Ecabet Free Base | CAS# 33159-27-2 (free base) | dry eye syndrome

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

MedKoo CAT#: 413988

CAS#: 33159-27-2 (free base)

Description: Ecabet Free Base is a prescription eye drop for the treatment of dry eye syndrome. Ecabet represents a new class of molecules that increases the quantity and quality of mucin produced by conjunctival goblet cells and corneal epithelia. Mucin is a glycoprotein component of tear film that lubricates while retarding moisture loss from tear evaporation. Ecabet is currently marketed in Japan as an oral agent for treatment of gastric ulcers and gastritis.

Chemical Structure

Ecabet Free Base

CAS# 33159-27-2 (free base)

Instruction

Theoretical Analysis

MedKoo Cat#: 413988
Name: Ecabet Free Base
CAS#: 33159-27-2 (free base)
Chemical Formula: C20H28O5S
Exact Mass: 380.17
Molecular Weight: 380.490
Elemental Analysis: C, 63.13; H, 7.42; O, 21.02; S, 8.43

Price and Availability

Size	Price	Availability
100mg	USD 285	2 Weeks
250mg	USD 500	2 Weeks
1g	USD 950	2 Weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Related CAS #: 33159-27-2 (free) 86408-72-2 (sodium) 219773-47-4 (sodium hydrate) 219773-47-4 (sodium pentahydrate)

Synonym: Ecabet Free Base; Ecabetum

IUPAC/Chemical Name: 13-Isopropyl-12-sulfopodocarpa-8,11,13-trien-15-oic acid

InChi Key: IWCWQNVIUXZOMJ-RLLQIKCJSA-N

InChi Code: InChI=1S/C20H28O5S/c1-12(2)14-10-13-6-7-17-19(3,8-5-9-20(17,4)18(21)22)15(13)11-16(14)26(23,24)25/h10-12,17H,5-9H2,1-4H3,(H,21,22)(H,23,24,25)/t17-,19-,20+/m1/s1

SMILES Code: C[C@]1(C(O)=O)CCC[C@]2(C)C3=C(C=C(C(C)C)C(S(=O)(O)=O)=C3)CC[C@@]12[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: To be determined

Shelf Life: >2 years if stored properly

Drug Formulation: To be determined

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:

Instruction:

View handling instruction

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 380.49 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.

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:
In vitro protocol:
In vivo protocol:

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1: Wang Y, Wang B, Lv ZF, Yang Y, Wang F, Wang H, Chen S, Xie Y, Zhou X. Efficacy and safety of ecabet sodium as an adjuvant therapy for Helicobacter pylori eradication: a systematic review and meta-analysis. Helicobacter. 2014 Oct;19(5):372-81. doi: 10.1111/hel.12136. Epub 2014 May 14. PMID: 24826809.

2: Takahashi S, Tanaka A. [Ecabet sodium]. Nihon Rinsho. 2002 Feb;60 Suppl 2:711-6. Japanese. PMID: 11979876.

3: Ito Y, Shibata K, Hongo A, Kinoshita M. Ecabet sodium, a locally acting antiulcer drug, inhibits urease activity of Helicobacter pylori. Eur J Pharmacol. 1998 Mar 19;345(2):193-8. doi: 10.1016/s0014-2999(97)01622-1. PMID: 9600637.

4: Lawrance IC. Ecabet sodium: a potential new agent in the management of distal colitis. J Gastroenterol Hepatol. 2010 Jul;25(7):1182-4. doi: 10.1111/j.1440-1746.2010.06339.x. PMID: 20594242.

5: Kusumoto K, Kawahara T, Kuwano Y, Teshima-Kondo S, Morita K, Kishi K, Rokutan K. Ecabet sodium inhibits Helicobacter pylori lipopolysaccharide-induced activation of NADPH oxidase 1 or apoptosis of guinea pig gastric mucosal cells. Am J Physiol Gastrointest Liver Physiol. 2005 Feb;288(2):G300-7. doi: 10.1152/ajpgi.00274.2004. Epub 2004 Sep 30. PMID: 15458921.

6: Kinoshita M, Endo M, Yasoshima A, Saito N, Yamasaki K, Chishima S, Narita H. Ecabet sodium, a novel locally-acting anti-ulcer agent, protects the integrity of the gastric mucosal gel layer from pepsin-induced disruption in the rat. Aliment Pharmacol Ther. 1999 May;13(5):687-94. doi: 10.1046/j.1365-2036.1999.00502.x. PMID: 10233194.

7: Okuyama K, Saito N, Kume E, Noto T, Nagasaki M. Ecabet sodium prevents esophageal lesions induced by the reflux of gastric juice in rats. Inflammopharmacology. 2007 Apr;15(2):90-4. doi: 10.1007/s10787-006-1538-0. PMID: 17450449.

8: Kim JY, Kim DH, Min KA, Maeng HJ, Jang DJ, Cho KH. Preparation, Characterization, and In Vitro Release of Chitosan-Ecabet Electrolyte Complex for the Mucosal Delivery. J Nanosci Nanotechnol. 2019 Feb 1;19(2):640-645. doi: 10.1166/jnn.2019.15961. PMID: 30360135.

9: Rah YC, Choi J, Yoo MH, Yum G, Park S, Oh KH, Lee SH, Kwon SY, Cho SH, Kim S, Park HC. Ecabet sodium alleviates neomycin-induced hair cell damage. Free Radic Biol Med. 2015 Dec;89:1176-83. doi: 10.1016/j.freeradbiomed.2015.11.007. Epub 2015 Nov 10. PMID: 26561773.

10: Katagiri F, Inoue S, Sato Y, Itoh H, Takeyama M. Ecabet sodium raises plasma levels of calcitonin generelated peptide and substance P in healthy humans. J Pharm Pharmacol. 2005 Jun;57(6):799-805. doi: 10.1211/0022357056271. PMID: 15969937.

11: Shimoyama T, Fukuda S, Liu Q, Nakaji S, Munakata A, Sugawara K. Ecabet sodium inhibits the ability of Helicobacter pylori to induce neutrophil production of reactive oxygen species and interleukin-8. J Gastroenterol. 2001 Mar;36(3):153-7. doi: 10.1007/s005350170122. PMID: 11291877.

12: Kagaya H, Kato M, Asaka M. [Ecabet sodium (ECA) + PPI + AMPC therapy for clarithromycin-resistant Helicobacter pylori infections]. Nihon Rinsho. 2002 Feb;60 Suppl 2:455-9. Japanese. PMID: 11979827.

13: Munakata W, Liu Q, Shimoyama T, Sawaya M, Umeda T, Sugawara K. Ecabet sodium attenuates reactive oxygen species produced by neutrophils after priming with bacterial lipopolysaccharides. Luminescence. 2003 Nov-Dec;18(6):330-3. doi: 10.1002/bio.745. PMID: 14694422.

14: Ito Y, Hongo A, Kinoshita M, Tamaki H. Mechanism of anti-urease action by the anti-ulcer drug ecabet sodium. Biol Pharm Bull. 1995 Jun;18(6):850-3. doi: 10.1248/bpb.18.850. PMID: 7550119.

15: Liang J, Li J, Han Y, Xia J, Yang Y, Li W, Zhang S, Wu Y, Yuan Y, Li Z, Du Y, Chen M, Chen B, Jiang B, Bai Y, Wen Q, Wu K, Fan D. Helicobacter pylori eradication with ecabet sodium, omeprazole, amoxicillin, and clarithromycin versus bismuth, omeprazole, amoxicillin, and clarithromycin quadruple therapy: a randomized, open-label, phase IV trial. Helicobacter. 2012 Dec;17(6):458-65. doi: 10.1111/j.1523-5378.2012.00971.x. Epub 2012 Jul 2. PMID: 23066868.

16: Kawakami K, Yasuda M, Ishii K, Kokusenya Y, Sato T. A kinetic study of protein binding to ecabet sodium using quartz-crystal microbalance. Chem Pharm Bull (Tokyo). 1999 Jul;47(7):919-22. doi: 10.1248/cpb.47.919. PMID: 10434394.

17: Shimoyama T, Fukuda Y, Fukuda S, Munakata A, Yoshida Y, Shimoyama T. Ecabet sodium eradicates Helicobacter pylori infection in gastric ulcer patients. J Gastroenterol. 1996 Nov;31 Suppl 9:59-62. PMID: 8959522.

18: Hayashi S, Sugiyama T, Yokota K, Isogai H, Isogai E, Shimomura H, Oguma K, Asaka M, Hirai Y. Combined effect of rebamipide and ecabet sodium on Helicobacter pylori adhesion to gastric epithelial cells. Microbiol Immunol. 2000;44(7):557-62. doi: 10.1111/j.1348-0421.2000.tb02534.x. PMID: 10981828.

19: Kim J, Kim K, Lee JS, Kim SY, Kim KO, Kim YJ, Kwon KA, Park DK, Chung JW. [The Efficacy of Rebamipide or Ecabet Sodium Supplementation for Helicobacter pylori Eradication Therapy Compared with Quadruple (Concomitant) Regimen]. Korean J Gastroenterol. 2018 Apr 25;71(4):204-212. Korean. doi: 10.4166/kjg.2018.71.4.204. PMID: 29684969.

20: Ito Y, Onoda Y, Nakamura S, Tagawa K, Fukushima T, Sugawara Y, Takaiti O. Effects of the new anti-ulcer drug ecabet sodium (TA-2711) on pepsin activity. II. Interaction with substrate protein. Jpn J Pharmacol. 1993 Jun;62(2):175-81. doi: 10.1254/jjp.62.175. PMID: 8371516.

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