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Chemistry

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Also known as: 160970-54-7, Rapaflo, Urief, Silodyx, Urorec, Kmd-3213
Molecular Formula
C25H32F3N3O4
Molecular Weight
495.5  g/mol
InChI Key
PNCPYILNMDWPEY-QGZVFWFLSA-N
FDA UNII
CUZ39LUY82

Silodosin
Silodosin is an orally available, alpha-1 adrenoreceptor (alpha-1a) selective antagonist that can be used to relieve symptoms of benign prostate hyperplasia (BPH). Upon administration, silodosin selectively binds alpha-1a receptors located in the human prostate and bladder with high affinity and blocks signaling pathways mediated by alpha-1a. Blockade of these receptors causes smooth muscle relaxation, lowers intraurethral pressure, and results in improved urine flow and a reduction in the symptoms of BPH, such as difficulty with urinating, painful urination, urinary frequency and incomplete bladder emptying. In addition, silodosin may be used to improve lower urinary tract symptoms, which can occur after receiving radiation therapy for prostate cancer.
Silodosin is an alpha-Adrenergic Blocker. The mechanism of action of silodosin is as an Adrenergic alpha-Antagonist.
1 2D Structure

Silodosin

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
1-(3-hydroxypropyl)-5-[(2R)-2-[2-[2-(2,2,2-trifluoroethoxy)phenoxy]ethylamino]propyl]-2,3-dihydroindole-7-carboxamide
2.1.2 InChI
InChI=1S/C25H32F3N3O4/c1-17(30-8-12-34-21-5-2-3-6-22(21)35-16-25(26,27)28)13-18-14-19-7-10-31(9-4-11-32)23(19)20(15-18)24(29)33/h2-3,5-6,14-15,17,30,32H,4,7-13,16H2,1H3,(H2,29,33)/t17-/m1/s1
2.1.3 InChI Key
PNCPYILNMDWPEY-QGZVFWFLSA-N
2.1.4 Canonical SMILES
CC(CC1=CC2=C(C(=C1)C(=O)N)N(CC2)CCCO)NCCOC3=CC=CC=C3OCC(F)(F)F
2.1.5 Isomeric SMILES
C[C@H](CC1=CC2=C(C(=C1)C(=O)N)N(CC2)CCCO)NCCOC3=CC=CC=C3OCC(F)(F)F
2.2 Other Identifiers
2.2.1 UNII
CUZ39LUY82
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 1-(3-hydroxypropyl)-5-(2-(2-(2-(2,2,2-trifluoroethoxy)phenoxy)ethylamino)propyl)indoline-7-carboxamide

2. Kmd 3213

3. Kmd-3213

4. Rapaflo

2.3.2 Depositor-Supplied Synonyms

1. 160970-54-7

2. Rapaflo

3. Urief

4. Silodyx

5. Urorec

6. Kmd-3213

7. Kmd 3213

8. Rapilif

9. Silodal

10. Kad 3213

11. Kad-3213

12. Kso-0400

13. Cuz39luy82

14. Chembl24778

15. 1-(3-hydroxypropyl)-5-[(2r)-2-[2-[2-(2,2,2-trifluoroethoxy)phenoxy]ethylamino]propyl]-2,3-dihydroindole-7-carboxamide

16. 2,3-dihydro-1-(3-hydroxypropyl)-5-[(2r)-2-[[2-[2-(2,2,2-trifluoroethoxy)phenoxy]ethyl]amino]propyl]-1h-indole-7-carboxamide

17. (-)-1-(3-hydroxypropyl)-5-[(2r)-2-[[2-[2-(2,2,2-trifluoroethoxy)phenoxy]ethyl]amino]propyl]-2,3-di-hydro-1h-indole-7-carboxamide

18. Rapflo

19. Silodosin [inn]

20. ( C)-1-(3-hydroxypropyl)-5-[(2r)-2-[[2-[2-(2,2,2-trifluoroethoxy)phenoxy]ethyl]amino]propyl]-2,3-di-hydro-1h-indole-7-carboxamide

21. (-)-1-(3-hydroxypropyl)-5-((2r)-2-((2-(2-(2,2,2-trifluoroethoxy)phenoxy)ethyl)amino)propyl)-2,3-dihydro-1h-indole-7-carboxamide

22. 1-(3-hydroxypropyl)-5-[(2r)-2-({2-[2-(2,2,2-trifluoroethoxy)phenoxy]ethyl}amino)propyl]-2,3-dihydro-1h-indole-7-carboxamide

23. 1h-indole-7-carboxamide, 2,3-dihydro-1-(3-hydroxypropyl)-5-[(2r)-2-[[2-[2-(2,2,2-trifluoroethoxy)phenoxy]ethyl]amino]propyl]-

24. Silodosin [inn:ban]

25. Unii-cuz39luy82

26. Urief, Rapaflo

27. 2,3-dihydro-1-(3-hydroxypropyl)-5-((2r)-2-((2-(2-(2,2,2-trifluoroethoxy)phenoxy)ethyl)amino)propyl)-1h-indole-7-carboxamide

28. Rapaflo (tn)

29. Silodosin (rapaflo)

30. Urief (tn)

31. Silodosin (r-isomer)

32. Silodosin [jan]

33. Silodosin [mi]

34. Silodosin [vandf]

35. Silodosin (jp17/inn)

36. Silodosin [mart.]

37. Silodosin [who-dd]

38. Gtpl493

39. Silodosin [ema Epar]

40. Mls006010022

41. Schembl136973

42. Silodosin [orange Book]

43. Silodosin, >=98% (hplc)

44. Dtxsid40167045

45. Kmd3213

46. Chebi:135929

47. Hms3715b06

48. Hms3884o21

49. Bcp02143

50. Zinc3806063

51. Bdbm50160154

52. Mfcd00930170

53. S1613

54. Akos005145899

55. Kad 3213;kmd 3213

56. Bs-1011

57. Ccg-221202

58. Cs-0284

59. Db06207

60. Ncgc00345882-03

61. 1-(3-hydroxypropyl)-5-(2-(2-(2-(2,2,2-trifluoroethoxy)phenoxy)ethylamino)propyl)indoline-7-carboxamide

62. Ac-22605

63. Hy-10122

64. Smr004701206

65. Am20090780

66. I1128

67. Sw219765-1

68. D01965

69. 970s649

70. A810210

71. Q411770

72. Sr-01000944157

73. Q-102517

74. Sr-01000944157-1

75. (r)-1-(3-hydroxypropyl)-5-(2-(2-(2-(2,2,2-trifluoroethoxy)phenoxy)ethylamino)propyl)indoline-7-carboxamide

76. (r)-5-[2-[[2-[2-(2,2,2-trifluoro-ethoxy)phenoxy]ethyl]amino]propyl]-1-(3-hydroxypropyl)-2,3-dihydro-1h-indole-7-carboxamide

77. 1-(3-hydroxy-propyl)-5-((r)-2-{2-[2-(2,2,2-trifluoro-ethoxy)-phenoxy]-ethylamino}-propyl)-2,3-dihydro-1h-indole-7-carboxylic Acid Amide

78. 1-(3-hydroxypropyl)-5-[(2r)-2-({2-[2-(2,2,2-trifluoroethoxy)phenoxy]-ethyl}amino)propyl]-2,3-dihydro-1h-indole-7-carboxamide

79. 1-(3-hydroxypropyl)-5-[(2r)-2-[[2-[2-(2,2,2-trifluoroethoxy)phenoxy]ethyl]amino]propyl]-2,3-dihydro-1h-indole-7-carboxamide; 1-(3-hydroxypropyl)-5-[(2r)-2-({2-[2-(2,2,2-trifluoroethoxy)phenoxy]ethyl}amino)propyl]-2,3-dihydro-1h-indole-7-carboxamide; (-)-1

2.4 Create Date
2005-06-24
3 Chemical and Physical Properties
Molecular Weight 495.5 g/mol
Molecular Formula C25H32F3N3O4
XLogP33.6
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count9
Rotatable Bond Count13
Exact Mass495.23449100 g/mol
Monoisotopic Mass495.23449100 g/mol
Topological Polar Surface Area97 Ų
Heavy Atom Count35
Formal Charge0
Complexity654
Isotope Atom Count0
Defined Atom Stereocenter Count1
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Information
1 of 2  
Drug NameRapaflo
PubMed HealthSilodosin (By mouth)
Drug ClassesBenign Prostatic Hypertrophy Agent
Drug LabelRAPAFLO is the brand name for silodosin, a selective antagonist of alpha-1 adrenoreceptors. The chemical name of silodosin is 1-(3-Hydroxypropyl)-5-[(2R)-2-({2-[2-(2,2,2-trifluoroethoxy)phenoxy]ethyl}amino)propyl]-2,3-dihydro-1H-indole-7-carboxamide...
Active IngredientSilodosin
Dosage FormCapsule
RouteOral
Strength8mg; 4mg
Market StatusPrescription
CompanyWatson Labs

2 of 2  
Drug NameRapaflo
PubMed HealthSilodosin (By mouth)
Drug ClassesBenign Prostatic Hypertrophy Agent
Drug LabelRAPAFLO is the brand name for silodosin, a selective antagonist of alpha-1 adrenoreceptors. The chemical name of silodosin is 1-(3-Hydroxypropyl)-5-[(2R)-2-({2-[2-(2,2,2-trifluoroethoxy)phenoxy]ethyl}amino)propyl]-2,3-dihydro-1H-indole-7-carboxamide...
Active IngredientSilodosin
Dosage FormCapsule
RouteOral
Strength8mg; 4mg
Market StatusPrescription
CompanyWatson Labs

4.2 Drug Indication

Silodosin is indicated for the treatment of the signs and symptoms of benign prostatic hyperplasia (BPH). It is not indicated for the treatment of hypertension.


FDA Label


Treatment of the signs and symptoms of benign prostatic hyperplasia (BPH)


Treatment of the signs and symptoms of benign prostatic hyperplasia (BPH).


Treatment of the signs and symptoms of benign prostatic hyperplasia (BPH) in adult men.


5 Pharmacology and Biochemistry
5.1 Pharmacology

Silodosin is an antagonist of 1-adrenoceptors. It has the highest selectivity for the 1A-adrenoceptor subtype, with a 162-fold greater affinity than 1B-adrenoceptor and about a 50-fold greater affinity than for 1D-adrenoceptor. In clinical trials, silodosin improved maximum urinary flow rate, voiding symptoms, and storage symptoms of benign prostatic hyperplasia. Following oral administration, silodosin had a rapid onset of effect in men, with early effects of relieving lower urinary tract symptoms occurring within two to six hours post-dose. Silodosin inhibited the human ether-a-go-go-related gene (HERG) tail current; however, it has weak cardiovascular effects. As with all 1-adrenoceptor antagonists blocking 1-adrenoceptors in the iris dilator muscle, silodosin may cause intraoperative floppy iris syndrome (IFIS), which is characterized by small pupils and iris billowing during cataract surgery in patients taking 1-AR antagonists.


5.2 MeSH Pharmacological Classification

Adrenergic alpha-1 Receptor Antagonists

Drugs that bind to and block the activation of ADRENERGIC ALPHA-1 RECEPTORS. (See all compounds classified as Adrenergic alpha-1 Receptor Antagonists.)


Urological Agents

Drugs used in the treatment of urological conditions and diseases such as URINARY INCONTINENCE and URINARY TRACT INFECTIONS. (See all compounds classified as Urological Agents.)


5.3 FDA Pharmacological Classification
5.3.1 Active Moiety
SILODOSIN
5.3.2 FDA UNII
CUZ39LUY82
5.3.3 Pharmacological Classes
alpha-Adrenergic Blocker [EPC]; Adrenergic alpha-Antagonists [MoA]
5.4 ATC Code

G04CA04


G04CA04


G04CA04


G04CA04

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

G04CA - Alpha-adrenoreceptor antagonists

G04CA04 - Silodosin


5.5 Absorption, Distribution and Excretion

Absorption

The absolute bioavailability is approximately 32%. Following oral administration of silodosin 8 mg once daily in healthy male subjects, Cmax was 61.6 27.54 ng/mL and AUC was 373.4 164.94 ng x hr/mL. The Tmax was 2.6 0.90 hours. Silodosin glucuronide or KMD-3213G, the main metabolite of silodosin, has an AUC three- or four fold higher than for the parent compound. A moderate fat or calorie meal reduces Cmax by 18% to 43% and AUC by 4% to 49%, as well as Tmax by about one hour. However, the US prescribing information recommends drug intake with meals to avoid the potential adverse effects associated with high plasma drug concentrations.


Route of Elimination

At 10 days following oral administration of radiolabelled silodosin, about 33.5% of the dose was recovered in urine and 54.9% was recovered in feces.


Volume of Distribution

Silodosin has an apparent volume of distribution of 49.5 L.


Clearance

After intravenous administration, the plasma clearance of silodosin was approximately 10 L/hour.


5.6 Metabolism/Metabolites

The main metabolite of silodosin is silodosin glucuronide (KMD-3213G), which is a pharmacologically active metabolite formed by direct glucuronide conjugation mediated by UDP-glucuronosyltransferase 2B7 (UGT2B7). Silodosin glucuronide reaches plasma exposure (AUC) approximately four times greater than that of silodosin. The second major metabolite, KMD-3293, is formed from dehydrogenation catalyzed by alcohol and aldehyde dehydrogenases. KMD-3293 has negligible pharmacological activity and reaches plasma exposures similar to that of silodosin. Silodosin is also metabolized by CYP3A4, which catalyzes the oxidation reaction. Other than glucuronidation, dehydrogenation, and oxidation as its main metabolic pathways, silodosin can also undergo dealkylation (KMD-3289), N-dealkylation, hydroxylation, glucosylation, and sulfate conjugation. Metabolites of silodosin can undergo a series of further metabolic pathways.


5.7 Biological Half-Life

The elimination half-life of silodosin is 13.3 8.07 hours. KMD-3213G, the main metabolite of silodosin, has an extended half-life of approximately 24 hours.


5.8 Mechanism of Action

The pathogenesis of benign prostatic hyperplasia is not fully understood: it is believed to involve several pathways, including inflammation, apoptosis, and cellular proliferation. Most drug therapies aim to alleviate symptoms of benign prostatic hyperplasia, silodosin included. Lower urinary tract symptoms of benign prostatic hyperplasia are categorized into three main groups: voiding or obstructive (hesitancy, slow stream, intermittency, incomplete emptying), storage or irritative (frequency, urgency, nocturia, urge urinary incontinence), and postmicturition (postvoid dribbling). Prostate contraction is the main contributor to lower urinary tract symptoms of benign prostatic hyperplasia. The smooth muscle tone of the prostate is regulated by 1A-adrenoceptors, which are the most highly expressed subtype of 1adrenoceptors in the human prostate tissue. It has been reported that blockade of 1A-adrenoceptors relieves bladder outlet obstruction. Blockade of 1D-adrenoceptors, another subtype found in prostate tissue, is believed to alleviate storage symptoms due to detrusor overactivity. 1-adrenoceptors are G protein-coupled receptors: upon binding of its natural ligand, norepinephrine and epinephrine, leads to the activation of phospholipase C and downstream signalling molecules, including inositol triphosphate and diacylglycerol. Ultimately, there is an increase in intracellular calcium levels and, consequently, smooth muscle contraction. Silodosin is an antagonist of 1-adrenoceptors, with the highest selectivity for the 1A-adrenoceptor subtype. By blocking the 1A-adrenoceptor signalling pathway, silodosin promotes prostatic and urethral smooth muscle relaxation, thereby improving lower urinary tract symptoms such as voiding. Silodosin also targets afferent nerves in the bladder, relieving bladder overactivity and storage symptoms.


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06-Jan-2021
22-Oct-2024
KGS
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DOSAGE - CAPSULE;ORAL - 4MG

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