Details of the Drug

General Information of Drug (ID: DMB6871)

Drug Name
Testosterone enanthate
Synonyms
Testanthate; Testate; Testenate; Testinon; Testoenant; Testonenant; Testosterone 17-enanthate; Testosterone enantate; Testosterone heptanoate; Testosterone heptoate; Testosterone heptylate; Testosterone oenanthate; Testostroval; testosterone enanthate; 17-Hydroxyandrost-4-en-3-one, 17-heptanoate; 315-37-7; Andro L.A. 200; Andropository; Androtardyl; Atlatest; DePatestrye; Delatest; Depo-Testro Med; Ditate; Durathate; Everone; Exten test; Malogen L.A.; Malogen L.A.200; NSC-17591; Orquisteron-E; Primotestone; Reposo TMD; Reposo-TMD
Affected Organisms
Humans and other mammals
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 1 Molecular Weight (mw) 400.6
Logarithm of the Partition Coefficient (xlogp) 6.3
Rotatable Bond Count (rotbonds) 7
Hydrogen Bond Donor Count (hbonddonor) 0
Hydrogen Bond Acceptor Count (hbondacc) 3
ADMET Property
Absorption Cmax
The maximum plasma concentration (Cmax) of drug is 1200 mcg/L [1]
Elimination
About 90% of a dose of testosterone given intramuscularly is excreted in the urine as glucuronic and sulfuric acid conjugates of testosterone and its metabolites; about 6% of a dose is excreted in the feces, mostly in the unconjugated form [2]
Half-life
The concentration or amount of drug in body reduced by one-half in 7 - 9 days [3]
Metabolism
The drug is metabolized via the enzymes in the bloodstream [2]
Vd
The volume of distribution (Vd) of drug is 1 L/kg [4]
Chemical Identifiers
Formula
C26H40O3
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] heptanoate
Canonical SMILES
CCCCCCC(=O)OC1CCC2C1(CCC3C2CCC4=CC(=O)CCC34C)C
InChI
VOCBWIIFXDYGNZ-IXKNJLPQSA-N
InChIKey
1S/C26H40O3/c1-4-5-6-7-8-24(28)29-23-12-11-21-20-10-9-18-17-19(27)13-15-25(18,2)22(20)14-16-26(21,23)3/h17,20-23H,4-16H2,1-3H3/t20-,21-,22-,23-,25-,26-/m0/s1
Cross-matching ID
PubChem CID
9416
ChEBI ID
CHEBI:9464
CAS Number
315-37-7
UNII
7Z6522T8N9
DrugBank ID
DB13944
INTEDE ID
DR1565

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 [5]
Mephenytoin 4-hydroxylase (CYP2C19) DEGTFWK CP2CJ_HUMAN Substrate [6]
Cytochrome P450 3A5 (CYP3A5) DEIBDNY CP3A5_HUMAN Substrate [7]
Cytochrome P450 2B6 (CYP2B6) DEPKLMQ CP2B6_HUMAN Substrate [8]
Cytochrome P450 2C8 (CYP2C8) DES5XRU CP2C8_HUMAN Substrate [9]
Cytochrome P450 3A7 (CYP3A7) DERD86B CP3A7_HUMAN Substrate [10]
Steroid 5-alpha-reductase 2 (SRD5A2) DEPTJ3D S5A2_HUMAN Substrate [11]
Phosphodiesterase 7B (PDE7B) DEON3ED PDE7B_HUMAN Substrate [12]
Steroid 5-alpha-reductase 3 (SRD5A3) DEZGVDW PORED_HUMAN Substrate [11]
Steroid 5-alpha-reductase 1 (SRD5A1) DEOG15F S5A1_HUMAN Substrate [11]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
14-3-3 protein beta/alpha OTGBS3RF 1433B_HUMAN Gene/Protein Processing [13]
17S U2 SnRNP complex component HTATSF1 (HTATSF1) OTLQ1ZLS HTSF1_HUMAN Gene/Protein Processing [13]
2'-5'-oligoadenylate synthase 2 (OAS2) OT64CCTM OAS2_HUMAN Gene/Protein Processing [13]
2-amino-3-ketobutyrate coenzyme A ligase, mitochondrial (GCAT) OT6WZPWV KBL_HUMAN Gene/Protein Processing [13]
2-oxoglutarate and iron-dependent oxygenase domain-containing protein 2 (OGFOD2) OTTXP61X OGFD2_HUMAN Gene/Protein Processing [13]
2-oxoglutarate dehydrogenase complex component E1 (OGDH) OTHGTQWF ODO1_HUMAN Gene/Protein Processing [13]
3',5'-cyclic-AMP phosphodiesterase 7B (PDE7B) OTK3SHT2 PDE7B_HUMAN Biotransformations [14]
3-hydroxyisobutyryl-CoA hydrolase, mitochondrial (HIBCH) OTU2VHWR HIBCH_HUMAN Gene/Protein Processing [13]
5'-AMP-activated protein kinase catalytic subunit alpha-2 (PRKAA2) OTU1KZPV AAPK2_HUMAN Gene/Protein Processing [13]
5'-AMP-activated protein kinase subunit beta-2 (PRKAB2) OTLVN68B AAKB2_HUMAN Gene/Protein Processing [13]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

1 Shoskes JJ, Wilson MK, Spinner ML: Pharmacology of testosterone replacement therapy preparations. Transl Androl Urol. 2016 Dec;5(6):834-843. doi: 10.21037/tau.2016.07.10.
2 Pfizer monograph
3 Pharmacokinetic Profile of Subcutaneous Testosterone Enanthate Delivered via a Novel, Prefilled Single-Use Autoinjector: A Phase II Study. Sex Med. 2015 Sep 17;3(4):269-79. doi: 10.1002/sm2.80. eCollection 2015 Dec.
4 Pfizer monograph
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 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.
7 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.
8 Insights into CYP2B6-mediated drug-drug interactions. Acta Pharm Sin B. 2016 Sep;6(5):413-425.
9 Role of cytochrome P450 2C8 in drug metabolism and interactions. Pharmacol Rev. 2016 Jan;68(1):168-241.
10 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.
11 Molecular analysis of the SRD5A1 and SRD5A2 genes in patients with benign prostatic hyperplasia with regard to metabolic parameters and selected hormone levels. Int J Environ Res Public Health. 2017 Oct 30;14(11).
12 PDE7B is involved in nandrolone decanoate hydrolysis in liver cytosol and its transcription is up-regulated by androgens in HepG2. Front Pharmacol. 2014 May 30;5:132.
13 Transcriptional profiling of testosterone-regulated genes in the skeletal muscle of human immunodeficiency virus-infected men experiencing weight loss. J Clin Endocrinol Metab. 2007 Jul;92(7):2793-802. doi: 10.1210/jc.2006-2722. Epub 2007 Apr 17.
14 Bioavailability of testosterone enanthate dependent on genetic variation in the phosphodiesterase 7B but not on the uridine 5'-diphospho-glucuronosyltransferase (UGT2B17) gene. Pharmacogenet Genomics. 2011 Jun;21(6):325-32. doi: 10.1097/FPC.0b013e328344c5c6.