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

General Information of Drug (ID: DR1418)
Drug Name
Rifabutin
Synonyms
Rifabutina; Rifabutina [Spanish]; Rifabutine; Rifabutine [French]; Rifabutinum; Rifabutinum [Latin]; 1,4-Dihydro-1-deoxy-1',4-didehydro-5'-(2-methylpropyl)-1-oxorifamycin XIV; 4-Deoxo-3,4-(2-spiro(N-isobutyl-4-piperidyl)-2,5-dihydro-1H-imidazo)-rifamycin S; Alfacid; Ansamycin; Ansatipin; Ansatipine; Antibiotic LM 427; LM 427; LM-427; Mycobutin; Mycobutin (TN); RIFABUTIN; 4-N-isobutylspiropiperidylrifamycin S; 72559-06-9; BRN 3584778; DRG-0085; DSSTox_RID_79103; HSDB 3577; NCGC00090762-01; ATEBXHFBFRCZMA-VXTBVIBXSA-N; RBT
Indication Pulmonary tuberculosis [ICD11: 1B10] Approved [1]
Structure
3D MOL is unavailable 2D MOL
Pharmaceutical Properties Molecular Weight 847 Topological Polar Surface Area 209
Heavy Atom Count 61 Rotatable Bond Count 5
Hydrogen Bond Donor Count 5 Hydrogen Bond Acceptor Count 14
Cross-matching ID
PubChem CID
135398743
ChEBI ID
CHEBI:45367
CAS Number
72559-06-9
TTD Drug ID
D05CHI
Formula
C46H62N4O11
Canonical SMILES
CC1C=CC=C(C(=O)N=C2C(=C3C(=C4C2=NC5(N4)CCN(CC5)CC(C)C)C6=C(C(=C3O)C)OC(C6=O)(OC=CC(C(C(C(C(C(C1O)C)O)C)OC(=O)C)C)OC)C)O)C
InChI
1S/C46H62N4O11/c1-22(2)21-50-18-16-46(17-19-50)48-34-31-32-39(54)28(8)42-33(31)43(56)45(10,61-42)59-20-15-30(58-11)25(5)41(60-29(9)51)27(7)38(53)26(6)37(52)23(3)13-12-14-24(4)44(57)47-36(40(32)55)35(34)49-46/h12-15,20,22-23,25-27,30,37-38,41,48,52-55H,16-19,21H2,1-11H3/b13-12+,20-15+,24-14-,47-36?/t23-,25+,26+,27+,30-,37-,38+,41+,45-/m0/s1
InChIKey
ZWBTYMGEBZUQTK-PVLSIAFMSA-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
20-Hydroxyrifabutin DM017905 N. A. Oxidation - Hydroxylation 1 [3]
25-O-deacetylrifabutin DM016632
135472677
Oxidation - Deacetylation 1 [2]
27-O-demethylrifabutin DM016848
156908058
Oxidation - 27-O-demethylation 1 [3]
31-Hydroxyrifabutin DM016631
135459776
Oxidation - Hydroxylation 1 [3]
32-Hydroxyrifabutin DM016671
136703936
Oxidation - Hydroxylation 1 [3]
Unclear DM009999 N. A. Unclear - Unclear 1 [4]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR013056 Rifabutin 27-O-demethylrifabutin Oxidation - 27-O-demethylation Unclear [3]
MR013057 Rifabutin 25-O-deacetylrifabutin Oxidation - Deacetylation CYP3A4 [2]
MR013058 Rifabutin 31-Hydroxyrifabutin Oxidation - Hydroxylation Unclear [3]
MR013059 Rifabutin 32-Hydroxyrifabutin Oxidation - Hydroxylation Unclear [3]
MR013060 Rifabutin 20-Hydroxyrifabutin Oxidation - Hydroxylation Unclear [3]
MR013061 Rifabutin Unclear Unclear - Unclear Unclear [4]
⏷ Show the Full List of 6 MR(s)
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 Rifabutin was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Tolerance and pharmacokinetic interactions of rifabutin and clarithromycin in human immunodeficiency virus-infected volunteers
3 Isolation and identification of major urinary metabolites of rifabutin in rats and humans
4 The effect of multiple doses of ritonavir on the pharmacokinetics of rifabutin. Clin Pharmacol Ther. 1998 Apr;63(4):414-21.

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