Details of the Active Pharmaceutical Ingredient (API)

General Information of API (ID: D01146)
Name
Ibrutinib
Synonyms    Click to Show/Hide the Synonyms of This API
Ibrutinib; 936563-96-1; PCI-32765; IMBRUVICA; PCI 32765; Ibrutinib (PCI-32765); PCI-32765 (Ibrutinib); UNII-1X70OSD4VX; CRA-032765; Pc-32765; 1X70OSD4VX; (R)-1-(3-(4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)piperidin-1-yl)prop-2-en-1-one; CHEBI:76612; PCI32765; 1-[(3R)-3-[4-Amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-1-piperidinyl]-2-propen-1-one; 1-[(3R)-3-[4-amino-3-(4-phenoxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]piperidin-1-yl]prop-2-en-1-one; 1-{(3R)-3-[4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]piperidin-1-yl}prop-2-en-1-one; (R)-1-(3-(4-Amino-3-(4-phenoxyphenyl)-1H-pyrazolo-[3,4-d]pyrimidin-1-yl)piperidin-1-yl)prop-2-en-1-one; (R)-1-(3-(4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)piperidin-1-yl)prop-2-en-1-one.; 2-Propen-1-one, 1-((3R)-3-(4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo(3,4-d)pyrimidin-1-yl)-1-piperidinyl)-; Ibrutinib [USAN:INN]; ibrutinibum; JNJ 02; Imbruvica (TN); 1-[(3R)-3-[4-Amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]piperidin-1-yl]prop-2-en-1-one; 2-Propen-1-one, 1-[(3R)-3-[4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-1-piperidinyl]-; CRA 032765; PCI-32765-00; Ibrutinib (JAN/USAN); Ibrutinib/PCI-32765; Ibrutinib (PCI32765); Imbruvica; PCI-32765; PCI-32765(Ibrutinib); MLS006010041; SCHEMBL201859; GTPL6912; CHEMBL1873475; HSDB 8260; DTXSID60893450; EX-A066; AMY27873; AOB87789; ABP000965; BDBM50357312; MFCD20261150; NSC800769; ZINC35328014; AKOS022185476; ACN-030256; DB09053; EBD2165770; EX-5960; NSC-800769; QC-4573; SB14736; NCGC00187912-01; NCGC00187912-02; NCGC00187912-03; NCGC00187912-12; 1-((3R)-3-(4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo(3,4-d)pyrimidin-1-yl)piperidin-1- yl)prop-2-en-1-one; AC-26942; HY-10997; SMR004701213; AB0008168; SW218096-2; X7513; D10223; S-7810; A1-01649; J-523872; Q5984881; (R)-3-(4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)piperidin-1-ylprop-2-en-1-one; 1-((R)-3-(4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)piperidin-1-yl)prop-2-en-1-one; 1-[(3R)-3-[4-Amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-1-piperidinyl]-2-propen-1-one1-[(3R)-3-[4-AMino-3-(4-phenoxyphenyl)pyrazolo[3, 4-d]pyriMidin-1-yl]; 1-[(3R)-3-[4-Amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]piperidin-1-yl]-2-propen-1-one; 1-[(3R)-3-[4-Amino-3-(4-phenoxyphenyl)pyrazolo[3, 4-d]pyrimidin-1-yl]piperidin-1-yl]prop-2-en-1-one; IbrutinibCI-32765mbruvica(R)-1-(3-(4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)piperidin-1-yl)prop-2-en-1-one; piperidin-1-yl]prop-2-en-1-one1-{3-[4-AMino-3-(4-phenoxy-phenyl)-pyrazolo[3,4-d]pyriMidin-1-yl]-piperidin-1-yl}-propenone
Clinical Status
Approved
PubChem CID
24821094
Formula
C25H24N6O2
Canonical SMILES
C=CC(=O)N1CCC[C@H](C1)N2C3=NC=NC(=C3C(=N2)C4=CC=C(C=C4)OC5=CC=CC=C5)N
InChI
1S/C25H24N6O2/c1-2-21(32)30-14-6-7-18(15-30)31-25-22(24(26)27-16-28-25)23(29-31)17-10-12-20(13-11-17)33-19-8-4-3-5-9-19/h2-5,8-13,16,18H,1,6-7,14-15H2,(H2,26,27,28)/t18-/m1/s1
InChIKey
XYFPWWZEPKGCCK-GOSISDBHSA-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=24821094"></iframe>
3D MOL is unavailable 2D MOL
Physicochemical Properties Molecular Weight 440.5 Topological Polar Surface Area 99.2
XlogP 3.6 Complexity 678
Heavy Atom Count 33 Rotatable Bond Count 5
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 6
Full List of Drug Formulations (DFMs) Containing This API
          Ibrutinib 280mg 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; Sodium Lauryl Sulfate; Ferrosoferric Oxide; Polyvinyl Alcohol; Polyethylene Glycol; Red Iron Oxide; Talc; Titanium Dioxide
                   Dosage Form Tablet
                   Company Pharmacyclics
                   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) [1]
Polyvinyl alcohol DIG Info Debrisoquine 4-hydroxylase (EC50 = 354.8 uM) [2]
Povidone DIG Info Cholesterol 25-hydroxylase (IC50 = 78.3 uM) [2]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [3]
Carmellose sodium DIG Info Albendazole monooxygenase (Protein expression upregulation) [3]
Polyethylene glycol 4000 DIG Info Albendazole monooxygenase (Inhibition ratio < 40 %) [4]
          Ibrutinib 140mg 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; Sodium Lauryl Sulfate; Ferrosoferric Oxide; Polyvinyl Alcohol; Polyethylene Glycol; Talc; Titanium Dioxide; Yellow Iron Oxide
                   Dosage Form Tablet
                   Company Pharmacyclics
                   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) [1]
Polyvinyl alcohol DIG Info Debrisoquine 4-hydroxylase (EC50 = 354.8 uM) [2]
Povidone DIG Info Cholesterol 25-hydroxylase (IC50 = 78.3 uM) [2]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [3]
Carmellose sodium DIG Info Albendazole monooxygenase (Protein expression upregulation) [3]
Polyethylene glycol 4000 DIG Info Albendazole monooxygenase (Inhibition ratio < 40 %) [4]
          Ibrutinib 560mg 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; Sodium Lauryl Sulfate; Polyvinyl Alcohol; Polyethylene Glycol; Red Iron Oxide; Talc; Titanium Dioxide; Yellow Iron Oxide
                   Dosage Form Tablet
                   Company Pharmacyclics
                   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) [1]
Polyvinyl alcohol DIG Info Debrisoquine 4-hydroxylase (EC50 = 354.8 uM) [2]
Povidone DIG Info Cholesterol 25-hydroxylase (IC50 = 78.3 uM) [2]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [3]
Carmellose sodium DIG Info Albendazole monooxygenase (Protein expression upregulation) [3]
Polyethylene glycol 4000 DIG Info Albendazole monooxygenase (Inhibition ratio < 40 %) [4]
          Ibrutinib 420mg 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; Sodium Lauryl Sulfate; Ferrosoferric Oxide; Polyvinyl Alcohol; Talc; Titanium Dioxide; Yellow Iron Oxide
                   Dosage Form Tablet
                   Company Pharmacyclics
                   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) [1]
Polyvinyl alcohol DIG Info Debrisoquine 4-hydroxylase (EC50 = 354.8 uM) [2]
Povidone DIG Info Cholesterol 25-hydroxylase (IC50 = 78.3 uM) [2]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [3]
Carmellose sodium DIG Info Albendazole monooxygenase (Protein expression upregulation) [3]
          Ibrutinib 70mg 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
Croscarmellose Sodium; Magnesium Stearate; Microcrystalline Cellulose; Sodium Lauryl Sulfate; Gelatin; Titanium Dioxide; Black Ink; Yellow Iron Oxide
                   Dosage Form Capsule
                   Company Pharmacyclics
                   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) [1]
Gelatin DIG Info Mephenytoin 4-hydroxylase (EC50 = 20.5 uM) [2]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [3]
Carmellose sodium DIG Info Albendazole monooxygenase (Protein expression upregulation) [3]
          Ibrutinib 140mg 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
Croscarmellose Sodium; Magnesium Stearate; Microcrystalline Cellulose; Sodium Lauryl Sulfate; Gelatin; Titanium Dioxide; Black Ink
                   Dosage Form Capsule
                   Company Pharmacyclics
                   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) [1]
Gelatin DIG Info Mephenytoin 4-hydroxylase (EC50 = 20.5 uM) [2]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [3]
Carmellose sodium DIG Info Albendazole monooxygenase (Protein expression upregulation) [3]
References
1 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.
2 Mediation of in vitro cytochrome p450 activity by common pharmaceutical excipients. Mol Pharm. 2013 Jul 1;10(7):2739-48.
3 Effects of commonly used excipients on the expression of CYP3A4 in colon and liver cells. Pharm Res. 2010 Aug;27(8):1703-12.
4 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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