Details of the Active Pharmaceutical Ingredient (API)

General Information of API (ID: D00605)
Name
Rolapitant
Synonyms    Click to Show/Hide the Synonyms of This API
Rolapitant; 552292-08-7; Sch 619734; Varubi; SCH-619734; UNII-NLE429IZUC; Rolapitant free base; NLE429IZUC; 5552292-08-7 (free base); (5S,8S)-8-(((R)-1-(3,5-bis(trifluoromethyl)phenyl)ethoxy)methyl)-8-phenyl-1,7-diazaspiro[4.5]decan-2-one; 914462-92-3; Varubi (TN); (5S,8S)-8-[[(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethoxy]methyl]-8-phenyl-1,9-diazaspiro[4.5]decan-2-one; Rolapitant [USAN:INN]; Varuby; Rolapitant (USAN/INN); Rolapitant(sch619734); SCHEMBL354305; GTPL5749; CHEMBL3707331; CHEBI:90908; DTXSID90203740; BCP09609; EX-A1288; ZINC3816514; MFCD23105917; ACN-055567; CCG-269691; CS-6387; DB09291; PB37313; SB20554; AC-30924; HY-14751; QC-11703; D10742; Q-4560; (5S,8S)-8-({(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethoxy}methyl)-8-phenyl-1,7-diazaspiro[4.5]decan-2-one
Clinical Status
Approved
Disease Indication Functional nausea/vomiting ICD-11: DD90 [1]
PubChem CID
10311306
Formula
C25H26F6N2O2
Canonical SMILES
C[C@H](C1=CC(=CC(=C1)C(F)(F)F)C(F)(F)F)OC[C@]2(CC[C@]3(CCC(=O)N3)CN2)C4=CC=CC=C4
InChI
1S/C25H26F6N2O2/c1-16(17-11-19(24(26,27)28)13-20(12-17)25(29,30)31)35-15-23(18-5-3-2-4-6-18)10-9-22(14-32-23)8-7-21(34)33-22/h2-6,11-13,16,32H,7-10,14-15H2,1H3,(H,33,34)/t16-,22-,23-/m1/s1
InChIKey
FIVSJYGQAIEMOC-ZGNKEGEESA-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=10311306"></iframe>
3D MOL 2D MOL
Physicochemical Properties Molecular Weight 500.5 Topological Polar Surface Area 50.4
XlogP 4.4 Complexity 731
Heavy Atom Count 35 Rotatable Bond Count 5
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 9
Full List of Drug Formulations (DFMs) Containing This API
          Rolapitant Hydrochloride eq 90mg base tablet Click to Show/Hide the Full List of Formulation(s):          1 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
Colloidal Silicon Dioxide; Croscarmellose Sodium; Lactose Monohydrate; Magnesium Stearate; Microcrystalline Cellulose; Povidone; Pregelatinized Starch; Fd&C Blue No. 2-Indigo Carmine Lake; Polyethylene Glycol; Polysorbate 80; Polyvinyl Alcohol; Talc; Titanium Dioxide
                   Dosage Form Tablet
                   Company Tersera
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
FD&C blue no. 2 DIG Info Adenosine receptor A3 (IC50 = 1 uM) [2]
Polysorbate 80 DIG Info Prostaglandin G/H synthase 1 (IC50 = 1 uM) [2]
Polyvinyl alcohol DIG Info Debrisoquine 4-hydroxylase (EC50 = 354.8 uM) [3]
Povidone DIG Info Cholesterol 25-hydroxylase (IC50 = 78.3 uM) [3]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
Carmellose sodium DIG Info Albendazole monooxygenase (Protein expression upregulation) [4]
Polyethylene glycol 4000 DIG Info Albendazole monooxygenase (Inhibition ratio < 40 %) [5]
Pregelatinized starch DIG Info Multidrug resistance protein 1 (Protein expression downregulation) [4]
          Rolapitant 90 mg tablet Click to Show/Hide the Full List of Formulation(s):          1 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
Lactose monohydrate; Magnesium stearate; Croscarmellose sodium; Silicon dioxide; Microcrystalline cellulose; Povidone, unspecified; Starch, corn
                   Dosage Form Oral Tablet
                   Company TESARO
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
Carmellose sodium DIG Info Albendazole monooxygenase (Protein expression upregulation) [4]
Silicon dioxide DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
          Rolapitant Hydrochloride eq 166.5mg base/92.5ml Emulsion Click to Show/Hide the Full List of Formulation(s):          1 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
Dibasic Sodium Phosphate Anhydrous; Medium Chain Triglycerides; Polyoxyl 15 Hydroxystearate; Sodium Chloride; Soybean Oil; Water For Injection
                   Dosage Form Emulsion
                   Company Tersera
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Polyoxyl 15 hydroxystearate DIG Info Albendazole monooxygenase (EC50 = 88.3 uM) [3]
Medium-chain triglyceride DIG Info Colon cancer Caco-2 cells (Inhibition ratio > 36 %) [6]
References
1 FDA label for approved rolapitant from the official website of the U.S. Food and Drug Administration.
2 The activities of drug inactive ingredients on biological targets. Science. 2020 Jul 24;369(6502):403-413.
3 Mediation of in vitro cytochrome p450 activity by common pharmaceutical excipients. Mol Pharm. 2013 Jul 1;10(7):2739-48.
4 Effects of commonly used excipients on the expression of CYP3A4 in colon and liver cells. Pharm Res. 2010 Aug;27(8):1703-12.
5 Pharmaceutical excipients inhibit cytochrome P450 activity in cell free systems and after systemic administration. Eur J Pharm Biopharm. 2008 Sep;70(1):279-88.
6 Interactions between human multidrug resistance related protein (MRP2; ABCC2) and excipients commonly used in self-emulsifying drug delivery systems (SEDDS). Int J Pharm. 2013 Apr 15;447(1-2):192-8.

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