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Chemistry

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Also known as: 63590-64-7, Terazosine, Hytrin, Terazosina, Terazosinum, Flumarc
Molecular Formula
C19H25N5O4
Molecular Weight
387.4  g/mol
InChI Key
VCKUSRYTPJJLNI-UHFFFAOYSA-N
FDA UNII
8L5014XET7

Terazosin
Terazosin is a quinazoline derivative alpha-1-selective adrenergic blocking agent indicated for benign prostatic hyperplasia and hypertension. Terazosin blocks adrenaline's action on alpha-1 adrenergic receptors, causing relaxation of smooth muscle in blood vessels and the prostate.
Terazosin is an alpha-Adrenergic Blocker. The mechanism of action of terazosin is as an Adrenergic alpha-Antagonist.
1 2D Structure

Terazosin

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
[4-(4-amino-6,7-dimethoxyquinazolin-2-yl)piperazin-1-yl]-(oxolan-2-yl)methanone
2.1.2 InChI
InChI=1S/C19H25N5O4/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/h10-11,14H,3-9H2,1-2H3,(H2,20,21,22)
2.1.3 InChI Key
VCKUSRYTPJJLNI-UHFFFAOYSA-N
2.1.4 Canonical SMILES
COC1=C(C=C2C(=C1)C(=NC(=N2)N3CCN(CC3)C(=O)C4CCCO4)N)OC
2.2 Other Identifiers
2.2.1 UNII
8L5014XET7
2.3 Synonyms
2.3.1 MeSH Synonyms

1. A 45975

2. Adecur

3. Apo-terazosin

4. Deflox

5. Dysalfa

6. Flotrin

7. Heitrin

8. Hytrin

9. Hytrin Bph

10. Hytrine

11. Magnurol

12. Novo-terazosin

13. Nu-terazosin

14. Pms-terazosin

15. Ratio-terazosin

16. Sutif

17. Tazusin

18. Terazoflo

19. Terazosin Azu

20. Terazosin Hexal

21. Terazosin Hydrochloride

22. Terazosin Hydrochloride Anhydrous

23. Terazosin, Monohydrochloride, Dihydrate

24. Terazosina Alter

25. Terazosina Kern

26. Terazosina Qualix

27. Zayasel

2.3.2 Depositor-Supplied Synonyms

1. 63590-64-7

2. Terazosine

3. Hytrin

4. Terazosina

5. Terazosinum

6. Flumarc

7. Vasomet

8. Terazosine [inn-french]

9. Terazosinum [inn-latin]

10. Terazosina [inn-spanish]

11. Terazosabb

12. Terazosin Hcl

13. Terazosin (inn)

14. 1-(4-amino-6,7-dimethoxy-2-quinazolinyl)-4-((tetrahydro-2-furanyl)carbonyl)piperazine

15. Chembl611

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

17. Mls000069703

18. Chebi:9445

19. 141269-44-5

20. Terazosin (hydrochloride)

21. 8l5014xet7

22. 141269-45-6

23. Smr000058309

24. Terazosin [inn]

25. Terazosin [inn:ban]

26. 1-(4-amino-6,7-dimethoxy-2-quinazolinyl)-4-(tetrahydro-2-furoyl)piperazine

27. 6,7-dimethoxy-2-[4-(oxolane-2-carbonyl)piperazin-1-yl]quinazolin-4-amine

28. (4-(4-amino-6,7-dimethoxyquinazolin-2-yl)piperazin-1-yl)(tetrahydrofuran-2-yl)methanone

29. [4-(4-amino-6,7-dimethoxyquinazolin-2-yl)piperazin-1-yl](tetrahydrofuran-2-yl)methanone

30. 6,7-dimethoxy-2-[4-(tetrahydrofuran-2-ylcarbonyl)piperazin-1-yl]quinazolin-4-amine

31. Abbott 45975

32. 1-(4-amino-6,7-dimethoxy-2-quinazolinyl)-4-[(tetrahydro-2-furanyl)carbonyl]piperazine

33. 1-(4-amino-6,7-dimethoxy-2-quinazolinyl)-4-{(tetnaphydro-2-furanyl)carbonyl}piperazine

34. 1-(4-amino-6,7-dimethoxy-2-quinazolinyl)4-[(tetrahydro-2-furanyl)carbonyl]piperazine

35. Terazosabb (tn)

36. 6,7-dimethoxy-2-[4-(tetrahydrofuran-2-ylcarbonyl)piperazin-1-yl]quinazolin-4-amine Hydrochloride

37. Terazosin A

38. Unii-8l5014xet7

39. Terazosinhydrochloride

40. Terazosin [mi]

41. 1-(4-amino-6,7-dimethoxy-2-quinazolinyl)4-[(tetrahydro-2-furanyl)carbonyl]piperazine Hydrochloride

42. Opera_id_1910

43. Prestwick0_000751

44. Prestwick1_000751

45. Prestwick2_000751

46. Prestwick3_000751

47. Terazosin [vandf]

48. Schembl6528

49. Terazosin [who-dd]

50. Lopac0_001138

51. Regid_for_cid_5401

52. Bspbio_000762

53. Mls001201836

54. Mls006011889

55. Spbio_002701

56. Bpbio1_000840

57. Gtpl7302

58. Dtxsid3023639

59. Hms2090p21

60. Hms2232n21

61. Hms3259f04

62. Hms3369p14

63. Hms3371e20

64. Hms3742i09

65. Hy-b0371

66. Bbl010743

67. Bdbm50033111

68. Stk567029

69. Akos005266642

70. Ccg-205212

71. Db01162

72. Nc00689

73. Sdccgsbi-0051105.p002

74. 6,7-bis(methyloxy)-2-[4-(tetrahydrofuran-2-ylcarbonyl)piperazin-1-yl]quinazolin-4-amine

75. Piperazine, 1-(4-amino-6,7-dimethoxy-2-quinazolinyl)-4-((tetrahydro-2-furanyl)carbonyl)-

76. Ncgc00016026-04

77. Ncgc00016026-05

78. Ncgc00016026-08

79. Ncgc00016026-11

80. Ncgc00025191-03

81. Ac-11120

82. Ls-14728

83. Ft-0630739

84. C07127

85. D08569

86. 590t647

87. A834201

88. L000692

89. Q280786

90. Brd-a22256192-003-03-7

91. Brd-a22256192-003-14-4

92. Z1172269406

93. 1-(4-amino-6,7-dimethoxy-2-quinazolinyl)-4-(2-tetrahydrofuroyl)piperazine

94. 1-(4-amino-6,7-dimethoxy-2-quinazolinyl)-4-(2-tetrahydrofuroyl)-piperazine

95. 6,7-dimethoxy-2-[4-(oxolane-2-carbonyl)piperazin-1-yl]-3,4-dihydroquinazolin-4-imine

96. 6,7-dimethoxy-2-[4-(tetrahydro-2-furanylcarbonyl)-1-piperazinyl]-4-quinazolinamine #

97. 6,7-dimethoxy-2-{4-[(oxolan-2-yl)carbonyl]piperazin-1-yl}quinazolin-4-amine

98. 1-(4-amino-6,7-dimethoxy-2-quinazolinyl)-4-[(tetrahydro-2-furanyl)carbonyl]-piperazinehydrochloride

99. 1-(4-amino-6,7-dimethoxyquinazolin-2-yl)-4-[[(2rs)-2,3,4,5-tetrahydrofuran-2-yl]carbonyl]piperazine

2.4 Create Date
2005-03-25
3 Chemical and Physical Properties
Molecular Weight 387.4 g/mol
Molecular Formula C19H25N5O4
XLogP31.4
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count8
Rotatable Bond Count4
Exact Mass387.19065430 g/mol
Monoisotopic Mass387.19065430 g/mol
Topological Polar Surface Area103 Ų
Heavy Atom Count28
Formal Charge0
Complexity544
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 Indication

Terazosin is indicated for use in treating symptomatic benign prostatic hyperplasia and hypertension.


FDA Label


5 Pharmacology and Biochemistry
5.1 Pharmacology

Terazosin is a quinazoline derivative alpha-1-selective adrenergic blocker.


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
TERAZOSIN
5.3.2 FDA UNII
8L5014XET7
5.3.3 Pharmacological Classes
alpha-Adrenergic Blocker [EPC]; Adrenergic alpha-Antagonists [MoA]
5.4 ATC Code

G04CA03

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

G04CA03 - Terazosin


5.5 Absorption, Distribution and Excretion

Absorption

Approximately 90%.


Route of Elimination

Approximately 10% of the oral dose is excreted unchanged in the urine and approximately 20% is excreted in the feces. 40% of the total dose is eliminated in urine and 60% of the total dose is eliminated in the feces.


Volume of Distribution

25L to 30L.


Clearance

Plasma clearance is 80mL/min and renal clearance is 10mL/min.


5.6 Metabolism/Metabolites

The majority of terazosin is hepatically metabolized. The metabolites recovered include 6-O-demethyl terazosin, 7-O-methyl terazosin, a piperozine derivative, and a diamine derivative.


5.7 Biological Half-Life

Terazosin has a mean half life 12 hours though this can be as high as 14 hours in patients over 70 years and as low as 11.4 hours in patients 20 to 39 years old.


5.8 Mechanism of Action

Terazosin is selective for alpha-1-adrenoceptors but not their individual subtypes. Inhibition of these alpha-1-adrenoceptors results in relaxation of smooth muscle in blood vessels and the prostate, lowering blood pressure and improving urinary flow. Smooth muscle cells accounts for roughly 40% of the volume of the prostate and so their relaxation reduces pressure on the urethra. It has also been shown that catecholamines induce factors responsible for mitogenesis and alpha-1-adrenergic receptor blockers inhibit this effect. A final long term mechanism of terazosin and other alpha-1-adrenergic receptor blockers is the induction of apoptosis of prostate cells. Treatment with terazosin enhances the expression of transforming growth factor beta-1 (TGF-beta1), which upregulates p27kip1, and the caspase cascade.


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DEAFARMA

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DEAFARMA

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Terazosin

About the Company : In the dinamic pharmaceutical field, DEAFARMA is the reference point for primaries Pharmaceutical Laboratories for over twenty years, even in the national and international territo...

In the dinamic pharmaceutical field, DEAFARMA is the reference point for primaries Pharmaceutical Laboratories for over twenty years, even in the national and international territory. DEAFARMA works with success in the pharmaceutical raw materials field through Agencies and professional relations with the most important European and Asiatic factories. Our partners are well known, reliable producers and all of them are operating in accordance with the latest GMP Rules. The APIs mentioned in the DEAFARMA catalogue are always supported by DMF and/or CEP.
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Terazosin

About the Company : Hoventa Pharma is in the business of manufacturing APIs for over three decades.We offer various kinds of services in addition to supplies of APIs, we undertake long-term contracts ...

Hoventa Pharma is in the business of manufacturing APIs for over three decades.We offer various kinds of services in addition to supplies of APIs, we undertake long-term contracts for manufacturing intermediates and development of new Active Pharmaceutical Ingredients as per your requirement. We have a sharp focus on giving value added services to our customers cost effectively. We are supplying APIs to the global pharmaceutical companies in India and abroad since the last 3 decades. Some of our major customers operate in India and export to their products to other countries.
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SPA","supplierCountry":"ITALY","foreign_port":"SEGRATE","customer":"AJANTA PHARMA LIMITED","customerCountry":"INDIA","quantity":"36.00","actualQuantity":"36","unit":"KGS","unitRateFc":"1913","totalValueFC":"69772.5","currency":"USD","unitRateINR":"162417.3","date":"13-Sep-2024","totalValueINR":"5847023","totalValueInUsd":"69772.5","indian_port":"Dahez-SEZ","hs_no":"29349990","bill_no":"1004564","productDescription":"API","marketType":"REGULATED MARKET","country":"ITALY","selfForZScoreResived":"Pharma Grade","supplierPort":"SEGRATE","supplierAddress":"BIOINDUSTRIA LABORATORIO ITALIANO MEDICINAL S.P.A.VIA DE AMBROSIIS,2\/ 4\/6,15067 NOVI LIGUREAL ITALY","customerAddress":"98, GOVT.INDUSTRIAL AREA,"}]
02-Mar-2021
13-Sep-2024
KGS
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Quantity (KGS) & Unit rate (USD/KGS) over time

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