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CAS 81403-80-7 manufacturers and suppliers on PharmaCompass

PharmaCompass
  • Chemistry
Prestwick3_000322
Also known as: 81403-80-7, Alfuzosina, Alfuzosine, Alfuzosinum, Sl 77499, Alfluzocin
Molecular Formula
C19H27N5O4
Molecular Weight
389.4  g/mol
InChI Key
WNMJYKCGWZFFKR-UHFFFAOYSA-N
FDA UNII
90347YTW5F

Alfuzosin is a synthetic quinazoline compound with smooth muscle relaxing activity. Alfuzosin selectively binds to and antagonizes alpha-1-adrenergic receptors in smooth muscle of the bladder neck and prostate, thereby relaxing the smooth muscle and decreasing the obstruction and urethral resistance seen with benign prostate hyperplasia (BPH) and prostate cancer. This agent also blocks alpha-1-adrenergic receptors in peripheral vascular smooth muscle, which leads to vasodilatation and a subsequent decrease in peripheral vascular resistance.
Alfuzosin is an alpha-Adrenergic Blocker. The mechanism of action of alfuzosin is as an Adrenergic alpha-Antagonist.
1 2D Structure

Prestwick3_000322

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
N-[3-[(4-amino-6,7-dimethoxyquinazolin-2-yl)-methylamino]propyl]oxolane-2-carboxamide
2.1.2 InChI
InChI=1S/C19H27N5O4/c1-24(8-5-7-21-18(25)14-6-4-9-28-14)19-22-13-11-16(27-3)15(26-2)10-12(13)17(20)23-19/h10-11,14H,4-9H2,1-3H3,(H,21,25)(H2,20,22,23)
2.1.3 InChI Key
WNMJYKCGWZFFKR-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CN(CCCNC(=O)C1CCCO1)C2=NC3=CC(=C(C=C3C(=N2)N)OC)OC
2.2 Other Identifiers
2.2.1 UNII
90347YTW5F
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Alfetim

2. Alfusozine

3. Alfuzosin Hydrochloride

4. Alphuzosine

5. Benestan

6. N-(3-((4-amino-6,7-dimethoxy-2-quinazolinyl)methylamino)propyl)tetrahydro-2-furancarboxamide

7. Urion

8. Uroxatral

9. Xatral

2.3.2 Depositor-Supplied Synonyms

1. 81403-80-7

2. Alfuzosina

3. Alfuzosine

4. Alfuzosinum

5. Sl 77499

6. Alfluzocin

7. Alfluzosin

8. Alfuzosin (inn)

9. N-[3-[(4-amino-6,7-dimethoxyquinazolin-2-yl)-methylamino]propyl]oxolane-2-carboxamide

10. Chembl709

11. Nsc-760065

12. Chebi:51141

13. 90347ytw5f

14. N-(3-((4-amino-6,7-dimethoxy-2-quinazolinyl)methylamino)propyl)tetrahydro-2-furancarboxamide

15. N-{3-[(4-amino-6,7-dimethoxyquinazolin-2-yl)(methyl)amino]propyl}tetrahydrofuran-2-carboxamide

16. Alfuzosine [french]

17. Alfuzosinum [latin]

18. Alfusosine

19. Alfuzosin [inn]

20. Alfuzosina [spanish]

21. Alfuzosin [inn:ban]

22. 2-furancarboxamide,n-[3-[(4-amino-6,7-dimethoxy-2-quinazolinyl)methylamino]propyl]tetrahydro-

23. Sl 77499-10

24. N-[3-[(4-amino-6,7-dimethoxy-2-quinazolinyl)methylamino]propyl]tetrahydro-2-furancarboxamide

25. N-(3-((4-amino-6,7-dimethoxyquinazolin-2-yl)(methyl)amino)propyl)tetrahydrofuran-2-carboxamide

26. Smr000466340

27. Xatral (tn)

28. Hsdb 7290

29. Sl 77-499

30. Sl-7749910

31. Unii-90347ytw5f

32. N-(3-((4-amino-6,7-dimethoxyquinazolin-2-yl)

33. Sr-01000759345

34. Alfuzosin- Bio-x

35. Alfuzosin-[d7]

36. Alfuzosin [mi]

37. Alfuzosin [hsdb]

38. Prestwick0_000322

39. Prestwick1_000322

40. Prestwick2_000322

41. Prestwick3_000322

42. Spectrum2_000505

43. Spectrum3_001063

44. Spectrum4_001208

45. Spectrum5_000817

46. Alfuzosin [vandf]

47. Alfuzosin [who-dd]

48. Schembl34477

49. Bspbio_000323

50. Bspbio_002646

51. Kbiogr_001616

52. Mls000759449

53. Mls001424027

54. Mls006011887

55. Spectrum1505263

56. Spbio_000429

57. Spbio_002244

58. Bpbio1_000357

59. Gtpl7109

60. Dtxsid6048549

61. Kbio3_001866

62. Hms1922p11

63. Hms2051i10

64. Hms2093o06

65. Hms2235o22

66. Hms3369k03

67. Hms3393i10

68. Hms3749i05

69. Hms3886o22

70. Pharmakon1600-01505263

71. Act03219

72. Hy-b0192

73. Bdbm50033110

74. Ccg-39585

75. Mfcd00865792

76. Nsc760065

77. S5766

78. Stk643675

79. Akos005574697

80. Ccg-100859

81. Db00346

82. Nc00109

83. Nsc 760065

84. Sdccgsbi-0206735.p002

85. N-{3-[(4-amino-6,7-dimethoxyquinazolin-2-yl)(methyl)amino]propyl}oxolane-2-carboxamide

86. Ncgc00095152-01

87. Ncgc00095152-02

88. Ncgc00095152-03

89. Ncgc00095152-04

90. Ncgc00095152-05

91. Ncgc00095152-07

92. Ncgc00095152-19

93. 2-furancarboxamide, N-(3-((4-amino-6,7-dimethoxy-2-quinazolinyl)methylamino)propyl)tetrahydro-

94. Ba164145

95. Sbi-0206735.p001

96. Db-056523

97. Ab00514667

98. Ft-0630891

99. D07124

100. Ab00514667-07

101. Ab00514667-09

102. Ab00514667-10

103. Ab00514667_11

104. Ab00514667_12

105. (methyl)amino)propyl)tetrahydrofuran-2-carboxamide

106. 403a807

107. A840122

108. L001317

109. Q2736873

110. Sr-01000759345-4

111. Brd-a09056319-001-02-2

112. Brd-a09056319-001-05-5

113. Brd-a09056319-003-03-6

114. (+/-)-n-(3-((4-amino-6,7-dimethoxyquinazolin-2-yl)(methyl)amino)propyl)tetrahydrofuran-2-carboxamide

115. (+/-)-n-[3-[(4-amino-6,7-dimethoxy-2-quinazolinyl)methylamino]propyl]tetrahydro-2-furamide

116. 1100050-87-0

117. 2-furancarboxamide, (+/-)-n-(3-((4-amino-6,7-dimethoxy-2-quinazolinyl)methylamino)propyl)tetrahydro-

118. N-[3-[(4-amino-6,7-dimethoxy-quinazolin-2-yl)- Methyl-amino]propyl] Tetrahydrofuran- 2-carboxamide

119. N-[3-[(4-amino-6,7-dimethoxy-quinazolin-2-yl)-methyl-amino]propyl]tetrahydrofuran-2-carboxamide;alfuzosin

120. N-{3-[(4-imino-6,7-dimethoxy-3,4-dihydroquinazolin-2-yl)(methyl)amino]propyl}oxolane-2-carboximidic Acid

2.4 Create Date
2005-03-25
3 Chemical and Physical Properties
Molecular Weight 389.4 g/mol
Molecular Formula C19H27N5O4
XLogP31.7
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count8
Rotatable Bond Count8
Exact Mass389.20630436 g/mol
Monoisotopic Mass389.20630436 g/mol
Topological Polar Surface Area112 Ų
Heavy Atom Count28
Formal Charge0
Complexity511
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count1
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Therapeutic Uses

Antihypertensive

O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. 13th Edition, Whitehouse Station, NJ: Merck and Co., Inc., 2001., p. 46


Alfuzosin hydrochloride is used for the symptomatic management of benign prostatic hyperplasia (BPH, benign prostatic hypertrophy). Alfuzosin relieves moderate to severe irritative (e.g., frequency, urgency, nocturia) and obstructive (e.g., hesitancy, interrupted or weak stream, sensation of incomplete bladder emptying or straining) manifestations and improves urinary flow rates in a substantial proportion of patients.

McEvoy, G.K. (ed.). American Hospital Formulary Service- Drug Information 2004. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2004 (Plus Supplements)., p. 3698


Uroxatal is not indicated for the treatment of hypertension. /Alfuzosin Hydrochloride/

Physicians Desk Reference. 58th ed. Thomson PDR. Montvale, NJ 2004., p. 3037


4.2 Drug Warning

In a study of QT effect in 45 healthy males, the QT effect appeared less with alfuzosin 10 mg than with 40 mg, and the effect of alfuzosin 40 mg did not appear as large as that of the active control moxifloxacin at its therapeutic dose. This observation should be considered in clinical decisions to prescribe Uroxatral for patients with a known history of QT prolongation or patients who are taking medications known to prolong QT, although there has been no signal of Torsades de Pointe in the extensive postmarketing experience with alfuzosin outside the United States. There are no known PK/PD studies of the effects of other alpha blockers on cardiac repolarization. /Alfuzosin Hydrochloride/

Physicians Desk Reference. 58th ed. Thomson PDR. Montvale, NJ 2004., p. 3037


Postural hypotension with or without symptoms (e.g., dizziness) may develop within a few hours following administration of Uroxatral (alfuzosin HCl extended-release tablets). As with other alpha-blockers, there is a potential for syncope. Patients should be warned of the possible occurrence of such events and should avoid situations where injury could result should syncope occur. Care should be taken when Uroxatral is administered to patients with symptomatic hypotension or patients who have had a hypotensive response to other medications.

Physicians Desk Reference. 58th ed. Thomson PDR. Montvale, NJ 2004., p. 3037


Carcinoma of the prostate and benign prostatic hyperplasia cause many of the same symptoms. These two diseases frequently coexist. Therefore, patients thought to have benign prostatic hyperplasia should be examined prior to starting therapy with Uroxatral (alfuzosin HCl extended-release tablets) to rule out the presence of carcinoma of the prostate.

Physicians Desk Reference. 58th ed. Thomson PDR. Montvale, NJ 2004., p. 3037


If symptoms of angina pectoris should newly appear or worsen, Uroxatral should be discontinued. /Extended Release Alfuzosin Hydrochloride/

Physicians Desk Reference. 58th ed. Thomson PDR. Montvale, NJ 2004., p. 3037


For more Drug Warnings (Complete) data for ALFUZOSIN (16 total), please visit the HSDB record page.


4.3 Drug Indication

Alfuzosin is used to treat the signs and symptoms of benign prostatic hyperplasia (BPH).


FDA Label


5 Pharmacology and Biochemistry
5.1 Pharmacology

By selectively inhibiting alpha adrenergic receptors in the lower urinary tract, alfuzosin causes smooth muscle relaxation in the bladder neck and prostate, improving urine flow, thereby reducing BPH symptoms. Additionally, alfuzosin reduces the vasoconstrictor effect of catecholamines (epinephrine and norepinephrine), leading to peripheral vasodilation. This leads to a risk of postural hypotension/syncope, and prescribing information warns that caution should be exercised in patients who take nitrates, antihypertensives, or have experienced decreased blood pressure after using other medications.


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
ALFUZOSIN
5.3.2 FDA UNII
90347YTW5F
5.3.3 Pharmacological Classes
Established Pharmacologic Class [EPC] - alpha-Adrenergic Blocker
5.4 ATC Code

G04CA01

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

G04CA01 - Alfuzosin


5.5 Absorption, Distribution and Excretion

Absorption

Alfuzosin is readily absorbed in the gastrointestinal tract and the absolute bioavailability under fed conditions is 49%. In patients over 75 years of age, alfuzosin is absorbed more rapidly and peak plasma levels are higher. One source mentions a bioavailability of 64%. After multiple doses under fed conditions, Cmax is achieved in 8 hours. Cmax and AUC0-24 values are about 13.6 ng/mL and 194 ngh/mL, respectively. Steady-state plasma concentrations are achieved after the second dose and are 1.2 to 1.6 times higher than after a single dose. With the extended-release formulation, alfuzosin release is sustained over 20 hours with a rate of dissolution ranging between 2 and 12 hours.


Route of Elimination

It is partially metabolised and excreted mainly in the bile and faeces. Following oral administration of a radiolabeled alfuzosin solution, the detection of radioactivity after one week was 69% in the feces and 24% in the urine.


Volume of Distribution

The volume of distribution of alfuzosin after intravenous administration in healthy volunteers is about 3.2 L/kg. Alfuzosin distributes heavily to the tissues of the prostate.


Clearance

Exercise caution if renal clearance is < 30 mL/min. The clearance of alfuzosin is increased in renal insufficiency (with or without dialysis), due to an increase in the free fraction.


Following oral administration of (14)C-labeled alfuzosin solution, the recovery of radioactivity after 7 days (expressed as a percentage of the administered dose) was 69% in feces and 24% in urine. /Alfuzosin Hydrochloride/

Physicians Desk Reference. 58th ed. Thomson PDR. Montvale, NJ 2004., p. 3036


The volume of distribution following intravenous administration in healthy male middle-aged volunteers was 3.2 L/kg. Results of in vitro studies indicate that alfuzosin is moderately bound to human plasma proteins (82% to 90%), with linear binding over a wide concentration range (5 to 5,000 ng/mL). /Alfuzosin Hydrochloride/

Physicians Desk Reference. 58th ed. Thomson PDR. Montvale, NJ 2004., p. 3036


The extent of absorption is 50% lower under fasting conditions. Therefore, Uroxatral should be taken immediately following a meal. /Alfuzosin Hydrochloride/

Physicians Desk Reference. 58th ed. Thomson PDR. Montvale, NJ 2004., p. 3036


The absolute bioavailability of Uroxatral 10 mg tablets under fed conditions is 49%. Following multiple dosing of 10 mg Uroxatral under fed conditions, the time to maximum concentration is 8 hours. Cmax and AUC0-24 are 13.6 (SD = 5.6) ng/mL and 194 (SD = 75) ng.h/mL, respectively.Uroxatral exhibits linear kinetics following single and multiple dosing up to 30 mg. Steady-state plasma levels are reached by with the second dose of Uroxatral administration. Steady-state alfuzosin plasma concentrations are 1.2- to 1.6-fold higher than those observed after a single administration. /Extended Release Alfuzosin Hydrochloride/

Physicians Desk Reference. 58th ed. Thomson PDR. Montvale, NJ 2004., p. 3036


For more Absorption, Distribution and Excretion (Complete) data for ALFUZOSIN (6 total), please visit the HSDB record page.


5.6 Metabolism/Metabolites

Alfuzosin undergoes extensive hepatic metabolism; only 11% of the administered dose is detected unchanged in the urine. Alfuzosin is metabolism occurs via three metabolic pathways: oxidation, O-demethylations, and N-dealkylation. Metabolites of alfuzosin are not pharmacologically active and CYP3A4 is main hepatic cytochrome enzyme responsible for its metabolism.


Alfuzosin undergoes extensive metabolism by the liver, with only 11% of the administered dose excreted unchanged in the urine. Alfuzosin is metabolized by three metabolic pathways: oxidation, O-demethylation, and N-dealkylation. The metabolites are not pharmacologically active. CYP3A4 is the principal hepatic enzyme isoform involved in its metabolism. /Alfuzosin Hydrochloride/

Physicians Desk Reference. 58th ed. Thomson PDR. Montvale, NJ 2004., p. 3036


5.7 Biological Half-Life

The apparent elimination half-life of alfuzosin after oral administration is about 10 hours. The terminal half-life is 3-5 hours.


Following oral administration of Uroxatral 10 mg tablets, the apparent elimination half-life is 10 hours. /Extended Release Alfuzosin Hydrochloride/

Physicians Desk Reference. 58th ed. Thomson PDR. Montvale, NJ 2004., p. 3036


5.8 Mechanism of Action

Alpha(1)-adrenoreceptors are found in the prostate, bladder base, bladder neck, prostatic capsule, and prostatic urethra; their activation may lead to contraction of smooth muscle and urinary symptoms in patients with BPH. Alfuzosin selectively binds to and inhibits alpha(1)-adrenergic receptors in the lower urinary tract. This leads to the relaxation of smooth muscle in both the prostate and bladder neck, resulting in the improvement in urine flow and a reduction of urinary symptoms.


Alfuzosin hydrochloride, a quinazoline-derivative alpha1-adrenergic blocking agent, is structurally and pharmacologically related to prazosin. Alfuzosin is a non-subtype-specific alpha1-adrenergic blocking agent that exhibits selectivity for alpha1-adrenergic receptors in the lower urinary tract (e.g., bladder base, bladder neck, prostate, prostatic capsule, prostatic urethra). Blockade of these adrenoreceptors can cause relaxation of smooth muscle in the bladder neck and prostate, resulting in improvement in urine flow and a reduction in symptoms of benign prostatic hyperplasia (BPH).

McEvoy, G.K. (ed.). American Hospital Formulary Service- Drug Information 2004. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2004 (Plus Supplements)., p. 3698


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