Proglumetacin maleate

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MedKoo CAT#: 573953

CAS#: 59209-40-4 (maleate)

Description: 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 not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales or click below button.
Note: Price will be listed if it is available in the future.

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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 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

Preparing Stock Solutions

The following data is based on the product molecular weight 1076.59 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.

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

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1: Alves VM, Bobrowski T, Melo-Filho CC, Korn D, Auerbach S, Schmitt C, Muratov EN, Tropsha A. QSAR Modeling of SARS-CoV Mpro Inhibitors Identifies Sufugolix, Cenicriviroc, Proglumetacin, and other Drugs as Candidates for Repurposing against SARS-CoV-2. Mol Inform. 2021 Jan;40(1):e2000113. doi: 10.1002/minf.202000113. Epub 2020 Aug 24. PMID: 33405340.

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4: Marcos Sánchez F, Parrilla Herranz P, Veitia Fernández R, Arranz Nieto MJ, Durán Pérez-Navarro A. Proglumetacina en el tratamiento de la artritis reumatoide [Proglumetacin in the treatment of rheumatoid arthritis]. 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. Indagine clinico-statistica a breve termine sull'attività antiinfiammatoria della proglumetacina nella pratica ambulatoriale odontostomatologica [Short-term clinico-statistical study of the anti- inflammatory activity of proglumetacin in ambulatory dental practice]. Minerva Stomatol. 1985 May-Jun;34(3):573-8. Italian. PMID: 3860726.

20: Gusso MI, Guzzo GC, Pennisi M. La proglumetacina: potenziale farmaco di prima scelta nella terapia dei disturbi ortopedico-traumatologici [Proglumetacin: possible first choice in the treatment of orthopedic- traumatologic disorders]. Minerva Med. 1985 Mar 24;76(12):567-73. Italian. PMID: 3887221.