Pirenzepine

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Pirenzepine
Systematic (IUPAC) name
221px
11-[(4-methylpiperazin-1-yl)acetyl]-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one
Identifiers
CAS Number	28797-61-7
ATC code	A02BX03 (WHO)
PubChem	CID 4848
IUPHAR/BPS	328
DrugBank	APRD00515
Chemical data
Formula	C₁₉H₂₁N₅O₂
Molar mass	351.403 g/mol[[Script error: No such module "String".]]

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Pirenzepine (Gastrozepin) is used in the treatment of peptic ulcers, as it reduces gastric acid secretion and reduces muscle spasm. It is in a class of drugs known as muscarinic receptor antagonists - acetylcholine being the neurotransmitter of the parasympathetic nervous system which initiates the rest-and-digest state (as opposed to fight-or-flight), the result being an increase in gastric motility and digestion. It has no effects on the brain and spinal cord as it cannot diffuse through the blood-brain barrier.

Pirenzepine has been investigated for use in myopia control.^[1]

References

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Drugs for acid related disorders: Drugs for peptic ulcer and GERD/GORD (A02B)

H₂ antagonists ("-tidine")

Cimetidine · Famotidine · Lafutidine · Loxtidine · Niperotidine · Nizatidine · Ranitidine · Roxatidine

Prostaglandins (E)/analogues ("-prost-")

Misoprostol · Enprostil

Proton-pump inhibitors ("-prazole")

Dexlansoprazole · Esomeprazole · Lansoprazole · Omeprazole · Pantoprazole · Rabeprazole · Tenatoprazole

Other

Acetoxolone · Alginic acid · Carbenoxolone · Cetraxate · Gefarnate · Pirenzepine · Proglumide · Sucralfate · Sulglicotide · Teprenone · Troxipide · Zolimidine · Rebamipide ·

See also: Helicobacter pylori eradication protocols

M: DIG

anat(t, g, p)/phys/devp/cell

noco/cong/tumr, sysi/epon

proc, drug(A2A/2B/3/4/5/6/7/14/16)

Cholinergics

Receptor ligands

mAChR

Agonists: 77-LH-28-1 • AC-42 • AC-260,584 • Aceclidine • Acetylcholine • AF30 • AF150(S) • AF267B • AFDX-384 • Alvameline • AQRA-741 • Arecoline • Bethanechol • Butyrylcholine • Carbachol • CDD-0034 • CDD-0078 • CDD-0097 • CDD-0098 • CDD-0102 • Cevimeline • cis-Dioxolane • Ethoxysebacylcholine • LY-593,039 • L-689,660 • LY-2,033,298 • McNA343 • Methacholine • Milameline • Muscarine • NGX-267 • Ocvimeline • Oxotremorine • PD-151,832 • Pilocarpine • RS86 • Sabcomeline • SDZ 210-086 • Sebacylcholine • Suberylcholine • Talsaclidine • Tazomeline • Thiopilocarpine • Vedaclidine • VU-0029767 • VU-0090157 • VU-0152099 • VU-0152100 • VU-0238429 • WAY-132,983 • Xanomeline • YM-796
Antagonists: 3-Quinuclidinyl Benzilate • 4-DAMP • Aclidinium Bromide • Anisodamine • Anisodine • Atropine • Atropine Methonitrate • Benactyzine • Benzatropine (Benztropine) • Benzydamine • BIBN 99 • Biperiden • Bornaprine • CAR-226,086 • CAR-301,060 • CAR-302,196 • CAR-302,282 • CAR-302,368 • CAR-302,537 • CAR-302,668 • CS-27349 • Cyclobenzaprine • Cyclopentolate • Darifenacin • DAU-5884 • Dimethindene • Dexetimide • DIBD • Dicyclomine (Dicycloverine) • Ditran • EA-3167 • EA-3443 • EA-3580 • EA-3834 • Elemicin • Etanautine • Etybenzatropine (Ethylbenztropine) • Flavoxate • Himbacine • HL-031,120 • Ipratropium • J-104,129 • Hyoscyamine • Mamba Toxin 3 • Mamba Toxin 7 • Mazaticol • Mebeverine • Methoctramine • Metixene • Myristicin • N-Ethyl-3-Piperidyl Benzilate • N-Methyl-3-Piperidyl Benzilate • Orphenadrine • Otenzepad • Oxybutynin • PBID • PD-102,807 • Phenglutarimide • Phenyltoloxamine • Pirenzepine • Piroheptine • Procyclidine • Profenamine • RU-47,213 • SCH-57,790 • SCH-72,788 • SCH-217,443 • Scopolamine (Hyoscine) • Solifenacin • Telenzepine • Tiotropium • Tolterodine • Trihexyphenidyl • Tripitamine • Tropatepine • Tropicamide • WIN-2299 • Xanomeline • Zamifenacin; Others: 1st Generation Antihistamines (Brompheniramine, chlorpheniramine, cyproheptadine, dimenhydrinate, diphenhydramine, doxylamine, mepyramine/pyrilamine, phenindamine, pheniramine, tripelennamine, triprolidine, etc) • Tricyclic Antidepressants (Amitriptyline, doxepin, trimipramine, etc) • Tetracyclic Antidepressants (Amoxapine, maprotiline, etc) • Typical Antipsychotics (Chlorpromazine, thioridazine, etc) • Atypical Antipsychotics (Clozapine, olanzapine, quetiapine, etc)

nAChR

Agonists: 5-HIAA • A-84,543 • A-366,833 • A-582,941 • A-867,744 • ABT-202 • ABT-418 • ABT-560 • ABT-894 • Acetylcholine • Altinicline • Anabasine • AR-R17779 • Butyrylcholine • Carbachol • Cotinine • Cytisine • Decamethonium • Desformylflustrabromine • Dianicline • Dimethylphenylpiperazinium • Epibatidine • Epiboxidine • Ethanol • Ethoxysebacylcholine • EVP-4473 • EVP-6124 • Galantamine • GTS-21 • Ispronicline • Lobeline • MEM-63,908 (RG-3487) • Nicotine • NS-1738 • PHA-543,613 • PHA-709,829 • PNU-120,596 • PNU-282,987 • Pozanicline • Rivanicline • Sazetidine A • Sebacylcholine • SIB-1508Y • SIB-1553A • SSR-180,711 • Suberylcholine • TC-1698 • TC-1734 • TC-1827 • TC-2216 • TC-5214 • TC-5619 • TC-6683 • Tebanicline • Tropisetron • UB-165 • Varenicline • WAY-317,538 • XY-4083
Antagonists: 18-Methoxycoronaridine • α-Bungarotoxin • α-Conotoxin • Alcuronium • Amantadine • Anatruxonium • Atracurium • Bupropion (Amfebutamone) • Chandonium • Chlorisondamine • Cisatracurium • Coclaurine • Coronaridine • Dacuronium • Decamethonium • Dextromethorphan • Dextropropoxyphene • Dextrorphan • Diadonium • DHβE • Dimethyltubocurarine (Metocurine) • Dipyrandium • Dizocilpine (MK-801) • Doxacurium • Duador • Esketamine • Fazadinium • Gallamine • Hexafluronium • Hexamethonium (Benzohexonium) • Ibogaine • Isoflurane • Ketamine • Kynurenic acid • Laudexium (Laudolissin) • Levacetylmethadol • Malouetine • Mecamylamine • Memantine • Methadone • Methorphan (Racemethorphan) • Methyllycaconitine • Metocurine • Mivacurium • Morphanol (Racemorphanol) • Neramexane • Nitrous Oxide • Pancuronium • Pempidine • Pentamine • Pentolinium • Phencyclidine • Pipecuronium • Radafaxine • Rapacuronium • Rocuronium • Surugatoxin • Suxamethonium (Succinylcholine) • Thiocolchicoside • Toxiferine • Trimethaphan • Tropeinium • Tubocurarine • Vecuronium • Xenon

Reuptake inhibitors

Plasmalemmal

CHT Inhibitors	Hemicholinium-3 (Hemicholine; HC3) • Triethylcholine

Vesicular

VAChT Inhibitors	Vesamicol

Enzyme inhibitors

Anabolism

ChAT inhibitors	1-(-Benzoylethyl)pyridinium • 2-(α-Naphthoyl)ethyltrimethylammonium • 3-Chloro-4-stillbazole • 4-(1-Naphthylvinyl)pyridine • Acetylseco hemicholinium-3 • Acryloylcholine • AF64A • B115 • BETA • CM-54,903 • N,N-Dimethylaminoethylacrylate • N,N-Dimethylaminoethylchloroacetate

Catabolism

AChE inhibitors

Reversible: Carbamates: Aldicarb • Bendiocarb • Bufencarb • Carbaryl • Carbendazim • Carbetamide • Carbofuran • Chlorbufam • Chloropropham • Ethienocarb • Ethiofencarb • Fenobucarb • Fenoxycarb • Formetanate • Furadan • Ladostigil • Methiocarb • Methomyl • Miotine • Oxamyl • Phenmedipham • Pinmicarb • Pirimicarb • Propamocarb • Propham • Propoxur; Stigmines: Ganstigmine • Neostigmine • Phenserine • Physostigmine • Pyridostigmine • Rivastigmine; Others: Acotiamide • Ambenonium • Donepezil • Edrophonium • Galantamine • Huperzine A • Minaprine • Tacrine • Zanapezil
Irreversible: Organophosphates: Acephate • Azinphos-methyl • Bensulide • Cadusafos • Chlorethoxyfos • Chlorfenvinphos • Chlorpyrifos • Chlorpyrifos-Methyl • Coumaphos • Cyclosarin (GF) • Demeton • Demeton-S-Methyl • Diazinon • Dichlorvos • Dicrotophos • Diisopropyl fluorophosphate (Guthion) • Diisopropylphosphate • Dimethoate • Dioxathion • Disulfoton • EA-3148 • Echothiophate • Ethion • Ethoprop • Fenamiphos • Fenitrothion • Fenthion • Fosthiazate • GV • Isofluorophate • Isoxathion • Malaoxon • Malathion • Methamidophos • Methidathion • Metrifonate • Mevinphos • Monocrotophos • Naled • Novichok agent • Omethoate • Oxydemeton-Methyl • Paraoxon • Parathion • Parathion-Methyl • Phorate • Phosalone • Phosmet • Phostebupirim • Phoxim • Pirimiphos-Methyl • Sarin (GB) • Soman (GD) • Tabun (GA) • Temefos • Terbufos • Tetrachlorvinphos • Tribufos • Trichlorfon • VE • VG • VM • VR • VX; Others: Demecarium • Onchidal (Onchidella binneyi)

BChE inhibitors

* Many of the acetylcholinesterase inhibitors listed above act as butyrylcholinesterase inhibitors.

Others

Precursors	Choline (Lecithin) • Citicoline • Cyprodenate • Dimethylethanolamine (DMAE, deanol) • Glycerophosphocholine • Meclofenoxate (Centrophenoxine) • Phosphatidylcholine • Phosphatidylethanolamine • Phosphorylcholine • Pirisudanol
Cofactors	Acetic acid • Acetylcarnitine • Acetyl-coA • Vitamin B₅ (Pantethine, Pantetheine, Panthenol)
Others	Acetylcholine releasing agents: α-Latrotoxin • β-Bungarotoxin; Acetylcholine release inhibitors: Botulinum toxin (Botox); Acetylcholinesterase reactivators: Asoxime • Obidoxime • Pralidoxime

v t e Piperazines
Simple piperazines (no additional rings)	1-Cyclohexylpiperazine • Aminoethylpiperazine • Diethylcarbamazine • HEPPS • Midafotel • Piperazine • PIPES
Phenylpiperazines	Acaprazine • Antrafenine • Aripiprazole • Batoprazine • Bifeprunox • BRL-15,572 • Ciprofloxacin • CSP-2503 • Dapiprazole • DCPP • DMPP • Dropropizine • EGIS-12,233 • Elopiprazole • Eltoprazine • Enpiprazole • Ensaculin • Etoperidone • Flesinoxan • Flibanserin • Fluprazine • Itraconazole • Ketoconazole • Levodropropizine • Lorpiprazole • mCPP • MeOPP • Mepiprazole • Naftopidil • Naphthylpiperazine • Nefazodone • Niaprazine • Oxypertine • Pardoprunox • pCPP • pFPP • Posaconazole • PRX-00023 • S-14,506 • S-14,671 • S-15,535 • SB-258,585 • SB-271,046 • SB-357,134 • SB-399,885 • Sonepiprazole • TFMPP • Tolpiprazole • Trazodone • Urapidil • Vesnarinone • Vilazodone • WAY-100,135 • WAY-100,635
Benzylpiperazines	2C-B-BZP • Befuraline • Bifeprunox • Buclizine • BZP • Chlorbenzoxamine • DBZP • Fipexide • Imatinib • MBZP • MDBZP • Meclozine • Piberaline • Piribedil • Trimetazidine • Vesnarinone
Diphenylalkylpiperazines (benzhydrylalkylpiperazines)	Almitrine • Amperozide • BRL-15,572 • Buclizine • BW373U86 • Cetirizine • Chlorbenzoxamine • Chlorcyclizine • Cinnarizine • Clocinizine • Cyclizine • DBL-583 • Diphenylmethylpiperazine • Dotarizine • DPI-221 • DPI-287 • DPI-3290 • GBR-12,783 • GBR-12,935 • GBR-13,069 • GBR-13,098 • GBR-13,119 • Hydroxyzine • Lidoflazine • Manidipine • Meclozine • Oxatomide • SNC-80 • Vanoxerine
Pyrimidinylpiperazines	Buspirone • Dasatinib • Eptapirone • Gepirone • Ipsapirone • Piribedil • Pyrimidinylpiperazine • Revospirone • Tandospirone • Tirilazad • Trimazosin • Umespirone • Zalospirone
Pyridinylpiperazines	Atevirdine • Azaperone • Pyridinylpiperazine
Benzo(iso)thiazolyl piperazines	Lurasidone • Perospirone • Revospirone • Tiospirone • Ziprasidone
Tricyclics (piperazine attached via side chain)	Amoxapine • Clopenthixol • Clozapine • Flupentixol • Fluphenazine • Loxapine • Olanzapine • Opipramol • Perazine • Perphenazine • Pirenzepine • Prochlorperazine • Thiethylperazine • Thiothixene • Trifluoperazine • Zuclopenthixol
Others	6-Nitroquipazine • Azimilide • Cinepazet • Cyclohexylpiperazine • Hexocyclium • Indinavir • JNJ-7777120 • Lodenafil • Mirodenafil • PB-28 • Quipazine • Ranolazine • SA-4503 • Sildenafil • Tadalafil • Vardenafil • VUF-6002 • Zipeprol

v t e Tricyclics
Classes	Acridine • Anthracene • Dibenzazepine • Dibenzocycloheptene • Dibenzodiazepine • Dibenzothiazepine • Dibenzothiepin • Dibenzoxazepine • Dibenzoxepin • Phenothiazine • Pyridazinobenzoxazine • Pyridinobenzodiazepine • Thioxanthene
Antidepressants	7-OH-Amoxapine • Amezepine • Amineptine • Amitriptyline • Amitriptylinoxide • Amoxapine • Aptazapine • Azepindole • Azipramine • Butriptyline • Cianopramine • Ciclazindol • Ciclopramine • Clomipramine • Cotriptyline • Cyanodothiepin • Demexiptiline • Depramine/Balipramine • Desipramine • Dibenzepine • Dimetacrine • Dosulepin/Dothiepin • Doxepin • Enprazepine • Esmirtazapine • Fluotracen • Hepzidine • Homopipramol • Imipramine • Imipraminoxide • Intriptyline • Iprindole • Ketipramine • Litracen • Lofepramine • Losindole • Loxapine • Maprotiline • Mariptiline • Mazindol • Melitracen • Metapramine • Mezepine • Mianserin • Mirtazapine • Naranol • Nitroxazepine • Nortriptyline • Noxiptiline • Octriptyline • Opipramol • Oxaprotiline • Pipofezine • Pirandamine • Propizepine • Protriptyline • Quinupramine • Setiptiline/Teciptiline • Tandamine • Tampramine • Tianeptine • Tienopramine • Trimipramine
Antihistamines	Alimemazine • Azatadine • Clobenzepam • Cyproheptadine • Dacemazine • Deptropine • Desloratadine • Epinastine • Etymemazine • Hydroxyethylpromethazine • Isopromethazine • Isothipendyl • Ketotifen • Latrepirdine • Loratadine • Mebhydrolin • Mequitazine • Methdilazine • Olopatadine • Oxomemazine • Phenindamine • Pimethixene • Promethazine • Propiomazine • Rupatadine • Thiazinamium
Antipsychotics	Acetophenazine • Amoxapine • Asenapine • Butaclamol • Butaperazine • Carphenazine • Carpipramine • Chlorpromazine • Chlorprothixene • Ciclindole • Clocapramine • Clomacran • Clotiapine • Clozapine • Flucindole • Fluotracen • Flupentixol • Fluphenazine • Gevotroline • Homopipramol • Levomepromazine/Methotrimeprazine • Loxapine • Maroxepin • Mesoridazine • Metitepine/Methiothepin • Metoxepin • Mosapramine • Naranol • Olanzapine • Perazine • Perphenazine • Periciazine • Piperacetazine • Pipotiazine • Piquindone • Prochlorperazine • Promazine • Prothipendyl • Quetiapine • Sulforidazine • Thiethylperazine • Thiopropazate • Thioridazine • Thiothixene • Trifluoperazine • Triflupromazine • Zotepine • Zuclopenthixol
Others	Atiprosin • Carbamazepine • Carvedilol • Cyclobenzaprine • Licarbazepine • Methylene Blue • Monatepil • Oxcarbazepine • Oxitriptyline • Pirenzepine • Pirolate • Pitrazepin • Pizotifen • Profenamine