Details of the Drug

General Information of Drug (ID: DMZO10Y)

Drug Name
Testosterone undecanoate
Synonyms Restandol (TN)
Indication
Disease Entry ICD 11 Status REF
Hypogonadism 5A61.0 Approved [1]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 2 Molecular Weight (mw) 456.7
Logarithm of the Partition Coefficient (xlogp) 8.5
Rotatable Bond Count (rotbonds) 11
Hydrogen Bond Donor Count (hbonddonor) 0
Hydrogen Bond Acceptor Count (hbondacc) 3
ADMET Property
Elimination
90% of an intramuscularly administered dose of testosterone is conjugated and eliminated in the urine, and approximately 6% of the dose is eliminated primarily unconjugated in the feces []
Half-life
The concentration or amount of drug in body reduced by one-half in 33.9 days [2]
Metabolism
The drug is metabolized via the non specific esterases [3]
Chemical Identifiers
Formula
C30H48O3
IUPAC Name
[(8R,9S,10R,13S,14S,17S)-10,13-dimethyl-3-oxo-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl] undecanoate
Canonical SMILES
CCCCCCCCCCC(=O)O[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CCC4=CC(=O)CC[C@]34C)C
InChI
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
Cross-matching ID
PubChem CID
65157
ChEBI ID
CHEBI:135741
CAS Number
5949-44-0
DrugBank ID
DB13946
TTD ID
D02AXG
INTEDE ID
DR1566
Combinatorial Drugs (CBD) Click to Jump to the Detailed CBD Information of This Drug

Molecular Interaction Atlas of This Drug


Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 2C9 (CYP2C9) DE5IED8 CP2C9_HUMAN Substrate [4]
Mephenytoin 4-hydroxylase (CYP2C19) DEGTFWK CP2CJ_HUMAN Substrate [5]
Cytochrome P450 3A5 (CYP3A5) DEIBDNY CP3A5_HUMAN Substrate [6]
Cytochrome P450 2B6 (CYP2B6) DEPKLMQ CP2B6_HUMAN Substrate [7]
Cytochrome P450 2C8 (CYP2C8) DES5XRU CP2C8_HUMAN Substrate [8]
Cytochrome P450 3A7 (CYP3A7) DERD86B CP3A7_HUMAN Substrate [9]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
15-hydroxyprostaglandin dehydrogenase (HPGD) OTYZI6JB PGDH_HUMAN Gene/Protein Processing [10]
ADP-ribosylation factor-like protein 9 (ARL9) OTCP868V ARL9_HUMAN Gene/Protein Processing [10]
Alpha-protein kinase 2 (ALPK2) OTWZZDQ9 ALPK2_HUMAN Gene/Protein Processing [10]
AMP deaminase 3 (AMPD3) OT5SP1KJ AMPD3_HUMAN Gene/Protein Processing [10]
Apoptosis facilitator Bcl-2-like protein 14 (BCL2L14) OT87E7HW B2L14_HUMAN Gene/Protein Processing [10]
Atrial natriuretic peptide-converting enzyme (CORIN) OT4SK7DK CORIN_HUMAN Gene/Protein Processing [10]
C-C motif chemokine 18 (CCL18) OT7JYSK9 CCL18_HUMAN Gene/Protein Processing [10]
C-X-C motif chemokine 10 (CXCL10) OTTLQ6S0 CXL10_HUMAN Gene/Protein Processing [10]
Calcineurin B homologous protein 2 (CHP2) OT4UMKUR CHP2_HUMAN Gene/Protein Processing [10]
CCN family member 3 (CCN3) OTOW5YL4 CCN3_HUMAN Gene/Protein Processing [10]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

1 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015
2 Intramuscular injection of testosterone undecanoate for the treatment of male hypogonadism: phase I studies. Eur J Endocrinol. 1999 May;140(5):414-9.
3 Bruce RB, Turnbull LB, Newman JH: Metabolism of methocarbamol in the rat, dog, and human. J Pharm Sci. 1971 Jan;60(1):104-6.
4 Human cytochrome p450 induction and inhibition potential of clevidipine and its primary metabolite h152/81. Drug Metab Dispos. 2006 May;34(5):734-7.
5 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.
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 Insights into CYP2B6-mediated drug-drug interactions. Acta Pharm Sin B. 2016 Sep;6(5):413-425.
8 Role of cytochrome P450 2C8 in drug metabolism and interactions. Pharmacol Rev. 2016 Jan;68(1):168-241.
9 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.
10 Levonorgestrel enhances spermatogenesis suppression by testosterone with greater alteration in testicular gene expression in men. Biol Reprod. 2009 Mar;80(3):484-92.