Details of the Drug

General Information of Drug (ID: DMC1TEV)

Drug Name
Testosterone cypionate
Synonyms
Testodrin prolongatum; Testosterone 17beta-cyclopentylpropionate; Testosterone 17beta-cypionate; Testosterone cyclopentanepropionate; Testosterone cyclopentylpropionate; Testosterone cypionate [USP]; Testandrone; Testiculosterone; Testim; Testobase; Testoderm; Testogel; Testopropon; Testosteroid; Testosteron; Testosterona; Testosteronum; Testostosterone; Testoviron; Testoviron Schering; Testoviron T; Testrone; Testryl; Virormone; Virosterone; testosterone; trans-Testosterone; 58-22-0; AndroGel; Androderm; Androlin; Andronaq; Andropatch; Andrusol; Cristerona T; Cristerone T; Homosteron; Homosterone; LibiGel; Malerone; Mertestate; Neotestis; Oreton; Orquisteron; Perandren; Primotest; Primoteston; Relibra; Sustanon; Sustanone; Synandrol F; Teslen; UNII-M0XW1UBI14; depAndro 100; depAndro 200; 58-20-8; Andro-Cyp; Androst-4-en-3-one, 17-(3-cyclopentyl-1-oxopropoxy)-, (17b)-; CHEBI:9463; DEPO; Dep-Test; Depo-Testadiol; Depo-Testosterone; Depotest; Depovirin; Durandro; Jectatest; M0XW1UBI14; Malogen CYP; NSC 9157; Pertestis; T-Ionate-P.A; TESTOSTERONE CYPIONATE
Affected Organisms
Humans and other mammals
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 1 Molecular Weight (mw) 412.6
Logarithm of the Partition Coefficient (xlogp) 6.4
Rotatable Bond Count (rotbonds) 5
Hydrogen Bond Donor Count (hbonddonor) 0
Hydrogen Bond Acceptor Count (hbondacc) 3
ADMET Property
Absorption Cmax
The maximum plasma concentration (Cmax) of drug is 11220 ng/L [1]
Absorption Tmax
The time to maximum plasma concentration (Tmax) is 4-5 days [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 8 days [1]
Metabolism
The drug is metabolized via the enzymes in the bloodstream [2]
Vd
The volume of distribution (Vd) of drug is 1 L/kg [3]
Chemical Identifiers
Formula
C27H40O3
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] 3-cyclopentylpropanoate
Canonical SMILES
CC12CCC3C(C1CCC2OC(=O)CCC4CCCC4)CCC5=CC(=O)CCC35C
InChI
InChI=1S/C27H40O3/c1-26-15-13-20(28)17-19(26)8-9-21-22-10-11-24(27(22,2)16-14-23(21)26)30-25(29)12-7-18-5-3-4-6-18/h17-18,21-24H,3-16H2,1-2H3/t21-,22-,23-,24-,26-,27-/m0/s1
InChIKey
HPFVBGJFAYZEBE-ZLQWOROUSA-N
Cross-matching ID
PubChem CID
441404
ChEBI ID
CHEMBL9463
CAS Number
58-20-8
UNII
M0XW1UBI14
DrugBank ID
DB13943
INTEDE ID
DR1564
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Drug ADMET Endpoint Profile (DAE)NEW Click to Jump to the Detailed DAE Information of This Drug
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Molecular Interaction Atlas of This Drug


Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 3A4 (CYP3A4) DE4LYSA CP3A4_HUMAN Substrate [4]
Cytochrome P450 2C9 (CYP2C9) DE5IED8 CP2C9_HUMAN Substrate [5]
Cytochrome P450 1A1 (CYP1A1) DE6OQ3W CP1A1_HUMAN Substrate [6]
Mephenytoin 4-hydroxylase (CYP2C19) DEGTFWK CP2CJ_HUMAN Substrate [7]
Cytochrome P450 3A5 (CYP3A5) DEIBDNY CP3A5_HUMAN Substrate [8]
Cytochrome P450 1B1 (CYP1B1) DE9QHP6 CP1B1_HUMAN Substrate [9]
Aromatase (CYP19A1) DEQX145 CP19A_HUMAN Substrate [10]
Cytochrome P450 2B6 (CYP2B6) DEPKLMQ CP2B6_HUMAN Substrate [11]
Cytochrome P450 2C8 (CYP2C8) DES5XRU CP2C8_HUMAN Substrate [12]
Cytochrome P450 3A7 (CYP3A7) DERD86B CP3A7_HUMAN Substrate [13]
Steroid 5-alpha-reductase 2 (SRD5A2) DEPTJ3D S5A2_HUMAN Substrate [14]
Cytochrome P450 4B1 (CYP4B1) DEMF740 CP4B1_HUMAN Substrate [15]
Cytochrome P450 2A13 (CYP2A13) DEXZA9U CP2AD_HUMAN Substrate [16]
Cytochrome P450 3A43 (CYP3A43) DEO1IE3 CP343_HUMAN Substrate [17]
Cholesterol 24-hydroxylase (CYP46A1) DEKP5HX CP46A_HUMAN Substrate [18]
Steroid 5-alpha-reductase 3 (SRD5A3) DEZGVDW PORED_HUMAN Substrate [14]
Steroid 5-alpha-reductase 1 (SRD5A1) DEOG15F S5A1_HUMAN Substrate [14]
Farnesol dehydrogenase (AKR1B15) DER0XCH AK1BF_HUMAN Substrate [19]
Cytochrome P450 MEG (cyp106) DEZ1H4L CPXM_BACME Substrate [20], [21]
Dehydrogenase/reductase retSDR3 (HSD17B14) DEGTB1K DHB14_HUMAN Substrate [22]
Cytochrome P450 154C2 (cyp154) DEHDW40 A0A345AH95_STRSQ Substrate [23], [24]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

1 Dailymed
2 Pfizer monograph
3 Pfizer monograph
4 Digging deeper into CYP3A testosterone metabolism: kinetic, regioselectivity, and stereoselectivity differences between CYP3A4/5 and CYP3A7. Drug Metab Dispos. 2017 Dec;45(12):1266-1275.
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 Allelic variants of human cytochrome P450 1A1 (CYP1A1): effect of T461N and I462V substitutions on steroid hydroxylase specificity. Pharmacogenetics. 2000 Aug;10(6):519-30.
7 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.
8 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.
9 Catalytic properties of polymorphic human cytochrome P450 1B1 variants. Carcinogenesis. 1999 Aug;20(8):1607-13.
10 Loss of aromatase cytochrome P450 function as a risk factor for Parkinson's disease? Brain Res Rev. 2008 Mar;57(2):431-43.
11 Insights into CYP2B6-mediated drug-drug interactions. Acta Pharm Sin B. 2016 Sep;6(5):413-425.
12 Role of cytochrome P450 2C8 in drug metabolism and interactions. Pharmacol Rev. 2016 Jan;68(1):168-241.
13 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.
14 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).
15 Steroid hormone hydroxylase specificities of eleven cDNA-expressed human cytochrome P450s. Arch Biochem Biophys. 1991 Oct;290(1):160-6.
16 Effects of 8-methoxypsoralen on cytochrome P450 2A13. Carcinogenesis. 2005 Mar;26(3):621-9.
17 cDNA cloning and initial characterization of CYP3A43, a novel human cytochrome P450. Mol Pharmacol. 2001 Feb;59(2):386-92.
18 Broad substrate specificity of human cytochrome P450 46A1 which initiates cholesterol degradation in the brain. Biochemistry. 2003 Dec 9;42(48):14284-92.
19 Aldo-keto Reductase 1B15 (AKR1B15): a mitochondrial human aldo-keto reductase with activity toward steroids and 3-keto-acyl-CoA conjugates. J Biol Chem. 2015 Mar 6;290(10):6531-45.
20 acillus megaterium SF185 spores exert protective effects against oxidative stress in vivo and in vitro. Sci Rep. 2019 Aug 19;9(1):12082.
21 A Novel NADPH-dependent flavoprotein reductase from Bacillus megaterium acts as an efficient cytochrome P450 reductase. J Biotechnol. 2016 Aug 10;231:83-94.
22 Expression patterns of 17beta-hydroxysteroid dehydrogenase 14 in human tissues. Horm Metab Res. 2012 Dec;44(13):949-56.
23 Regio- and stereoselective hydroxylation of testosterone by a novel cytochrome P450 154C2 from Streptomyces avermitilis. Biochem Biophys Res Commun. 2020 Feb 5;522(2):355-361.
24 The metagenome of Caracolus marginella gut microbiome using culture independent approaches and shotgun sequencing. Data Brief. 2017 Nov 22;16:501-505.