Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR1338)
Drug Name
Pretomanid
Synonyms
Pretomanid; Pretomanid (PA-824); Pretomanid (USAN/INN); Pretomanid [USAN:INN]; PA 824; PA-824; PA-824(Pretomanid); (6S)-2-nitro-6-[[4-(trifluoromethoxy)phenyl]methoxy]-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine; (6S)-6,7-Dihydro-2-nitro-6-[[4-(trifluoromethoxy)phenyl]methoxy]-5H-imidazo[2,1-b][1,3]oxazine; (S)-2-Nitro-6-((4-(trifluoromethoxy)benzyl)oxy)-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine; (S)-PA 824; 187235-37-6; 2XOI31YC4N; AC1L9UFX; AK161427; C14H12F3N3O5; CHEMBL227875; MLS006011141; MMV688755; PA824; UNII-2XOI31YC4N
Indication Pulmonary tuberculosis [ICD11: 1B10] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 359.26 Topological Polar Surface Area 91.3
Heavy Atom Count 25 Rotatable Bond Count 4
Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 9
Cross-matching ID
PubChem CID
456199
PubChem SID
602759 ; 11568219 ; 14754667 ; 56314347 ; 74512488 ; 92309397 ; 103516892 ; 109718929 ; 129919200 ; 134340334 ; 135143585 ; 136345878 ; 136348779 ; 136967299 ; 139347532 ; 144229765 ; 162223093 ; 162474735 ; 164046419 ; 164764023 ; 174006653 ; 174007389 ; 175426953 ; 179231147 ; 188889470 ; 196409666 ; 198982738 ; 210274726 ; 210280360 ; 223384013 ; 223554904 ; 223700553 ; 223705177 ; 223726250 ; 229040932 ; 241383546 ; 249855633 ; 250224263 ; 251971002 ; 252066562 ; 252434136 ; 252450233 ; 252553552
CAS Number
187235-37-6
TTD Drug ID
D02AYL
Formula
C14H12F3N3O5
Canonical SMILES
C1C(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
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
Des-nitroso derivative, Pretomanid DM002952 N. A. Reduction - Reduction 1 [3]
Unclear DM009999 N. A. Unclear 1 [4]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR002133 Pretomanid Des-nitroso derivative, Pretomanid Reduction - Reduction SAML1065 [3]
MR002134 Pretomanid . Unclear CYP3A4 [4]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[2]
Deazaflavin-dependent nitroreductase (SAML1065) DMEN058 Streptomyces ambofaciens
A3KK16_STRA7
5.1.3.1
[3]
References
1 Pretomanid was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 FDA briefing document - pretomanid tablet, 200 mg meeting of the antimicrobial drugs advisory committee (AMDAC).
3 Antitubercular Nitroimidazoles Revisited: Synthesis and Activity of the Authentic 3-Nitro Isomer of Pretomanid ACS Med Chem Lett. 2017 Nov 13;8(12):1275-1280. doi: 10.1021/acsmedchemlett.7b00356.
4 FDA:Pretomanid

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