Finasteride
(right click,save link as to download,it is a temp file,please download as soon as possible, you can also use CTRL+S to save the whole html page)
Basic Info
| Common Name | Finasteride(F05528) |
| 2D Structure | |
| Description | An orally active testosterone 5-alpha-reductase inhibitor. It is used as a surgical alternative for treatment of benign prostatic hyperplasia. |
| FRCD ID | F05528 |
| CAS Number | 98319-26-7 |
| PubChem CID | 57363 |
| Formula | C23H36N2O2 |
| IUPAC Name | (1S,3aS,3bS,5aR,9aR,9bS,11aS)-N-tert-butyl-9a,11a-dimethyl-7-oxo-1,2,3,3a,3b,4,5,5a,6,9b,10,11-dodecahydroindeno[5,4-f]quinoline-1-carboxamide |
| InChI Key | DBEPLOCGEIEOCV-WSBQPABSSA-N |
| InChI | InChI=1S/C23H36N2O2/c1-21(2,3)25-20(27)17-8-7-15-14-6-9-18-23(5,13-11-19(26)24-18)16(14)10-12-22(15,17)4/h11,13-18H,6-10,12H2,1-5H3,(H,24,26)(H,25,27)/t14-,15-,16-,17+,18+,22-,23+/m0/s1 |
| Canonical SMILES | CC12CCC3C(C1CCC2C(=O)NC(C)(C)C)CCC4C3(C=CC(=O)N4)C |
| Isomeric SMILES | C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2C(=O)NC(C)(C)C)CC[C@@H]4[C@@]3(C=CC(=O)N4)C |
| Wikipedia | Finasteride |
| Synonyms |
Finastid
Finasterida
finasteride
98319-26-7
Proscar
Propecia
Prostide
Chibro-Proscar
MK-906
Finasteridum
|
| Classifies |
Predicted: Pesticide
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Lipids and lipid-like molecules |
| Class | Steroids and steroid derivatives |
| Subclass | Androstane steroids |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Androgens and derivatives |
| Alternative Parents | |
| Molecular Framework | Aliphatic heteropolycyclic compounds |
| Substituents | 20-hydroxysteroid - Androgen-skeleton - 3-hydroxysteroid - Hydroxysteroid - 4-azasteroid - Azasteroid - Cyclic carboximidic acid - Carboximidic acid - Carboximidic acid derivative - Azacycle - Organoheterocyclic compound - Propargyl-type 1,3-dipolar organic compound - Organic 1,3-dipolar compound - Organic oxygen compound - Organopnictogen compound - Organonitrogen compound - Organooxygen compound - Hydrocarbon derivative - Organic nitrogen compound - Aliphatic heteropolycyclic compound |
| Description | This compound belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 372.553 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 2 |
| Rotatable Bond Count | 2 |
| Complexity | 678 |
| Monoisotopic Mass | 372.278 |
| Exact Mass | 372.278 |
| XLogP | 3 |
| Formal Charge | 0 |
| Heavy Atom Count | 27 |
| Defined Atom Stereocenter Count | 7 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
ADMET
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB+ | 0.9777 |
| Human Intestinal Absorption | HIA+ | 0.9952 |
| Caco-2 Permeability | Caco2- | 0.5496 |
| P-glycoprotein Substrate | Substrate | 0.7639 |
| P-glycoprotein Inhibitor | Inhibitor | 0.7258 |
| Non-inhibitor | 0.5558 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.7854 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.6018 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8062 |
| CYP450 2D6 Substrate | Non-substrate | 0.9116 |
| CYP450 3A4 Substrate | Substrate | 0.7407 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.9045 |
| CYP450 2C9 Inhibitor | Inhibitor | 0.8948 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9230 |
| CYP450 2C19 Inhibitor | Inhibitor | 0.8994 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.9176 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.7841 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9901 |
| Non-inhibitor | 0.8734 | |
| AMES Toxicity | Non AMES toxic | 0.8581 |
| Carcinogens | Non-carcinogens | 0.9436 |
| Fish Toxicity | High FHMT | 0.9137 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9569 |
| Honey Bee Toxicity | Low HBT | 0.6619 |
| Biodegradation | Not ready biodegradable | 1.0000 |
| Acute Oral Toxicity | II | 0.7306 |
| Carcinogenicity (Three-class) | Non-required | 0.5603 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -3.5859 | LogS |
| Caco-2 Permeability | 1.2934 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 2.9188 | LD50, mol/kg |
| Fish Toxicity | 1.5503 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.3836 | pIGC50, ug/L |
Targets
- General Function:
- Steroid binding
- Specific Function:
- Efficiently catalyzes the reduction of progesterone, androstenedione, 17-alpha-hydroxyprogesterone and testosterone to 5-beta-reduced metabolites. The bile acid intermediates 7-alpha,12-alpha-dihydroxy-4-cholesten-3-one and 7-alpha-hydroxy-4-cholesten-3-one can also act as substrates.
- Gene Name:
- AKR1D1
- Uniprot ID:
- P51857
- Molecular Weight:
- 37376.615 Da
References
- Drury JE, Di Costanzo L, Penning TM, Christianson DW: Inhibition of human steroid 5beta-reductase (AKR1D1) by finasteride and structure of the enzyme-inhibitor complex. J Biol Chem. 2009 Jul 24;284(30):19786-90. doi: 10.1074/jbc.C109.016931. Epub 2009 Jun 10. [19515843 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Steroid hormone receptors are ligand-activated transcription factors that regulate eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Transcription factor activity is modulated by bound coactivator and corepressor proteins. Transcription activation is down-regulated by NR0B2. Activated, but not phosphorylated, by HIPK3 and ZIPK/DAPK3.
- Gene Name:
- AR
- Uniprot ID:
- P10275
- Molecular Weight:
- 98987.9 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Ligand-activated transcription factor. Receptor that binds peroxisome proliferators such as hypolipidemic drugs and fatty acids. Has a preference for poly-unsaturated fatty acids, such as gamma-linoleic acid and eicosapentanoic acid. Once activated by a ligand, the receptor binds to promoter elements of target genes. Regulates the peroxisomal beta-oxidation pathway of fatty acids. Functions as transcription activator for the acyl-CoA oxidase gene. Decreases expression of NPC1L1 once activated by a ligand.
- Gene Name:
- PPARD
- Uniprot ID:
- Q03181
- Molecular Weight:
- 49902.99 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Ligand-activated transcription factor. Receptor for bile acids such as chenodeoxycholic acid, lithocholic acid and deoxycholic acid. Represses the transcription of the cholesterol 7-alpha-hydroxylase gene (CYP7A1) through the induction of NR0B2 or FGF19 expression, via two distinct mechanisms. Activates the intestinal bile acid-binding protein (IBABP). Activates the transcription of bile salt export pump ABCB11 by directly recruiting histone methyltransferase CARM1 to this locus.
- Gene Name:
- NR1H4
- Uniprot ID:
- Q96RI1
- Molecular Weight:
- 55913.915 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
- General Function:
- Sterol 5-alpha reductase activity
- Specific Function:
- Converts testosterone (T) into 5-alpha-dihydrotestosterone (DHT) and progesterone or corticosterone into their corresponding 5-alpha-3-oxosteroids. It plays a central role in sexual differentiation and androgen physiology.
- Gene Name:
- SRD5A2
- Uniprot ID:
- P31213
- Molecular Weight:
- 28393.015 Da
References
- Suzuki R, Satoh H, Ohtani H, Hori S, Sawada Y: Saturable binding of finasteride to steroid 5alpha-reductase as determinant of nonlinear pharmacokinetics. Drug Metab Pharmacokinet. 2010;25(2):208-13. [20460827 ]
- General Function:
- Electron carrier activity
- Specific Function:
- Converts testosterone into 5-alpha-dihydrotestosterone and progesterone or corticosterone into their corresponding 5-alpha-3-oxosteroids. It plays a central role in sexual differentiation and androgen physiology.
- Gene Name:
- SRD5A1
- Uniprot ID:
- P18405
- Molecular Weight:
- 29458.18 Da
References
- Thigpen AE, Russell DW: Four-amino acid segment in steroid 5 alpha-reductase 1 confers sensitivity to finasteride, a competitive inhibitor. J Biol Chem. 1992 Apr 25;267(12):8577-83. [1314830 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Orphan receptor that acts as transcription activator in the absence of bound ligand. Binds specifically to an estrogen response element and activates reporter genes controlled by estrogen response elements (By similarity). Induces the expression of PERM1 in the skeletal muscle.
- Gene Name:
- ESRRG
- Uniprot ID:
- P62508
- Molecular Weight:
- 51305.485 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Nuclear receptor that binds DNA as a monomer to ROR response elements (RORE) containing a single core motif half-site 5'-AGGTCA-3' preceded by a short A-T-rich sequence. Considered to have intrinsic transcriptional activity, have some natural ligands such as all-trans retinoic acid (ATRA) and other retinoids which act as inverse agonists repressing the transcriptional activity. Required for normal postnatal development of rod and cone photoreceptor cells. Modulates rod photoreceptors differentiation at least by inducing the transcription factor NRL-mediated pathway. In cone photoreceptor cells, regulates transcription of OPN1SW. Involved in the regulation of the period length and stability of the circadian rhythm. May control cytoarchitectural patterning of neocortical neurons during development. May act in a dose-dependent manner to regulate barrel formation upon innervation of layer IV neurons by thalamocortical axons. May play a role in the suppression of osteoblastic differentiation through the inhibition of RUNX2 transcriptional activity (By similarity).Isoform 1 is critical for hindlimb motor control and for the differentiation of amacrine and horizontal cells in the retina. Regulates the expression of PTF1A synergistically with FOXN4 (By similarity).
- Gene Name:
- RORB
- Uniprot ID:
- Q92753
- Molecular Weight:
- 53219.385 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]