DT-Web

DB00984 - Nandrolone phenpropionate


Identification
Name Nandrolone phenpropionate
Accession Number DB00984 (APRD00134)
Type small molecule
Description C18 steroid with androgenic and anabolic properties. It is generally prepared from alkyl ethers of estradiol to resemble testosterone but less one carbon at the 19 position. It is a schedule III drug in the U.S.
Structure
MOL SDF PDB SMILES InChI
Categories (*)
Molecular Weight 406.5571
Groups illicit
Monoisotopic Weight 406.250794954
Pharmacology
Indication For the treatment of refractory deficient red cell production anemias, breast carcinoma, hereditary angioedema, antithrombin III deficiency, fibrinogen excess, growth failure and Turner's syndrome. It is also indicated in the prophylaxis of hereditary angioedema.
Mechanism of action Nandrolone is an androgen receptor agonist. The drug bound to the receptor complexes which allows it to enter the 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 The absorption after oral dosing is rapid for testosterone and probably for other anabolic steroids, but there is extensive first-pass hepatic metabolism for all anabolic steroids except those that are substituted at the 17-alpha position. The rate of absorption from subcutaneous or intramuscular depots depends on the product and its formulation. Absorption is slow for the lipid-soluble esters such as the cypionate or enanthate, and for oily suspensions.
Protein binding 58%
Biotransformation Nandrolone is unusual in that unlike most anabolic steroids, it is not broken down into the more reactive DHT by the enzyme 5?-reductase, but rather into a less effective product known as Dihydronandrolone.
Route of elimination Not Available
Toxicity Not Available
Affected organisms
  • Humans and other mammals
Interactions
Drug Interactions
Drug Mechanism of interaction
Warfarin Nandrolone may increase the serum concentration and anticoagulant effect of warfarin. Monitor for changes in prothrombin time and therapeutic effects of warfarin if nandrolone 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
  • Cen Y, Li K, Liu XX: [Effect of nandrolone phenylpropionate on expression of hepatic albumin-mRNA and androgen receptor in burned rats] Zhongguo Xiu Fu Chong Jian Wai Ke Za Zhi. 2003 Nov;17(6):439-41. - Pubmed
  • Li K, Cen Y, Liu X, Luo X: [The effects of nandrolone phenylpropionate on androgen receptor of liver and sexual glands in burned rats] Sichuan Da Xue Xue Bao Yi Xue Ban. 2003 Oct;34(4):708-10. - Pubmed
  • Burger LL, Haisenleder DJ, Wotton GM, Aylor KW, Dalkin AC, Marshall JC: The regulation of FSHbeta transcription by gonadal steroids: testosterone and estradiol modulation of the activin intracellular signaling pathway. Am J Physiol Endocrinol Metab. 2007 Jul;293(1):E277-85. Epub 2007 Apr 3. - Pubmed
  • Fujii Y, Kawakami S, Okada Y, Kageyama Y, Kihara K: Regulation of prostate-specific antigen by activin A in prostate cancer LNCaP cells. Am J Physiol Endocrinol Metab. 2004 Jun;286(6):E927-31. Epub 2004 Feb 3. - Pubmed
  • Yan W, Burns KH, Matzuk MM: Genetic engineering to study testicular tumorigenesis. APMIS. 2003 Jan;111(1):174-81; discussion 182-3. - Pubmed
  • Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. - Pubmed
DTHybrid score 1.0933

Enzymes


Cytochrome P450 19A1
Name Cytochrome P450 19A1
Gene Name CYP19A1
Actions substrate
References
  • Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. - Pubmed
DTHybrid score 0.3771

Predictions


Id Partner name Gene Name Score
4512 Cytochrome P450 3A4 CYP3A4 0.0745
756 Sex hormone-binding globulin SHBG 0.0669
136 Estrogen receptor ESR1 0.0464
614 Progesterone receptor PGR 0.0393
6016 Cytochrome P450 2C19 CYP2C19 0.0313
6017 Cholesterol side-chain cleavage enzyme, mitochondrial CYP11A1 0.0301
4757 Cytochrome P450 2C9 CYP2C9 0.0276
4200 Cytochrome P450 1A2 CYP1A2 0.0273
1588 Multidrug resistance protein 1 ABCB1 0.0268
737 Mineralocorticoid receptor NR3C2 0.0267
4924 Cytochrome P450 2C8 CYP2C8 0.0249
226 Gonadotropin-releasing hormone receptor GNRHR 0.0248
871 Glucocorticoid receptor NR3C1 0.0239
6030 Cytochrome P450 2B6 CYP2B6 0.0221
260 Cytochrome P450 51 ERG11 0.0214
761 Cytochrome P450 51 ERG11 0.0214
3163 Cytochrome P450 51 cyp51 0.0214
563 Thyroid peroxidase TPO 0.0207
4116 Dihydropteroate synthetase Not Available 0.0199
6013 Cytochrome P450 2E1 CYP2E1 0.0191
148 Lutropin-choriogonadotropic hormone receptor LHCGR 0.0175
5718 Cytochrome P450 2A6 CYP2A6 0.0167
3941 Amine oxidase [flavin-containing] A MAOA 0.0165
596 3-oxo-5-alpha-steroid 4-dehydrogenase 1 SRD5A1 0.0161
3939 Amine oxidase [flavin-containing] B MAOB 0.0148
3810 Catechol O-methyltransferase COMT 0.0145
6139 Solute carrier organic anion transporter family member 1A2 SLCO1A2 0.0142
4118 Cytochrome P450 3A5 CYP3A5 0.0138
4119 Cytochrome P450 2D6 CYP2D6 0.0137
805 Cytochrome P450 11B1, mitochondrial CYP11B1 0.0136
290 Prostaglandin G/H synthase 2 PTGS2 0.0133
380 Cytochrome P450 17A1 CYP17A1 0.0131
381 Prolactin receptor PRLR 0.013
6241 Nuclear receptor coactivator 2 NCOA2 0.013
1649 Small inducible cytokine A2 CCL2 0.0125
3923 Cholinesterase BCHE 0.0125
217 Estradiol 17-beta-dehydrogenase 1 HSD17B1 0.0123
6044 Serum paraoxonase/lactonase 3 PON3 0.0118
6024 Cytochrome P450 1A1 CYP1A1 0.0112
1898 Cytochrome P450 1B1 CYP1B1 0.011
6107 Cytochrome P450 3A7 CYP3A7 0.011
6022 UDP-glucuronosyltransferase 1-1 UGT1A1 0.0108
6142 Solute carrier family 22 member 8 SLC22A8 0.0102
587 Serum albumin ALB 0.0094
869 Estrogen receptor beta ESR2 0.0079
3957 Adenosine deaminase ADA 0.0079
1735 Canalicular multispecific organic anion transporter 1 ABCC2 0.0078
1680 Solute carrier family 2, facilitated glucose transporter member 1 SLC2A1 0.0078
373 Transthyretin TTR 0.0076
4120 NADPH--cytochrome P450 reductase POR 0.0074
650 Aldo-keto reductase family 1 member C3 AKR1C3 0.0071
1656 CYP2B protein CYP2B 0.0068
1732 ATP-binding cassette sub-family G member 2 ABCG2 0.0066
6023 Cytochrome P450 11B2, mitochondrial CYP11B2 0.0065
20 Prostaglandin G/H synthase 1 PTGS1 0.0062
6078 Neuronal acetylcholine receptor subunit beta-4 CHRNB4 0.006
847 Mu-type opioid receptor OPRM1 0.0056
6079 Neuronal acetylcholine receptor subunit alpha-3 CHRNA3 0.0054
6220 Aryl hydrocarbon receptor AHR 0.0053
3947 Xanthine dehydrogenase/oxidase XDH 0.005
144 Hemoglobin subunit alpha HBA1 0.0049
3809 Estrogen-related receptor gamma ESRRG 0.0048
564 Cellular retinoic acid-binding protein 1 CRABP1 0.0047
776 Bile salt export pump ABCB11 0.0047
6020 Aldehyde oxidase AOX1 0.0047
629 Alpha-2B adrenergic receptor ADRA2B 0.0047
5934 Cytochrome P450 26A1 CYP26A1 0.0047
1010 Cytochrome P450 51A1 CYP51A1 0.0046
1729 Solute carrier family 22 member 6 SLC22A6 0.0046
1178 Adenosine A2a receptor ADORA2A 0.0045
780 Retinoic acid receptor RXR-gamma RXRG 0.0043
229 Retinoic acid receptor beta RARB 0.0043
634 Squalene monooxygenase SQLE 0.0043
7196 Squalene monooxygenase ERG1 0.0043
730 Retinoic acid receptor alpha RARA 0.0042
6031 Cytochrome P450 3A43 CYP3A43 0.0041
872 Gamma-aminobutyric-acid receptor subunit alpha-1 GABRA1 0.004
462 Intermediate conductance calcium-activated potassium channel protein 4 KCNN4 0.004
459 Retinoic acid receptor RXR-alpha RXRA 0.004
88 Retinoic acid receptor RXR-beta RXRB 0.0039
162 Retinoic acid receptor gamma-1 RARG 0.0039
567 Receptor tyrosine-protein kinase erbB-2 ERBB2 0.0038
2782 Complement C1s subcomponent C1S 0.0037
6014 Cytochrome P450 2A13 CYP2A13 0.0035
3815 Complement C1q subcomponent subunit A C1QA 0.0034
3816 Complement C1q subcomponent subunit B C1QB 0.0034
3817 Complement C1q subcomponent subunit C C1QC 0.0034
3818 Low affinity immunoglobulin gamma Fc region receptor III-A FCGR3A 0.0034
3819 Low affinity immunoglobulin gamma Fc region receptor II-a FCGR2A 0.0034
1102 Low affinity immunoglobulin gamma Fc region receptor III-B FCGR3B 0.0034
3821 Low affinity immunoglobulin gamma Fc region receptor II-c FCGR2C 0.0034
3814 Complement C1r subcomponent C1R 0.0034
3830 Calreticulin CALR 0.0034
3820 Low affinity immunoglobulin gamma Fc region receptor II-b FCGR2B 0.0034
474 Acetylcholinesterase ACHE 0.0033
784 High affinity immunoglobulin gamma Fc receptor I FCGR1A 0.0032
6143 Solute carrier family 22 member 7 SLC22A7 0.0032
6035 Nuclear receptor ROR-beta RORB 0.0032
6034 Hydroxyindole O-methyltransferase ASMT 0.0032
6036 Eosinophil peroxidase EPX 0.0032
6025 UDP-glucuronosyltransferase 1-4 UGT1A4 0.0029
6145 Solute carrier family 22 member 1 SLC22A1 0.0029
844 Epidermal growth factor receptor EGFR 0.0028
765 Indoleamine 2,3-dioxygenase IDO1 0.0027
6141 Sodium/bile acid cotransporter SLC10A1 0.0027
571 Melatonin receptor type 1A MTNR1A 0.0026
362 Melatonin receptor type 1B MTNR1B 0.0026
5923 Microtubule-associated protein tau MAPT 0.0024
5924 Microtubule-associated protein 4 MAP4 0.0024
458 Neuronal acetylcholine receptor subunit alpha-10 CHRNA10 0.0023
267 Plasminogen activator inhibitor 1 SERPINE1 0.0023
1852 Microtubule-associated protein 2 MAP2 0.0023
833 Organic cation/carnitine transporter 1 SLC22A4 0.0022
7 Nitric oxide synthase, inducible NOS2 0.0022
6147 Solute carrier family 22 member 3 SLC22A3 0.0022
6931 Calcium-activated potassium channel subunit beta-1 KCNMB1 0.0022
6933 Calcium-activated potassium channel subunit beta-4 KCNMB4 0.0022
6932 Calcium-activated potassium channel subunit beta-3 KCNMB3 0.0022
6934 Small conductance calcium-activated potassium channel protein 1 KCNN1 0.0022
6935 Small conductance calcium-activated potassium channel protein 2 KCNN2 0.0022
6936 Small conductance calcium-activated potassium channel protein 3 KCNN3 0.0022
273 Apoptosis regulator Bcl-2 BCL2 0.0021
6221 Steroid hormone receptor ERR1 ESRRA 0.0021
1490 Solute carrier organic anion transporter family member 1B1 SLCO1B1 0.0021
6002 Prostaglandin E2 receptor EP4 subtype PTGER4 0.002
706 Glutamate [NMDA] receptor subunit 3A GRIN3A 0.002
243 Ribosyldihydronicotinamide dehydrogenase [quinone] NQO2 0.0019
5463 Calcium-activated potassium channel subunit beta 2 KCNMB2 0.0019
29 Tubulin beta-1 chain TUBB1 0.0019
84 Nuclear receptor 0B1 NR0B1 0.0019
4131 Prostaglandin E2 receptor, EP3 subtype PTGER3 0.0018
1457 Long-chain-fatty-acid--CoA ligase 4 ACSL4 0.0018
406 Prostaglandin E2 receptor, EP2 subtype PTGER2 0.0018
6106 Cytochrome P450 2C18 CYP2C18 0.0018
469 Annexin A1 ANXA1 0.0018
6167 Organic solute transporter subunit beta OSTB 0.0018
6166 Organic solute transporter subunit alpha OSTA 0.0018
467 Delta-type opioid receptor OPRD1 0.0018
1192 Sulfotransferase 1A1 SULT1A1 0.0018
1284 Nuclear receptor subfamily 1 group I member 2 NR1I2 0.0018
1757 Myeloperoxidase MPO 0.0017
6104 Dimethylaniline monooxygenase [N-oxide-forming] 1 FMO1 0.0017
465 Calmodulin CALM1 0.0017
6181 UDP-glucuronosyltransferase 1-8 UGT1A8 0.0016
6148 Multidrug resistance-associated protein 7 ABCC10 0.0016
6177 UDP-glucuronosyltransferase 1-10 UGT1A10 0.0016
73 Prostaglandin E2 receptor, EP1 subtype PTGER1 0.0016
1709 Canalicular multispecific organic anion transporter 2 ABCC3 0.0016
514 Potassium voltage-gated channel subfamily H member 6 KCNH6 0.0015
772 Potassium voltage-gated channel subfamily H member 7 KCNH7 0.0015
6160 Solute carrier organic anion transporter family member 3A1 SLCO3A1 0.0015
6153 Solute carrier organic anion transporter family member 4A1 SLCO4A1 0.0015
6157 Solute carrier organic anion transporter family member 1B3 SLCO1B3 0.0014
6101 Dimethylaniline monooxygenase [N-oxide-forming] 3 FMO3 0.0014
2222 Equilibrative nucleoside transporter 1 SLC29A1 0.0014
6152 Solute carrier organic anion transporter family member 2A1 SLCO2A1 0.0014
610 Calcium-activated potassium channel subunit alpha 1 KCNMA1 0.0014
6158 Solute carrier organic anion transporter family member 1C1 SLCO1C1 0.0014
468 Cytochrome P450 4A11 CYP4A11 0.0014
6136 Multidrug resistance-associated protein 5 ABCC5 0.0013
6176 UDP-glucuronosyltransferase 1-3 UGT1A3 0.0013
862 Multidrug resistance-associated protein 1 ABCC1 0.0013
4604 Liver carboxylesterase 1 CES1 0.0012
6018 UDP-glucuronosyltransferase 1-9 UGT1A9 0.0012
6178 UDP-glucuronosyltransferase 2B7 UGT2B7 0.0012
1632 Solute carrier organic anion transporter family member 2B1 SLCO2B1 0.0012
101 Potassium voltage-gated channel subfamily H member 2 KCNH2 0.0012
238 Peroxisome proliferator-activated receptor gamma PPARG 0.0012
1024 Solute carrier family 22 member 11 SLC22A11 0.0011
2164 Multidrug resistance-associated protein 4 ABCC4 0.0011
291 Nitric-oxide synthase, endothelial NOS3 0.0011
6144 Solute carrier family 22 member 2 SLC22A2 0.001
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