| Record Information |
|---|
| Version |
3.5 |
| Creation Date |
2006-05-22 08:17:30 -0600 |
| Update Date |
2013-05-29 13:33:10 -0600 |
| HMDB ID |
HMDB01984 |
| Secondary Accession Numbers |
|
| Metabolite Identification |
|---|
| Common Name |
Finasteride |
| Description |
Finasteride is only found in individuals that have used or taken this drug. Finasteride is an androgen antagonist. It is an orally active testosterone 5-alpha-reductase inhibitor. Finasteride is one of the currently available pharmacologic treatment modalities with proven efficacy for treatment of androgenetic 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. Androgenetic alopecia (AGA), or male pattern hair loss, affects approximately 50% of the male population. AGA is an androgen-related condition in genetically predisposed individuals. There is no treatment to completely reverse AGA in advanced stages, but with medical treatment (e.g., finasteride), the progression can be arrested and partly reversed in the majority of patients who have mild to moderate AGA. Finasteride is also used as a surgical alternative for treatment of benign prostatic hyperplasia. [PubChem]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). Finasteride may increase the sensitivity of prostate specific antigen to detect prostate cancer. At present, finasteride remains the only intervention shown in long-term prospective phase III clinical trials to reduce the incidence of prostate cancer. (PMID: 18044109  , 17543725 , 17414641 , 17415094 , 17394699 ). |
| Structure |
Download:
MOL |
SDF |
SMILES |
InChI
Display:
2D Structure |
3D Structure
|
| Synonyms |
- Chibro-proscar
- Finasterida
- Finasteridum
- Finastid
- Finpecia
- Propecia
- Proscar
- Prostide
|
| Chemical Formula |
C23H36N2O2 |
| Average Molecular Weight |
372.5441 |
| Monoisotopic Molecular Weight |
372.277678406 |
| IUPAC Name |
(1S,2R,7R,10S,11S,14S,15S)-N-tert-butyl-2,15-dimethyl-5-oxo-6-azatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-3-ene-14-carboxamide |
| Traditional IUPAC Name |
finasteride |
| CAS Registry Number |
98319-26-7 |
| SMILES |
[H][C@@]12CC[C@H](C(=O)NC(C)(C)C)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])NC(=O)C=C[C@]12C |
| 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 |
| InChI Key |
DBEPLOCGEIEOCV-WSBQPABSSA-N |
| Chemical Taxonomy |
|---|
| Kingdom |
Organic Compounds |
| Super Class |
Lipids |
| Class |
Prenol Lipids |
| Sub Class |
Diterpenes |
| Other Descriptors |
- Aliphatic Heteropolycyclic Compounds
|
| Substituents |
- Benzoquinoline
- Carboxamide Group
- Cyclohexane
- Decaline
- Lactam
- Quinoline
- Secondary Carboxylic Acid Amide
|
| Direct Parent |
Diterpenes |
| Ontology |
|---|
| Status |
Expected and Not Quantified |
| Origin |
|
| Biofunction |
- Anti-baldness Agents
- Antihyperplasia Agents
- Cell signalling
- Enzyme Inhibitors
- Fuel and energy storage
- Fuel or energy source
- Hormones, Membrane component
- Membrane integrity/stability
- Skin and Mucous Membrane Agents
|
| Application |
- Nutrients
- Pharmaceutical
- Stabilizers
- Surfactants and Emulsifiers
|
| Cellular locations |
|
| Physical Properties |
|---|
| State |
Solid |
| Experimental Properties |
| Property |
Value |
Reference |
| Melting Point |
252 - 254 °C |
Not Available |
| Boiling Point |
Not Available |
Not Available |
| Water Solubility |
1.98e-03 g/L |
Not Available |
| LogP |
3.03 |
HANSCH,C ET AL. (1995) |
|
| Predicted Properties |
|
| Spectra |
|---|
|
Not Available
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| Biological Properties |
|---|
| Cellular Locations |
|
| Biofluid Locations |
Not Available
|
| Tissue Location |
Not Available
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| Pathways |
Not Available
|
| Normal Concentrations |
|---|
|
Not Available |
| Abnormal Concentrations |
|---|
|
Not Available |
| Associated Disorders and Diseases |
|---|
| Disease References |
None |
| Associated OMIM IDs |
None |
| External Links |
|---|
| DrugBank ID |
DB01216 |
| DrugBank Metabolite ID |
Not Available |
| Phenol Explorer Compound ID |
Not Available |
| Phenol Explorer Metabolite ID |
Not Available |
| FoodDB ID |
FDB022782 |
| KNApSAcK ID |
Not Available |
| Chemspider ID |
51714 |
| KEGG Compound ID |
Not Available |
| BioCyc ID |
Not Available |
| BiGG ID |
Not Available |
| Wikipedia Link |
Finasteride |
| NuGOwiki Link |
HMDB01984 |
| Metagene Link |
HMDB01984 |
| METLIN ID |
Not Available |
| PubChem Compound |
57363 |
| PDB ID |
Not Available |
| ChEBI ID |
5062 |
| References |
|---|
| Synthesis Reference |
Peng, Dongming; Huang, Kelong; Liu, Yanfei. Improved synthesis of finasteride. Zhongguo Yaowu Huaxue Zazhi (2005), 15(5), 288-290. |
| Material Safety Data Sheet (MSDS) |
Download (PDF)
|
| General References |
- Trueb RM: Pharmacologic interventions in aging hair. Clin Interv Aging. 2006;1(2):121-9.
Pubmed: 18044109
- Otberg N, Finner AM, Shapiro J: Androgenetic alopecia. Endocrinol Metab Clin North Am. 2007 Jun;36(2):379-98.
Pubmed: 17543725
- Lin AM, Small EJ: Prostate cancer update: 2006. Curr Opin Oncol. 2007 May;19(3):229-33.
Pubmed: 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.
Pubmed: 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.
Pubmed: 17394699
|
