Details of the Active Pharmaceutical Ingredient (API)

General Information of API (ID: D01360)
Name
Pretomanid
Synonyms    Click to Show/Hide the Synonyms of This API
PA-824; Pretomanid; 187235-37-6; PA 824; PA824; (S)-2-Nitro-6-((4-(trifluoromethoxy)benzyl)oxy)-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine; UNII-2XOI31YC4N; 2XOI31YC4N; CHEMBL227875; MMV688755; (6S)-2-nitro-6-[[4-(trifluoromethoxy)phenyl]methoxy]-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine; (6S)-2-nitro-6-{[4-(trifluoromethoxy)benzyl]oxy}-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine; (S)-PA 824; Pretomanid [USAN:INN]; C14H12F3N3O5; Pretomanid (TN); PA-824(Pretomanid); Pretomanid (USAN/INN); MLS006011141; SCHEMBL2983011; DTXSID8041163; GTPL11172; AOB1594; EX-A1749; ZINC3821675; BDBM50363237; MFCD06809939; s1162; AKOS024464713; CCG-268145; DB05154; DS-7321; QC-5184; SB22927; 2-nitro-6-(4-(trifluoromethoxy)benzyloxy)-6,7-dihydro-5H-imidazo(2,1-b)(1,3)oxazine; NCGC00346682-01; NCGC00346682-02; AC-25501; HY-10844; SMR004702918; AB0033407; SW220281-1; X6951; A11401; D10722; Q7118312; (S)-2-nitro-6-(4-(trifluoromethoxy)benzyloxy)-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine; {4-[((3S)-6-Nitro(2H,3H,4H-imidazolo[2,1-b]1,3-oxazaperhydroin-3-yloxy))methyl]phenoxy}trifluoromethane; 5H-Imidazo(2,1-b)(1,3)oxazine, 6,7-dihydro-2-nitro-6-((4-(trifluoromethoxy)phenyl)methoxy)-, (6S)-; PA-824; ; ; (6S)-2-Nitro-6-[[4-(trifluoromethoxy)phenyl]methoxy]-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine
Clinical Status
Approved
PubChem CID
456199
Formula
C14H12F3N3O5
Canonical SMILES
C1[C@@H](COC2=NC(=CN21)[N+](=O)[O-])OCC3=CC=C(C=C3)OC(F)(F)F
InChI
1S/C14H12F3N3O5/c15-14(16,17)25-10-3-1-9(2-4-10)7-23-11-5-19-6-12(20(21)22)18-13(19)24-8-11/h1-4,6,11H,5,7-8H2/t11-/m0/s1
InChIKey
ZLHZLMOSPGACSZ-NSHDSACASA-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=456199"></iframe>
3D MOL is unavailable 2D MOL
Physicochemical Properties Molecular Weight 359.26 Topological Polar Surface Area 91.3
XlogP 2.8 Complexity 468
Heavy Atom Count 25 Rotatable Bond Count 4
Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 9
Full List of Drug Formulations (DFMs) Containing This API
          Pretomanid 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
Colloidal Silicon Dioxide; Lactose Monohydrate; Magnesium Stearate; Microcrystalline Cellulose; Povidone; Sodium Lauryl Sulfate; Sodium Starch Glycolate
                   Dosage Form Tablet
                   Company Mylan Specialty L.P.
                   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]
Povidone DIG Info Cholesterol 25-hydroxylase (IC50 = 78.3 uM) [2]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [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.

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