Acotiamide

Chemical compound

A03FA10 (WHO) QA03FA10 (WHO)

JP: Rx-only

Pharmacokinetic dataProtein binding84.21–85.95%MetabolismUGT1A8 and 1A9 (major)Elimination half-life10.9–21.7 hoursExcretionFeces (92.7%), urine (5.3%)^[1]Identifiers

IUPAC name

N-{2-[bis(1-Methylethyl)amino]ethyl}-2-{[(2-hydroxy-4,5-dimethoxyphenyl)carbonyl]amino}-1,3-thiazole-4-carboxamide

CAS Number

185106-16-5^N

PubChem CID

5282338

ChemSpider

4445505^Y

UNII

D42OWK5383

KEGG

D08838^N

ChEMBL

ChEMBL2107723^N

Chemical and physical dataFormulaC₂₁H₃₀N₄O₅SMolar mass450.55 g·mol⁻¹3D model (JSmol)

Interactive image

SMILES

O=C(Nc1nc(C(=O)NCCN(C(C)C)C(C)C)cs1)c2cc(OC)c(OC)cc2O

InChI

InChI=1S/C21H30N4O5S/c1-12(2)25(13(3)4)8-7-22-20(28)15-11-31-21(23-15)24-19(27)14-9-17(29-5)18(30-6)10-16(14)26/h9-13,26H,7-8H2,1-6H3,(H,22,28)(H,23,24,27)^Y
Key:TWHZNAUBXFZMCA-UHFFFAOYSA-N^Y

^NY (what is this?) (verify)

Acotiamide, sold under the brand name Acofide,^[2]^[3] is a medication manufactured and approved in Japan for the treatment of postprandial fullness, upper abdominal bloating, and early satiation due to functional dyspepsia.^[4] It acts as an acetylcholinesterase inhibitor.

References

^ "Acofide (acotiamide hydrochloride hydrate) Tablets Review Report" (PDF). Retrieved 29 December 2016.
^ Nowlan ML, Scott LJ (August 2013). "Acotiamide: first global approval". Drugs. 73 (12): 1377–83. doi:10.1007/s40265-013-0100-9. PMID 23881665. S2CID 20383853.
^ Matsunaga Y, Tanaka T, Saito Y, Kato H, Takei M (February 2014). "[Pharmacological and clinical profile of acotiamide hydrochloride hydrate (Acofide(®) Tablets 100 mg), a novel therapeutic agent for functional dyspepsia (FD)]". Nihon Yakurigaku Zasshi. Folia Pharmacologica Japonica (in Japanese). 143 (2): 84–94. doi:10.1254/fpj.143.84. PMID 24531902.
^ Matsueda K, Hongo M, Tack J, Aoki H, Saito Y, Kato H (June 2010). "Clinical trial: dose-dependent therapeutic efficacy of acotiamide hydrochloride (Z-338) in patients with functional dyspepsia - 100 mg t.i.d. is an optimal dosage". Neurogastroenterology and Motility. 22 (6): 618–e173. doi:10.1111/j.1365-2982.2009.01449.x. PMID 20059698. S2CID 41298446.

Drugs for functional gastrointestinal disorders (A03)

Drugs for
functional
bowel
disorders

Antimuscarinics

Tertiary amino group	Oxyphencyclimine Camylofin Mebeverine Trimebutine Rociverine Dicycloverine Dihexyverine Difemerine Piperidolate
Quaternary ammonium compounds	Benzilone Mepenzolate Pipenzolate Glycopyrronium Oxyphenonium Penthienate Methantheline Propantheline Otilonium Tridihexethyl Isopropamide Hexocyclium Poldine Bevonium Diphemanil Tiemonium Prifinium Timepidium Fenpiverinium

Phosphodiesterase
inhibitors

Acting on
serotonin receptors

5-HT₃ antagonists
- Alosetron
- Cilansetron
5-HT₄ agonists
- Mosapride

Other

Belladonna
and derivatives
(antimuscarinics)

Tertiary amines: Atropine
Hyoscyamine

Propulsives

Primarily dopamine antagonists
5-HT₄ agonists
- Cinitapride
- Cisapride

Acetylcholine metabolism and transport modulators

Enzyme
(modulators)

ChATTooltip Choline acetyltransferase	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
AChETooltip Acetylcholinesterase	Inhibitors: Reversible: Carbamates: Aldicarb Aminocarb Bendiocarb Bufencarb Carbaryl Carbendazim Carbetamide Carbofuran Carbosulfan Chlorbufam Chloropropham Dimetilan Ethienocarb Ethiofencarb Fenobucarb Formetanate Formparanate Methiocarb Methomyl Metolcarb Miotine Oxamyl Phenmedipham Pinmicarb Pirimicarb Promecarb Propamocarb Propham Propoxur Thiodicarb Thiofanox; Stigmines: Distigmine Eptastigmine Ganstigmine Neostigmine +glycopyrronium bromide Phenserine Physostigmine Pyridostigmine Quilostigmine Rivastigmine Terestigmine; Others: Acotiamide Ambenonium Caffeine Donepezil EA-3990 EA-4056 Edrophonium Galantamine Huperzine A Huprine W Huprine X Huprine Y Ipidacrine Itopride Ladostigil Minaprine Octamethylene-bis(5-dimethylcarbamoxyisoquinolinium bromide) T-1123 T-1152 T-1194 TL-599 TL-1238 Tacrine Zanapezil Irreversible: Organophosphates: 2-Ethoxycarbonyl-1-methylvinyl cyclohexyl methylphosphonate Acephate Armine Azinphos-ethyl Azinphos-methyl BAY-29952 Bensulide Cadusafos Carbophenothion Chlorethoxyfos Chlorfenvinphos Chlorpyrifos Chlorpyrifos-methyl Coumaphos Crotylsarin Cyanophos Cyclosarin (GF) Demephion Demeton Demeton-S-methyl Dialifor Diazinon Dichlorvos Dicrotophos Dicyclohexyl phosphorofluoridate Diisopropylphosphate Diisopropyl fluorophosphate Dimefox Dimethoate Dimethyl 4-(methylthio)phenyl phosphate Dioxathion Disulfoton EA-2012 EA-2054 EA-2098 EA-2192 EA-2613 EA-3148 EA-4352 Echothiophate Ethylsarin (GE) Endothion EPN Ethion Ethoprop Fenamiphos Fenitrothion Fenthion Fluorotabun Fonofos Formothion Fosthiazate GD-42 GH GT-45 GV Guanitoxin Hexaethyl tetraphosphate (HETP) Isofluorophate Isoxathion Leptophos Malaoxon Malathion Mazidox Methamidophos Methidathion Methyl phenkapton Methylfluorophosphonylcholine (MFPCh) Metrifonate Mevinphos Mipafox Monocrotophos MSPI Naled Novichok agent Omethoate Oxydemeton-methyl Paraoxon Parathion Parathion-methyl Phorate Phosalone Phosfolan Phosmet Phosphamidon Phoxim Pirimiphos-methyl Profenofos Prothoate R-16661 Ro 3-0340 Ro 3-0346 Ro 3-0347 Ro 3-0351 Ro 3-0352 Ro 3-0397 Ro 3-0411 Ro 3-0412 Ro 3-0417 Ro 3-0419 Ro 3-0422 Ro 3-0433 Ronnel Sarin (GB) Schradan Soman (GD) Sulfotep (TEDP) Tabun (GA) Tebupirimfos Temefos Terbufos Tetrachlorvinphos Tetraethyl pyrophosphate (TEPP) Triazofos Tribufos Trichlorfon Trichloronate Tricresyl phosphate VE VG VM VP VS VR VX; Others: Demecarium Fasciculins (green mamba toxins) (1, 2, 3, 4) Onchidal (Onchidella binneyi) Methanesulfonyl fluoride Unsorted: α-Pinene α-Viniferin Affinine Affinisine Arisugacin A Bulbocapnine Conodurine Coronaridine Corydaline Corynoline Crimidine Cyclanoline Cymserine Harmaline Kobophenol A Lactucopicrin Lycorine Phosacetim Rosmarinic acid Stercuronium iodide Taspine Tetrahydrocannabinol Ungeremine Ungiminorine Dimethylcarbamoyl fluoride BW284C51 TMTFA 3152 CT Reactivators: Asoxime chloride Methoxime Obidoxime Pralidoxime Trimedoxime bromide
BChETooltip Butyrylcholinesterase	Inhibitors: Affinine Affinisine Conodurine Cymserine Ladostigil Profenamine (ethopropazine) Rivastigmine Tacrine ZINC-12613047 Many of the other AChE inhibitors listed above

Transporter
(modulators)

CHTTooltip Choline transporter	Inhibitors: Hemicholinium-3 (hemicholine) Triethylcholine Enhancers: Coluracetam
VAChTTooltip Vesicular acetylcholine transporter	Inhibitors: Vesamicol

Release
(modulators)

Inhibitors	SNAP-25Tooltip Synaptosomal-associated protein 25 inactivators: Botulinum toxin (A, C, E) VAMPTooltip Vesicle-associated membrane protein inactivators: Botulinum toxin (B, D, F, G) Others: Bungarotoxins (β-bungarotoxin, γ-bungarotoxin)
Enhancers	LPHNTooltip Latrophilin agonists: α-Latrotoxin Others: Atracotoxins (e.g., robustoxin, versutoxin) Crotoxin