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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 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 Formula	C₁₉H₂₅N₅O₄
Molecular Weight	387.4 g/mol
XLogP3	1.4
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	8
Rotatable Bond Count	4
Exact Mass	387.19065430 g/mol
Monoisotopic Mass	387.19065430 g/mol
Topological Polar Surface Area	103 Å²
Heavy Atom Count	28
Formal Charge	0
Complexity	544
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	1
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

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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