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

General Information of Drug (ID: DR1419)
Drug Name
KRM-1648
Synonyms
Benzoxazinorifamycin; KRM-1648; Krm 1648; Rifalazil; Rifalazil [USAN:INN]; S1976TE8QK; (2S,16Z,18E,20S,21S,22R,23R,24R,25S,26R,27S,28E)-5,12,21,23,25-Pentahydroxy-10-(4-isobutyl-1-piperazinyl)-27-methoxy-2,4,16,20,22,24,26-heptamethyl-2,7-(epoxypentadeca(1,11,13)trienimino)-6H-benzofuro(4,5-a)phenoxazine-1(2H),6,15-trione 25-acetate; 129791-92-0; 3'-Hydroxy-5'-(4-isobutylpiperazinyl)benzoxazinorifamycin; ABI 1648; UNII-S1976TE8QK
Indication Chlamydial lymphogranuloma [ICD11: 1A80] Phase 3 [1]
Structure
3D MOL is unavailable 2D MOL
Pharmaceutical Properties Molecular Weight 941.1 Topological Polar Surface Area 226
Heavy Atom Count 68 Rotatable Bond Count 6
Hydrogen Bond Donor Count 5 Hydrogen Bond Acceptor Count 16
Cross-matching ID
PubChem CID
135431094
CAS Number
129791-92-0
TTD Drug ID
D0XW9L
Formula
C51H64N4O13
Canonical SMILES
CC1C=CC=C(C(=O)NC2=C3C(=C4C(=C(C(=C5C4=C(C(O5)(OC=CC(C(C(C(C(C(C1O)C)O)C)OC(=O)C)C)OC)C)O)C)O)C2=O)N=C6C(=CC(=CC6=O)N7CCN(CC7)CC(C)C)O3)C
InChI
1S/C51H64N4O13/c1-24(2)23-54-16-18-55(19-17-54)32-21-33(57)39-35(22-32)67-48-40(52-39)36-37-44(60)30(8)47-38(36)49(62)51(10,68-47)65-20-15-34(64-11)27(5)46(66-31(9)56)29(7)43(59)28(6)42(58)25(3)13-12-14-26(4)50(63)53-41(48)45(37)61/h12-15,20-22,24-25,27-29,34,42-43,46,58-60,62H,16-19,23H2,1-11H3,(H,53,63)/b13-12+,20-15+,26-14-/t25-,27+,28+,29+,34-,42-,43+,46+,51-/m0/s1
InChIKey
IXSVOCGZBUJEPI-HTQYORAHSA-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
25-deacetyl-benzoxazinorifamycin DM003246 N. A. Oxidation - 25-deacetylation 1 [3] , [4]
30-hydroxy-benzoxazinorifamycin DM003248 N. A. Oxidation - Oxidationn 1 [4]
32-hydroxy-benzoxazinorifamycin. DM003249 N. A. Oxidation - 32-hydroxylation 1 [5]
25-deacetyl- 30-hydroxy-benzoxazinorifamycin. DM003247 N. A. Oxidation - Deacetylation 2 [4]
25-deacetyl- 30-hydroxy-benzoxazinorifamycin. DM003247 N. A. Oxidation - Oxidationn 2 [4]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR013338 KRM-1648 25-deacetyl-benzoxazinorifamycin Oxidation - 25-deacetylation Unclear [3], [4]
MR013340 KRM-1648 30-hydroxy-benzoxazinorifamycin Oxidation - Oxidationn Unclear [4]
MR013342 KRM-1648 32-hydroxy-benzoxazinorifamycin. Oxidation - 32-hydroxylation CYP3A4 [5]
MR013339 25-deacetyl-benzoxazinorifamycin 25-deacetyl- 30-hydroxy-benzoxazinorifamycin. Oxidation - Oxidationn Unclear [4]
MR013341 30-hydroxy-benzoxazinorifamycin 25-deacetyl- 30-hydroxy-benzoxazinorifamycin. Oxidation - Deacetylation Unclear [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]
References
1 ClinicalTrials.gov (NCT00251849) PROVIDENCE-1: Study of Rifalazil in Chlamydia Pneumoniae Seropositive Patients.
2 Identification of enzymes responsible for rifalazil metabolism in human liver microsomes. Xenobiotica. 2000 Jun;30(6):565-74.
3 Pharmacokinetics of KRM-1648, a new benzoxazinorifamycin, in rats and dogs
4 Identification and antimicrobial activity of urinary metabolites of a rifamycin derivative in dog
5 DrugBank : KRM-1648

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