Details of the Active Pharmaceutical Ingredient (API)

General Information of API (ID: D00367)
Name
Linezolid
Synonyms    Click to Show/Hide the Synonyms of This API
linezolid; 165800-03-3; (S)-N-((3-(3-fluoro-4-morpholinophenyl)-2-oxooxazolidin-5-yl)methyl)acetamide; Zyvoxid; PNU-100766; U-100766; Zyvoxam; PNU 100766; U 100766; C16H20FN3O4; UNII-ISQ9I6J12J; N-(((S)-3-(3-Fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl)methyl)acetamide; CHEMBL126; ISQ9I6J12J; CHEBI:63607; Linezolid, 98%; MFCD00937825; U-100,766; (S)-N-[[3-(3-fluoro-4-morpholinylphenyl)-2-oxo-5-oxazolidinyl]methyl]acetamide; Zivoxid; Zyvoxa; N-[[(5S)-3-(3-fluoro-4-morpholino-phenyl)-2-oxo-oxazolidin-5-yl]methyl]acetamide; SMR000466335; Zyvox (TN); HSDB 7478; SR-01000759376; Linezolid & VRC3375; Linezoid; Linezolid (JAN/USAN/INN); Linezolid [USAN:INN:BAN]; (S)-N-[[3-(3-Fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl]methyl]acetamide; NCGC00164628-01; Linezolid (Zyvox); PNU100766; 111GE017; CPD000466335; NDA 21-130 Zyvox (linezolid tablets); SCHEMBL5027; DSSTox_CID_26489; DSSTox_RID_81660; DSSTox_GSID_46489; cc-154; MLS000759444; MLS001424075; BIDD:GT0404; Benzotriazol-2-yl-acetonitrile; cid_441401; Linezolid (PNU-100766); QCR-88; DTXSID5046489; Linezolid, >=98% (HPLC); NDA 21-131 Zyvox for injection (linezolid injection); GTPL10827; SYN3021; HMS2051F08; HMS2089K06; HMS3260C14; HMS3713K10; NDA 21-132 Zyvox oral suspension (linzolid oral suspension); BCP05586; ZINC2008866; Tox21_112246; Tox21_500096; BDBM50116067; AKOS016340522; AM84567; BCP9000855; CCG-101009; CS-0756; DB00601; KS-1178; NC00259; (R)-N-((3-(3-fluoro-4-morpholinophenyl)-2-oxooxazolidin-5-yl)methyl)acetamide; Linezolid 100 microg/mL in Acetonitrile; NCGC00260781-01; NCGC00263531-03; NCGC00263531-05; NCGC00263531-10; HY-10394; AB0012049; CAS-165800-03-3; SW197639-3; C08146; D00947; J90009; M-8338; AB00639994-06; AB00639994-08; AB00639994-09; AB00639994_10; AB00639994_11; 800L033; A810662; Q411377; Q-201308; SR-01000759376-4; SR-01000759376-5; Linezolid, United States Pharmacopeia (USP) Reference Standard; (S)-N-((3-fluoro-4-morpholinophenyl)-2-oxaoxazolidin-5-yl)methyl)acetamide; Linezolid, Pharmaceutical Secondary Standard; Certified Reference Material; N-[3-(3-Fluoro-4-morpholin-4-yl-phenyl)-2-oxo-oxazolidin-5-ylmethyl]-acetamide
Clinical Status
Approved
Disease Indication Streptococcus bacterial infection ICD-11: 1C41 [1]
PubChem CID
441401
Formula
C16H20FN3O4
Canonical SMILES
CC(=O)NC[C@H]1CN(C(=O)O1)C2=CC(=C(C=C2)N3CCOCC3)F
InChI
1S/C16H20FN3O4/c1-11(21)18-9-13-10-20(16(22)24-13)12-2-3-15(14(17)8-12)19-4-6-23-7-5-19/h2-3,8,13H,4-7,9-10H2,1H3,(H,18,21)/t13-/m0/s1
InChIKey
TYZROVQLWOKYKF-ZDUSSCGKSA-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=441401"></iframe>
3D MOL 2D MOL
Physicochemical Properties Molecular Weight 337.35 Topological Polar Surface Area 71.1
XlogP 0.7 Complexity 472
Heavy Atom Count 24 Rotatable Bond Count 4
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 6
Full List of Drug Formulations (DFMs) Containing This API
          Linezolid 600 mg tablet Click to Show/Hide the Full List of Formulation(s):        16 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; D&c yellow no. 10; Fd&c blue no. 2; Fd&c yellow no. 6; Magnesium stearate; Titanium dioxide; Triacetin; Croscarmellose sodium; Silicon dioxide; Hypromellose, unspecified; Microcrystalline cellulose; Polydextrose; Polyethylene glycol, unspecified
                   Dosage Form Oral Tablet
                   Company Mylan Pharamceuticals
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Sunset yellow FCF DIG Info Solute carrier SLCO2B1 (Ki = 68.4 uM) [2]
Sodium lauryl sulfate DIG Info Solute carrier SLCO2B1 (Ki = 1.98 uM) [2]
FD&C blue no. 2 DIG Info Adenosine receptor A3 (IC50 = 1 uM) [3]
Quinoline yellow WS DIG Info Estrogen receptor alpha (IC50 = 18 uM) [3]
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]
             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; D&c yellow no. 10; Fd&c blue no. 2; Fd&c yellow no. 6; Magnesium stearate; Titanium dioxide; Triacetin; Croscarmellose sodium; Silicon dioxide; Cellulose, microcrystalline; Hypromelloses; Polydextrose; Polyethylene glycols
                   Dosage Form Oral Tablet
                   Company Mylan Pharamceuticals
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Sunset yellow FCF DIG Info Solute carrier SLCO2B1 (Ki = 68.4 uM) [2]
Sodium lauryl sulfate DIG Info Solute carrier SLCO2B1 (Ki = 1.98 uM) [2]
FD&C blue no. 2 DIG Info Adenosine receptor A3 (IC50 = 1 uM) [3]
Quinoline yellow WS DIG Info Estrogen receptor alpha (IC50 = 18 uM) [3]
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]
             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
Diethyl phthalate; Magnesium stearate; Talc; Titanium dioxide; Croscarmellose sodium; Povidone; Silicon dioxide; Cellulose, microcrystalline; Ethylcelluloses; Hypromelloses
                   Dosage Form Oral Tablet
                   Company Amneal Pharmaceuticals
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Diethyl phthalate DIG Info Phosphodiesterase 4D (IC50 = 8.5 uM) [3]
Povidone DIG Info Cholesterol 25-hydroxylase (IC50 = 78.3 uM) [5]
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]
             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
Magnesium stearate; Mannitol; Titanium dioxide; Croscarmellose sodium; Polyethylene glycol 400; Hypromellose 2910 (5 mpa.s); Povidone k90; Starch, corn
                   Dosage Form Oral Tablet
                   Company Teva Pharmaceuticals
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Mannitol DIG Info Glycine receptor alpha-1 (EC50 = 12589.25 nM) [6]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
Carmellose sodium DIG Info Albendazole monooxygenase (Protein expression upregulation) [4]
Polyethylene glycol 400 DIG Info Albendazole monooxygenase (IC50 = 10.77 mg.mL-1) [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
Sodium stearyl fumarate; Mannitol; Titanium dioxide; Polyethylene glycol 400; Silicon dioxide; Copovidone k25-31; Hypromellose 2910 (6 mpa.s); Starch, corn
                   Dosage Form Oral Tablet
                   Company American Health Packaging; Ascend Laboratories; AvPAK; Major Pharmaceuticals
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Mannitol DIG Info Glycine receptor alpha-1 (EC50 = 12589.25 nM) [6]
Sodium stearyl fumarate DIG Info Leukemia K562 cells (IC50 = 20.2 ug.mL-1) [8]
Polyethylene glycol 400 DIG Info Albendazole monooxygenase (IC50 = 10.77 mg.mL-1) [7]
Silicon dioxide DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
             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
Sodium stearyl fumarate; Titanium dioxide; Croscarmellose sodium; Polyethylene glycol 400; Silicon dioxide; Cellulose, microcrystalline; Hydroxypropyl cellulose (type e); Hydroxypropyl cellulose, low substituted; Hypromelloses
                   Dosage Form Oral Tablet
                   Company Alembic Pharmaceuticals
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Sodium stearyl fumarate DIG Info Leukemia K562 cells (IC50 = 20.2 ug.mL-1) [8]
Carmellose sodium DIG Info Albendazole monooxygenase (Protein expression upregulation) [4]
Polyethylene glycol 400 DIG Info Albendazole monooxygenase (IC50 = 10.77 mg.mL-1) [7]
Silicon dioxide DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
             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
Magnesium stearate; Titanium dioxide; Triacetin; Crospovidone; Polyethylene glycol 1000; Cellulose, microcrystalline; Hydroxypropyl cellulose (type h); Hypromellose 2208 (100 mpa.s); Polydextrose
                   Dosage Form Oral Tablet
                   Company Novel Laboratories
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Polyethylene glycol 1000 DIG Info Cytochrome P450 2E1 (IC50 = 75.3 uM) [5]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
Crospovidone DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
             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
Lactose monohydrate; Magnesium stearate; Titanium dioxide; Croscarmellose sodium; Polyethylene glycol 400; Hypromellose, unspecified; Povidone, unspecified
                   Dosage Form Oral Tablet
                   Company Glenmark Pharmaceutials
                   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]
Polyethylene glycol 400 DIG Info Albendazole monooxygenase (IC50 = 10.77 mg.mL-1) [7]
             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
Magnesium stearate; Titanium dioxide; Crospovidone; Silicon dioxide; Cellulose, microcrystalline; Hydroxypropyl cellulose (type h); Hypromelloses; Polyethylene glycols
                   Dosage Form Oral Tablet
                   Company Cadila Healthcare; Zydus Pharmaceuticals
                   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]
Crospovidone DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
Silicon dioxide DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
             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
Lactose monohydrate; Magnesium stearate; Titanium dioxide; Silicon dioxide; Carnauba wax; Hypromellose, unspecified; Polacrilin potassium; Polyethylene glycol, unspecified
                   Dosage Form Oral Tablet
                   Company American Health Packaging
                   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]
Silicon dioxide DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
             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
Lactose monohydrate; Magnesium stearate; Titanium dioxide; Silicon dioxide; Carnauba wax; Hypromelloses; Polacrilin potassium; Polyethylene glycols
                   Dosage Form Oral Tablet
                   Company RemedyRepack
                   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]
Silicon dioxide DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
             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
Lactose monohydrate; Magnesium stearate; Titanium dioxide; Carnauba wax; Colloidal silicon dioxide; Hypromelloses; Polacrilin potassium; Polyethylene glycols
                   Dosage Form Oral Tablet
                   Company Camber Pharmaceuticals
                   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]
             Drug Formulation 13 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
Magnesium stearate; Titanium dioxide; Carnauba wax; Cellulose, microcrystalline; Hydroxypropyl cellulose (type h); Hypromelloses; Polyethylene glycols; Starch, corn
                   Dosage Form Oral Tablet
                   Company RemedyRepack
                   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]
             Drug Formulation 14 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
Magnesium stearate; Titanium dioxide; Carnauba wax; Cellulose, microcrystalline; Hydroxypropyl cellulose; Hypromelloses; Polyethylene glycol; Sodium starch glycolate type a potato; Starch, corn
                   Dosage Form Oral Tablet
                   Company Cardinal Health
                   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]
             Drug Formulation 15 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
Magnesium stearate; Titanium dioxide; Carnauba wax; Hydroxypropyl cellulose (1200000 mw); Hypromellose, unspecified; Microcrystalline cellulose; Polyethylene glycol, unspecified; Starch, corn
                   Dosage Form Oral Tablet
                   Company Greenstone; Pharmacia and Upjohn Company
                   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]
             Drug Formulation 16 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
Magnesium stearate; Titanium dioxide; Carnauba wax; Cellulose, microcrystalline; Hydroxypropyl cellulose; Hypromelloses; Polyethylene glycol; Starch, corn
                   Dosage Form Oral Tablet
                   Company Rebel Distributors
                   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]
References
1 FDA label for approved linezolid 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 The activities of drug inactive ingredients on biological targets. Science. 2020 Jul 24;369(6502):403-413.
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 Mediation of in vitro cytochrome p450 activity by common pharmaceutical excipients. Mol Pharm. 2013 Jul 1;10(7):2739-48.
6 Pharmacological property optimization for allosteric ligands: A medicinal chemistry perspective. Bioorg Med Chem Lett. 2017 Jun 1; 27(11):2239-2258.
7 Pharmaceutical excipients inhibit cytochrome P450 activity in cell free systems and after systemic administration. Eur J Pharm Biopharm. 2008 Sep;70(1):279-88.
8 Synthesis and evaluation of (-)-Massoialactone and analogues as potential anticancer and anti-inflammatory agents. Eur J Med Chem. 2014 Apr 9; 76:291-300.

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