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Chemistry

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Also known as: 74191-85-8, Doxazosine, Doxazosinum, Doxazosina, Doxazosin (inn), [4-(4-amino-6,7-dimethoxyquinazolin-2-yl)piperazin-1-yl]-(2,3-dihydro-1,4-benzodioxin-3-yl)methanone
Molecular Formula
C23H25N5O5
Molecular Weight
451.5  g/mol
InChI Key
RUZYUOTYCVRMRZ-UHFFFAOYSA-N
FDA UNII
NW1291F1W8

Cardura
A prazosin-related compound that is a selective alpha-1-adrenergic blocker.
Doxazosin is an alpha-Adrenergic Blocker. The mechanism of action of doxazosin is as an Adrenergic alpha-Antagonist.
1 2D Structure

Cardura

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
[4-(4-amino-6,7-dimethoxyquinazolin-2-yl)piperazin-1-yl]-(2,3-dihydro-1,4-benzodioxin-3-yl)methanone
2.1.2 InChI
InChI=1S/C23H25N5O5/c1-30-18-11-14-15(12-19(18)31-2)25-23(26-21(14)24)28-9-7-27(8-10-28)22(29)20-13-32-16-5-3-4-6-17(16)33-20/h3-6,11-12,20H,7-10,13H2,1-2H3,(H2,24,25,26)
2.1.3 InChI Key
RUZYUOTYCVRMRZ-UHFFFAOYSA-N
2.1.4 Canonical SMILES
COC1=C(C=C2C(=C1)C(=NC(=N2)N3CCN(CC3)C(=O)C4COC5=CC=CC=C5O4)N)OC
2.2 Other Identifiers
2.2.1 UNII
NW1291F1W8
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 1 (4-amino-6,7-dimethoxy-2-quinazolinyl)-4-((2,3-dihydro-1,4-benzodioxin-2-yl)carbonyl)piperazine

2. Alfamedin

3. Apo Doxazosin

4. Apo-doxazosin

5. Cardular

6. Cardura

7. Carduran

8. Carduran Neo

9. Ct, Doxazosin Von

10. Diblocin

11. Doxa Puren

12. Doxa-puren

13. Doxacor

14. Doxagamma

15. Doxamax

16. Doxatensa

17. Doxauro

18. Doxazomerck

19. Doxazosin Al

20. Doxazosin Apogepha

21. Doxazosin Azu

22. Doxazosin Beta

23. Doxazosin Findusfit

24. Doxazosin Heumann

25. Doxazosin Klast

26. Doxazosin Mesylate

27. Doxazosin Monohydrochloride

28. Doxazosin Ratiopharm

29. Doxazosin Stada

30. Doxazosin Von Ct

31. Doxazosin Wolff

32. Doxazosin-ratiopharm

33. Doxazosin-wolff

34. Doxazosina Alter

35. Doxazosina Cinfa

36. Doxazosina Combino Pharm

37. Doxazosina Geminis

38. Doxazosina Normon

39. Doxazosina Pharmagenus

40. Doxazosina Ratiopharm

41. Doxazosina Ur

42. Gen Doxazosin

43. Gen-doxazosin

44. Jutalar

45. Mesylate, Doxazosin

46. Monohydrochloride, Doxazosin

47. Mtw Doxazosin

48. Mtw-doxazosin

49. Neo, Carduran

50. Novo Doxazosin

51. Novo-doxazosin

52. Progandol Neo

53. Ratio Doxazosin

54. Ratio-doxazosin

55. Ratiopharm, Doxazosina

56. Uk 33274

57. Uk-33274

58. Uk33274

59. Uriduct

60. Von Ct, Doxazosin

61. Zoxan

2.3.2 Depositor-Supplied Synonyms

1. 74191-85-8

2. Doxazosine

3. Doxazosinum

4. Doxazosina

5. Doxazosin (inn)

6. [4-(4-amino-6,7-dimethoxyquinazolin-2-yl)piperazin-1-yl]-(2,3-dihydro-1,4-benzodioxin-3-yl)methanone

7. Uk 33274

8. Uk-33274

9. 1-(4-amino-6,7-dimethoxy-2-quinazolinyl)-4-(1,4-benzodioxan-2-ylcarbonyl)piperazin

10. 1-(4-amino-6,7-dimethoxy-2-chinazolinyl)-4-(2,3-dihydro-1,4-benzodioxixin-2-ylcarbonyl)piperazin

11. Chebi:4708

12. (rs)-2-{4-[(2,3-dihydro-1,4-benzodioxin-2-yl)carbonyl]piperazin-1-yl}-6,7-dimethoxyquinazolin-4-amine

13. Doxazosine [french]

14. C02ca04

15. Nw1291f1w8

16. (4-(4-amino-6,7-dimethoxyquinazolin-2-yl)piperazin-1-yl)(2,3-dihydrobenzo[b][1,4]dioxin-2-yl)methanone

17. Doxazosinum [latin]

18. Doxazosin [inn]

19. Doxazosina [spanish]

20. Doxazosin [inn:ban]

21. Piperazine, 1-(4-amino-6,7-dimethoxy-2-quinazolinyl)-4-((2,3-dihydro-1,4-benzodioxin-2-yl)carbonyl)-

22. 2-[4-(2,3-dihydro-1,4-benzodioxin-2-ylcarbonyl)piperazin-1-yl]-6,7-bis(methyloxy)quinazolin-4-amine

23. Methanone, [4-(4-amino-6,7-dimethoxy-2-quinazolinyl)-1-piperazinyl](2,3-dihydro-1,4-benzodioxin-2-yl)-

24. Cardura Xl (tn)

25. Supress

26. Unii-nw1291f1w8

27. Methanone, (4-(4-amino-6,7-dimethoxy-2-quinazolinyl)-1-piperazinyl)(2,3-dihydro-1,4-benzodioxin-2-yl)-

28. Piperazine, 1-(4-amino-6,7-dimethoxy-2-quinazolinyl)-4-[(2,3-dihydro-1,4-benzodioxin-2-yl)carbonyl]-

29. 2-[4-(2,3-dihydro-1,4-benzodioxin-2-ylcarbonyl)piperazin-1-yl]-6,7-dimethoxyquinazolin-4-amine

30. Cpd000097306

31. Doxazosin [mi]

32. Prestwick0_000858

33. Prestwick1_000858

34. Prestwick2_000858

35. Prestwick3_000858

36. Doxazosin [vandf]

37. Chemdiv2_005017

38. Chembl707

39. Ec 616-059-6

40. Doxazosin [who-dd]

41. (+/-)-doxazosin

42. Lopac0_000474

43. Oprea1_259518

44. Schembl34111

45. Bspbio_000875

46. Doxazosin-d8(piperazine-d8)

47. 2-{4-[(2,3-dihydro-1,4-benzodioxin-2-yl)carbonyl]piperazin-1-yl}-6,7-dimethoxyquinazolin-4-amine

48. Spbio_002796

49. Bpbio1_000963

50. Gtpl7170

51. Dtxsid7022964

52. Bdbm86731

53. Hms1383e01

54. Hms2090c20

55. Hms3259n21

56. Hms3372l09

57. Hms3886j03

58. Bcp12228

59. Hy-b0098

60. Zca19185

61. (4-benzylmorpholin-2-yl)-aceticacid

62. Nsc768144

63. Nsc768145

64. S5782

65. Akos001681453

66. Akos017343634

67. Ccg-118218

68. Cs-1831

69. Db00590

70. Nc00685

71. Nsc-768144

72. Nsc-768145

73. Sdccgsbi-0050459.p003

74. Idi1_003732

75. Ncgc00018158-02

76. Ncgc00018158-03

77. Ncgc00018158-05

78. Ncgc00018158-06

79. Ncgc00018158-08

80. Ncgc00018158-11

81. Ncgc00018158-20

82. Ncgc00089775-02

83. Ac-11062

84. As-77104

85. Sbi-0050459.p002

86. Cas_74191-85-8

87. Db-055848

88. Uk 33,274

89. Ft-0630831

90. Uk-3327427

91. En300-53055

92. C06970

93. D07874

94. 191d858

95. A838054

96. L000738

97. Q419939

98. Brd-a13188892-066-03-3

99. Brd-a13188892-066-13-2

100. (4-(4-amino-6,7-dimethoxy-2-quinazolinyl)-1-piperazinyl)(2,3-dihydro-1,4-benzodioxin-2-yl)methanone

101. (4-(4-amino-6,7-dimethoxyquinazolin-2-yl)piperazin-1-yl)(2,3-dihydro-1,4-benzodioxin-2-yl)methanone

102. [4-(4-amino-6,7-dimethoxy-2-quinazolinyl)-1-piperazinyl]-[(3s)-2,3-dihydro-1,4-benzodioxin-3-yl]methanone

103. 1-(4-amino-6,7-dimethoxy-2-quinazolinyl)-4-(1,4-benzodioxan-2-ylcarbonyl)piperazine

104. 1-(4-amino-6,7-dimethoxy-2-quinazolinyl)-4-[(2,3-dihydro-1,4-benzodioxin-2-yl)carbonyl]piperazine

105. 137888-77-8

106. 2-[4-(2,3-dihydro-1,4-benzodioxine-2-carbonyl)piperazin-1-yl]-6,7-dimethoxy-3,4-dihydroquinazolin-4-imine

2.4 Create Date
2005-03-25
3 Chemical and Physical Properties
Molecular Weight 451.5 g/mol
Molecular Formula C23H25N5O5
XLogP32.5
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count9
Rotatable Bond Count4
Exact Mass451.18556891 g/mol
Monoisotopic Mass451.18556891 g/mol
Topological Polar Surface Area112 Ų
Heavy Atom Count33
Formal Charge0
Complexity678
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 Drug Information
1 of 2  
Drug NameCardura
PubMed HealthDoxazosin (By mouth)
Drug ClassesAntihypertensive, Benign Prostatic Hypertrophy Agent, Cardiovascular Agent
Drug LabelCARDURA (doxazosin mesylate) is a quinazoline compound that is a selective inhibitor of the alpha1 subtype of alpha-adrenergic receptors. The chemical name of doxazosin mesylate is 1-(4-amino-6,7-dimethoxy-2-quinazolinyl)-4-(1,4-benzodioxan-2-ylcar...
Active IngredientDoxazosin mesylate
Dosage FormTablet
RouteOral
Strengtheq 4mg base; eq 2mg base; eq 1mg base; eq 8mg base
Market StatusPrescription
CompanyPfizer

2 of 2  
Drug NameCardura
PubMed HealthDoxazosin (By mouth)
Drug ClassesAntihypertensive, Benign Prostatic Hypertrophy Agent, Cardiovascular Agent
Drug LabelCARDURA (doxazosin mesylate) is a quinazoline compound that is a selective inhibitor of the alpha1 subtype of alpha-adrenergic receptors. The chemical name of doxazosin mesylate is 1-(4-amino-6,7-dimethoxy-2-quinazolinyl)-4-(1,4-benzodioxan-2-ylcar...
Active IngredientDoxazosin mesylate
Dosage FormTablet
RouteOral
Strengtheq 4mg base; eq 2mg base; eq 1mg base; eq 8mg base
Market StatusPrescription
CompanyPfizer

4.2 Drug Indication

Doxazosin is indicated to treat the symptoms of benign prostatic hypertrophy, which may include urinary frequency, urgency, and nocturia, among other symptoms. In addition, doxazosin is indicated alone or in combination with various antihypertensive agents for the management of hypertension. Off-label uses of doxazosin include the treatment of pediatric hypertension and the treatment of ureteric calculi.


5 Pharmacology and Biochemistry
5.1 Pharmacology

Doxazosin decreases standing and supine blood pressure and relieves the symptoms of benign prostatic hypertrophy through the inhibition of alpha-1 receptors. Doxazosin may cause hypotension due to its pharmacological actions. This frequently occurs in the upright position, leading to a feeling of dizziness or lightheadedness. The first dose of doxazosin may lead to such effects, however, subsequent doses may also cause them. The risk of these effects is particularly high when dose adjustments occur or there are long intervals between doxazosin doses. Treatment should be started with the 1 mg dose of doxazosin, followed by slow titration to the appropriate dose. Patients must be advised of this risk and to avoid situations in which syncope and dizziness could be hazardous following the ingestion of doxazosin. Interestingly doxazosin exerts beneficial effects on plasma lipids. It reduces LDL (low-density lipoprotein) cholesterol and triglyceride levels and increases HDL (high-density lipoprotein) cholesterol levels. A note on priapism risk In rare cases, doxazosin and other alpha-1 blockers may cause priapism, a painful occurrence of persistent and unrelievable penile erection that can lead to impotence if medical attention is not sought as soon as possible. Patients must be advised of the priapism risk associated with doxazosin and to seek medical attention immediately if it is suspected.


5.2 MeSH Pharmacological Classification

Antihypertensive Agents

Drugs used in the treatment of acute or chronic vascular HYPERTENSION regardless of pharmacological mechanism. Among the antihypertensive agents are DIURETICS; (especially DIURETICS, THIAZIDE); ADRENERGIC BETA-ANTAGONISTS; ADRENERGIC ALPHA-ANTAGONISTS; ANGIOTENSIN-CONVERTING ENZYME INHIBITORS; CALCIUM CHANNEL BLOCKERS; GANGLIONIC BLOCKERS; and VASODILATOR AGENTS. (See all compounds classified as Antihypertensive Agents.)


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.)


5.3 FDA Pharmacological Classification
5.3.1 Active Moiety
DOXAZOSIN
5.3.2 FDA UNII
NW1291F1W8
5.3.3 Pharmacological Classes
alpha-Adrenergic Blocker [EPC]; Adrenergic alpha-Antagonists [MoA]
5.4 ATC Code

C - Cardiovascular system

C02 - Antihypertensives

C02C - Antiadrenergic agents, peripherally acting

C02CA - Alpha-adrenoreceptor antagonists

C02CA04 - Doxazosin


5.5 Absorption, Distribution and Excretion

Absorption

Doxazosin is rapidly absorbed in the gastrointestinal tract and peak concentrations are achieved within 2-3 hours after administration. The bioavailability is about 60%-70%. The intake of food with doxazosin is not expected to cause clinically significant effects.


Route of Elimination

In a pharmacokinetic study using a 1 mg IV radiolabeled dose and a 2 mg oral dose, 63% of the ingested doxazosin was found to be excreted in the feces and about 9% of the dose was found to be excreted in the urine. Traces of radiolabeled unchanged drug were found in the urine and about 5% of the administered drug was found as unchanged drug excreted in the feces.


Volume of Distribution

The volume of distribution of doxazosin is 1.0-1.9 L/kg. In a study of radiolabeled doxazosin administered to pregnant rats, doxazosin was found to cross the placenta.


Clearance

The clearance of doxazosin is low and ranges from approximately 1-2 ml/min/kg.


5.6 Metabolism/Metabolites

Hepatic metabolism of doxazosin produces inactive O-demethylated and C-hydroxylated metabolites. Metabolism occurs via O-demethylation of the quinazoline nucleus of doxazosin or via hydroxylation of its benzodioxan portion. The enzymes involved in the metabolism of doxazosin include CYP2C19, CYP2D6, CYP2C19, and CYP3A4, which is the primary metabolizing enzyme. Doxazosin itself is considered to be mainly responsible for its pharmacological action, however, some active metabolites have been identified whose pharmacokinetics have not been adequately characterized.


5.7 Biological Half-Life

The terminal elimination half-life of doxazosin has been estimated at 9-12 hours according to some resources. The FDA label indicates the elimination half-life of doxazosin is 22 hours.


5.8 Mechanism of Action

Doxazosin selectively inhibits the postsynaptic alpha-1 receptors on vascular smooth muscle by nonselectively blocking the alpha-1a, alpha-1b, and alpha-1d subtypes. This action on blood vessels decreases systemic peripheral vascular resistance, reducing blood pressure, exerting minimal effects on the heart rate due to its receptor selectivity. Norepinephrine-activated alpha-1 receptors located on the prostate gland and bladder neck normally cause contraction of regional muscular tissue, obstructing urinary flow and contributing to the symptoms of benign prostatic hypertrophy. Alpha-1 antagonism causes smooth muscle relaxation in the prostate and bladder, effectively relieving urinary frequency, urgency, weak urinary stream, and other unpleasant effects of BPH. Recently, doxazosin was found to cause apoptosis of hERG potassium channels in an in vitro setting, possibly contributing to a risk of heart failure with doxazosin use.


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