Record Information |
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Version | 2.0 |
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Creation Date | 2014-09-11 05:18:00 UTC |
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Update Date | 2014-12-24 20:26:57 UTC |
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Accession Number | T3D4820 |
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Identification |
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Common Name | Finasteride |
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Class | Small Molecule |
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Description | An orally active testosterone 5-alpha-reductase inhibitor. It is used as a surgical alternative for treatment of benign prostatic hyperplasia. |
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Compound Type | - 5-alpha Reductase Inhibitor
- Amide
- Amine
- Drug
- Ester
- Food Toxin
- Metabolite
- Organic Compound
- Skin and Mucous Membrane Agent
- Synthetic Compound
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Chemical Structure | |
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Synonyms | Synonym | (5alpha,17beta)-(1,1-Dimethylethyl)-3-oxo-4-azaandrost-1-ene-17-carboxamide | Chibro-proscar | Finasterida | Finasteridum | Finastid | Finpecia | Propecia | Proscar | Prostide |
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Chemical Formula | C23H36N2O2 |
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Average Molecular Mass | 372.544 g/mol |
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Monoisotopic Mass | 372.278 g/mol |
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CAS Registry Number | 98319-26-7 |
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IUPAC Name | (1S,2R,7R,10S,11S,14S,15S)-N-tert-butyl-2,15-dimethyl-5-oxo-6-azatetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-3-ene-14-carboxamide |
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Traditional Name | (1S,2R,7R,10S,11S,14S,15S)-N-tert-butyl-2,15-dimethyl-5-oxo-6-azatetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-3-ene-14-carboxamide |
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SMILES | [H][C@@]1(CC[C@@]2([H])[C@]3([H])CC[C@@]4([H])N=C(O)C=C[C@]4(C)[C@@]3([H])CC[C@]12C)C(O)=NC(C)(C)C |
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InChI Identifier | 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 |
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InChI Key | InChIKey=DBEPLOCGEIEOCV-WSBQPABSSA-N |
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Chemical Taxonomy |
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Description | 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. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Steroids and steroid derivatives |
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Sub Class | Androstane steroids |
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Direct Parent | Androgens and derivatives |
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Alternative Parents | |
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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
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Molecular Framework | Aliphatic heteropolycyclic compounds |
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External Descriptors | |
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Biological Properties |
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Status | Detected and Not Quantified |
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Origin | Exogenous |
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Cellular Locations | |
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Biofluid Locations | Not Available |
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Tissue Locations | Not Available |
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Pathways | Not Available |
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Applications | Not Available |
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Biological Roles | Not Available |
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Chemical Roles | Not Available |
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Physical Properties |
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State | Solid |
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Appearance | White powder. |
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Experimental Properties | Property | Value |
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Melting Point | 252-254°C | Boiling Point | Not Available | Solubility | 11.7 mg/L | LogP | 3.03 |
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Predicted Properties | |
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Spectra |
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Spectra | Spectrum Type | Description | Splash Key | Deposition Date | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0a4i-1579000000-3a73a92e1d34b87c3e4c | 2017-09-01 | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-qTof , Positive | splash10-0a4i-5910000000-7dd7b7fbb29b6ae08f4c | 2017-09-14 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-0ab9-1319000000-9f18f09bea4e9168f1df | 2017-09-14 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-0002-5900000000-3ad6a0d10c51f9892144 | 2017-09-14 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-0a4i-0119000000-f683db304300c01e907a | 2017-09-14 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-0a4i-0129000000-a097bfd2187d4d4c97c6 | 2017-09-14 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - , positive | splash10-00xr-0119000000-43c6646bf19d62255966 | 2017-09-14 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - , positive | splash10-01b9-2539000000-c47506144391db372c4b | 2017-09-14 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QFT , positive | splash10-014i-0900000000-a55cf309ee5a976c5e45 | 2017-09-14 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - 90V, Positive | splash10-0aou-9400000000-e2d92afbb0c688a7c65f | 2021-09-20 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - 50V, Positive | splash10-0a4i-0936000000-473b441c435f8a167da5 | 2021-09-20 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - 40V, Positive | splash10-05fr-0109000000-a6753fafb9b44a98b5ea | 2021-09-20 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - 75V, Positive | splash10-0aor-9500000000-2323be14f82809784cbb | 2021-09-20 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - 15V, Positive | splash10-00di-0009000000-5429921102770ed801ec | 2021-09-20 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - 30V, Positive | splash10-00di-0009000000-42255449abab8a1efb5b | 2021-09-20 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - 30V, Positive | splash10-00di-0009000000-5f84c9991fe026c30104 | 2021-09-20 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - 20V, Positive | splash10-00di-0009000000-832f340612f54390180c | 2021-09-20 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - 35V, Positive | splash10-00di-0009000000-acfb1d6450dbdd3c37ce | 2021-09-20 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - 10V, Positive | splash10-00di-0009000000-47e745329afb05408179 | 2021-09-20 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - 55V, Positive | splash10-0ab9-0219000000-040ec285d4c909fdf035 | 2021-09-20 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-00di-0009000000-a6be7718311b4f11aad5 | 2016-08-02 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0zmi-0439000000-e0a2fad4c18c6da72e1c | 2016-08-02 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0uej-3790000000-df2f90aa3664e0df8776 | 2016-08-02 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-00di-0009000000-be3980c97e5b8f8767a6 | 2016-08-03 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-00di-3029000000-5489b391a47dec8eb0f1 | 2016-08-03 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-00dl-9131000000-a1b8897126899f67f5fb | 2016-08-03 | View Spectrum |
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Toxicity Profile |
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Route of Exposure | Not Available |
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Mechanism of Toxicity | The mechanism of action of Finasteride is based on its preferential inhibition of Type II 5a-reductase through the formation of a stable complex with the enzyme. Inhibition of Type II 5a-reductase blocks the peripheral conversion of testosterone to DHT, resulting in significant decreases in serum and tissue DHT concentrations, minimal to moderate increase in serum testosterone concentrations, and substantial increases in prostatic testosterone concetrations. As DHT appears to be the principal androgen responsible for stimulation of prostatic growth, a decrease in DHT concentrations will result in a decrease in prostatic volume (approximately 20-30% after 6-24 months of continued therapy). In men with androgenic alopecia, the mechanism of action has not been fully determined, but finasteride has shown to decrease scalp DHT concentration to the levels found in hairy scalp, reduce serum DHT, increase hair regrowth, and slow hair loss. |
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Metabolism | Drug is extensively metabolized, primarily in the liver via CYP3A4. Two metabolites have been identified with дЉ_20% of the activity of finasteride.
Route of Elimination: Following an oral dose of 14C-finasteride in man (n = 6), a mean of 39% (range, 32 to 46%) of the dose was excreted in the urine in the form of metabolites; 57% (range, 51 to 64%) was excreted in the feces. Urinary excretion of metabolites was decreased in patients with renal impairment. This decrease was associated with an increase in fecal excretion of metabolites.
Half Life: 4.5 hours (range 3.3-13.4 hours) |
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Toxicity Values | Not Available |
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Lethal Dose | Not Available |
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Carcinogenicity (IARC Classification) | No indication of carcinogenicity to humans (not listed by IARC). |
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Uses/Sources | For the treatment of symptomatic benign prostatic hyperplasia (BPH) in men with an enlarged prostate to: Improve symptoms, reduce the risk of acute urinary retention, reduce the risk of the need for surgery including transurethral resection of the prostate. Also used for the stimulation of regrowth of hair in men with mild to moderate androgenetic alopecia (male pattern alopecia, hereditary alopecia, common male baldness). |
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Minimum Risk Level | Not Available |
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Health Effects | Not Available |
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Symptoms | Not Available |
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Treatment | Not Available |
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Normal Concentrations |
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| Not Available |
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Abnormal Concentrations |
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| Not Available |
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External Links |
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DrugBank ID | DB01216 |
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HMDB ID | HMDB01984 |
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PubChem Compound ID | 57363 |
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ChEMBL ID | CHEMBL710 |
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ChemSpider ID | 51714 |
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KEGG ID | Not Available |
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UniProt ID | Not Available |
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OMIM ID | |
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ChEBI ID | 5062 |
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BioCyc ID | Not Available |
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CTD ID | Not Available |
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Stitch ID | Not Available |
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PDB ID | Not Available |
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ACToR ID | Not Available |
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Wikipedia Link | Finasteride |
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References |
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Synthesis Reference | Roman Davis, Alan Millar, “Method for preparing finasteride.” U.S. Patent US5670643, issued October, 1992. |
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MSDS | Link |
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General 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 ]
- Smith AB, Carson CC: Finasteride in the treatment of patients with benign prostatic hyperplasia: a review. Ther Clin Risk Manag. 2009 Jun;5(3):535-45. Epub 2009 Jul 12. [19707263 ]
- Trueb RM: Pharmacologic interventions in aging hair. Clin Interv Aging. 2006;1(2):121-9. [18044109 ]
- Otberg N, Finner AM, Shapiro J: Androgenetic alopecia. Endocrinol Metab Clin North Am. 2007 Jun;36(2):379-98. [17543725 ]
- Lin AM, Small EJ: Prostate cancer update: 2006. Curr Opin Oncol. 2007 May;19(3):229-33. [17414641 ]
- Dunn BK, Ford LG: Hormonal interventions to prevent hormonal cancers: breast and prostate cancers. Eur J Cancer Prev. 2007 Jun;16(3):232-42. [17415094 ]
- Thorpe JF, Jain S, Marczylo TH, Gescher AJ, Steward WP, Mellon JK: A review of phase III clinical trials of prostate cancer chemoprevention. Ann R Coll Surg Engl. 2007 Apr;89(3):207-11. [17394699 ]
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Gene Regulation |
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Up-Regulated Genes | Not Available |
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Down-Regulated Genes | Not Available |
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