Details of the Active Pharmaceutical Ingredient (API)

General Information of API (ID: D01197)
Name
Larotrectinib
Synonyms    Click to Show/Hide the Synonyms of This API
Larotrectinib; LOXO-101; 1223403-58-4; (S)-N-(5-((R)-2-(2,5-difluorophenyl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-hydroxypyrrolidine-1-carboxamide; ARRY-470; LOXO 101; Larotrectinib free base; UNII-PF9462I9HX; LOXO101; PF9462I9HX; 1223403-58-4 (free base); (3S)-N-[5-[(2R)-2-(2,5-difluorophenyl)pyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-3-yl]-3-hydroxypyrrolidine-1-carboxamide; 1-Pyrrolidinecarboxamide, N-[5-[(2R)-2-(2,5-difluorophenyl)-1-pyrrolidinyl]pyrazolo[1,5-a]pyrimidin-3-yl]-3-hydroxy-, (3S)-; Vitrakvi; ARRY 470; 1-Pyrrolidinecarboxamide, N-(5-((2R)-2-(2,5-difluorophenyl)-1-pyrrolidinyl)pyrazolo(1,5-a)pyrimidin-3-yl)-3-hydroxy-, (3S)-; ARRY-470; larotrectinib; Larotrectinib (USAN/INN); Larotrectinib [USAN:INN]; ARRY470; AMY264; GTPL8909; SCHEMBL2241012; CHEMBL3889654; BDBM136597; BCP16262; EX-A1981; MFCD28902192; NSC785570; NSC801004; Larotrectinib (LOXO-101 free base); example 14 [US8865698 B2]; ZINC118399834; BAY2757556; CS-5722; DB14723; NSC-785570; NSC-801004; BAY-2757556; AS-35231; HY-12866; J3.628.138C; D11137; US8865698, 14; Q27081513; ARRY-470;ARRY 470 : LOXO-101; LOXO101; Larotrectinib; ARRY470;ARRY-470;ARRY 470;LOXO 101;LOXO101;Larotrectinib; (3S)-N-(5-((2R)-2-(2,5-Difluorophenyl)pyrrolidin-1-yl)pyrazolo(1,5-a)pyrimidin-3-yl)-3-hydroxypyrrolidine- 1-carboxamide; (S)-N-(5 -((R)-2-(2,5-difluorophenyl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-hydroxypyrrolidine-1-carboxamide; (S)-N-(5-((R)-2-(2,5-difluorophenyl)pyrrolidin -1-yl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-hydroxypyrrolidine-1-carboxamide; (S)-N-(5-((R)-2-(2,5-difluorophenyl)pyrrolidin-1-yl)-pyrazolo[1,5-a]pyrimidin-3-yl)-3-hydroxypyrrolidine-1-carboxamide; (S)-N-(5-((R)-2-(2,5-difluorophenyl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidin-3 yl)-3-hydroxypyrrolidine-1-carboxamide
Clinical Status
Approved
PubChem CID
46188928
Formula
C21H22F2N6O2
Canonical SMILES
C1C[C@@H](N(C1)C2=NC3=C(C=NN3C=C2)NC(=O)N4CC[C@@H](C4)O)C5=C(C=CC(=C5)F)F
InChI
1S/C21H22F2N6O2/c22-13-3-4-16(23)15(10-13)18-2-1-7-28(18)19-6-9-29-20(26-19)17(11-24-29)25-21(31)27-8-5-14(30)12-27/h3-4,6,9-11,14,18,30H,1-2,5,7-8,12H2,(H,25,31)/t14-,18+/m0/s1
InChIKey
NYNZQNWKBKUAII-KBXCAEBGSA-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=46188928"></iframe>
3D MOL is unavailable 2D MOL
Physicochemical Properties Molecular Weight 428.4 Topological Polar Surface Area 86
XlogP 1.7 Complexity 659
Heavy Atom Count 31 Rotatable Bond Count 3
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 7
Full List of Drug Formulations (DFMs) Containing This API
          Larotrectinib 20 mg/ml solution 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
Purified Water; Hydroxypropyl Betadex; Sucrose; Glycerin; Sorbitol; Citric Acid; Sodium Phosphate; Sodium Citrate Dihydrate; Propylene Glycol; Flavoring; Methylparaben; Potassium Sorbate
                   Dosage Form Solution
                   Company Bayer Healthcare Pharmaceuticals ; Loxo Oncology;
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
methylparaben DIG Info Carbonic anhydrase VII (Ki = 780 nM) [1]
Kyselina citronova DIG Info Perilipin-1 (IC50 = 3708 nM) [2]
Propylene glycol DIG Info Albendazole monooxygenase (Inhibition ratio < 20 %) [3]
          Larotrectinib 100 mg capsule 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
Gelatin; Titanium Dioxide; Edible Ink
                   Dosage Form Capsule
                   Company Bayer Healthcare Pharmaceuticals ; Loxo Oncology
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Gelatin DIG Info Mephenytoin 4-hydroxylase (EC50 = 20.5 uM) [4]
          Larotrectinib 25 mg capsule 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
Gelatin; Titanium Dioxide; Edible Ink
                   Dosage Form Capsule
                   Company Bayer Healthcare Pharmaceuticals ; Loxo Oncology
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Gelatin DIG Info Mephenytoin 4-hydroxylase (EC50 = 20.5 uM) [4]
References
1 Mono-/dihydroxybenzoic acid esters and phenol pyridinium derivatives as inhibitors of the mammalian carbonic anhydrase isoforms I, II, VII, IX, XII and XIV. Bioorg Med Chem. 2013 Mar 15; 21(6):1564-9.
2 PubChem BioAssay data set.
3 Pharmaceutical excipients inhibit cytochrome P450 activity in cell free systems and after systemic administration. Eur J Pharm Biopharm. 2008 Sep;70(1):279-88.
4 Mediation of in vitro cytochrome p450 activity by common pharmaceutical excipients. Mol Pharm. 2013 Jul 1;10(7):2739-48.

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