General Information of Drug (ID: DR1564)
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
Indication Testosterone deficiency [ICD11: 5A81] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 412.6 Topological Polar Surface Area 43.4
Heavy Atom Count 30 Rotatable Bond Count 5
Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 3
Cross-matching ID
PubChem CID
441404
ChEBI ID
CHEBI:9463
CAS Number
58-20-8
Formula
C27H40O3
Canonical SMILES
CC12CCC3C(C1CCC2OC(=O)CCC4CCCC4)CCC5=CC(=O)CCC35C
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
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
Testosterone DM001963
6013
Hydrolysis - Hydrolyation 1 [23]
5alpha-dihydrotestosterone DM002519
10635
Unclear 2 [23]
3alpha-Androstanediol glucuronide DM001573
53480451
Unclear 3 [24]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR004896 Testosterone cypionate Testosterone Hydrolysis - Hydrolyation Unclear [23]
MR004894 Testosterone 5alpha-dihydrotestosterone Unclear SRD5A2 [23]
MR004895 5alpha-dihydrotestosterone 3alpha-Androstanediol glucuronide Unclear Unclear [24]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Aromatase (CYP19A1) DME0002 Homo sapiens
CP19A_HUMAN
1.14.14.14
[2]
Cholesterol 24-hydroxylase (CYP46A1) DME0028 Homo sapiens
CP46A_HUMAN
1.14.14.25
[3]
Cytochrome P450 154C2 (cyp154) DME1466 Streptomyces avermitilis
A0A345AH95_STRSQ
1.14.14.1
[4] , [5]
Cytochrome P450 1A1 (CYP1A1) DME0006 Homo sapiens
CP1A1_HUMAN
1.14.14.1
[6]
Cytochrome P450 1B1 (CYP1B1) DME0023 Homo sapiens
CP1B1_HUMAN
1.14.14.1
[7]
Cytochrome P450 2A13 (CYP2A13) DME0030 Homo sapiens
CP2AD_HUMAN
1.14.14.1
[8]
Cytochrome P450 2B6 (CYP2B6) DME0020 Homo sapiens
CP2B6_HUMAN
1.14.14.1
[9]
Cytochrome P450 2C8 (CYP2C8) DME0018 Homo sapiens
CP2C8_HUMAN
1.14.14.1
[10]
Cytochrome P450 2C9 (CYP2C9) DME0019 Homo sapiens
CP2C9_HUMAN
1.14.14.1
[11]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[12]
Cytochrome P450 3A43 (CYP3A43) DME0022 Homo sapiens
CP343_HUMAN
1.14.14.1
[13]
Cytochrome P450 3A5 (CYP3A5) DME0012 Homo sapiens
CP3A5_HUMAN
1.14.14.1
[14]
Cytochrome P450 3A7 (CYP3A7) DME0015 Homo sapiens
CP3A7_HUMAN
1.14.14.1
[15]
Cytochrome P450 4B1 (CYP4B1) DME0010 Homo sapiens
CP4B1_HUMAN
1.14.14.1
[16]
Cytochrome P450 MEG (cyp106) DME1072 Bacillus megaterium
CPXM_BACME
1.14.15.8
[17] , [18]
Dehydrogenase/reductase retSDR3 (HSD17B14) DME0609 Homo sapiens
DHB14_HUMAN
1.1.1.62
[19]
Farnesol dehydrogenase (AKR1B15) DME0399 Homo sapiens
AK1BF_HUMAN
1.1.1.54
[20]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[21]
Steroid 5-alpha-reductase 1 (SRD5A1) DME0204 Homo sapiens
S5A1_HUMAN
1.3.1.22
[22]
Steroid 5-alpha-reductase 2 (SRD5A2) DME0218 Homo sapiens
S5A2_HUMAN
1.3.1.22
[22]
Steroid 5-alpha-reductase 2 (SRD5A2) DME0218 Homo sapiens
S5A2_HUMAN
1.3.1.22
[23]
Steroid 5-alpha-reductase 3 (SRD5A3) DME0219 Homo sapiens
PORED_HUMAN
1.3.1.22
[22]
⏷ Show the Full List of 22  DME(s)
Experimental Enzyme Kinetic Data of This Drug
DME Name DME Info Kinetic Data Uniprot ID REF
Farnesol dehydrogenase (AKR1B15) DME0399 Km = 0.0071 microM
AK1BF_HUMAN
[20]
Cytochrome P450 154C2 (cyp154) DME1466 Km = 160 microM
A0A345AH95_STRSQ
[4] , [5]
References
1 Testosterone Cypionate was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Loss of aromatase cytochrome P450 function as a risk factor for Parkinson's disease? Brain Res Rev. 2008 Mar;57(2):431-43.
3 Broad substrate specificity of human cytochrome P450 46A1 which initiates cholesterol degradation in the brain. Biochemistry. 2003 Dec 9;42(48):14284-92.
4 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.
5 The metagenome of Caracolus marginella gut microbiome using culture independent approaches and shotgun sequencing. Data Brief. 2017 Nov 22;16:501-505.
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 Catalytic properties of polymorphic human cytochrome P450 1B1 variants. Carcinogenesis. 1999 Aug;20(8):1607-13.
8 Effects of 8-methoxypsoralen on cytochrome P450 2A13. Carcinogenesis. 2005 Mar;26(3):621-9.
9 Insights into CYP2B6-mediated drug-drug interactions. Acta Pharm Sin B. 2016 Sep;6(5):413-425.
10 Role of cytochrome P450 2C8 in drug metabolism and interactions. Pharmacol Rev. 2016 Jan;68(1):168-241.
11 Human cytochrome p450 induction and inhibition potential of clevidipine and its primary metabolite h152/81. Drug Metab Dispos. 2006 May;34(5):734-7.
12 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.
13 cDNA cloning and initial characterization of CYP3A43, a novel human cytochrome P450. Mol Pharmacol. 2001 Feb;59(2):386-92.
14 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.
15 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.
16 Steroid hormone hydroxylase specificities of eleven cDNA-expressed human cytochrome P450s. Arch Biochem Biophys. 1991 Oct;290(1):160-6.
17 acillus megaterium SF185 spores exert protective effects against oxidative stress in vivo and in vitro. Sci Rep. 2019 Aug 19;9(1):12082.
18 A Novel NADPH-dependent flavoprotein reductase from Bacillus megaterium acts as an efficient cytochrome P450 reductase. J Biotechnol. 2016 Aug 10;231:83-94.
19 Expression patterns of 17beta-hydroxysteroid dehydrogenase 14 in human tissues. Horm Metab Res. 2012 Dec;44(13):949-56.
20 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.
21 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.
22 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).
23 The history of synthetic testosterone
24 DrugBank(Pharmacology-Metabolism):Testosterone cypionate

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