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1. 17beta-n-(2,5-bis(trifluoromethyl))phenyl-carbamoyl-4-aza-5alpha-androst-1-en-3-one
2. 745, Gg
3. Avodart
4. Gg 745
5. Gg-745
6. Gg745
7. Gi198745
1. 164656-23-9
2. Avodart
3. Avolve
4. Gg-745
5. Gi 198745
6. Gi-198745
7. Gg 745
8. Duastride
9. (1s,3as,3bs,5ar,9ar,9bs,11as)-n-[2,5-bis(trifluoromethyl)phenyl]-9a,11a-dimethyl-7-oxo-1,2,3,3a,3b,4,5,5a,6,9b,10,11-dodecahydroindeno[5,4-f]quinoline-1-carboxamide
10. Nsc-740477
11. O0j6xjn02i
12. (5alpha,17beta)-n-(2,5-bis(trifluoromethyl)phenyl)-3-oxo-4-azaandrost-1-ene-17-carboxamide
13. Alpha,alpha,alpha,alpha',alpha',alpha'-hexafluoro-3-oxo-4-aza-5alpha-androst-1-ene-17beta-carboxy-2',5'-xylidide
14. Chembl1200969
15. Chebi:521033
16. Nsc-759880
17. (1s,3as,3bs,5ar,9ar,11as)-n-[2,5-bis(trifluoromethyl)phenyl]-9a,11a-dimethyl-7-oxo-1,2,3,3a,3b,4,5,5a,6,9b,10,11-dodecahydroindeno[5,4-f]quinoline-1-carboxamide
18. (4ar,4bs,6as,7s,9as,9bs,11ar)-n-(2,5-bis(trifluoromethyl)phenyl)-4a,6a-dimethyl-2-oxo-2,4a,4b,5,6,6a,7,8,9,9a,9b,10,11,11a-tetradecahydro-1h-indeno[5,4-f]quinoline-7-carboxamide
19. (1s,2r,7r,10s,11s,14s,15s)-n-[2,5-bis(trifluoromethyl)phenyl]-2,15-dimethyl-5-oxo-6-azatetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-3-ene-14-carboxamide
20. Dutasteride [usan]
21. Duagen
22. 1h-indeno[5,4-f]quinoline-7-carboxamide, N-[2,5-bis(trifluoromethyl)phenyl]-2,4a,4b,5,6,6a,7,8,9,9a,9b,10,11,11a-tetradecahydro-4a,6a-dimethyl-2-oxo-, (4ar,4bs,6as,7s,9as,9bs,11ar)-
23. Avodart (tn)
24. Unii-o0j6xjn02i
25. Avidart
26. Gi198745
27. Dutasteride [usan:inn:ban]
28. Ncgc00164571-01
29. (5alpha,17beta)-n-[2,5-bis(trifluoromethyl)phenyl]-3-oxo-4-azaandrost-1-ene-17-carboxamide
30. 1h-indeno(5,4-f)quinoline-7-carboxamide, N-(2,5-bis(trifluoromethyl)phenyl)-2,4a,4b,5,6,6a,7,8,9,9a,9b,10,11,11a-tetradecahydro-4a,6a-dimethyl-2-oxo-, (4ar,4bs,6as,7s,9as,9bs,11ar)-
31. Dutasteride- Bio-x
32. Gi-198745x
33. Dutasteride [mi]
34. Dutasteride [inn]
35. Dutasteride [jan]
36. Dutasteride [vandf]
37. Schembl5903
38. Dsstox_cid_26452
39. Dsstox_rid_81626
40. Dutasteride [mart.]
41. Dsstox_gsid_46452
42. Dutasteride [usp-rs]
43. Dutasteride [who-dd]
44. Dutasteride (jan/usp/inn)
45. Gtpl7457
46. Dtxsid8046452
47. Dutasteride, >=98% (hplc)
48. Dutasteride [orange Book]
49. Dutasteride For System Suitability
50. Jalyn Component Dutasteride
51. Bcpp000248
52. Dutasteride [ep Monograph]
53. Dutasteride [usp Monograph]
54. Bcp02344
55. Ex-a1952
56. Zinc3932831
57. Tox21_112199
58. Bdbm50340481
59. Mfcd00937869
60. Nsc740477
61. S1202
62. Dutasteride Component Of Jalyn
63. Akos015920136
64. Akos015924431
65. Bcp9000630
66. Ccg-269904
67. Cs-1542
68. Db01126
69. Gs-3565
70. Nsc 740477
71. Nsc 759880
72. N-[2,5-bis(trifluoromethyl)phenyl]-3-oxo-4-aza-5alpha-androst-1-ene-17beta-carboxamide
73. Bd164398
74. Hy-13613
75. Cas-164656-23-9
76. D5973
77. D03820
78. Ab01274774-01
79. Ab01274774_02
80. 656d239
81. A810580
82. Q424760
83. Q-201052
84. Brd-k30373883-001-02-8
85. Z1563146168
86. Dutasteride, European Pharmacopoeia (ep) Reference Standard
87. Dutasteride, United States Pharmacopeia (usp) Reference Standard
88. 4-azaandrost-1-ene-17-carboxamide, N-[2,5-bis(trifluoromethyl)phenyl]-3-oxo-, (5a,17b)-
89. Dutasteride For System Suitability, European Pharmacopoeia (ep) Reference Standard
90. (4ar,4bs,6as,7s,9as,9bs,11ar)-n-[2,5-bis(trifluoromethyl)phenyl]-2,4a,4b,5,6,6a,7,8,9,9a,9b,10,11,11a-tetradecahydro-4a,6a-dimethyl-2-oxo-1h-indeno[5,4-f]quinoline-7-carboxamide
91. (5.alpha.,17.beta.)-n-(2,5-bis(trifluoromethyl)phenyl)-3-oxo-4-azaandrost-1-ene-17-carboxamide
92. (5.alpha.,5 Bis(trifluoromethyl)phenyl}-3-oxo-4-azaandrost-1-ene-17-carboxamide;dutasteride;avodart;
93. (5alpha,17beta)-n-{2,5-bis(trifluoromethyl)-phenyl}-3-oxo-4-azaandrost-1-ene-17-carboxamide
94. .alpha.,.alpha.,.alpha.,.alpha.',.alpha.',.alpha.'-hexafluoro-3-oxo-4-aza-5.alpha.-androst-1-ene-17.beta.-carboxy-2',5'-xylidide
| Molecular Weight | 528.5 g/mol |
|---|---|
| Molecular Formula | C27H30F6N2O2 |
| XLogP3 | 5.4 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 8 |
| Rotatable Bond Count | 2 |
| Exact Mass | 528.22114718 g/mol |
| Monoisotopic Mass | 528.22114718 g/mol |
| Topological Polar Surface Area | 58.2 Ų |
| Heavy Atom Count | 37 |
| Formal Charge | 0 |
| Complexity | 964 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 7 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Covalently Bonded Unit Count | 1 |
| 1 of 4 | |
|---|---|
| Drug Name | Avodart |
| PubMed Health | Dutasteride (By mouth) |
| Drug Classes | Benign Prostatic Hypertrophy Agent |
| Drug Label | AVODART is a synthetic 4-azasteroid compound that is a selective inhibitor of both the type 1 and type 2 isoforms of steroid 5 alpha-reductase, an intracellular enzyme that converts testosterone to DHT. Dutasteride is chemically designated as (5,17... |
| Active Ingredient | Dutasteride |
| Dosage Form | Capsule |
| Route | Oral |
| Strength | 0.5mg |
| Market Status | Prescription |
| Company | Glaxosmithkline |
| 2 of 4 | |
|---|---|
| Drug Name | Dutasteride |
| PubMed Health | Dutasteride (By mouth) |
| Drug Classes | Benign Prostatic Hypertrophy Agent |
| Drug Label | AVODART is a synthetic 4-azasteroid compound that is a selective inhibitor of both the type 1 and type 2 isoforms of steroid 5 alpha-reductase, an intracellular enzyme that converts testosterone to DHT. Dutasteride is chemically designated as (5,17... |
| Active Ingredient | Dutasteride |
| Dosage Form | Capsule |
| Route | oral; Oral |
| Strength | 0.5mg |
| Market Status | Tentative Approval; Prescription |
| Company | Endo Pharms; Sandoz; Banner Pharmacaps; Roxane; Barr |
| 3 of 4 | |
|---|---|
| Drug Name | Avodart |
| PubMed Health | Dutasteride (By mouth) |
| Drug Classes | Benign Prostatic Hypertrophy Agent |
| Drug Label | AVODART is a synthetic 4-azasteroid compound that is a selective inhibitor of both the type 1 and type 2 isoforms of steroid 5 alpha-reductase, an intracellular enzyme that converts testosterone to DHT. Dutasteride is chemically designated as (5,17... |
| Active Ingredient | Dutasteride |
| Dosage Form | Capsule |
| Route | Oral |
| Strength | 0.5mg |
| Market Status | Prescription |
| Company | Glaxosmithkline |
| 4 of 4 | |
|---|---|
| Drug Name | Dutasteride |
| PubMed Health | Dutasteride (By mouth) |
| Drug Classes | Benign Prostatic Hypertrophy Agent |
| Drug Label | AVODART is a synthetic 4-azasteroid compound that is a selective inhibitor of both the type 1 and type 2 isoforms of steroid 5 alpha-reductase, an intracellular enzyme that converts testosterone to DHT. Dutasteride is chemically designated as (5,17... |
| Active Ingredient | Dutasteride |
| Dosage Form | Capsule |
| Route | oral; Oral |
| Strength | 0.5mg |
| Market Status | Tentative Approval; Prescription |
| Company | Endo Pharms; Sandoz; Banner Pharmacaps; Roxane; Barr |
Indicated for the treatment of symptomatic benign prostatic hyperplasia (BPH) in men with an enlarged prostate gland to improve symptoms, and reduce the risk of acute urinary retention and the need for BPH-related surgery alone or in combination with [tamsulosin].
Dutasteride is a synthetic 4-azasteroid compound that selectively inhibits both the type I and type II isoforms of steroid 5-reductase, an intracellular enzyme that converts testosterone to 5-dihydrotestosterone (DHT). Dutasteride works by reducing the levels of circulating DHT. It was also shown to reduce the size of the prostate gland, improve urinary flow, and symptoms of benign prostatic hyperplasia alone or in combination with tamsulosin. The effect of the reduction of DHT by dutasteride is dose-dependent, with the maximum effect observed within 1-2 weeks following initial administration. After 1 and 2 weeks of daily dosing with dutasteride 0.5 mg, median serum DHT concentrations were reduced by 85% and 90%, respectively. The serum concentrations of DHT were maintained to be decreased by more than 90% in 85% of patients following 1 years' administration of oral dutasteride 0.5 mg/day. As evident from the clinical studies, dutasteride may also cause decreases in serum PSA in the presence of prostate cancer.
5-alpha Reductase Inhibitors
Drugs that inhibit 3-OXO-5-ALPHA-STEROID 4-DEHYDROGENASE. They are commonly used to reduce the production of DIHYDROTESTOSTERONE. (See all compounds classified as 5-alpha Reductase Inhibitors.)
G04CB02
S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355
G - Genito urinary system and sex hormones
G04 - Urologicals
G04C - Drugs used in benign prostatic hypertrophy
G04CB - Testosterone-5-alpha reductase inhibitors
G04CB02 - Dutasteride
Absorption
Following oral administration of a single dose of 0.5 mg dutasteride, the peak serum concentrations were reached within 2 to 3 hours. Following daily oral administration of 0.5 mg dutasteride, the steady-state concentration of 40 ng/mL is expected to be achieved at 6 months following initial administration. In healthy subjects, the absolute bioavailability was 60%, ranging from 40% to 94%. While food intake reduced the maximum serum concentrations by 10 to 15%, food intake is reported to have a negligible effect on the bioavailability of the drug.
Route of Elimination
Dutasteride and its metabolites mainly undergo fecal excretion. About 1-15% of the dose is excreted as the unchanged parent compound, while 2-90% of the total dose is excreted in the form of dutasteride-related metabolites in the feces. Trace amounts of unchanged dutasteride, with less than 1%, can also be detected in the urine. Therefore, on average, the dose unaccounted for approximated 55%, with a range between 5% and 97%.
Volume of Distribution
Dutasteride displays a large volume of distribution ranging from 300 to 500 L. Following daily oral administration of 0.5 mg dutasteride healthy subjects for 12 months, the semen dutasteride concentrations averaged 3.4 ng/mL (range: 0.4 to 14 ng/mL) with 11.5% of serum dutasteride concentrations being partitioned into semen.
Clearance
In a study of healthy volunteers receiving single oral doses of dutasteride ranging from 0.01 to 40 mg, dutasteride displayed a low linear clearance of 0.58 L/h. The estimated inter-individual variability for the linear clearance was high.
Dutasteride undergoes extensive hepatic metabolism mediated by CYP3A4 and CYP3A5. 4-hydroxydutasteride, 6-hydroxydutasteride, 6,4-dihydroxydutasteride, 1,2-dihydrodutasteride, and 15-hydroxydutasteride metabolites are formed. 2 minor metabolites - 6,4-dihydroxydutasteride and 15-hydroxydutasteride - can also be detected. According to _in vitro_ studies, 4-hydroxydutasteride and 1,2-dihydrodutasteride mediated inhibitory actions against both isoforms of 5-reductase but with lower potency when compared to the parent drug. The activity of 6-hydroxydutasteride is comparable to that of dutasteride.
The terminal elimination half-life of dutasteride is approximately 5 weeks at steady state. This long half-life accounts for the serum concentrations remaining detectable for up to 4 to 6 months after discontinuation of treatment.
The 5-reductase is a nuclear-bound steroid intracellular enzyme primarily located in the prostatic stromal cell that converts the androgen testosterone into the more active metabolite, 5-dihydrotestosterone (DHT). DHT is considered to be the primary androgen playing a role in the initial development and subsequent enlargement of the prostate gland. It serves as the hormonal mediator for the hyperplasia upon accumulation within the prostate gland. DHT displays a higher affinity towards androgen receptors in the prostate gland compared to testosterone and by acting on the androgen receptors, DHT modulates genes that are responsible for cell proliferation. Responsible for the synthesis of approximately one-third of circulating DHT, type I 5-reductase is predominant in the sebaceous glands of most regions of skin, including the scalp, and liver. The type II 5a-reductase isozyme is primarily found in the prostate, seminal vesicles, epididymides, and hair follicles as well as liver, and is responsible for two-thirds of circulating DHT. Due to its dual inhibition of both isoenzymes of 5-reductase, dutasteride causes a near-complete suppression of DHT. Compared to a 70% reduction of serum DHT levels caused by [finasteride], a near-complete suppression of serum DHT-more than 90% is seen with dutasteride. By forming a stable complex with both type II and type II 5-reductase, dutasteride inhibits its enzymatic action of converting testosterone to 5-dihydrotestosterone (DHT), which is the androgen primarily responsible for the initial development and subsequent enlargement of the prostate gland. It is proposed that DHT is the principal androgen responsible for prostatic growth in later life-normal masculinization of the external genitalia and maturation of the prostate gland during development-thus reducing the serum DHT levels results in reduced prostatic volume and increased epithelial apoptosis. Dutasteride is a competitive and specific inhibitor of both Type I and Type II 5-reductase isoenzymes and when evaluated under _in vitro_ and _in vivo_ conditions, the dissociation of the drug from the drug-enzyme complex is reported to be extremely slow. Dutasteride does not bind to the human androgen receptor.
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