MedKoo Cat#: 328914 | Name: Ethenzamide
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Ethenzamide, also known as HP-209, is an anti-inflammatory used and to reduce fever and pain.

Chemical Structure

Ethenzamide
Ethenzamide
CAS#938-73-8

Theoretical Analysis

MedKoo Cat#: 328914

Name: Ethenzamide

CAS#: 938-73-8

Chemical Formula: C9H11NO2

Exact Mass: 165.0790

Molecular Weight: 165.19

Elemental Analysis: C, 65.44; H, 6.71; N, 8.48; O, 19.37

Price and Availability

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25g USD 250.00 2 Weeks
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Related CAS #
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Synonym
Ethenzamide; 2-ethoxybenzamide; o-Ethoxybenzamide; Ethbenzamide; Ethenzamid; Etosalicyl; Protopyrin; Trancalgyl; HP-209; HP 209; HP209; NSC-28787; NSC28787; NSC 28787
IUPAC/Chemical Name
2-ethoxybenzamide
InChi Key
SBNKFTQSBPKMBZ-UHFFFAOYSA-N
InChi Code
InChI=1S/C9H11NO2/c1-2-12-8-6-4-3-5-7(8)9(10)11/h3-6H,2H2,1H3,(H2,10,11)
SMILES Code
O=C(N)C1=CC=CC=C1OCC
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
Product Data
Biological target:
2-Ethoxybenzamide is widely used as an antipyretic anodyne.
In vitro activity:
To investigate the effect on stomach motility, the effects of ETZ (ethenzamide) on 5HT- or α-methyl-5HT-induced contractions of rat-isolated gastric fundus were examined. 5HT (Fig. 1a) or α-methyl-5HT (Fig. 1b) resulted in the contraction of the tissue strips in a concentration-dependent manner. The 5HT- or α-methyl-5HT-induced contractions were suppressed by ETZ. The concentration–response curves of 5HT or α-methyl-5HT were shifted to the right in a concentration-dependent manner (Figs. 1a, b). In addition, the slopes of the Schlid regression of ETZ in 5HT and α-methyl-5HT were 1.11 and 1.32, respectively. The pA2 values of ETZ in 5HT and α-methyl-5HT were 4.63 and 4.36, respectively. Reference: Biol Pharm Bull. 2021 Mar 1;44(3):332-337. https://pubmed.ncbi.nlm.nih.gov/33342935/
In vivo activity:
Oral administration of ETZ (ethenzamide) reduced the second-phase nociceptive behaviors in the rat formalin test in a dose-dependent manner (Fig. 2a). The results of immunohistochemical analysis revealed that the number of c-Fos-positive cells in the superficial laminae of the spinal dorsal horn was significantly increased in the formalin-injected animals (vehicle group) as compared to the saline-injected animals (normal group) (Fig. 2b). Furthermore, in the animals administered ETZ at 400 mg/kg (ETZ group), the number of c-Fos-positive cells in the superficial laminae of the spinal dorsal horn induced by formalin injection was significantly decreased as compared to that in the vehicle-treated animals (vehicle group) (Figs. 2b, c). Reference: Biol Pharm Bull. 2020 May 1;43(5):839-847. https://pubmed.ncbi.nlm.nih.gov/32147623/
Solvent mg/mL mM
Solubility
DMSO 47.0 284.52
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 165.19 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. Nikaido T, Muroga S, Maruyama C, Fujimaru Y, Asano T, Takaoka A. Ethenzamide Exerts Protective Effects against Ibuprofen-Induced Gastric Mucosal Damage in Rats by Suppressing Gastric Contraction. Biol Pharm Bull. 2021 Mar 1;44(3):332-337. doi: 10.1248/bpb.b20-00479. Epub 2020 Dec 19. PMID: 33342935. 2. Nikaido T, Maruyama C, Hamanaka M, Yamaguchi C, Fujimaru Y, Nakanishi Y, Asano T, Takaoka A. Ethenzamide Exerts Analgesic Effect at the Spinal Cord via Multiple Mechanisms of Action Including the 5HT2B Receptor Blockade in the Rat Formalin Test. Biol Pharm Bull. 2020 May 1;43(5):839-847. doi: 10.1248/bpb.b19-01050. Epub 2020 Mar 6. PMID: 32147623.
In vitro protocol:
1. Nikaido T, Muroga S, Maruyama C, Fujimaru Y, Asano T, Takaoka A. Ethenzamide Exerts Protective Effects against Ibuprofen-Induced Gastric Mucosal Damage in Rats by Suppressing Gastric Contraction. Biol Pharm Bull. 2021 Mar 1;44(3):332-337. doi: 10.1248/bpb.b20-00479. Epub 2020 Dec 19. PMID: 33342935. 2. Nikaido T, Maruyama C, Hamanaka M, Yamaguchi C, Fujimaru Y, Nakanishi Y, Asano T, Takaoka A. Ethenzamide Exerts Analgesic Effect at the Spinal Cord via Multiple Mechanisms of Action Including the 5HT2B Receptor Blockade in the Rat Formalin Test. Biol Pharm Bull. 2020 May 1;43(5):839-847. doi: 10.1248/bpb.b19-01050. Epub 2020 Mar 6. PMID: 32147623.
In vivo protocol:
1. Nikaido T, Muroga S, Maruyama C, Fujimaru Y, Asano T, Takaoka A. Ethenzamide Exerts Protective Effects against Ibuprofen-Induced Gastric Mucosal Damage in Rats by Suppressing Gastric Contraction. Biol Pharm Bull. 2021 Mar 1;44(3):332-337. doi: 10.1248/bpb.b20-00479. Epub 2020 Dec 19. PMID: 33342935. 2. Nikaido T, Maruyama C, Hamanaka M, Yamaguchi C, Fujimaru Y, Nakanishi Y, Asano T, Takaoka A. Ethenzamide Exerts Analgesic Effect at the Spinal Cord via Multiple Mechanisms of Action Including the 5HT2B Receptor Blockade in the Rat Formalin Test. Biol Pharm Bull. 2020 May 1;43(5):839-847. doi: 10.1248/bpb.b19-01050. Epub 2020 Mar 6. PMID: 32147623.
1: Przybyłek M, Ziółkowska D, Mroczyńska K, Cysewski P. Propensity of salicylamide and ethenzamide cocrystallization with aromatic carboxylic acids. Eur J Pharm Sci. 2016 Mar 31;85:132-40. doi: 10.1016/j.ejps.2016.02.010. Epub 2016 Feb 17. PubMed PMID: 26898408. 2: Moribe K, Tsuchiya M, Tozuka Y, Yamaguchi K, Oguchi T, Yamamoto K. Grinding-induced equimolar complex formation between thiourea and ethenzamide. Chem Pharm Bull (Tokyo). 2004 May;52(5):524-9. PubMed PMID: 15133201. 3: Darias V, Bravo L, Abdallah SS, Sánchez Mateo CC, Expósito-Orta MA, Lissavetsky J, Manzanares J. Synthesis and preliminary pharmacological study of thiophene analogues of the antipyretic and analgesic agent ethenzamide. Arch Pharm (Weinheim). 1992 Feb;325(2):83-7. PubMed PMID: 1605721. 4: Aitipamula S, Chow PS, Tan RB. Ethenzamide-gentisic acid-acetic acid (2/1/1). Acta Crystallogr Sect E Struct Rep Online. 2010 Apr 10;66(Pt 5):o1045-6. doi: 10.1107/S1600536810012407. PubMed PMID: 21579106; PubMed Central PMCID: PMC2979229. 5: Fukunaka T, Golman B, Shinohara K. Batch grinding kinetics of Ethenzamide particles by fluidized-bed jet-milling. Int J Pharm. 2006 Mar 27;311(1-2):89-96. Epub 2006 Jan 20. PubMed PMID: 16427749. 6: Uehara H, Otsuka H, Izumi K. Modifying effects of a mixture of acetaminophen, aspirin, dipyrone and ethenzamide on a multiorgan initiation model and its carcinogenicity in male F344 rats. Cancer Lett. 1999 Jan 8;135(1):83-90. PubMed PMID: 10077225. 7: Fujimaki Y, Matsubara T, Sakamoto T, Sasakura D, Miura T, Takekawa M, Hiyama Y. Distribution of ethenzamide and other ingredients on granule surfaces studied by Raman microspectroscopy and mapping. Pharmazie. 2009 May;64(5):316-22. PubMed PMID: 19530442. 8: Ozawa M, Hasegawa K, Yonezawa Y, Sunada H. Preparation of solid dispersion for ethenzamide-carbopol and theophylline-carbopol systems using a twin screw extruder. Chem Pharm Bull (Tokyo). 2002 Jun;50(6):802-7. PubMed PMID: 12045335. 9: Aoki S, Mizutani T, Danjo K. Studies on the number of contacts between ibuprofen and ethenzamide using thermal analysis. Chem Pharm Bull (Tokyo). 2000 Jan;48(1):140-1. PubMed PMID: 10705490. 10: Hirasawa N, Okamoto H, Danjo K. Lactose as a low molecular weight carrier of solid dispersions for carbamazepine and ethenzamide. Chem Pharm Bull (Tokyo). 1999 Mar;47(3):417-20. PubMed PMID: 10212391. 11: Shibasaki J, Konishi R, Takemura M, Fukushima E, Nakamura J, Sasaki H. Comparison of the first-pass metabolism of ethenzamide and salicylamide in rats. J Pharmacobiodyn. 1984 Nov;7(11):804-10. PubMed PMID: 6530645. 12: Fukunaka T, Golman B, Shinohara K. Continuous grinding kinetics of ethenzamide particles by fluidized-bed jet-milling. Drug Dev Ind Pharm. 2006 Mar;32(3):347-55. PubMed PMID: 16556539. 13: Asada S, Fujii H, Nakae H. [Application of multi-lines fitting technic for ethenzamide elimination with capacity-limited process in the rabbit plasma]. Yakugaku Zasshi. 1989 Jul;109(7):499-504. Japanese. PubMed PMID: 2585261. 14: Kawano O, Sawabe T, Misaki N, Fukawa K. Studies on combination dosing (III). Aspirin and ethenzamide. Jpn J Pharmacol. 1978 Dec;28(6):829-35. PubMed PMID: 745307. 15: Kondo K, Kato A, Niwa T. Development of a novel pelletization technique through an extremely high-shear process using a mechanical powder processor to produce high-dose small core granules suitable for film coating. Int J Pharm. 2015 Apr 10;483(1-2):101-9. doi: 10.1016/j.ijpharm.2015.02.026. Epub 2015 Feb 11. PubMed PMID: 25681728.