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
InChI=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
InChIKey
VOCBWIIFXDYGNZ-IXKNJLPQSA-N
Cross-matching ID
PubChem CID
9416
ChEBI ID
CHEMBL9464
CAS Number
315-37-7
UNII
7Z6522T8N9
DrugBank ID
DB13944
INTEDE ID
DR1565
Drug Pharmacogenomic Perturbation (DPP)NEW Click to Jump to the Detailed DPP Information of This Drug
Drug ADMET Endpoint Profile (DAE)NEW Click to Jump to the Detailed DAE 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 [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-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]
5,6-dihydroxyindole-2-carboxylic acid oxidase OTRK49R4 TYRP1_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.