DT-Web

DB01420 - Testosterone Propionate


Identification
Name Testosterone Propionate
Accession Number DB01420
Type small molecule
Description An ester of testosterone with a propionate substitution at the 17-beta position. [PubChem]
Structure
MOL SDF PDB SMILES InChI
Categories (*)
Molecular Weight 344.4877
Groups approved
Monoisotopic Weight 344.23514489
Pharmacology
Indication Testosterone propionate is an anabolic steroid and a short ester form of testosterone that becomes active in the body. It is often used for muscle mass building.
Mechanism of action The effects of testosterone in humans and other vertebrates occur by way of two main mechanisms: by activation of the androgen receptor (directly or as DHT), and by conversion to estradiol and activation of certain estrogen receptors. Free testosterone (T) is transported into the cytoplasm of target tissue cells, where it can bind to the androgen receptor, or can be reduced to 5α-dihydrotestosterone (DHT) by the cytoplasmic enzyme 5α-reductase. DHT binds to the same androgen receptor even more strongly than T, so that its androgenic potency is about 2.5 times that of T. The T-receptor or DHT-receptor complex undergoes a structural change that allows it to move into the cell nucleus and bind directly to specific nucleotide sequences of the chromosomal DNA. The areas of binding are called hormone response elements (HREs), and influence transcriptional activity of certain genes, producing the androgen effects.
Absorption Not Available
Protein binding 40% of testosterone in plasma is bound to sex hormone-binding globulin and 2% remains unbound and the rest is bound to albumin and other proteins.
Biotransformation Testosterone propionate is rapidly hydrolysed into testosterone. Testosterone is metabolized to 17-keto steroids through two different pathways. The major active metabolites are estradiol and dihydrotestosterone (DHT).
Route of 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.
Toxicity Side effects include amnesia, anxiety, discolored hair, dizziness, dry skin, hirsutism, hostility, impaired urination, paresthesia, penis disorder, peripheral edema, sweating, and vasodilation.
Affected organisms
  • Humans and other mammals
Interactions
Drug Interactions
Drug Mechanism of interaction
Acenocoumarol The androgen, Testosterone, may incrase the anticoagulant effect of the Vitamin K antagonist, Acenocoumarol. Monitor for changes in the therapeutic effect of Acenocoumarol if Testosterone is initiated, discontinued or dose changed.
Cyclosporine The androgen, Testosterone, may increase the hepatotoxicity of Cyclosporine. Testosterone may also elevate serum concentrations of Cyclosporine. Consider alternate therapy or monitor for signs of renal and hepatic toxicity.
Docetaxel Testosterone propionate may increase the serum levels and toxicity of docetaxel.
Warfarin The androgen, Testosterone, may incrase the anticoagulant effect of the Vitamin K antagonist, Warfarin. Monitor for changes in the therapeutic effect of Warfarin if Testosterone is initiated, discontinued or dose changed.
Food Interactions Not Available

Targets


Androgen receptor
Name Androgen receptor
Gene Name AR
Pharmacological action yes
Actions agonist
References
  • Small EJ, Ryan CJ: The case for secondary hormonal therapies in the chemotherapy age. J Urol. 2006 Dec;176(6 Pt 2):S66-71. - Pubmed
  • Omwancha J, Brown TR: Selective androgen receptor modulators: in pursuit of tissue-selective androgens. Curr Opin Investig Drugs. 2006 Oct;7(10):873-81. - Pubmed
  • Petraki CD, Sfikas CP: Histopathological changes induced by therapies in the benign prostate and prostate adenocarcinoma. Histol Histopathol. 2007 Jan;22(1):107-18. - Pubmed
  • Maudsley S, Davidson L, Pawson AJ, Freestone SH, Lopez de Maturana R, Thomson AA, Millar RP: Gonadotropin-releasing hormone functionally antagonizes testosterone activation of the human androgen receptor in prostate cells through focal adhesion complexes involving Hic-5. Neuroendocrinology. 2006;84(5):285-300. Epub 2007 Jan 4. - Pubmed
  • Lapauw B, Goemaere S, Crabbe P, Kaufman JM, Ruige JB: Is the effect of testosterone on body composition modulated by the androgen receptor gene CAG repeat polymorphism in elderly men? Eur J Endocrinol. 2007 Mar;156(3):395-401. - Pubmed
  • Yin D, Gao W, Kearbey JD, Xu H, Chung K, He Y, Marhefka CA, Veverka KA, Miller DD, Dalton JT: Pharmacodynamics of selective androgen receptor modulators. J Pharmacol Exp Ther. 2003 Mar;304(3):1334-40. - Pubmed
DTHybrid score 1.0628

Enzymes


Catechol O-methyltransferase
Name Catechol O-methyltransferase
Gene Name COMT
Actions inhibitor
References
  • Ladosky W, Schneider HT: Changes in hypothalamic catechol-O-methyl-transferase during sexual differentiation of the brain. Braz J Med Biol Res. 1981 Dec;14(6):409-13. - Pubmed
DTHybrid score 0.7981
UDP-glucuronosyltransferase 1-1
Name UDP-glucuronosyltransferase 1-1
Gene Name UGT1A1
Actions inducer
References
  • Stern ST, Tallman MN, Miles KK, Ritter JK, Smith PC: Androgen regulation of renal uridine diphosphoglucuronosyltransferase 1A1 in rats. Drug Metab Dispos. 2008 Sep;36(9):1737-9. doi: 10.1124/dmd.108.020610. Epub 2008 May 30. - Pubmed
DTHybrid score 0.1756

Predictions


Id Partner name Gene Name Score
3811 Cytochrome P450 19A1 CYP19A1 0.0686
6018 UDP-glucuronosyltransferase 1-9 UGT1A9 0.0629
4757 Cytochrome P450 2C9 CYP2C9 0.0609
5455 Arylsulfatase A ARSA 0.0518
4512 Cytochrome P450 3A4 CYP3A4 0.0476
1588 Multidrug resistance protein 1 ABCB1 0.046
6178 UDP-glucuronosyltransferase 2B7 UGT2B7 0.0438
4924 Cytochrome P450 2C8 CYP2C8 0.0434
756 Sex hormone-binding globulin SHBG 0.0407
6176 UDP-glucuronosyltransferase 1-3 UGT1A3 0.0377
3939 Amine oxidase [flavin-containing] B MAOB 0.0327
3941 Amine oxidase [flavin-containing] A MAOA 0.0327
6016 Cytochrome P450 2C19 CYP2C19 0.0326
614 Progesterone receptor PGR 0.0297
4200 Cytochrome P450 1A2 CYP1A2 0.0273
766 Beta-2 adrenergic receptor ADRB2 0.0271
737 Mineralocorticoid receptor NR3C2 0.0267
6026 Alcohol dehydrogenase 6 ADH6 0.0266
1490 Solute carrier organic anion transporter family member 1B1 SLCO1B1 0.0264
290 Prostaglandin G/H synthase 2 PTGS2 0.0263
4118 Cytochrome P450 3A5 CYP3A5 0.0232
1732 ATP-binding cassette sub-family G member 2 ABCG2 0.0226
136 Estrogen receptor ESR1 0.0223
6139 Solute carrier organic anion transporter family member 1A2 SLCO1A2 0.0215
587 Serum albumin ALB 0.0214
4119 Cytochrome P450 2D6 CYP2D6 0.0212
6030 Cytochrome P450 2B6 CYP2B6 0.0211
193 Beta-1 adrenergic receptor ADRB1 0.0201
1539 Oligopeptide transporter, small intestine isoform SLC15A1 0.0198
20 Prostaglandin G/H synthase 1 PTGS1 0.0198
1735 Canalicular multispecific organic anion transporter 1 ABCC2 0.0195
318 Alpha-2A adrenergic receptor ADRA2A 0.0184
6013 Cytochrome P450 2E1 CYP2E1 0.0164
1729 Solute carrier family 22 member 6 SLC22A6 0.0159
871 Glucocorticoid receptor NR3C1 0.0158
330 Spermidine synthase SRM 0.0149
3038 Spermidine synthase speE 0.0149
381 Prolactin receptor PRLR 0.013
6241 Nuclear receptor coactivator 2 NCOA2 0.013
113 S-adenosylmethionine decarboxylase proenzyme AMD1 0.0128
453 S-adenosylmethionine synthetase isoform type-1 MAT1A 0.0126
334 S-adenosylmethionine synthetase isoform type-2 MAT2A 0.0126
6024 Cytochrome P450 1A1 CYP1A1 0.0126
26 Vascular endothelial growth factor receptor 3 FLT4 0.0125
411 Glycine N-methyltransferase GNMT 0.0122
5718 Cytochrome P450 2A6 CYP2A6 0.0121
5880 Thrombopoietin receptor MPL 0.012
32 Vascular endothelial growth factor receptor 1 FLT1 0.0119
838 Inosine-5'-monophosphate dehydrogenase 1 IMPDH1 0.0119
796 Inosine-5'-monophosphate dehydrogenase 2 IMPDH2 0.0118
358 Cystathionine beta-synthase CBS 0.0117
373 Transthyretin TTR 0.0116
6181 UDP-glucuronosyltransferase 1-8 UGT1A8 0.0116
6177 UDP-glucuronosyltransferase 1-10 UGT1A10 0.011
2164 Multidrug resistance-associated protein 4 ABCC4 0.011
862 Multidrug resistance-associated protein 1 ABCC1 0.0109
6180 UDP-glucuronosyltransferase 2B4 UGT2B4 0.0105
504 Mast/stem cell growth factor receptor KIT 0.0104
6157 Solute carrier organic anion transporter family member 1B3 SLCO1B3 0.0101
6142 Solute carrier family 22 member 8 SLC22A8 0.0099
6107 Cytochrome P450 3A7 CYP3A7 0.0097
407 Vascular endothelial growth factor receptor 2 KDR 0.0096
1898 Cytochrome P450 1B1 CYP1B1 0.0095
319 Opioid receptor, sigma 1 OPRS1 0.0094
1632 Solute carrier organic anion transporter family member 2B1 SLCO2B1 0.0094
1709 Canalicular multispecific organic anion transporter 2 ABCC3 0.0093
3809 Estrogen-related receptor gamma ESRRG 0.0092
631 3-hydroxy-3-methylglutaryl-coenzyme A reductase HMGCR 0.0084
3387 3-hydroxy-3-methylglutaryl-coenzyme A reductase mvaA 0.0084
596 3-oxo-5-alpha-steroid 4-dehydrogenase 1 SRD5A1 0.0082
467 Delta-type opioid receptor OPRD1 0.0081
696 Kappa-type opioid receptor OPRK1 0.0081
847 Mu-type opioid receptor OPRM1 0.0077
4120 NADPH--cytochrome P450 reductase POR 0.0074
6220 Aryl hydrocarbon receptor AHR 0.0074
6147 Solute carrier family 22 member 3 SLC22A3 0.0073
4162 Potassium voltage-gated channel subfamily KQT member 3 KCNQ3 0.0072
650 Aldo-keto reductase family 1 member C3 AKR1C3 0.0071
4164 Potassium voltage-gated channel subfamily KQT member 5 KCNQ5 0.0069
4163 Potassium voltage-gated channel subfamily KQT member 4 KCNQ4 0.0069
6102 Arylamine N-acetyltransferase 2 NAT2 0.0069
3923 Cholinesterase BCHE 0.0069
1024 Solute carrier family 22 member 11 SLC22A11 0.0069
1086 Potassium voltage-gated channel subfamily KQT member 2 KCNQ2 0.0067
869 Estrogen receptor beta ESR2 0.0066
217 Estradiol 17-beta-dehydrogenase 1 HSD17B1 0.0066
228 Beta platelet-derived growth factor receptor PDGFRB 0.0065
6025 UDP-glucuronosyltransferase 1-4 UGT1A4 0.0065
1649 Small inducible cytokine A2 CCL2 0.0063
380 Cytochrome P450 17A1 CYP17A1 0.0062
6164 POU domain, class 5, transcription factor 1 POU5F1 0.0061
6017 Cholesterol side-chain cleavage enzyme, mitochondrial CYP11A1 0.0061
1284 Nuclear receptor subfamily 1 group I member 2 NR1I2 0.0057
6141 Sodium/bile acid cotransporter SLC10A1 0.0056
17 Proto-oncogene tyrosine-protein kinase ABL1 ABL1 0.0055
226 Gonadotropin-releasing hormone receptor GNRHR 0.0054
4604 Liver carboxylesterase 1 CES1 0.0054
890 Niemann-Pick C1-like protein 1 NPC1L1 0.0054
6158 Solute carrier organic anion transporter family member 1C1 SLCO1C1 0.0053
4752 Peroxisomal trans-2-enoyl-CoA reductase PECR 0.0052
2751 Holliday junction ATP-dependent DNA helicase ruvB ruvB 0.0052
4755 Holliday junction ATP-dependent DNA helicase ruvB ruvB 0.0052
6155 ATP-binding cassette transporter sub-family C member 11 ABCC11 0.005
950 Alpha platelet-derived growth factor receptor PDGFRA 0.0049
805 Cytochrome P450 11B1, mitochondrial CYP11B1 0.0048
6288 Low molecular weight phosphotyrosine protein phosphatase ACP1 0.0048
1760 Aminopeptidase N ANPEP 0.0047
6843 Aminopeptidase N pepN 0.0047
153 Dopamine beta-hydroxylase DBH 0.0047
6832 Serine/threonine-protein kinase SRPK2 SRPK2 0.0046
117 Sterol O-acyltransferase 1 SOAT1 0.0046
6145 Solute carrier family 22 member 1 SLC22A1 0.0046
6153 Solute carrier organic anion transporter family member 4A1 SLCO4A1 0.0044
6179 UDP-glucuronosyltransferase 2B17 UGT2B17 0.0043
40 RAF proto-oncogene serine/threonine-protein kinase RAF1 0.0043
4692 A/G-specific adenine glycosylase mutY 0.0043
4606 Purine trans deoxyribosylase ptd 0.0042
4177 Proto-oncogene tyrosine-protein kinase receptor ret RET 0.0041
3804 Sodium channel protein type 4 subunit alpha SCN4A 0.0041
3679 MTA/SAH nucleosidase mtnN 0.004
1958 S-methyl-5-thioadenosine phosphorylase MTAP 0.004
775 Acetyl-CoA carboxylase 2 ACACB 0.004
6149 Solute carrier family 22 member 10 SLC22A10 0.004
128 Adenine phosphoribosyltransferase APRT 0.0038
238 Peroxisome proliferator-activated receptor gamma PPARG 0.0038
3854 Basic fibroblast growth factor receptor 1 FGFR1 0.0038
6144 Solute carrier family 22 member 2 SLC22A2 0.0037
6167 Organic solute transporter subunit beta OSTB 0.0037
6166 Organic solute transporter subunit alpha OSTA 0.0037
698 B-Raf proto-oncogene serine/threonine-protein kinase BRAF 0.0037
3856 Fibroblast growth factor receptor 3 FGFR3 0.0037
1630 Integrin beta-2 ITGB2 0.0036
163 D(1B) dopamine receptor DRD5 0.0036
2450 Tyrosine-protein kinase ITK/TSK ITK 0.0035
6137 Multidrug resistance-associated protein 6 ABCC6 0.0035
432 D(4) dopamine receptor DRD4 0.0034
6085 Fatty acid-binding protein, intestinal FABP2 0.0034
638 D(3) dopamine receptor DRD3 0.0033
6143 Solute carrier family 22 member 7 SLC22A7 0.0033
713 Sodium-dependent dopamine transporter SLC6A3 0.0033
844 Epidermal growth factor receptor EGFR 0.0032
102 DNA topoisomerase I, mitochondrial TOP1MT 0.0032
6148 Multidrug resistance-associated protein 7 ABCC10 0.0031
6160 Solute carrier organic anion transporter family member 3A1 SLCO3A1 0.0031
2264 Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase cobT 0.0031
2981 Phospholipase A2, membrane associated PLA2G2A 0.003
23 D(1A) dopamine receptor DRD1 0.003
6044 Serum paraoxonase/lactonase 3 PON3 0.0029
6136 Multidrug resistance-associated protein 5 ABCC5 0.0029
118 Organic cation/carnitine transporter 2 SLC22A5 0.0029
2021 Thrombomodulin THBD 0.0028
6031 Cytochrome P450 3A43 CYP3A43 0.0028
831 D(2) dopamine receptor DRD2 0.0028
5798 Mitogen-activated protein kinase 11 MAPK11 0.0028
6106 Cytochrome P450 2C18 CYP2C18 0.0027
572 Integrin alpha-L ITGAL 0.0027
1353 DNA topoisomerase 1 TOP1 0.0027
3552 DNA topoisomerase 1 topA 0.0027
1192 Sulfotransferase 1A1 SULT1A1 0.0027
70 Type-1 angiotensin II receptor AGTR1 0.0026
267 Plasminogen activator inhibitor 1 SERPINE1 0.0026
1275 Estrogen sulfotransferase SULT1E1 0.0025
4122 Histone deacetylase 2 HDAC2 0.0025
760 Fibroblast growth factor 1 FGF1 0.0025
3802 Sodium channel protein type 2 subunit alpha SCN2A 0.0025
1050 Bile salt sulfotransferase SULT2A1 0.0024
776 Bile salt export pump ABCB11 0.0024
4192 DNA topoisomerase 2-beta TOP2B 0.0024
6221 Steroid hormone receptor ERR1 ESRRA 0.0024
811 Translocator protein TSPO 0.0024
908 Glutathione S-transferase theta-1 GSTT1 0.0023
3937 Fatty-acid amide hydrolase FAAH 0.0022
1181 Alpha-1-acid glycoprotein 1 ORM1 0.0022
936 Ephrin type-A receptor 2 EPHA2 0.0021
6042 Prostaglandin reductase 2 PTGR2 0.0021
1618 High affinity nerve growth factor receptor NTRK1 0.0021
5787 Angiopoietin-1 receptor TEK 0.0021
165 FL cytokine receptor FLT3 0.0021
1457 Long-chain-fatty-acid--CoA ligase 4 ACSL4 0.0021
823 Fibroblast growth factor receptor 2 FGFR2 0.002
6206 DNA-directed RNA polymerase subunit beta' rpoC 0.002
1792 Tissue-type plasminogen activator PLAT 0.002
389 Amiloride-sensitive cation channel 2, neuronal ACCN2 0.0019
6043 Putative G-protein coupled receptor 44 GPR44 0.0019
2184 Cystic fibrosis transmembrane conductance regulator CFTR 0.0019
841 Gamma-aminobutyric-acid receptor subunit alpha-6 GABRA6 0.0019
273 Apoptosis regulator Bcl-2 BCL2 0.0019
530 Gamma-aminobutyric-acid receptor subunit alpha-4 GABRA4 0.0019
904 Glutathione S-transferase P GSTP1 0.0019
284 DNA-directed RNA polymerase beta chain rpoB 0.0018
5773 DNA-directed RNA polymerase beta chain rpoB 0.0018
580 Gamma-aminobutyric-acid receptor subunit alpha-3 GABRA3 0.0018
523 Gamma-aminobutyric-acid receptor subunit alpha-5 GABRA5 0.0018
423 Gamma-aminobutyric-acid receptor subunit alpha-2 GABRA2 0.0018
6014 Cytochrome P450 2A13 CYP2A13 0.0018
817 DNA topoisomerase 2-alpha TOP2A 0.0018
4100 Gamma-aminobutyric-acid receptor subunit beta-2 GABRB2 0.0016
1313 Lactoylglutathione lyase GLO1 0.0016
2222 Equilibrative nucleoside transporter 1 SLC29A1 0.0016
4099 Gamma-aminobutyric-acid receptor subunit beta-3 GABRB3 0.0016
468 Cytochrome P450 4A11 CYP4A11 0.0015
275 Arachidonate 5-lipoxygenase ALOX5 0.0014
952 Dipeptidyl peptidase 4 DPP4 0.0014
833 Organic cation/carnitine transporter 1 SLC22A4 0.0011
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