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    terazosin hydrochloride anhydrous

    ACTIVE PHARMA INGREDIENTS

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    2D Structure
    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

    2D Structure

    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.