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

General Information of Drug (ID: DR1421)
Drug Name
Rifapentine
Synonyms
Rifapentin; Rifapentina [Spanish]; Rifapentinum; Rifapentinum [Latin]; XJM390A33U; 3-(((4-Cyclopentyl-1-piperazinyl)imino)methyl)rifamycin; Cyclopentyl rifampin; Cyclopentylrifampicin; DL 473; MDL 473; MDL-473; Priftin; Priftin (TN); RIFAPENTINE; Rifamycin AF/ACPP; 61379-65-5; CHEBI:45304; KTC 1; RPT; UNII-XJM390A33U
Indication Pulmonary tuberculosis [ICD11: 1B10] Approved [1]
Structure
3D MOL is unavailable 2D MOL
Pharmaceutical Properties Molecular Weight 877 Topological Polar Surface Area 220
Heavy Atom Count 63 Rotatable Bond Count 6
Hydrogen Bond Donor Count 6 Hydrogen Bond Acceptor Count 15
Cross-matching ID
PubChem CID
135403821
ChEBI ID
CHEBI:20502
CAS Number
61379-65-5
TTD Drug ID
D0G9IU
Formula
C47H64N4O12
Canonical SMILES
CC1C=CC=C(C(=O)NC2=C(C(=C3C(=C2O)C(=C(C4=C3C(=O)C(O4)(OC=CC(C(C(C(C(C(C1O)C)O)C)OC(=O)C)C)OC)C)C)O)O)C=NN5CCN(CC5)C6CCCC6)C
InChI
1S/C47H64N4O12/c1-24-13-12-14-25(2)46(59)49-37-32(23-48-51-20-18-50(19-21-51)31-15-10-11-16-31)41(56)34-35(42(37)57)40(55)29(6)44-36(34)45(58)47(8,63-44)61-22-17-33(60-9)26(3)43(62-30(7)52)28(5)39(54)27(4)38(24)53/h12-14,17,22-24,26-28,31,33,38-39,43,53-57H,10-11,15-16,18-21H2,1-9H3,(H,49,59)/b13-12+,22-17+,25-14-,48-23+/t24-,26+,27+,28+,33-,38-,39+,43+,47-/m0/s1
InChIKey
WDZCUPBHRAEYDL-GZAUEHORSA-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-desacetyl rifapentine DM005413
135483774
Other reaction - Deacylation 1 [2] , [3]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR005746 Rifapentine 25-desacetyl rifapentine Other reaction - Deacylation AADAC [2], [3]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Arylacetamide deacetylase (AADAC) DMEN272 Homo sapiens
AAAD_HUMAN
3.1.1.3
[2] , [3]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[4]
References
1 Rifapentine was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Isoniazid level and flu-like symptoms during rifapentine-based tuberculosis preventive therapy: A population pharmacokinetic analysis. Br J Clin Pharmacol. 2023 Feb;89(2):714-726. doi: 10.1111/bcp.15527.
3 Human arylacetamide deacetylase is responsible for deacetylation of rifamycins: rifampicin, rifabutin, and rifapentine. Biochem Pharmacol. 2011 Dec 1;82(11):1747-56.
4 Inhibitory potential of twenty five anti-tuberculosis drugs on CYP activities in human liver microsomes. Biol Pharm Bull. 2015;38(9):1425-9.

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