Details of the Active Pharmaceutical Ingredient (API)

General Information of API (ID: D00337)
Name
Itraconazole
Synonyms    Click to Show/Hide the Synonyms of This API
Oriconazole; 84625-61-6; Sporanox; Itrizole (TN); Sporanox (TN); ITCZ; Itraconazole (Sporanox); Itraconazol [Spanish]; Itraconazolum [Latin]; CHEMBL22587; C35H38Cl2N8O4; cis-Itraconazole; CHEBI:6076; 2-butan-2-yl-4-[4-[4-[4-[[(2R,4S)-2-(2,4-dichlorophenyl)-2-(1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]piperazin-1-yl]phenyl]-1,2,4-triazol-3-one; ITZ; DSSTox_CID_3180; DSSTox_RID_76908; DSSTox_GSID_23180; 1-(butan-2-yl)-4-{4-[4-(4-{[(2R,4S)-2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)piperazin-1-yl]phenyl}-4,5-dihydro-1H-1,2,4-triazol-5-one; 2-(butan-2-yl)-4-{4-[4-(4-{[(2R,4S)-2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)piperazin-1-yl]phenyl}-2,4-dihydro-3H-1,2,4-triazol-3-one; 4-[4-[4-[4-[[(2R,4S)-2-(2,4-dichlorophenyl)-2-(1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]piperazin-1-yl]phenyl]-2-sec-butyl-1,2,4-triazol-3-one; CAS-84625-61-6; R-51211; Intraconazole; Sporanox(TM); NCGC00018268-03; 4-(4-{4-[4-({[(2R,4S)-2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methyl}oxy)phenyl]piperazin-1-yl}phenyl)-2-(1-methylpropyl)-2,4-dihydro-3H-1,2,4-triazol-3-one; R51211; Itraconazole & Nyotran; Itraconazole (JP17/USP); SCHEMBL23934; 84604-65-9; MLS006011958; DTXSID3023180; GTPL11426; Pharmakon1600-01505756; Tox21_110854; 2485AH; AC-542; BDBM50127138; CI0042; MFCD00941396; NSC759239; s2476; AKOS015842738; AKOS015961385; Tox21_110854_1; CCG-270391; DB01167; KS-1268; MCULE-2446846552; NE57775; NSC-759239; NCGC00274068-01; NCGC00274068-02; NCGC00274068-07; 4-(4-(4-(4-(((2R,4S)-2-((1H-1,2,4-triazol-1-yl)methyl)-2-(2,4-dichlorophenyl)-1,3-dioxolan-4-yl)methoxy)phenyl)piperazin-1-yl)phenyl)-2-(sec-butyl)-2,4-dihydro-3H-1,2,4-triazol-3-one; 873066-43-4; HY-17514; SMR001827898; Itraconazole & Nyotran(Liposomal Nystatin); SBI-0206914.P001; AB0012897; SW219756-1; Itraconazole 2.0 mg/ml in Dimethyl Sulfoxide; D00350; 24236-EP2281816A1; 24236-EP2314590A1; AB01274818-01; AB01274818_02; AB01274818_03; Q411229; BRD-A23067620-001-01-7; 3H-1,2,4-Triazol-3-one, 4-[4-[4-[4-[[2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]-1-pipera-zinyl]phenyl]-2,4-dihydro-2-(1-methylpropyl); 4-[4-[4-[4-[[(2R,4S)-2-(2,4-Dichlorophenyl)-2-(1H-1,2,4-triazole-1-ylmethyl)-1,3-dioxolane-4-yl]methoxy]phenyl]piperazino]phenyl]-2-(1-methylpropyl)-4H-1,2,4-triazole-3(2H)-one
Clinical Status
Approved
Disease Indication Blastomycosis ICD-11: 1F22 [1]
PubChem CID
55283
Formula
C35H38Cl2N8O4
Canonical SMILES
CCC(C)N1C(=O)N(C=N1)C2=CC=C(C=C2)N3CCN(CC3)C4=CC=C(C=C4)OC[C@H]5CO[C@](O5)(CN6C=NC=N6)C7=C(C=C(C=C7)Cl)Cl
InChI
1S/C35H38Cl2N8O4/c1-3-25(2)45-34(46)44(24-40-45)29-7-5-27(6-8-29)41-14-16-42(17-15-41)28-9-11-30(12-10-28)47-19-31-20-48-35(49-31,21-43-23-38-22-39-43)32-13-4-26(36)18-33(32)37/h4-13,18,22-25,31H,3,14-17,19-21H2,1-2H3/t25?,31-,35-/m0/s1
InChIKey
VHVPQPYKVGDNFY-ZPGVKDDISA-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=55283"></iframe>
3D MOL 2D MOL
Physicochemical Properties Molecular Weight 705.6 Topological Polar Surface Area 101
XlogP 5.7 Complexity 1120
Heavy Atom Count 49 Rotatable Bond Count 11
Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 9
Full List of Drug Formulations (DFMs) Containing This API
          Itraconazole 100 mg capsule Click to Show/Hide the Full List of Formulation(s):        12 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; Fd&c red no. 40; Butyl alcohol; Fd&c blue no. 1; Isopropyl alcohol; Ammonia; Potassium hydroxide; Propylene glycol; Sucrose; Talc; Titanium dioxide; Fd&c red no. 3; Poloxamer 188; Polyethylene glycol 20000; Silicon dioxide; Alcohol; Gelatin; Hypromellose 2910 (5 mpa.s); Methylene chloride; Shellac; Starch, corn
                   Dosage Form Oral Capsule
                   Company NorthStar Rx
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Allura red AC dye DIG Info Solute carrier SLCO2B1 (Ki = 4.7 uM) [2]
FD&C blue no. 1 DIG Info Solute carrier SLCO2B1 (Ki = 13 uM) [3]
Sodium lauryl sulfate DIG Info Solute carrier SLCO2B1 (Ki = 1.98 uM) [3]
Allura red AC dye DIG Info Solute carrier SLCO2B1 (Ki = 2.59 uM) [3]
Isopropyl alcohol DIG Info Lymphoma P388/ADR cells (IC50 = 0.22 uM) [4]
Propylene glycol DIG Info Albendazole monooxygenase (Inhibition ratio < 20 %) [5]
FD&C red no. 3 DIG Info Phosphodiesterase 3A (IC50 = 0.092 uM) [2]
Poloxamer 188 DIG Info Albendazole monooxygenase (IC50 = 60 uM) [6]
Polyethylene glycol 20000 DIG Info Multidrug resistance protein 1 (Inhibition ratio = 72 %) [7]
Silicon dioxide DIG Info Albendazole monooxygenase (Protein expression downregulation) [8]
             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 red no. 40; Butyl alcohol; Fd&c blue no. 1; Isopropyl alcohol; Ammonia; Potassium hydroxide; Propylene glycol; Sucrose; Talc; Titanium dioxide; Fd&c red no. 3; Poloxamer 188; Polyethylene glycol 20000; Silicon dioxide; Alcohol; Gelatin; Hypromellose 2910 (5 mpa.s); Methylene chloride; Shellac
                   Dosage Form Oral Capsule
                   Company Ascend Laboratories
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Allura red AC dye DIG Info Solute carrier SLCO2B1 (Ki = 4.7 uM) [2]
FD&C blue no. 1 DIG Info Solute carrier SLCO2B1 (Ki = 13 uM) [3]
Sodium lauryl sulfate DIG Info Solute carrier SLCO2B1 (Ki = 1.98 uM) [3]
Allura red AC dye DIG Info Solute carrier SLCO2B1 (Ki = 2.59 uM) [3]
Isopropyl alcohol DIG Info Lymphoma P388/ADR cells (IC50 = 0.22 uM) [4]
Propylene glycol DIG Info Albendazole monooxygenase (Inhibition ratio < 20 %) [5]
FD&C red no. 3 DIG Info Phosphodiesterase 3A (IC50 = 0.092 uM) [2]
Poloxamer 188 DIG Info Albendazole monooxygenase (IC50 = 60 uM) [6]
Polyethylene glycol 20000 DIG Info Multidrug resistance protein 1 (Inhibition ratio = 72 %) [7]
Silicon dioxide DIG Info Albendazole monooxygenase (Protein expression downregulation) [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
D&c yellow no. 10; Fd&c red no. 40; Fd&c blue no. 1; Fd&c blue no. 2; Ferrosoferric oxide; Propylene glycol; Sucrose; Titanium dioxide; Gelatin; Hypromelloses; Polyethylene glycols; Shellac; Starch, corn
                   Dosage Form Oral Capsule
                   Company Eon Labs
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Allura red AC dye DIG Info Solute carrier SLCO2B1 (Ki = 4.7 uM) [2]
FD&C blue no. 1 DIG Info Solute carrier SLCO2B1 (Ki = 13 uM) [3]
FD&C blue no. 2 DIG Info Adenosine receptor A3 (IC50 = 1 uM) [2]
Quinoline yellow WS DIG Info Estrogen receptor alpha (IC50 = 18 uM) [2]
Allura red AC dye DIG Info Solute carrier SLCO2B1 (Ki = 2.59 uM) [3]
Propylene glycol DIG Info Albendazole monooxygenase (Inhibition ratio < 20 %) [5]
             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
D&c red no. 28; Fd&c blue no. 1; Fd&c blue no. 2; Sucrose; Talc; Titanium dioxide; Polyethylene glycol 20000; Gelatin; Hypromellose 2910 (5 mpa.s); Starch, corn
                   Dosage Form Oral Capsule
                   Company Accord Healthcare
                   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) [3]
FD&C blue no. 2 DIG Info Adenosine receptor A3 (IC50 = 1 uM) [2]
D&C red no. 28 DIG Info Organic anion transporter 1 (Ki = 0.064 uM) [2]
Polyethylene glycol 20000 DIG Info Multidrug resistance protein 1 (Inhibition ratio = 72 %) [7]
             Drug Formulation 5 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
D&c red no. 22; D&c red no. 28; Fd&c blue no. 1; Sucrose; Titanium dioxide; Polyethylene glycol 20000; Gelatin; Hypromelloses; Starch, corn
                   Dosage Form Oral Capsule
                   Company Alembic Pharmaceuticals
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
D&C red no. 22 DIG Info Organic anion transporter 1 (Ki = 89.13 nM) [9]
FD&C blue no. 1 DIG Info Solute carrier SLCO2B1 (Ki = 13 uM) [3]
D&C red no. 28 DIG Info Organic anion transporter 1 (Ki = 0.064 uM) [2]
Polyethylene glycol 20000 DIG Info Multidrug resistance protein 1 (Inhibition ratio = 72 %) [7]
             Drug Formulation 6 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
D&c red no. 22; D&c red no. 28; Fd&c blue no. 1; Fd&c blue no. 2; Sucrose; Titanium dioxide; Gelatin; Hypromelloses; Polyethylene glycols; Starch, corn
                   Dosage Form Oral Capsule
                   Company Bryant Ranch Prepack
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
D&C red no. 22 DIG Info Organic anion transporter 1 (Ki = 89.13 nM) [9]
FD&C blue no. 1 DIG Info Solute carrier SLCO2B1 (Ki = 13 uM) [3]
FD&C blue no. 2 DIG Info Adenosine receptor A3 (IC50 = 1 uM) [2]
D&C red no. 28 DIG Info Organic anion transporter 1 (Ki = 0.064 uM) [2]
             Drug Formulation 7 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
D&c red no. 22; D&c red no. 28; Fd&c blue no. 1; Fd&c blue no. 2; Sucrose; Titanium dioxide; Gelatin, unspecified; Hypromellose, unspecified; Polyethylene glycol, unspecified; Starch, corn
                   Dosage Form Oral Capsule
                   Company Janssen Pharmaceutical
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
D&C red no. 22 DIG Info Organic anion transporter 1 (Ki = 89.13 nM) [9]
FD&C blue no. 1 DIG Info Solute carrier SLCO2B1 (Ki = 13 uM) [3]
FD&C blue no. 2 DIG Info Adenosine receptor A3 (IC50 = 1 uM) [2]
D&C red no. 28 DIG Info Organic anion transporter 1 (Ki = 0.064 uM) [2]
             Drug Formulation 8 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; Ammonia; Ferrosoferric oxide; Potassium hydroxide; Propylene glycol; Sucrose; Titanium dioxide; Cellulose, microcrystalline; Dextrose; Gelatin; Hypromelloses; Polyethylene glycols; Shellac; Starch, corn
                   Dosage Form Oral Capsule
                   Company Amneal Pharmaceuticals
                   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) [3]
Sodium lauryl sulfate DIG Info Solute carrier SLCO2B1 (Ki = 1.98 uM) [3]
Propylene glycol DIG Info Albendazole monooxygenase (Inhibition ratio < 20 %) [5]
             Drug Formulation 9 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; Ammonia; Ferrosoferric oxide; Potassium hydroxide; Propylene glycol; Sucrose; Titanium dioxide; Dextrose, unspecified form; Gelatin, unspecified; Hypromellose, unspecified; Microcrystalline cellulose; Polyethylene glycol, unspecified; Shellac; Starch, corn
                   Dosage Form Oral Capsule
                   Company American Health Packaging
                   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) [3]
Sodium lauryl sulfate DIG Info Solute carrier SLCO2B1 (Ki = 1.98 uM) [3]
Propylene glycol DIG Info Albendazole monooxygenase (Inhibition ratio < 20 %) [5]
             Drug Formulation 10 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
Fd&c blue no. 1; Fd&c blue no. 2; Sucrose; Titanium dioxide; Polyethylene glycol 20000; Gelatin; Hypromelloses; Starch, corn
                   Dosage Form Oral Capsule
                   Company Jubilant Cadista Pharmaceuticals
                   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) [3]
FD&C blue no. 2 DIG Info Adenosine receptor A3 (IC50 = 1 uM) [2]
Polyethylene glycol 20000 DIG Info Multidrug resistance protein 1 (Inhibition ratio = 72 %) [7]
             Drug Formulation 11 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
Fd&c blue no. 2; Ferric oxide red; Ferric oxide yellow; Ferrosoferric oxide; Propylene glycol; Sodium hydroxide; Sucrose; Talc; Titanium dioxide; Gelatin, unspecified; Hypromellose, unspecified; Polyethylene glycol, unspecified; Povidone, unspecified; Shellac; Starch, corn
                   Dosage Form Oral Capsule
                   Company Mylan Pharamceuticals
                   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]
Propylene glycol DIG Info Albendazole monooxygenase (Inhibition ratio < 20 %) [5]
             Drug Formulation 12 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
Ferrosoferric oxide; Propylene glycol; Sucrose; Titanium dioxide; Polyethylene glycol 20000; Gelatin; Hypromellose 2910 (5 mpa.s); Shellac; Starch, corn
                   Dosage Form Oral Capsule
                   Company Par Pharmaceutical
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Propylene glycol DIG Info Albendazole monooxygenase (Inhibition ratio < 20 %) [5]
Polyethylene glycol 20000 DIG Info Multidrug resistance protein 1 (Inhibition ratio = 72 %) [7]
          Itraconazole 200 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; Magnesium stearate; Propylene glycol; Talc; Titanium dioxide; Crospovidone; Silicon dioxide; Cellulose, microcrystalline; Hypromelloses
                   Dosage Form Oral Tablet
                   Company Merz Pharmaceuticals
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Propylene glycol DIG Info Albendazole monooxygenase (Inhibition ratio < 20 %) [5]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [8]
Crospovidone DIG Info Albendazole monooxygenase (Protein expression downregulation) [8]
Silicon dioxide DIG Info Albendazole monooxygenase (Protein expression downregulation) [8]
References
1 FDA label for approved itraconazole 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 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.
4 Synthesis and evaluation of dihydropyrroloquinolines that selectively antagonize P-glycoprotein. J Med Chem. 2004 Mar 11; 47(6):1413-22.
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 Mediation of in vitro cytochrome p450 activity by common pharmaceutical excipients. Mol Pharm. 2013 Jul 1;10(7):2739-48.
7 Modulation of intestinal P-glycoprotein function by polyethylene glycols and their derivatives by in vitro transport and in situ absorption studies. Int J Pharm. 2006 Apr 26;313(1-2):49-56.
8 Effects of commonly used excipients on the expression of CYP3A4 in colon and liver cells. Pharm Res. 2010 Aug;27(8):1703-12.
9 Structural variation governs substrate specificity for organic anion transporter (OAT) homologs. Potential remote sensing by OAT family members. J Biol Chem. 2007 Aug 17; 282(33):23841-53.

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