Rotatable Bond Count 6
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 12
Full List of Drug Formulations (DFMs) Containing This API
          Aprepitant 125 mg capsule Click to Show/Hide the Full List of Formulation(s):          3 Formulation(s)
             Drug Formulation 1 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Sodium lauryl sulfate; Sodium stearyl fumarate; Mannitol; Ferrosoferric oxide; Potassium hydroxide; Titanium dioxide; Water; Fd&c red no. 3; Poloxamer 407; Silicon dioxide; Tocophersolan; Gelatin, unspecified; Hydroxyethyl cellulose (140 mpa.s at 5%); Microcrystalline cellulose; Povidone, unspecified; Shellac
                   Dosage Form Oral Capsule
                   Company Glenmark Pharmaceutials
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Sodium lauryl sulfate DIG Info Solute carrier SLCO2B1 (Ki = 1.98 uM) [2]
Mannitol DIG Info Glycine receptor alpha-1 (EC50 = 12589.25 nM) [3]
Sodium stearyl fumarate DIG Info Leukemia K562 cells (IC50 = 20.2 ug.mL-1) [4]
FD&C red no. 3 DIG Info Phosphodiesterase 3A (IC50 = 0.092 uM) [5]
Poloxamer 407 DIG Info Albendazole monooxygenase (EC50 = 32.8 uM) [6]
Tocophersolan DIG Info Albendazole monooxygenase (EC50 = 28.3 uM) [6]
Silicon dioxide DIG Info Albendazole monooxygenase (Protein expression downregulation) [7]
             Drug Formulation 2 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Sodium lauryl sulfate; Fd&c blue no. 1; Ferrosoferric oxide; Propylene glycol; Sucrose; Titanium dioxide; Cellulose, microcrystalline; Gelatin; Hydroxypropyl cellulose (type h); Shellac
                   Dosage Form Oral Capsule
                   Company Sandoz
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
FD&C blue no. 1 DIG Info Solute carrier SLCO2B1 (Ki = 13 uM) [2]
Sodium lauryl sulfate DIG Info Solute carrier SLCO2B1 (Ki = 1.98 uM) [2]
Propylene glycol DIG Info Albendazole monooxygenase (Inhibition ratio < 20 %) [8]
             Drug Formulation 3 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Sodium lauryl sulfate; Ferric oxide red; Ferric oxide yellow; Sucrose; Titanium dioxide; Silicon dioxide; Gelatin, unspecified; Hydroxypropyl cellulose (1200000 mw); Microcrystalline cellulose
                   Dosage Form Oral Capsule
                   Company Merck Sharp & Dohme
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Sodium lauryl sulfate DIG Info Solute carrier SLCO2B1 (Ki = 1.98 uM) [2]
Silicon dioxide DIG Info Albendazole monooxygenase (Protein expression downregulation) [7]
          Aprepitant 40 mg capsule Click to Show/Hide the Full List of Formulation(s):          4 Formulation(s)
             Drug Formulation 1 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Sodium lauryl sulfate; Sodium stearyl fumarate; Mannitol; Ferric oxide yellow; Ferrosoferric oxide; Potassium hydroxide; Titanium dioxide; Water; Poloxamer 407; Silicon dioxide; Tocophersolan; Gelatin, unspecified; Hydroxyethyl cellulose (140 mpa.s at 5%); Microcrystalline cellulose; Povidone, unspecified; Shellac
                   Dosage Form Oral Capsule
                   Company Glenmark Pharmaceutials
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Sodium lauryl sulfate DIG Info Solute carrier SLCO2B1 (Ki = 1.98 uM) [2]
Mannitol DIG Info Glycine receptor alpha-1 (EC50 = 12589.25 nM) [3]
Sodium stearyl fumarate DIG Info Leukemia K562 cells (IC50 = 20.2 ug.mL-1) [4]
Poloxamer 407 DIG Info Albendazole monooxygenase (EC50 = 32.8 uM) [6]
Tocophersolan DIG Info Albendazole monooxygenase (EC50 = 28.3 uM) [6]
Silicon dioxide DIG Info Albendazole monooxygenase (Protein expression downregulation) [7]
             Drug Formulation 2 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Sodium lauryl sulfate; Ferrosoferric oxide; Propylene glycol; Sucrose; Titanium dioxide; Cellulose, microcrystalline; Gelatin; Hydroxypropyl cellulose (type h); Shellac
                   Dosage Form Oral Capsule
                   Company Sandoz
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Sodium lauryl sulfate DIG Info Solute carrier SLCO2B1 (Ki = 1.98 uM) [2]
Propylene glycol DIG Info Albendazole monooxygenase (Inhibition ratio < 20 %) [8]
             Drug Formulation 3 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Sodium lauryl sulfate; Ferric oxide yellow; Sucrose; Titanium dioxide; Silicon dioxide; Cellulose, microcrystalline; Gelatin; Hydroxypropyl cellulose
                   Dosage Form Oral Capsule
                   Company Rebel Distributors
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Sodium lauryl sulfate DIG Info Solute carrier SLCO2B1 (Ki = 1.98 uM) [2]
Silicon dioxide DIG Info Albendazole monooxygenase (Protein expression downregulation) [7]
             Drug Formulation 4 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Sodium lauryl sulfate; Ferric oxide yellow; Sucrose; Titanium dioxide; Silicon dioxide; Gelatin, unspecified; Hydroxypropyl cellulose (1200000 mw); Microcrystalline cellulose
                   Dosage Form Oral Capsule
                   Company Merck Sharp & Dohme
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Sodium lauryl sulfate DIG Info Solute carrier SLCO2B1 (Ki = 1.98 uM) [2]
Silicon dioxide DIG Info Albendazole monooxygenase (Protein expression downregulation) [7]
          Aprepitant 80 mg capsule Click to Show/Hide the Full List of Formulation(s):          4 Formulation(s)
             Drug Formulation 1 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Sodium lauryl sulfate; Sodium stearyl fumarate; Mannitol; Ferrosoferric oxide; Potassium hydroxide; Titanium dioxide; Water; Poloxamer 407; Silicon dioxide; Tocophersolan; Gelatin, unspecified; Hydroxyethyl cellulose (140 mpa.s at 5%); Microcrystalline cellulose; Povidone, unspecified; Shellac
                   Dosage Form Oral Capsule
                   Company Glenmark Pharmaceutials
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Sodium lauryl sulfate DIG Info Solute carrier SLCO2B1 (Ki = 1.98 uM) [2]
Mannitol DIG Info Glycine receptor alpha-1 (EC50 = 12589.25 nM) [3]
Sodium stearyl fumarate DIG Info Leukemia K562 cells (IC50 = 20.2 ug.mL-1) [4]
Poloxamer 407 DIG Info Albendazole monooxygenase (EC50 = 32.8 uM) [6]
Tocophersolan DIG Info Albendazole monooxygenase (EC50 = 28.3 uM) [6]
Silicon dioxide DIG Info Albendazole monooxygenase (Protein expression downregulation) [7]
             Drug Formulation 2 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Sodium lauryl sulfate; Ferrosoferric oxide; Propylene glycol; Sucrose; Titanium dioxide; Cellulose, microcrystalline; Gelatin; Hydroxypropyl cellulose (type h); Shellac
                   Dosage Form Oral Capsule
                   Company Sandoz
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Sodium lauryl sulfate DIG Info Solute carrier SLCO2B1 (Ki = 1.98 uM) [2]
Propylene glycol DIG Info Albendazole monooxygenase (Inhibition ratio < 20 %) [8]
             Drug Formulation 3 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Sodium lauryl sulfate; Sucrose; Titanium dioxide; Silicon dioxide; Cellulose, microcrystalline; Gelatin; Hydroxypropyl cellulose
                   Dosage Form Oral Capsule
                   Company Physicians Total Care
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Sodium lauryl sulfate DIG Info Solute carrier SLCO2B1 (Ki = 1.98 uM) [2]
Silicon dioxide DIG Info Albendazole monooxygenase (Protein expression downregulation) [7]
             Drug Formulation 4 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Sodium lauryl sulfate; Sucrose; Titanium dioxide; Silicon dioxide; Gelatin, unspecified; Hydroxypropyl cellulose (1200000 mw); Microcrystalline cellulose
                   Dosage Form Oral Capsule
                   Company Merck Sharp & Dohme
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Sodium lauryl sulfate DIG Info Solute carrier SLCO2B1 (Ki = 1.98 uM) [2]
Silicon dioxide DIG Info Albendazole monooxygenase (Protein expression downregulation) [7]
References
1 FDA label for approved aprepitant from the official website of the U.S. Food and Drug Administration.
2 Bacterial metabolism rescues the inhibition of intestinal drug absorption by food and drug additives. Proc Natl Acad Sci U S A. 2020 Jul 7;117(27):16009-16018.
3 Pharmacological property optimization for allosteric ligands: A medicinal chemistry perspective. Bioorg Med Chem Lett. 2017 Jun 1; 27(11):2239-2258.
4 Synthesis and evaluation of (-)-Massoialactone and analogues as potential anticancer and anti-inflammatory agents. Eur J Med Chem. 2014 Apr 9; 76:291-300.
5 The activities of drug inactive ingredients on biological targets. Science. 2020 Jul 24;369(6502):403-413.
6 Mediation of in vitro cytochrome p450 activity by common pharmaceutical excipients. Mol Pharm. 2013 Jul 1;10(7):2739-48.
7 Effects of commonly used excipients on the expression of CYP3A4 in colon and liver cells. Pharm Res. 2010 Aug;27(8):1703-12.
8 Pharmaceutical excipients inhibit cytochrome P450 activity in cell free systems and after systemic administration. Eur J Pharm Biopharm. 2008 Sep;70(1):279-88.

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