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

General Information of Drug (ID: DR0434)
Drug Name
Delavirdine mesylate
Synonyms
Delavirdine (mesylate); Delavirdine mesilate; Delavirdine mesylate (USAN); Delavirdine mesylate [USAN]; Delavirdine monomethanesulfonate; N-(2-(4-(3-(isopropylamino)pyridin-2-yl)piperazine-1-carbonyl)-1H-indol-5-yl)methanesulfonamide methanesulfonate; U-90152S; UNII-421105KRQE; Delavirdine; Delavirdine (INN); Delavirdine [INN]; N-(2-(4-(3-(Isopropylamino)pyridin-2-yl)piperazine-1-carbonyl)-1H-indol-5-yl)methanesulfonamide; N-[2-({4-[3-(propan-2-ylamino)pyridin-2-yl]piperazin-1-yl}carbonyl)-1H-indol-5-yl]methanesulfonamide; U 90152; UNII-DOL5F9JD3E; U-90152; 136817-59-9; 2-(4-(5-Methanesulfonamido-1H-indol-2-ylcarbonyl)-1-piperazinyl)-N-(1-methylethyl)-3-pyridinamine; BHAP der; BHAP-U 90152; CHEMBL593; DLV; DOL5F9JD3E; 1-(3-(Isopropylamino)-2-pyridyl)-4-((5-methanesulfonamidoindol-2-yl)carbonyl)piperazine monomethanesulfonate; 147221-93-0; 421105KRQE; CHEBI:4379; DELAVIRDINE MESYLATE
Indication Human immunodeficiency virus infection [ICD11: 1C60] Approved [1]
Structure
3D MOL is unavailable 2D MOL
Pharmaceutical Properties Molecular Weight 552.7 Topological Polar Surface Area 182
Heavy Atom Count 37 Rotatable Bond Count 6
Hydrogen Bond Donor Count 4 Hydrogen Bond Acceptor Count 10
Cross-matching ID
PubChem CID
441386
ChEBI ID
CHEBI:4379
CAS Number
147221-93-0
TTD Drug ID
D0G6SD
Formula
C23H32N6O6S2
Canonical SMILES
CC(C)NC1=C(N=CC=C1)N2CCN(CC2)C(=O)C3=CC4=C(N3)C=CC(=C4)NS(=O)(=O)C.CS(=O)(=O)O
InChI
1S/C22H28N6O3S.CH4O3S/c1-15(2)24-19-5-4-8-23-21(19)27-9-11-28(12-10-27)22(29)20-14-16-13-17(26-32(3,30)31)6-7-18(16)25-20;1-5(2,3)4/h4-8,13-15,24-26H,9-12H2,1-3H3;1H3,(H,2,3,4)
InChIKey
MEPNHSOMXMALDZ-UHFFFAOYSA-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
Delavirdine mesylate MET-10 DM000775
60948
Unclear 1 [5]
Delavirdine mesylate MET-12 DM000776
10013750
Unclear 1 [5]
Delavirdine mesylate MET-16 DM000773 N. A. Oxidation - Hydroxylation; Glucuronidation 1 [5]
Delavirdine mesylate MET-17 DM000774 N. A. Conjugation - Glucuronidation 1 [5]
Delavirdine mesylate MET-7 DM000768
154700087
Oxidation - Hydroxylation 1 [5]
N-desalkyl delavirdine DM000763
468304
Oxidation - N-Dealkylation 1 [5]
Delavirdine mesylate MET-15d DM000766 N. A. Oxidation - Hydroxylation 2 [5]
Delavirdine mesylate MET-2 DM000772 N. A. Unclear 2 [5]
Delavirdine mesylate MET-4a DM000764 N. A. Conjugation - Sulfation 2 [5]
Delavirdine mesylate MET-4b DM000771
165429035
Conjugation - Sulfation 2 [5]
Delavirdine mesylate MET-4c DM000765 N. A. Conjugation - Glucuronidation 2 [5]
Delavirdine mesylate MET-4d DM000767
165429036
Conjugation - Sulfation 2 [5]
Delavirdine mesylate MET-6 DM000769 N. A. Conjugation - Glucuronidation 2 [5]
⏷ Show the Full List of 13  DM(s)
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR003133 Delavirdine mesylate Delavirdine mesylate MET-7 Oxidation - Hydroxylation Unclear [5]
MR003137 Delavirdine mesylate N-desalkyl delavirdine Oxidation - N-Dealkylation CYP3A4 [5]
MR003138 Delavirdine mesylate Delavirdine mesylate MET-16 Oxidation - Hydroxylation; Glucuronidation Unclear [5]
MR003139 Delavirdine mesylate Delavirdine mesylate MET-17 Conjugation - Glucuronidation Unclear [5]
MR003140 Delavirdine mesylate Delavirdine mesylate MET-10 Unclear Unclear [5]
MR003141 Delavirdine mesylate Delavirdine mesylate MET-12 Unclear Unclear [5]
MR003132 Delavirdine mesylate MET-7 Delavirdine mesylate MET-15d Oxidation - Hydroxylation Unclear [5]
MR003134 Delavirdine mesylate MET-7 Delavirdine mesylate MET-6 Conjugation - Glucuronidation Unclear [5]
MR003135 Delavirdine mesylate MET-7 Delavirdine mesylate MET-4b Conjugation - Sulfation Unclear [5]
MR003136 Delavirdine mesylate MET-7 Delavirdine mesylate MET-2 Unclear Unclear [5]
MR003128 N-desalkyl delavirdine Delavirdine mesylate MET-4a Conjugation - Sulfation Unclear [5]
MR003129 N-desalkyl delavirdine Delavirdine mesylate MET-4c Conjugation - Glucuronidation Unclear [5]
MR003130 N-desalkyl delavirdine Delavirdine mesylate MET-15d Oxidation - Hydroxylation Unclear [5]
MR003131 N-desalkyl delavirdine Delavirdine mesylate MET-4d Conjugation - Sulfation Unclear [5]
⏷ Show the Full List of 14 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[2]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[3]
Cytochrome P450 3A5 (CYP3A5) DME0012 Homo sapiens
CP3A5_HUMAN
1.14.14.1
[4]
Cytochrome P450 3A7 (CYP3A7) DME0015 Homo sapiens
CP3A7_HUMAN
1.14.14.1
[4]
References
1 Delavirdine Mesylate was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Inhibition of human cytochrome P450 isoforms by nonnucleoside reverse transcriptase inhibitors. J Clin Pharmacol. 2001 Jan;41(1):85-91.
3 Delavirdine: clinical pharmacokinetics and drug interactions. Clin Pharmacokinet. 2001;40(3):207-26.
4 Drug Interactions Flockhart Table
5 Identification of the metabolites of the HIV-1 reverse transcriptase inhibitor delavirdine in monkeys Drug Metab Dispos. 1997 Jul;25(7):814-27.

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