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

General Information of Drug (ID: DR1550)
Drug Name
Teniposide
Synonyms
Teniposide (Vumon); Teniposido; Teniposido [INN-Spanish]; Teniposidum; Teniposidum [INN-Latin]; Vee M-26; teniposide; 29767-20-2; 4'-Demethyl-epipodophyllotoxin-beta-D-thenylidene-glucoside; 4'-Demethylepipodophyllotoxin 9-(4,6-O-(R)-2-thenylidene-beta-D-glucopyranoside); 4'-Demethylepipodophyllotoxin-beta-D-thenylidine glucoside; 4'-Dimethyl-9-(4,6-O-2-thenyid)-epipodophyllotoxin; C32H32O13S; CCRIS 2058; EINECS 249-831-2; HSDB 6546; NSC 122819; UNII-957E6438QA; VM 26; VM-26; Vehem; Vumon
Indication Acute lymphoblastic leukemia [ICD11: 2B33] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 656.7 Topological Polar Surface Area 189
Heavy Atom Count 46 Rotatable Bond Count 6
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 14
Cross-matching ID
PubChem CID
452548
PubChem SID
597750 ; 7980753 ; 10300907 ; 14912717 ; 49965048 ; 51063681 ; 53788607 ; 57405354 ; 99030090 ; 99246079 ; 103589230 ; 104253379 ; 104645164 ; 118046116 ; 119526326 ; 124757497 ; 125164301 ; 135692278 ; 136178636 ; 137001864 ; 139137932 ; 140852399 ; 152035492 ; 162037723 ; 162174797 ; 163620769 ; 163686094 ; 175267905 ; 176484801 ; 178103449 ; 179116911 ; 184811965 ; 187072639 ; 223384958 ; 226396002 ; 241050196 ; 251887699 ; 252220258 ; 252390155 ; 252401148 ; 252451125
CAS Number
29767-20-2
TTD Drug ID
D01DBQ
Formula
C32H32O13S
Canonical SMILES
COC1=CC(=CC(=C1O)OC)C2C3C(COC3=O)C(C4=CC5=C(C=C24)OCO5)OC6C(C(C7C(O6)COC(O7)C8=CC=CS8)O)O
InChI
1S/C32H32O13S/c1-37-19-6-13(7-20(38-2)25(19)33)23-14-8-17-18(42-12-41-17)9-15(14)28(16-10-39-30(36)24(16)23)44-32-27(35)26(34)29-21(43-32)11-40-31(45-29)22-4-3-5-46-22/h3-9,16,21,23-24,26-29,31-35H,10-12H2,1-2H3/t16-,21+,23+,24-,26+,27+,28+,29+,31+,32-/m0/s1
InChIKey
NRUKOCRGYNPUPR-QBPJDGROSA-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
Cis-isomer of teniposide DM000497 N. A. Unclear 1 [6]
Glucuronide of the aglycone DM000498 N. A. Unclear 1 [6]
Hydroxy acid DM000496 N. A. Unclear 1 [6]
O-demethylated Teniposide DM000499 N. A. Unclear 1 [7]
Teniposide catechol derivative DM000493
101670240
Unclear 1 [7]
Teniposide catechol derivative DM000493
101670240
Oxidation - O-Demethylation 1 [5]
Unclear DM009999 N. A. Unclear 1 [8]
Teniposide o-quinone derivative DM000494 N. A. Unclear 2 [5]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR002393 Teniposide Teniposide catechol derivative Oxidation - O-Demethylation CYP3A4 ... [5]
MR002394 Teniposide Hydroxy acid Unclear Unclear [6]
MR002395 Teniposide Cis-isomer of teniposide Unclear Unclear [6]
MR002396 Teniposide Glucuronide of the aglycone Unclear Unclear [6]
MR002397 Teniposide O-demethylated Teniposide Unclear CYP3A4 ... [7]
MR002398 Teniposide . Unclear CYP2C19 [8]
MR002392 Teniposide catechol derivative Teniposide o-quinone derivative Unclear MPO [5]
⏷ Show the Full List of 7 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]
Cytochrome P450 3A5 (CYP3A5) DME0012 Homo sapiens
CP3A5_HUMAN
1.14.14.1
[3]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[4]
Myeloperoxidase (MPO) DME0096 Homo sapiens
PERM_HUMAN
1.11.2.2
[5]
References
1 Teniposide was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Screening for inhibitory effects of antineoplastic agents on CYP3A4 in human liver microsomes. Int J Clin Pharmacol Ther. 2001 Dec;39(12):517-28.
3 O-demethylation of epipodophyllotoxins is catalyzed by human cytochrome P450 3A4. Mol Pharmacol. 1994 Feb;45(2):352-8.
4 Drug Interactions Flockhart Table
5 DrugBank(Pharmacology-Metabolism)Teniposide
6 The clinical pharmacology of etoposide and teniposide Clin Pharmacokinet. 1987 Apr;12(4):223-52. doi: 10.2165/00003088-198712040-00001.
7 PubChem:Teniposide
8 Drug Interactions Flockhart Table:Docetaxel

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