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

General Information of Drug (ID: DR1566)
Drug Name
Testosterone undecanoate
Prodrug Info Testosterone undecanoate is the prodrug of Testosterone
Synonyms
Testosterone (undecanoate); Testosterone undecanoate; Testosterone undecanoate [USAN]; Testosterone undecylate; Testosterone, undecanoate (ester); UDSFVOAUHKGBEK-CNQKSJKFSA-N; UNII-H16A5VCT9C; Undestor; 17beta-Hydroxyandrost-4-en-3-one undecanoate; 3-Oxoandrost-4-en-17beta-yl undecanoate; 5-alpha-Androstan-3-one, 17-beta-hydroxy-, undecanoate; 5949-44-0; Andriol; Androst-4-en-3-one, 17-((1-oxoundecyl)oxy)-, (17-beta)-; BRN 3176734; EINECS 227-712-6; H16A5VCT9C; Nebido; Org 538; Pantestone; Restandol; T undecanoate
Indication Hypogonadism [ICD11: 5A61] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 456.7 Topological Polar Surface Area 43.4
Heavy Atom Count 33 Rotatable Bond Count 11
Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 3
Cross-matching ID
PubChem CID
65157
PubChem SID
8189552 ; 14906816 ; 14906817 ; 43121994 ; 47207745 ; 50049755 ; 50175053 ; 53786919 ; 57315356 ; 91616147 ; 104333040 ; 119501543 ; 126667397 ; 129353752 ; 135023127 ; 137117249 ; 160698246 ; 163413446 ; 163849167 ; 164234097 ; 175268717 ; 184552224 ; 198993637 ; 223675394 ; 226513522 ; 241089167 ; 250001622 ; 251887422 ; 252088562 ; 252122171 ; 252159067 ; 252357073
ChEBI ID
CHEBI:135741
CAS Number
5949-44-0
TTD Drug ID
D02AXG
Formula
C30H48O3
Canonical SMILES
CCCCCCCCCCC(=O)OC1CCC2C1(CCC3C2CCC4=CC(=O)CCC34C)C
InChI
1S/C30H48O3/c1-4-5-6-7-8-9-10-11-12-28(32)33-27-16-15-25-24-14-13-22-21-23(31)17-19-29(22,2)26(24)18-20-30(25,27)3/h21,24-27H,4-20H2,1-3H3/t24-,25-,26-,27-,29-,30-/m0/s1
InChIKey
UDSFVOAUHKGBEK-CNQKSJKFSA-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
Dihydrotestosterone undecanoate DM004576
56614500
Reduction - Reduction 1 [9]
Testosterone DM001963
6013
Hydrolysis - Esterase hydrolyzation 1 [9]
5alpha-dihydrotestosterone DM002519
10635
Unclear 2 [9]
Undecanoate DM004571
8180
Unclear 2 [10]
3-alpha-androstanediol DM004574
441301
Unclear 3 [2]
3-beta-androstenediol DM004575 N. A. Unclear 3 [2]
Acetyl Coenzyme A DM003095
444493
Oxidation - Oxidationn 3 [11]
3-alpha-androstanediol glucuronide DM007061
44263363
Unclear 4 [2]
Dihydrotestosterone glucuronide DM007062
162498
Unclear 4 [2]
Propionyl Coenzyme A DM004573
92753
Oxidation - Oxidationn 4 [11]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR004897 Testosterone undecanoate Testosterone Hydrolysis - Esterase hydrolyzation ES [9]
MR004906 Testosterone undecanoate Dihydrotestosterone undecanoate Reduction - Reduction SRD5A2 [9]
MR004907 Dihydrotestosterone undecanoate 5alpha-dihydrotestosterone Unclear Unclear [9]
MR004901 Testosterone 5alpha-dihydrotestosterone Unclear SRD5A2 [9]
MR004898 Testosterone undecanoate Undecanoate Unclear Unclear [10]
MR004902 5alpha-dihydrotestosterone 3-alpha-androstanediol Unclear AKR1C4 ... [2]
MR004904 5alpha-dihydrotestosterone 3-beta-androstenediol Unclear Unclear [2]
MR004899 Undecanoate Acetyl Coenzyme A Oxidation - Oxidationn Unclear [11]
MR004903 3-alpha-androstanediol 3-alpha-androstanediol glucuronide Unclear Unclear [2]
MR004905 3-beta-androstenediol Dihydrotestosterone glucuronide Unclear Unclear [2]
MR004900 Acetyl Coenzyme A Propionyl Coenzyme A Oxidation - Oxidationn Unclear [11]
⏷ Show the Full List of 11 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Aldo-keto reductase 1C4 (AKR1C4) DME0198 Homo sapiens
AK1C4_HUMAN
1.1.1.357
[2]
Cytochrome P450 2B6 (CYP2B6) DME0020 Homo sapiens
CP2B6_HUMAN
1.14.14.1
[3]
Cytochrome P450 2C8 (CYP2C8) DME0018 Homo sapiens
CP2C8_HUMAN
1.14.14.1
[4]
Cytochrome P450 2C9 (CYP2C9) DME0019 Homo sapiens
CP2C9_HUMAN
1.14.14.1
[5]
Cytochrome P450 3A5 (CYP3A5) DME0012 Homo sapiens
CP3A5_HUMAN
1.14.14.1
[6]
Cytochrome P450 3A7 (CYP3A7) DME0015 Homo sapiens
CP3A7_HUMAN
1.14.14.1
[7]
Dihydrotestosterone oxidoreductase (HSD3B1) DME0221 Homo sapiens
3BHS1_HUMAN
1.1.1.145
[2]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[8]
Steroid 5-alpha-reductase 2 (SRD5A2) DME0218 Homo sapiens
S5A2_HUMAN
1.3.1.22
[9]
⏷ Show the Full List of 9  DME(s)
References
1 Testosterone Undecanoate was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Metabolism of dihydrotestosterone in human liver: importance of 3alpha- and 3beta-hydroxysteroid dehydrogenase
3 Insights into CYP2B6-mediated drug-drug interactions. Acta Pharm Sin B. 2016 Sep;6(5):413-425.
4 Role of cytochrome P450 2C8 in drug metabolism and interactions. Pharmacol Rev. 2016 Jan;68(1):168-241.
5 Human cytochrome p450 induction and inhibition potential of clevidipine and its primary metabolite h152/81. Drug Metab Dispos. 2006 May;34(5):734-7.
6 In vitro metabolism of midazolam, triazolam, nifedipine, and testosterone by human liver microsomes and recombinant cytochromes p450: role of cyp3a4 and cyp3a5. Drug Metab Dispos. 2003 Jul;31(7):938-44.
7 Steroid hydroxylation by human fetal CYP3A7 and human NADPH-cytochrome P450 reductase coexpressed in insect cells using baculovirus. Res Commun Mol Pathol Pharmacol. 1998 Apr;100(1):15-28.
8 Progesterone and testosterone hydroxylation by cytochromes P450 2C19, 2C9, and 3A4 in human liver microsomes. Arch Biochem Biophys. 1997 Oct 1;346(1):161-9.
9 Importance of measuring testosterone in enzyme-inhibited plasma for oral testosterone undecanoate androgen replacement therapy clinical trials
10 Androgen Receptor Structure, Function and Biology: From Bench to Bedside
11 DrugBank(Pharmacology-Metabolism):Testosterone undecanoate

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