Proglumetacin maleate | CAS# 59209-40-4 | Biochemical

MedKoo Cat#: 573953 | Name: Proglumetacin maleate

Description:

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

Proglumetacin (PGM), aslo known as CR-604, Protacine and Protaxon, is a nonsteroidal anti-inflammatory drug (NSAID). It is metabolized in the body to indometacin (IND) and proglumide, a drug with antisecretory effects that helps prevent injury to the stomach lining. It was considered that the mode of action of PGM mainly depended on its active metabolite, IND. However, PGM was also active in the case of local administration into the sites of inflammation on rat hind paw edema. Therefore, it seemed that PGM had a different behavior than a so called "prodrug".

Chemical Structure

Proglumetacin maleate

CAS#59209-40-4 (maleate)

Theoretical Analysis

MedKoo Cat#: 573953

Name: Proglumetacin maleate

CAS#: 59209-40-4 (maleate)

Chemical Formula: C54H66ClN5O16

Exact Mass: 1075.4193

Molecular Weight: 1076.59

Elemental Analysis: C, 60.25; H, 6.18; Cl, 3.29; N, 6.51; O, 23.78

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

Bulk Inquiry

Related CAS #

57132-53-3 (free base) 59209-40-4 (maleate)

Synonym

CR-604; CR 604; CR604; Afloxan; Miridacin; Proglumetacin maleate; Protacine; Protacine; Protaxon; Proxil;

IUPAC/Chemical Name

1H-Indole-3-acetic acid, 1-(4-chlorobenzoyl)-5-methoxy-2-methyl-, 2-[4-[3-[[4-(benzoylamino)-5-(dipropylamino)-1,5-dioxopentyl]oxy]propyl]-1-piperazinyl]ethyl ester, (2Z)-2-butenedioate (1:2)

InChi Key

MKFWBVKQDGNXDW-SPIKMXEPSA-N

InChi Code

1S/C46H58ClN5O8.2C4H4O4/c1-5-21-51(22-6-2)46(57)40(48-44(55)34-11-8-7-9-12-34)18-20-42(53)59-29-10-23-49-24-26-50(27-25-49)28-30-60-43(54)32-38-33(3)52(41-19-17-37(58-4)31-39(38)41)45(56)35-13-15-36(47)16-14-35;2*5-3(6)1-2-4(7)8/h7-9,11-17,19,31,40H,5-6,10,18,20-30,32H2,1-4H3,(H,48,55);2*1-2H,(H,5,6)(H,7,8)/b;2*2-1-

SMILES Code

CCCN(C(=O)C(NC(=O)c1ccccc1)CCC(=O)OCCCN2CCN(CC2)CCOC(=O)Cc3c4c(n(c3C)C(=O)c5ccc(cc5)Cl)ccc(c4)OC)CCC.C(=C\C(=O)O)\C(=O)O.C(=C\C(=O)O)\C(=O)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

>3 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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 1,076.59 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

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An Med Interna. 1989 Apr;6(4):217. Spanish. PMID: 2491526. 5: Conti P, Reale M, Fiore S, Barbacane RC, Bongrazio M, Panara MR, Carratelli L. Enhanced natural killer cell activity by proglumetacin, a non-steroidal anti- inflammatory drug. Agents Actions. 1989 Jan;26(1-2):216-8. doi: 10.1007/BF02126615. PMID: 2653004. 6: Cianfanelli M, Fiermonte MA, Fiore D, Dardano B, Michela Zucco FR. La proglumetacina nel trattamento dell'artrite reumatoide e dell'artrosi [Proglumetacin in the treatment of rheumatoid arthritis and arthrosis]. Clin Ter. 1988 Aug 15;126(3):181-5. Italian. PMID: 2974384. 7: Ono N, Sunami A, Yamasaki Y, Yamamoto N, Miyake H. Effects of proglumetacin maleate and its major metabolites on allergic air pouch inflammation in rats. Eur J Pharmacol. 1987 Oct 13;142(2):245-51. doi: 10.1016/0014-2999(87)90113-0. PMID: 2826180. 8: Makovec F, Chisté R, Peris W, Setnikar I. Pharmacokinetics and metabolism of [14C]-proglumetacin after oral administration in the rat. Arzneimittelforschung. 1987 Jul;37(7):806-13. PMID: 3675676. 9: Setnikar I, Arigoni R, Chisté R, Makovec F, Revel L. Plasma levels of proglumetacin and its metabolites after intravenous or oral administration in the dog. Arzneimittelforschung. 1987 Jun;37(6):698-702. PMID: 3663267. 10: Imoto S, Aoki M, Shimpo K, Yamashita K. [Chronic oral toxicity study of proglumetacin maleate in beagle dogs]. J Toxicol Sci. 1987 Feb;12 Suppl 1:1-33. Japanese. doi: 10.2131/jts.12.supplementi_1. PMID: 3573082. 11: Ono N, Yamasaki Y, Yamamoto N, Sunami A, Miyake H. Pharmacological studies on proglumetacin maleate, a new non-steroidal anti-inflammatory drug (4). Mode of action on anti-inflammatory activity. Jpn J Pharmacol. 1986 Nov;42(3):431-9. doi: 10.1254/jjp.42.431. PMID: 3102823. 12: [Clinical evaluation of proglumetacin malate in rheumatoid arthritis--a multi-institutional cooperative study]. Ryumachi. 1986 Oct;26(5):377-88. Japanese. PMID: 3299753. 13: Ono N, Yamasaki Y, Yamamoto N, Sunami A, Miyake H. [Pharmacological studies on proglumetacin maleate, a new non-steroidal anti-inflammatory drug. (3) Damaging effects on the gastrointestinal tract]. Nihon Yakurigaku Zasshi. 1986 Sep;88(3):205-13. Japanese. doi: 10.1254/fpj.88.205. PMID: 3098653. 14: Ono N, Sunami A, Yamamoto N, Yamasaki Y, Miyake H. [Pharmacological studies on proglumetacin maleate, a new non-steroidal anti-inflammatory drug. (2). Analgesic and antipyretic effects]. Nihon Yakurigaku Zasshi. 1986 Aug;88(2):77-84. Japanese. doi: 10.1254/fpj.88.77. PMID: 3490420. 15: Ono N, Yamamoto N, Sunami A, Yamasaki Y, Miyake H. [Pharmacological studies on proglumetacin maleate, a new non-steroidal anti-inflammatory drug. (1). Anti- inflammatory effects]. Nihon Yakurigaku Zasshi. 1986 Jul;88(1):33-46. Japanese. doi: 10.1254/fpj.88.33. PMID: 3758875. 16: Conti P, Alesse E, Cifone MG. Comparative effects of indomethacin and proglumetacin on 6-oxo-PGF1 alpha released ex vivo by rat gastric mucosa. Int J Tissue React. 1986;8(1):31-4. PMID: 3512465. 17: Montrone F, Fumagalli M, Santandrea S, Boccassini L, Greco M, Caruso I. Studio aperto di confronto tra proglumetacina e diclofenac nel trattamento dell'artrosi dell'anca e del ginocchio [Comparative open study between proglumetacin and diclofenac in the treatment of arthrosis of the hip and the knee]. Clin Ter. 1985 Sep 30;114(6):475-9. Italian. PMID: 3905222. 18: Stargardt M, Kasper E. Behandlung der sekundären Synovialitis. Doppelblindstudie Proglumetacin versus Indometacin [Treatment of secondary synovitis. Double blind study of proglumetacin versus indomethacin]. Fortschr Med. 1985 Jul 25;103(27-28):717-20. German. PMID: 4029867. 19: Floris N, Pittau A, Porru S. 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