Acotiamide hydrochloride trihydrate
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MedKoo CAT#: 314263

CAS#: 773092-05-0 (HCl hydrate)

Description: Acotiamide, also known as YM-443 and Z-338, is a drug approved in Japan for the treatment of postprandial fullness, upper abdominal bloating, and early satiation due to functional dyspepsia. It acts as an acetylcholinesterase inhibitor. Note: The Approved drug API is a cotiamide HCl trihydrate (1:1:3)

Chemical Structure

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Acotiamide hydrochloride trihydrate
CAS# 773092-05-0 (HCl hydrate)
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 314263
Name: Acotiamide hydrochloride trihydrate
CAS#: 773092-05-0 (HCl hydrate)
Chemical Formula: C21H37ClN4O8S
Exact Mass: 0.00
Molecular Weight: 541.060
Elemental Analysis: C, 46.62; H, 6.89; Cl, 6.55; N, 10.36; O, 23.66; S, 5.93

Price and Availability

Size Price Availability Quantity
25mg USD 90 Ready to ship
50mg USD 150 Ready to ship
100mg USD 225 Ready to ship
200mg USD 350 Ready to ship
500mg USD 650 Ready to ship
1g USD 950 Ready to ship
2g USD 1450 Ready to ship
5g USD 2950 Ready to ship
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Related CAS #: 773092-05-0 (HCl hydrate)   185104-11-4 (HCl)   185106-16-5 (free base)    

Synonym: YM443; YM-443; YM 443; Z338; Z-338; Z 338; Acotiamide; Acotiamide hydrochloride trihydrate; Brand name: Acofide.

IUPAC/Chemical Name: N-(2-(diisopropylamino)ethyl)-2-(2-hydroxy-4,5-dimethoxybenzamido)thiazole-4-carboxamide hydrochloride trihydrate.

InChi Key: NPTDXIXCQCFGKC-UHFFFAOYSA-N

InChi Code: InChI=1S/C21H30N4O5S.ClH.3H2O/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);1H;3*1H2

SMILES Code: O=C(C1=CSC(NC(C2=CC(OC)=C(OC)C=C2O)=O)=N1)NCCN(C(C)C)C(C)C.[H]Cl.[H]O[H].[H]O[H].[H]O[H]

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO.

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info: Related CAS# CAS#773092-05-0 (Acotiamide HCl hydrate, 1:1:3); CAS#185104-11-4(Acotiamide HCl, 1:1); CAS#185106-16-5 (Acotiamide free base)

Biological target: Acotiamide monohydrochloride trihydrate enhances acetylcholine released by enteric neurons through muscarinic receptor antagonism and acetylcholinesterase (AChE) inhibition.
In vitro activity: TNF-α production in 1 μg/mL LPS-stimulated NR8383 cells treated with MCP-1 (100 pg/mL) was significantly elevated compared to that in LPS (1 μg/mL)-stimulated NR8383 cells (Figure 7A) (P < .01). Interestingly, acotiamide treatment (10, 30, and 100 μmol/L) significantly reduced TNF-α productions in LPS (1 μg/mL)-stimulated NR8383 cells treated with MCP-1 (100 pg/mL) (Figure 7A) (P < .05, respectively). IL-6 production in LPS (1 μg/mL)-stimulated NR8383 cells treated with MCP-1 (100 pg/ml) was significantly elevated compared to that in LPS (1 μg/mL)-stimulated NR8383 cells (Figure 7B) (P < .05). Interestingly, 30 μmol/L treatment with acotiamide significantly reduced IL-6 production in 1 μg/mL LPS-stimulated NR8383 cells treated with MCP-1 (100 pg/mL) (Figure 7B) (P < .05), and then, IL-4 productions were not increased in LPS alone or LPS-stimulated NR8383 cells treated with MCP-1 (Figure 7C). Reference: Neurogastroenterol Motil. 2020 Aug;32(8):e13813. https://pubmed.ncbi.nlm.nih.gov/32030855/
In vivo activity: As shown in Fig. 3A, Z-338 (10 µM) markedly enhanced the frequency of spontaneous unit discharges in AP rat neurons with relatively low (<1~2 unit discharges/sec) firing rates. The acceleratory effect of Z-338 was reversible, although the effects lasted for prolonged period (more than 1 hour) after wash out of Z-338. In neurons with relatively higher firing rates (>3~5 unit discharges/sec), on the other hand, Z-338 showed little effect on the firing rates (Fig. 3B). Reference: J Smooth Muscle Res. 2010;46(1):31-47. https://www.jstage.jst.go.jp/article/jsmr/46/1/46_1_31/_pdf/-char/en

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 112.5 207.93
Ethanol 20.0 36.96
Water 5.0 9.24

Preparing Stock Solutions

The following data is based on the product molecular weight 541.06 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. Yamawaki H, Futagami S, Sakasegawa N, Murakami M, Agawa S, Ikeda G, Noda H, Kirita K, Gudis K, Higuchi K, Kodaka Y, Ueki N, Iwakiri K. Acotiamide attenuates central urocortin 2-induced intestinal inflammatory responses, and urocortin 2 treatment reduces TNF-α productions in LPS-stimulated macrophage cell lines. Neurogastroenterol Motil. 2020 Aug;32(8):e13813. doi: 10.1111/nmo.13813. Epub 2020 Feb 7. PMID: 32030855. 2. Hashimoto K, Tashima K, Imai T, Matsumoto K, Horie S. The rodent model of impaired gastric motility induced by allyl isothiocyanate, a pungent ingredient of wasabi, to evaluate therapeutic agents for functional dyspepsia. J Pharmacol Sci. 2021 Jan;145(1):122-129. doi: 10.1016/j.jphs.2020.10.006. Epub 2020 Nov 11. PMID: 33357770. 3. Akaike H, Jang II, Hori N, Ogawa S, Ito Y, Akaike N. Effects of Z-338, a novel gastroprokinetic agent, on the actions of excitatory and inhibitory neurotransmitters on neurons in area postrema. J Smooth Muscle Res. 2010;46(1):31-47. doi: 10.1540/jsmr.46.31. PMID: 20383032.
In vitro protocol: 1. Yamawaki H, Futagami S, Sakasegawa N, Murakami M, Agawa S, Ikeda G, Noda H, Kirita K, Gudis K, Higuchi K, Kodaka Y, Ueki N, Iwakiri K. Acotiamide attenuates central urocortin 2-induced intestinal inflammatory responses, and urocortin 2 treatment reduces TNF-α productions in LPS-stimulated macrophage cell lines. Neurogastroenterol Motil. 2020 Aug;32(8):e13813. doi: 10.1111/nmo.13813. Epub 2020 Feb 7. PMID: 32030855.
In vivo protocol: 1. Hashimoto K, Tashima K, Imai T, Matsumoto K, Horie S. The rodent model of impaired gastric motility induced by allyl isothiocyanate, a pungent ingredient of wasabi, to evaluate therapeutic agents for functional dyspepsia. J Pharmacol Sci. 2021 Jan;145(1):122-129. doi: 10.1016/j.jphs.2020.10.006. Epub 2020 Nov 11. PMID: 33357770. 2. Akaike H, Jang II, Hori N, Ogawa S, Ito Y, Akaike N. Effects of Z-338, a novel gastroprokinetic agent, on the actions of excitatory and inhibitory neurotransmitters on neurons in area postrema. J Smooth Muscle Res. 2010;46(1):31-47. doi: 10.1540/jsmr.46.31. PMID: 20383032.

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1: Mayanagi S, Kishino M, Kitagawa Y, Sunamura M. Efficacy of acotiamide in combination with esomeprazole for functional dyspepsia refractory to proton-pump inhibitor monotherapy. Tohoku J Exp Med. 2014;234(3):237-40. PubMed PMID: 25382232.

2: Zai H, Matsueda K, Kusano M, Urita Y, Saito Y, Kato H. Effect of acotiamide on gastric emptying in healthy adult humans. Eur J Clin Invest. 2014 Dec;44(12):1215-21. doi: 10.1111/eci.12367. PubMed PMID: 25370953.

3: Xiao G, Xie X, Fan J, Deng J, Tan S, Zhu Y, Guo Q, Wan C. Efficacy and safety of acotiamide for the treatment of functional dyspepsia: systematic review and meta-analysis. ScientificWorldJournal. 2014;2014:541950. doi: 10.1155/2014/541950. Epub 2014 Aug 12. PubMed PMID: 25197703; PubMed Central PMCID: PMC4146483.

4: Sun Y, Song G, McCallum RW. Evaluation of acotiamide for the treatment of functional dyspepsia. Expert Opin Drug Metab Toxicol. 2014 Aug;10(8):1161-8. doi: 10.1517/17425255.2014.920320. Epub 2014 May 31. PubMed PMID: 24881488.

5: Matsunaga Y, Tanaka T, Saito Y, Kato H, Takei M. [Pharmacological and clinical profile of acotiamide hydrochloride hydrate (Acofide(®) Tablets 100 mg), a novel therapeutic agent for functional dyspepsia (FD)]. Nihon Yakurigaku Zasshi. 2014 Feb;143(2):84-94. Review. Japanese. PubMed PMID: 24531902.

6: Nowlan ML, Scott LJ. Acotiamide: first global approval. Drugs. 2013 Aug;73(12):1377-83. doi: 10.1007/s40265-013-0100-9. Erratum in: Drugs. 2014 Jun;74(9):1059. Nolan, Mary L [corrected to Nowlan, Mary L]. PubMed PMID: 23881665.

7: Altan E, Masaoka T, Farré R, Tack J. Acotiamide, a novel gastroprokinetic for the treatment of patients with functional dyspepsia: postprandial distress syndrome. Expert Rev Gastroenterol Hepatol. 2012 Sep;6(5):533-44. doi: 10.1586/egh.12.34. Review. PubMed PMID: 23061703.

8: Nagahama K, Matsunaga Y, Kawachi M, Ito K, Tanaka T, Hori Y, Oka H, Takei M. Acotiamide, a new orally active acetylcholinesterase inhibitor, stimulates gastrointestinal motor activity in conscious dogs. Neurogastroenterol Motil. 2012 Jun;24(6):566-74, e256. doi: 10.1111/j.1365-2982.2012.01912.x. Epub 2012 Mar 19. PubMed PMID: 22429221.

9: Kusunoki H, Haruma K, Manabe N, Imamura H, Kamada T, Shiotani A, Hata J, Sugioka H, Saito Y, Kato H, Tack J. Therapeutic efficacy of acotiamide in patients with functional dyspepsia based on enhanced postprandial gastric accommodation and emptying: randomized controlled study evaluation by real-time ultrasonography. Neurogastroenterol Motil. 2012 Jun;24(6):540-5, e250-1. doi: 10.1111/j.1365-2982.2012.01897.x. Epub 2012 Mar 4. PubMed PMID: 22385472.

10: McLarnon A. Dyspepsia: Acotiamide can relieve symptoms of functional dyspepsia. Nat Rev Gastroenterol Hepatol. 2012 Jan 17;9(2):62. doi: 10.1038/nrgastro.2011.262. PubMed PMID: 22249733.