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22 API Suppliers
16 USDMF
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$ API Reference Price

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87 FDF Dossiers, 57 FDA Orange Book, 3 Canada, 12 Australia, 3 South Africa, 12 Listed Dossiers

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3 Canada
12 Australia
3 South Africa
12 Listed Dossiers

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CAPSULE;ORAL - EQ 1MG BASE, CAPSULE;ORAL - EQ 2MG BASE, CAPSULE;ORAL - EQ 5MG BASE

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CAPSULE;ORAL - EQ 1MG BASE
CAPSULE;ORAL - EQ 2MG BASE
CAPSULE;ORAL - EQ 5MG BASE

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Nuray Prazosin HCL

Synopsis

ACTIVE PHARMA INGREDIENTS

22

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$

$ 719

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7

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87

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57

FDA Orange Book

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0

Europe

3

Canada

12

Australia

3

South Africa

12

Listed Dossiers

3DRUGS IN DEVELOPMENT

DRUG PRODUCT COMPOSITIONS

REF. STANDARDS OR IMPURITIES

2

EDQM

1

USP

2

JP

2

Others

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2

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Chemistry

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Also known as: 19237-84-4, Prazosin hcl, Minipress, Vasoflex, Peripress, Furazosin hydrochloride

Molecular Formula

C₁₉H₂₂ClN₅O₄

Molecular Weight

419.9 g/mol

InChI Key

WFXFYZULCQKPIP-UHFFFAOYSA-N

FDA UNII

X0Z7454B90

Prazosin Hydrochloride

A selective adrenergic alpha-1 antagonist used in the treatment of HEART FAILURE; HYPERTENSION; PHEOCHROMOCYTOMA; RAYNAUD DISEASE; PROSTATIC HYPERTROPHY; and URINARY RETENTION.

1 2D Structure

Prazosin Hydrochloride

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

[4-(4-amino-6,7-dimethoxyquinazolin-2-yl)piperazin-1-yl]-(furan-2-yl)methanone;hydrochloride

2.1.2 InChI

InChI=1S/C19H21N5O4.ClH/c1-26-15-10-12-13(11-16(15)27-2)21-19(22-17(12)20)24-7-5-23(6-8-24)18(25)14-4-3-9-28-14;/h3-4,9-11H,5-8H2,1-2H3,(H2,20,21,22);1H

2.1.3 InChI Key

WFXFYZULCQKPIP-UHFFFAOYSA-N

2.1.4 Canonical SMILES

COC1=C(C=C2C(=C1)C(=NC(=N2)N3CCN(CC3)C(=O)C4=CC=CO4)N)OC.Cl

2.2 Other Identifiers

2.2.1 UNII

X0Z7454B90

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Furazosin

2. Hcl, Prazosin

3. Hydrochloride, Prazosin

4. Minipress

5. Pratsiol

6. Prazosin

7. Prazosin Hcl

2.3.2 Depositor-Supplied Synonyms

1. 19237-84-4

2. Prazosin Hcl

3. Minipress

4. Vasoflex

5. Peripress

6. Furazosin Hydrochloride

7. Minipress Xl

8. Hypovase

9. 1-(4-amino-6,7-dimethoxy-2-quinazolinyl)-4-(2-furanylcarbonyl)piperazine Hydrochloride

10. Cp-12299-1

11. Prazosin (hydrochloride)

12. 1-(4-amino-6,7-dimethoxy-2-quinazolinyl)-4-(2-furoyl)piperazine Monohydrochloride

13. Cp-12,299-1

14. Prazosinhydrochloride

15. (4-(4-amino-6,7-dimethoxyquinazolin-2-yl)piperazin-1-yl)(furan-2-yl)methanone Hydrochloride

16. [4-(4-amino-6,7-dimethoxyquinazolin-2-yl)piperazin-1-yl]-(furan-2-yl)methanone;hydrochloride

17. Mls000028454

18. Piperazine, 1-(4-amino-6,7-dimethoxy-2-quinazolinyl)-4-(2-furanylcarbonyl)-, Monohydrochloride

19. Nsc-292810

20. X0z7454b90

21. Deprazolin

22. Hypovasole

23. Pratsiol

24. Sinetens

25. Smr000058384

26. Minipress (tn)

27. 19237-84-4 (hcl)

28. 2-(4-(2-furoyl)piperazin-1-yl)-4-amino-6,7-dimethoxyquinazoline Hydrochloride

29. 2-{4-[(furan-2-yl)carbonyl]piperazin-1-yl}-6,7-dimethoxyquinazolin-4-amine Hydrochloride

30. Chebi:8365

31. Hsdb 3298

32. Methanone, [4-(4-amino-6,7-dimethoxy-2-quinazolinyl)-1-piperazinyl]-2-furanyl-, Hydrochloride (1:1)

33. C19h21n5o4.hcl

34. Nsc 292810

35. Prazosin Clorhidrato [spanish]

36. Prazosine Hydrochloride

37. Sr-01000003052

38. Einecs 242-903-4

39. Mfcd00058177

40. Unii-x0z7454b90

41. Pressin And Hypovase

42. Prazosin Hydrochloride [usan:usp:jan]

43. Prazosin Hydrochloride;

44. Opera_id_370

45. Chembl1558

46. Piperazine, 1-(4-amino-6,7-dimethoxy-2-quinazolinyl)-4-(2-furoyl)-, Monohydrochloride

47. Schembl41257

48. Mls001148201

49. Mls001333696

50. Mls002153280

51. Mls002222304

52. Spectrum1500495

53. Prazosin Hcl (furazosin Hcl)

54. Piperazin-1-yl)(furan-2-yl)

55. Hy-b0193a

56. Dtxsid50172822

57. Hms1570n16

58. Hms1920j10

59. Pharmakon1600-01500495

60. Prazosin Hydrochloride [mi]

61. Bcp13643

62. Prazosin Hydrochloride (jp17/usp)

63. Prazosin Hydrochloride [jan]

64. Tox21_501002

65. Ac-699

66. Ccg-39227

67. Nsc292810

68. Nsc757286

69. Prazosin Hydrochloride [hsdb]

70. Prazosin Hydrochloride [usan]

71. S1424

72. Prazosin Hydrochloride [vandf]

73. Akos015895394

74. Prazosin Hydrochloride [mart.]

75. Af-0012

76. H37p844

77. Lp01002

78. Nsc-757286

79. Prazosin Hydrochloride [usp-rs]

80. Prazosin Hydrochloride [who-dd]

81. Sb17352

82. Prazosin Hydrochloride, >=99% (tlc)

83. Quinazoline, 4-amino-6,7-dimethoxy-2-(4-(2-furoyl)piperazin-1-yl)-, Hydrochloride

84. Ncgc00094296-01

85. Ncgc00094296-02

86. Ncgc00094296-03

87. Ncgc00094296-04

88. Ncgc00094296-05

89. Ncgc00261687-01

90. Ba164294

91. Db-044795

92. Prazosin Hydrochloride [ep Impurity]

93. Prazosin Hydrochloride [orange Book]

94. Eu-0101002

95. P0938

96. Prazosin Hydrochloride [ep Monograph]

97. Prazosin Hydrochloride [usp Monograph]

98. D00609

99. H11453

100. Minizide Component Prazosin Hydrochloride

101. Prazosin Hydrochloride 100 Microg/ml In Methanol

102. Prazosin Hydrochloride Component Of Minizide

103. Sr-01000003052-2

104. Sr-01000003052-8

105. W-107719

106. Q27108060

107. Piperazine,7-dimethoxy-2-quinazolinyl)-4-(2-furoyl)-, Monohydrochloride

108. Prazosin Hydrochloride, European Pharmacopoeia (ep) Reference Standard

109. Prazosin Hydrochloride, United States Pharmacopeia (usp) Reference Standard

110. 1-(4-amino-6,7-dimethoxy-2-quinazol Inyl)-4-(2-furanylcarbonyl)piperazine Hydrochloride

111. Piperazine,7-dimethoxy-2-quinazolinyl)-4-(2-furanylcarbonyl)-, Monohydrochloride

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₁₉H₂₂ClN₅O₄
Molecular Weight	419.9 g/mol
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	8
Rotatable Bond Count	4
Exact Mass	419.1360319 g/mol
Monoisotopic Mass	419.1360319 g/mol
Topological Polar Surface Area	107 Å²
Heavy Atom Count	29
Formal Charge	0
Complexity	544
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	2

4 Drug and Medication Information

4.1 Drug Information

1 of 2
Drug Name	Prazosin hydrochloride
Drug Label	Prazosin hydrochloride, a quinazoline derivative, is the first of a new chemical class of antihypertensives. It is the hydrochloride salt of 1-(4-amino-6,7-dimethoxy-2-quinazolinyl)-4-(2-furoyl) piperazine and its structural formula is:Prazosin hydro...
Active Ingredient	Prazosin hydrochloride
Dosage Form	Capsule
Route	oral; Oral
Strength	eq 5mg base; eq 2mg base; eq 1mg base
Market Status	Prescription
Company	Ivax Sub Teva Pharms; Teva Pharms; Mylan

2 of 2
Drug Name	Prazosin hydrochloride
Drug Label	Prazosin hydrochloride, a quinazoline derivative, is the first of a new chemical class of antihypertensives. It is the hydrochloride salt of 1-(4-amino-6,7-dimethoxy-2-quinazolinyl)-4-(2-furoyl) piperazine and its structural formula is:Prazosin hydro...
Active Ingredient	Prazosin hydrochloride
Dosage Form	Capsule
Route	oral; Oral
Strength	eq 5mg base; eq 2mg base; eq 1mg base
Market Status	Prescription
Company	Ivax Sub Teva Pharms; Teva Pharms; Mylan

4.2 Therapeutic Uses

Adrenergic alpha-Antagonists; Antihypertensive Agents; Sympatholytics

National Library of Medicine's Medical Subject Headings online file (MeSH, 1999)

Prazosin hydrochloride is used in the management of hypertension. Prazosin's efficacy in hypertensive patients is similar to that of thiazide diuretics, beta-adrenergic blocking agents, hydralazine, and centrally acting adrenergic inhibitors (eg, clonidine, methyldopa). ... Prazosin has been shown to be effective in the management of hypertension in patients undergoing chronic hemodialysis, and the drug may be particularly useful in the acute management of severe hypertension in patients with increased concentrations of circulating catecholamines.

McEvoy, G.K. (ed.). American Hospital Formulary Service- Drug Information 2002. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2002 (Plus Supplements)., p. 1860

Prazosin has been used with good results alone or in combination with a beta-adrenergic blocking agent for the preoperative management of the signs and symptoms of pheochromocytoma in a limited number of patients; however, these patients may be particularly susceptible to a marked hypotensive response to the initial dose of prazosin. Limited data also suggest that prazosin may be useful for the treatment of Raynaud's disease or phenomenon and ergotamine induced peripheral ischemia.

McEvoy, G.K. (ed.). American Hospital Formulary Service- Drug Information 2002. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2002 (Plus Supplements)., p. 1861

Prazosin may be used as an adjunct to digoxin and diuretics for the treatment of congestive heart failure. However, prazosin has not been shown to improve survival in these patients. /NOT included in US product labeling/

MICROMEDEX Thomson Health Care. USPDI - Drug Information for the Health Care Professional. 22nd ed. Volume 1. MICROMEDEX Thomson Health Care, Greenwood Village, CO. 2002. Content Reviewed and Approved by the U.S. Pharmacopeial Convention, Inc., p. 2430

For more Therapeutic Uses (Complete) data for PRAZOSIN HYDROCHLORIDE (11 total), please visit the HSDB record page.

4.3 Drug Warning

May cause syncope with sudden loss of consciousness, usually attributable to an excessive postural hypotensive effect; risk may be reduced by limiting the initial dose of the drug to 1 mg, and by subsequently increasing the dosage slowly. Adverse reactions include dizziness, drowsiness, and other CNS effects; patients should be cautioned regarding activities such as driving and operating machinery, as well as interactions with other CNS acting drugs including alcohol. Other adverse reactions include palpitations and nausea. The concurrent use of a beta-adrenergic blocking agent may increase the risk of hypotension. /Prazosin hydrochloride/

Hussar, D.A. (ed.). Modell's Drugs in Current Use and New Drugs. 38th ed. New York, NY: Springer Publishing Co., 1992., p. 135

When prazosin is used as a fixed-combination preparation that includes polythiazide, the cautions, precautions, and contraindications associated with thiazide diuretics must be considered in addition to those associated with prazosin.

McEvoy, G.K. (ed.). American Hospital Formulary Service- Drug Information 2002. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2002 (Plus Supplements)., p. 1862

Caution should be used when adding prazosin to a preexisting antihypertensive regimen or when adding other hypotensive agents to a prazosin regimen in order to avoid a possible rapid fall in blood pressure. Caution should be used when administering prazosin to patients with chronic renal failure as they may require only small doses of the drug.

McEvoy, G.K. (ed.). American Hospital Formulary Service- Drug Information 2002. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2002 (Plus Supplements)., p. 1862

Prazosin has been used alone or in combination with other hypotensive agents for the management of severe hypertension in a limited number of pregnant women without apparent adverse effect on the fetus. There are no adequate and well controlled studies to date using prazosin in pregnant women, however, and the drug should be used during pregnancy only when the potential benefits justify the possible risks to the fetus.

McEvoy, G.K. (ed.). American Hospital Formulary Service- Drug Information 2002. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2002 (Plus Supplements)., p. 1862

For more Drug Warnings (Complete) data for PRAZOSIN HYDROCHLORIDE (18 total), please visit the HSDB record page.

5 Pharmacology and Biochemistry

5.1 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.)

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.)

5.2 FDA Pharmacological Classification

5.2.1 Pharmacological Classes

alpha-Adrenergic Blocker [EPC]; Adrenergic alpha-Antagonists [MoA]

5.3 Absorption, Distribution and Excretion

There is intraindividual and interindividual variation in the rate of absorption and plasma concentrations of prazosin. The absolute oral bioavailability of prazosin is also variable but is reported to average about 60% (range: 43-82%). Results of one study indicate that the presence of food may delay absorption of the drug in some patients, but does not affect the extent of absorption.

McEvoy, G.K. (ed.). American Hospital Formulary Service- Drug Information 2002. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2002 (Plus Supplements)., p. 1863

Following oral administration of prazosin hydrochloride, plasma concentrations of the drug reach a peak in 2-3 hrs in most fasting patients. Plasma concentrations of prazosin generally do not correlate with therapeutic effect. One manufacturer reports that plasma concentrations of the drug after a single 5 mg dose range from 0.01-0.075 ug/ml. Blood pressure begins to decrease within 2 hr after an oral dose; the maximum decrease occurs in 2-4 hr. The hypotensive effect of prazosin lasts less than 24 hr.

McEvoy, G.K. (ed.). American Hospital Formulary Service- Drug Information 2002. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2002 (Plus Supplements)., p. 1863

Animal studies indicate that prazosin is widely distributed in body tissues. After iv administration in dogs, highest concentrations of the drug are found in the lungs, coronary arteries, aorta, paw arteries and heart; the lowest concentrations are in the brain. During prazosin therapy, approximately 97% of the drug in plasma is bound to proteins. It is not known whether the drug crosses the placenta. Prazosin is distributed into milk in small amounts.

McEvoy, G.K. (ed.). American Hospital Formulary Service- Drug Information 2002. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2002 (Plus Supplements)., p. 1863

Approximately 6-10% of a dose is excreted in urine and the remainder in feces via bile.

McEvoy, G.K. (ed.). American Hospital Formulary Service- Drug Information 2002. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2002 (Plus Supplements)., p. 1863

The drug /prazosin hydrochloride/ is tightly bound to plasma proteins (primarily alpha1-acid glycoprotein), and only 5% of the drug is free in the circulation; diseases that modify the concentration of this protein (e.g., inflammatory processes) may change the free fraction. Prazosin is extensively metabolized in the liver, and little unchanged drug is excreted by the kidneys.

Hardman, J.G., L.E. Limbird, P.B., A.G. Gilman. Goodman and Gilman's The Pharmacological Basis of Therapeutics. 10th ed. New York, NY: McGraw-Hill, 2001., p. 246

5.4 Metabolism/Metabolites

Animal studies show that prazosin hydrochloride is metabolized extensively in the liver, principally by demethylation and conjugation, and excreted as unchanged drug (5-11%) and metabolites. Four of the metabolites have been shown to possess 10-25% of the hypotensive activity of prazosin and they may contribute to the antihypertensive effect of the drug.

McEvoy, G.K. (ed.). American Hospital Formulary Service- Drug Information 2002. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2002 (Plus Supplements)., p. 1863

The 6-O-demethyl and 7-O-demethyl analogues of the new antihypertensive drug prazosin [2-[4-(2-furoyl)-piperazin-1-yl]-4-amino-6,7-dimethoxyquinazoline hydrochloride] have been unequivocally synthesized via separate 10-step reaction sequences starting from isovanillin and vanillin, respectively. The 6-O-demethyl derivative was found to be identical with the major prazosin metabolite formed in dog and rat, while the 7-O-demethyl derivative was identical with another, less prevalent but significant metabolite. Two minor metabolites of prazosin, 2-(1-piperazinyl)-4-amino-6,7-dimethoxyquinazoline and 2,4-diamino-6,7-dimethoxyquinazoline, are also described. All 4 metabolites are less potent blood pressure lowering agents in dogs than prazosin but may contribute to its antihypertensive effect, since they account for a major portion of the administered dose.

PMID:833813 Althius T, Hess H; J Med Chem 20 (1): 146-9 (1977)

5.5 Biological Half-Life

Elimination half-life approx 3 hr.

Haddad, L.M., Clinical Management of Poisoning and Drug Overdose. 2nd ed. Philadelphia, PA: W.B. Saunders Co., 1990., p. 1348

The plasma half-life of prazosin after oral administration has been reported to be 2-4 hr.

McEvoy, G.K. (ed.). American Hospital Formulary Service- Drug Information 2002. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2002 (Plus Supplements)., p. 1863

5.6 Mechanism of Action

Animal studies indicate that prazosin does not have its antihypertensive effect in the CNS. Prazosin does not interfere with nerve impulse transmission across sympathetic ganglia nor does it cause adrenergic neuronal blockade.

McEvoy, G.K. (ed.). American Hospital Formulary Service- Drug Information 2002. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2002 (Plus Supplements)., p. 1862

The exact mechanism of the hypotensive action of prazosin is unknown. Prazosin causes a decrease in total peripheral resistance and was originally thought to have a direct relaxant action on vascular smooth muscle. Animal studies have suggested that the vasodilator effect of prazosin is also related to blockade of postsynaptic alpha-adrenoceptors. The results of dog forelimb experiments demonstrate that that the peripheral vasodilator effect of prazosin is confined mainly to the level of the resistance vessels (arterioles). Unlike conventional alpha- blockers, the antihypertensive action of prazosin is usually not accompanied by reflex tachycardia.

Medical Economics Co; Physicians Desk Reference 56th ed p. 2699 (2002)

Prazosin ... is a very potent and selective alpha 1-adrenergic antagonist. ... Interestingly, the drug also is a relatively potent inhibitor of cyclic nucleotide phosphodiesterases...

Hardman, J.G., L.E. Limbird, P.B., A.G. Gilman. Goodman and Gilman's The Pharmacological Basis of Therapeutics. 10th ed. New York, NY: McGraw-Hill, 2001., p. 246

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SupplySide West 2024

Not Confirmed

09

EURAND

U.S.A

USDMF, CEP/COS, JDMF, EU-WC, NDC, KDMF, VMF, Others

SupplySide West 2024

Not Confirmed

10

Heumann

Germany

USDMF, CEP/COS, JDMF, EU-WC, NDC, KDMF, VMF, Others

SupplySide West 2024

Not Confirmed

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USDMF

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CEP/COS

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EU WC

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NDC API

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Listed Suppliers

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API Reference Price

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Number of Transactions

Total Quantity (KGS)

Total Value (USD)

Quantity (KGS) & Unit rate (USD/KGS) over time

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Importing Country	Total Quantity (KGS)	Average Price (USD/KGS)	Number of Transactions

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DOSAGE - CAPSULE;ORAL - EQ 1MG BASE

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