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MedKoo Cat#: 329638 | Name: Amtolmetin guacil
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Description:

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

Amtolmetin guacil, also known ST-679 and MED-15, is a non-acidic prodrug of tolmetin, having similar NSAID properties like tolmetin with additional analgesic, antipyretic, and gastro protective properties. Amtolmetin is formed by amidation of tolmetin by glycine. Amtolmetin guacil stimulates capsaicin receptors present on gastro intestinal walls, because of presence of vanillic moiety and also releases NO which is gastro protective. It also inhibits prostaglandin synthesis and cyclooxygenase (COX).

Chemical Structure

Amtolmetin guacil
Amtolmetin guacil
CAS#87344-06-7

Theoretical Analysis

MedKoo Cat#: 329638

Name: Amtolmetin guacil

CAS#: 87344-06-7

Chemical Formula: C24H24N2O5

Exact Mass: 420.1685

Molecular Weight: 420.47

Elemental Analysis: C, 68.56; H, 5.75; N, 6.66; O, 19.03

Price and Availability

Size Price Availability Quantity
100mg USD 450.00 2 Weeks
250mg USD 850.00 2 Weeks
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Related CAS #
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Synonym
Amtolmetin guacil; ST-679; ST 679; ST679; MED-15; MED 15; MED15; Eufans. Trade names: Amtoril®, Artricol®, Artromed®.
IUPAC/Chemical Name
2-methoxyphenyl (2-(1-methyl-5-(4-methylbenzoyl)-1H-pyrrol-2-yl)acetyl)glycinate
InChi Key
CWJNMKKMGIAGDK-UHFFFAOYSA-N
InChi Code
InChI=1S/C24H24N2O5/c1-16-8-10-17(11-9-16)24(29)19-13-12-18(26(19)2)14-22(27)25-15-23(28)31-21-7-5-4-6-20(21)30-3/h4-13H,14-15H2,1-3H3,(H,25,27)
SMILES Code
O=C(OC1=CC=CC=C1OC)CNC(CC2=CC=C(C(C3=CC=C(C)C=C3)=O)N2C)=O
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

Preparing Stock Solutions

The following data is based on the product molecular weight 420.47 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
1: Lin HC, Chen CJ, Chiang KH, Yen TY, Ho CM, Hwang KP, Su BH, Lin HC, Li TC, Lu JJ. Clonal dissemination of invasive and colonizing clonal complex 1 of serotype VI group B Streptococcus in central Taiwan. J Microbiol Immunol Infect. 2016 Dec;49(6):902-909. doi: 10.1016/j.jmii.2014.11.002. Epub 2014 Nov 11. PubMed PMID: 25560254. 2: Nappi C, Nolfe G, La Pinta M, Colace G, Ruotolo C, Affinito P. [The treatment of postoperative pain in obstetrical-gynecologic surgery. A comparative study between ST-679 and paracetamol]. Clin Ter. 1993 Jan;142(1 Pt 2):47-52. Italian. PubMed PMID: 8472521. 3: Donati G, Spinazzè R. [A clinical study to determine the optimal dosage of ST-679 in the treatment of rheumatic diseases]. Clin Ter. 1993 Jan;142(1 Pt 2):19-28. Italian. PubMed PMID: 8472517. 4: De Santis E, La Pinta M, Nolfe G. [An evaluation of the analgesic activity and tolerance of ST-679 in patients with pain following orthopedic and traumatological interventions]. Clin Ter. 1993 Jan;142(1 Pt 2):53-9. Italian. PubMed PMID: 8472522. 5: Lingetti M, Ciarimboli M, Porfido FA, Imparato L, Sorrentino GP, Garzya G, Saraceni G, Donati G, Nolfe G. [An evaluation of the therapeutic activity and tolerance of ST-679 in patients with osteoarthritis at different sites. A controlled double-blind study vs tolmetin]. Clin Ter. 1993 Jan;142(1 Pt 2):29-40. Italian. PubMed PMID: 8472518. 6: Arrigoni-Martelli E. Profile of activity of a new anti-inflammatory agent, ST 679 (MED 15). Drugs Exp Clin Res. 1990;16(2):63-6. PubMed PMID: 2401188. 7: Nanni G, Sarro G, Antoci G, Bianchi P, Gossetti F, Catarci M, La Pinta M, Negro P, Nolfe G. [The drug treatment of postoperative pain]. Clin Ter. 1993 Jan;142(1 Pt 2):41-6. Italian. PubMed PMID: 8472520. 8: Annunziato L, di Renzo G. [A bioequivalence study of tablet and powder formulations of the nonsteroidal anti-inflammatory drug 2-methoxyphenyl 1-methyl-5-(p-methylbenzoylpyrrol)-2-acetamidoacetate]. Clin Ter. 1993 Jan;142(1 Pt 2):11-7. Italian. PubMed PMID: 8472516. 9: Nagulapalli M, Maji S, Dwivedi N, Dahiya P, Thakur JK. Evolution of disorder in Mediator complex and its functional relevance. Nucleic Acids Res. 2016 Feb 29;44(4):1591-612. doi: 10.1093/nar/gkv1135. Epub 2015 Nov 20. PubMed PMID: 26590257; PubMed Central PMCID: PMC4770211. 10: Nakatsubo T, Nishitani S, Kikuchi Y, Iida S, Yamada K, Tanaka A, Ohkuma Y. Human mediator subunit MED15 promotes transcriptional activation. Drug Discov Ther. 2014 Oct;8(5):212-7. PubMed PMID: 25382556. 11: Shaikhibrahim Z, Menon R, Braun M, Offermann A, Queisser A, Boehm D, Vogel W, Rüenauver K, Ruiz C, Zellweger T, Svensson M, Andren O, Kristiansen G, Wernert N, Bubendorf L, Kirfel J, Biskup S, Perner S. MED15, encoding a subunit of the mediator complex, is overexpressed at high frequency in castration-resistant prostate cancer. Int J Cancer. 2014 Jul 1;135(1):19-26. doi: 10.1002/ijc.28647. Epub 2013 Dec 9. PubMed PMID: 24374838. 12: Rong Z, Xu Y, Zhang C, Xiang D, Li X, Liu D. Evaluation of intestinal absorption of amtolmetin guacyl in rats: breast cancer resistant protein as a primary barrier of oral bioavailability. Life Sci. 2013 Feb 27;92(3):245-51. doi: 10.1016/j.lfs.2012.12.010. Epub 2013 Jan 16. PubMed PMID: 23333829. 13: Hotha KK, Bharathi DV, Kumar SS, Reddy YN, Chatki P, Ravindranath LK, Veera KN, Mullangi R. Validation and clinical application of an LC-ESI-MS/MS method for simultaneous determination of tolmetin and MED5, the metabolites of amtolmetin guacil in human plasma. Biomed Chromatogr. 2010 Oct;24(10):1100-7. doi: 10.1002/bmc.1411. PubMed PMID: 20853464. 14: Annunziato L, di Renzo G. [A bioequivalence study in man of tablet and capsule formulations of the nonsteroidal anti-inflammatory compound 2-methoxyphenyl 1-methyl-5-(p-methylbenzoylpyrrol)-2-acetamidoacetate]. Clin Ter. 1993 Jan;142(1 Pt 2):3-10. Italian. PubMed PMID: 8472519. 15: Hotha KK, Dasari VB, Shaik AN, Syed M, Shivva V, Lakshmanarao RK, Korlakunta JN, Mullangi R. Species difference in the in vitro and in vivo metabolism of amtolmetin guacil. Arzneimittelforschung. 2010;60(11):667-74. doi: 10.1055/s-0031-1296345. PubMed PMID: 21175039. 16: Kirkova M, Alexandova A, Kesiova M, Todorov S. In vivo effects of amtolmetin guacyl on lipid peroxidation and antioxidant defence systems. Comparison with non-selective and COX-2 selective NSAIDs. Auton Autacoid Pharmacol. 2007 Apr;27(2):99-104. PubMed PMID: 17391279. 17: Kirkova M, Kesiova M, Konstantinova S, Alexandrova A, Petrov L, Tsvetanova E, Todorov S. In vivo effects of amtolmetin guacyl on lipid peroxidation and antioxidant defence systems in different models of gastrointestinal injury. Auton Autacoid Pharmacol. 2007 Jan;27(1):63-70. PubMed PMID: 17199877. 18: Kirkova M, Alexandova A, Kesiova M, Tsvetanova E, Georgieva A, Todorov S. Potential antioxidant activity of celecoxib and amtolmetin guacyl: in vitro studies. Auton Autacoid Pharmacol. 2007 Jan;27(1):13-8. PubMed PMID: 17199871. 19: Jajić Z, Malaise M, Nekam K, Koó E, Dankó K, Kovacs M, Scarpignato C. Gastrointestinal safety of amtolmetin guacyl in comparison with celecoxib in patients with rheumatoid arthritis. Clin Exp Rheumatol. 2005 Nov-Dec;23(6):809-18. PubMed PMID: 16396699. 20: Li YH, Li J, Huang Y, Lu XW, Jin Y. Gastroprotective effect and mechanism of amtolmetin guacyl in mice. World J Gastroenterol. 2004 Dec 15;10(24):3616-20. PubMed PMID: 15534917; PubMed Central PMCID: PMC4612003.