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    Pirenzepine

    ACTIVE PHARMA INGREDIENTS

    DIGITAL CONTENT

    PharmaCompass
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    2D Structure
    Also known as: 28797-61-7, Pirenzepinum, Pirenzepina, Pirenzepin, 11-[2-(4-methylpiperazin-1-yl)acetyl]-5h-pyrido[2,3-b][1,4]benzodiazepin-6-one, Pirenzepine (inn)
    Molecular Formula
    C19H21N5O2
    Molecular Weight
    351.4  g/mol
    InChI Key
    RMHMFHUVIITRHF-UHFFFAOYSA-N
    FDA UNII
    3G0285N20N
    An antimuscarinic agent that inhibits gastric secretion at lower doses than are required to affect gastrointestinal motility, salivary, central nervous system, cardiovascular, ocular, and urinary function. It promotes the healing of duodenal ulcers and due to its cytoprotective action is beneficial in the prevention of duodenal ulcer recurrence. It also potentiates the effect of other antiulcer agents such as CIMETIDINE and RANITIDINE. It is generally well tolerated by patients.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    11-[2-(4-methylpiperazin-1-yl)acetyl]-5H-pyrido[2,3-b][1,4]benzodiazepin-6-one
    2.1.2 InChI
    InChI=1S/C19H21N5O2/c1-22-9-11-23(12-10-22)13-17(25)24-16-7-3-2-5-14(16)19(26)21-15-6-4-8-20-18(15)24/h2-8H,9-13H2,1H3,(H,21,26)
    2.1.3 InChI Key
    RMHMFHUVIITRHF-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    CN1CCN(CC1)CC(=O)N2C3=CC=CC=C3C(=O)NC4=C2N=CC=C4
    2.2 Other Identifiers
    2.2.1 UNII
    3G0285N20N
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Dihydrochloride, Pirenzepine

    2. Gastrotsepin

    3. Gastrozepin

    4. L-s 519

    5. Ls 519

    6. Ls-519

    7. Ls519

    8. Piren Basan

    9. Piren-basan

    10. Pirenzepin

    11. Pirenzepin Ratiopharm

    12. Pirenzepin Von Ct

    13. Pirenzepin-ratiopharm

    14. Pirenzepine Dihydrochloride

    15. Pyrenzepine

    16. Ulcoprotect

    17. Ulgescum

    18. Von Ct, Pirenzepin

    2.3.2 Depositor-Supplied Synonyms

    1. 28797-61-7

    2. Pirenzepinum

    3. Pirenzepina

    4. Pirenzepin

    5. 11-[2-(4-methylpiperazin-1-yl)acetyl]-5h-pyrido[2,3-b][1,4]benzodiazepin-6-one

    6. Pirenzepine (inn)

    7. 11-((4-methyl-1-piperazinyl)acetyl)-5,11-dihydro-6h-pyrido(2,3-b)(1,4)benzodiazepin-6-one

    8. 11-[(4-methylpiperazin-1-yl)acetyl]-5,11-dihydro-6h-pyrido[2,3-b][1,4]benzodiazepin-6-one

    9. Chembl9967

    10. 5,11-dihydro-11-((4-methyl-1-piperazinyl)acetyl)-6h-pyrido(2,3-b)(1,4)benzodiazepin-6-one

    11. 6h-pyrido(2,3-b)(1,4)benzodiazepin-6-one, 5,11-dihydro-11-((4-methyl-1-piperazinyl)acetyl)-

    12. Aci-91

    13. Chebi:8247

    14. Pirenzepinedihydrochloridemonohydrate

    15. 3g0285n20n

    16. Ncgc00015836-08

    17. Pirenzepinum [inn-latin]

    18. Pirenzepina [inn-spanish]

    19. Pirenzepine [inn]

    20. Dsstox_cid_3487

    21. Pirenzepine [inn:ban]

    22. Dsstox_rid_77049

    23. Dsstox_gsid_23487

    24. Mls000069702

    25. 5,11-dihydro-11-[(4-methyl-1-piperazinyl)acetyl]-6h-pyrido[2,3-b][1,4]benzodiazepin-6-one

    26. 6h-pyrido[2,3-b][1,4]benzodiazepin-6-one, 5,11-dihydro-11-[(4-methyl-1-piperazinyl)acetyl]-

    27. 6h-pyrido[2,3-b][1,4]benzodiazepin-6-one, 5,11-dihydro-11-[(4-methyl-1-piperazinyl)acetyl]- (8ci,9ci)

    28. 6h-pyrido[2,3-b][1,4]benzodiazepin-6-one, 5,11-dihydro-11-[2-(4-methyl-1-piperazinyl)acetyl]-

    29. Cas-28797-61-7

    30. Smr000058502

    31. Einecs 249-228-4

    32. Ls-519

    33. Brn 0628987

    34. Unii-3g0285n20n

    35. Pirenzepine-[d8]

    36. Spectrum_001378

    37. Tocris-1071

    38. Starbld0016668

    39. Pirenzepine [mi]

    40. Prestwick0_000129

    41. Prestwick1_000129

    42. Prestwick2_000129

    43. Prestwick3_000129

    44. Spectrum2_001417

    45. Spectrum3_001453

    46. Spectrum4_000437

    47. Spectrum5_001344

    48. Lopac-p-7412

    49. Pirenzepine [vandf]

    50. Lopac0_000962

    51. Schembl41705

    52. Bspbio_000178

    53. Bspbio_002945

    54. Gtpl328

    55. Kbiogr_000794

    56. Kbioss_001858

    57. Pirenzepine [who-dd]

    58. Divk1c_000127

    59. Spbio_001494

    60. Spbio_002117

    61. Bpbio1_000196

    62. Cid_185248

    63. Dtxsid7023487

    64. Bdbm39341

    65. Kbio1_000127

    66. Kbio2_001858

    67. Kbio2_004426

    68. Kbio2_006994

    69. Kbio3_002445

    70. Ninds_000127

    71. Hms2089k21

    72. Hms3742e07

    73. Hms3742g13

    74. Bcp12188

    75. Tox21_110239

    76. Hy-17037a

    77. Pdsp1_000965

    78. Pdsp2_000949

    79. Zinc19632927

    80. Akos015969751

    81. Tox21_110239_1

    82. Ccg-205042

    83. Db00670

    84. Sdccgsbi-0050935.p004

    85. Idi1_000127

    86. Ncgc00015836-01

    87. Ncgc00015836-02

    88. Ncgc00015836-03

    89. Ncgc00015836-04

    90. Ncgc00015836-05

    91. Ncgc00015836-06

    92. Ncgc00015836-07

    93. Ncgc00015836-09

    94. Ncgc00015836-10

    95. Ncgc00015836-12

    96. Ncgc00015836-19

    97. Ncgc00024297-02

    98. Ncgc00024297-04

    99. Ncgc00024297-05

    100. Sbi-0050935.p003

    101. Cas-29868-97-1

    102. Ab00053603

    103. Cs-0013749

    104. Ft-0600051

    105. Ft-0673943

    106. 97p617

    107. C07508

    108. D08389

    109. Ab00053603-08

    110. Ab00053603_09

    111. L000485

    112. Q419550

    113. Brd-k89375097-300-05-4

    114. Brd-k89375097-300-06-2

    115. 11-[2-(4-methylpiperazino)acetyl]-5h-pyrido[2,3-b][1,4]benzodiazepin-6-one;hydrochloride

    116. 11-[(4-methyl-1-piperazinyl)acetyl]-5,11-dihydro-6h-pyrido[2,3-b][1,4]benzodiazepin-6-one #

    117. 11-[2-(4-methyl-1-piperazinyl)-1-oxoethyl]-5h-pyrido[2,3-b][1,4]benzodiazepin-6-one;hydrochloride

    118. 11-[2-(4-methyl-piperazin-1-yl)-acetyl]-5,11-dihydro-benzo[e]pyrido[3,2-b][1,4]diazepin-6-one

    119. 11-[2-(4-methylpiperazin-1-yl)-acetyl]-5,11-dihydro-6h-pyrido[2,3-b][1,4]benzodiazepin-6-one

    120. 11-[2-(4-methylpiperazin-1-yl)acetyl]-5h-pyrido[2,3-b][1,4]benzodiazepin-6-one;hydrochloride

    121. 11-[2-(4-methylpiperazin-1-yl)ethanoyl]-5h-pyrido[2,3-b][1,4]benzodiazepin-6-one;hydrochloride

    122. 2-[2-(4-methylpiperazin-1-yl)acetyl]-2,4,9-triazatricyclo[9.4.0.0^{3,8}]pentadeca-1(11),3,5,7,12,14-hexaen-10-one

    2.4 Create Date
    2005-03-25
    3 Chemical and Physical Properties
    Molecular Weight 351.4 g/mol
    Molecular Formula C19H21N5O2
    XLogP30.1
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count5
    Rotatable Bond Count2
    Exact Mass351.16952493 g/mol
    Monoisotopic Mass351.16952493 g/mol
    Topological Polar Surface Area68.8 Ų
    Heavy Atom Count26
    Formal Charge0
    Complexity534
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Indication

    For the treatment of peptic ulcer, gastric ulcer, and duodenal ulcer.

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Pirenzepine belongs to a group of medications called antispasmodics/anticholinergics. These medications are used to relieve cramps or spasms of the stomach, intestines, and bladder. Pirenzepine is used to treat duodenal or stomach ulcers or intestine problems. It can be used together with antacids or other medicine in the treatment of peptic ulcer. It may also be used to prevent nausea, vomiting, and motion sickness.

    5.2 MeSH Pharmacological Classification

    Anti-Ulcer Agents

    Various agents with different action mechanisms used to treat or ameliorate PEPTIC ULCER or irritation of the gastrointestinal tract. This has included ANTIBIOTICS to treat HELICOBACTER INFECTIONS; HISTAMINE H2 ANTAGONISTS to reduce GASTRIC ACID secretion; and ANTACIDS for symptomatic relief. (See all compounds classified as Anti-Ulcer Agents.)

    Muscarinic Antagonists

    Drugs that bind to but do not activate MUSCARINIC RECEPTORS, thereby blocking the actions of endogenous ACETYLCHOLINE or exogenous agonists. Muscarinic antagonists have widespread effects including actions on the iris and ciliary muscle of the eye, the heart and blood vessels, secretions of the respiratory tract, GI system, and salivary glands, GI motility, urinary bladder tone, and the central nervous system. (See all compounds classified as Muscarinic Antagonists.)

    5.3 ATC Code

    A - Alimentary tract and metabolism

    A02 - Drugs for acid related disorders

    A02B - Drugs for peptic ulcer and gastro-oesophageal reflux disease (gord)

    A02BX - Other drugs for peptic ulcer and gastro-oesophageal reflux disease (gord)

    A02BX03 - Pirenzepine

    5.4 Mechanism of Action

    Pirenzepine is a muscarinic receptor antagonist and binds to the muscarinic acetylcholine receptor. The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins.