Repirinast | MY-5116 | CAS#73080-51-0 | Mediator Release Inhibitor

MedKoo Cat#: 328334 | Name: Repirinast

Description:

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

Repirinast, also known as MY-5116, is a mediator release inhibitor used to treat asthma.

Chemical Structure

Repirinast

CAS#73080-51-0

Theoretical Analysis

MedKoo Cat#: 328334

Name: Repirinast

CAS#: 73080-51-0

Chemical Formula: C20H21NO5

Exact Mass: 355.1420

Molecular Weight: 355.39

Elemental Analysis: C, 67.59; H, 5.96; N, 3.94; O, 22.51

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Synonym

Repirinast; MY-5116; MY 5116; MY5116

IUPAC/Chemical Name

isopentyl 7,8-dimethyl-4,5-dioxo-5,6-dihydro-4H-pyrano[3,2-c]quinoline-2-carboxylate

InChi Key

NFQIAEMCQGTTIR-UHFFFAOYSA-N

InChi Code

InChI=1S/C20H21NO5/c1-10(2)7-8-25-20(24)15-9-14(22)16-18(26-15)13-6-5-11(3)12(4)17(13)21-19(16)23/h5-6,9-10H,7-8H2,1-4H3,(H,21,23)

SMILES Code

O=C(C(O1)=CC(C2=C1C3=C(NC2=O)C(C)=C(C)C=C3)=O)OCCC(C)C

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

Product Data

Instruction

View handling instruction

Biological target:

Repirinast (MY-5116) is an orally active anti-allergic agent. Repirinast inhibits histamine release. Repirinast can be used in the research of bronchial asthma.

In vitro activity:

The drugs, one being repirinast, in the culture medium stimulated the proliferation of B-1F cells to various extents. The results suggest that chronic administration of these drugs might enhance the proliferation of some kinds of tumor cells. However, there are significant differences between in vitro cultured animal cells and in vivo humans. Reference: Anticancer Res. 1996 May-Jun;16(3A):1241-5. https://pubmed.ncbi.nlm.nih.gov/8702244/

In vivo activity:

The inhibitory effect of repirinast on the infiltration of eosinophils and/or neutrophils into the airways of guinea pigs may reflect the inhibition of late pulmonary response and airway hyperresponsiveness. Reference: Int Arch Allergy Immunol. 1993;100(4):367-72. https://pubmed.ncbi.nlm.nih.gov/8386963/

Preparing Stock Solutions

The following data is based on the product molecular weight 355.39 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:

1. Nishizawa Y, Yamamoto T, Terada N, Fushiki S, Amakata Y, Nishizawa Y. Effects of antiallergic drugs on the proliferation of estrogen-sensitive mouse Leydig cell line. Anticancer Res. 1996 May-Jun;16(3A):1241-5. PMID: 8702244. 2. Yamada N, Kadowaki S, Takahashi K, Umezu K. MY-1250, a major metabolite of the anti-allergic drug repirinast, induces phosphorylation of a 78-kDa protein in rat mast cells. Biochem Pharmacol. 1992 Sep 25;44(6):1211-3. doi: 10.1016/0006-2952(92)90387-x. PMID: 1358073. 3. Yamada N, Ohgaki M, Muramatsu M. Repirinast inhibits antigen-induced early and late pulmonary responses and airway hyperresponsiveness in guinea pigs. Int Arch Allergy Immunol. 1993;100(4):367-72. doi: 10.1159/000236440. PMID: 8386963. 4. Takei M, Endo K, Takahashi K. Inhibition of histamine release from rat peritoneal mast cells by MY-1250, an active metabolite of Repirinast (MY-5116). Int Arch Allergy Appl Immunol. 1990;93(2-3):237-41. doi: 10.1159/000235307. PMID: 1712003.

In vitro protocol:

In vivo protocol:

1. Yamada N, Ohgaki M, Muramatsu M. Repirinast inhibits antigen-induced early and late pulmonary responses and airway hyperresponsiveness in guinea pigs. Int Arch Allergy Immunol. 1993;100(4):367-72. doi: 10.1159/000236440. PMID: 8386963. 2. Takei M, Endo K, Takahashi K. Inhibition of histamine release from rat peritoneal mast cells by MY-1250, an active metabolite of Repirinast (MY-5116). Int Arch Allergy Appl Immunol. 1990;93(2-3):237-41. doi: 10.1159/000235307. PMID: 1712003.

1: Shishikura T, Shito K, Uchida M, Inaba T. A late cutaneous response in actively sensitized rats: a new method for evaluating the efficacy of antiallergic drugs. J Pharmacol Sci. 2006 Aug;101(4):350-5. doi: 10.1254/jphs.fp0060519. Epub 2006 Aug 5. PMID: 16891762. 2: Kano H, Juji F, Shibuya N, Narita M, Naritaka S, Suko M, Morita Y, Iwata T. [Clinical courses of 18 cases with food-dependent exercise-induced anaphylaxis]. Arerugi. 2000 Jun;49(6):472-8. Japanese. PMID: 10916885. 3: Tominaga T, Watanbe A, Tsuji J, Koda A, Nagai H, Kumazawa Y, Shimada H. Effect of TYB-2285 on antigen-induced accumulation of eosinophils into the peritoneal cavity of rats sensitized with Ascaris suum extract. Gen Pharmacol. 1997 Mar;28(3):411-4. doi: 10.1016/s0306-3623(96)00298-4. PMID: 9068982. 4: Yamada N, Sugasawa K. Pharmacologic modulation of delayed-type hypersensitivity in mice. Arzneimittelforschung. 1996 Sep;46(9):884-6. PMID: 8876937. 5: Nishizawa Y, Yamamoto T, Terada N, Fushiki S, Amakata Y, Nishizawa Y. Effects of antiallergic drugs on the proliferation of estrogen-sensitive mouse Leydig cell line. Anticancer Res. 1996 May-Jun;16(3A):1241-5. PMID: 8702244. 6: Yamada N, Arai Y, Funayama K, Kadowaki S, Takahashi K, Umezu K. Effect of a major metabolite of the antiallergic drug repirinast on phosphodiesterase and adenylate cyclase activities. Arzneimittelforschung. 1995 Jan;45(1):33-5. PMID: 7534459. 7: Hojo M, Hamasaki Y, Fujita I, Koga H, Matsumoto S, Miyazaki S. Effects of anti-allergy drugs on fMet-Leu-Phe-stimulated superoxide generation in human neutrophils. Ann Allergy. 1994 Jul;73(1):21-6. PMID: 7913297. 8: Kurumaji Y, Shono M. Drug-induced solar urticaria due to repirinast. Dermatology. 1994;188(2):117-21. doi: 10.1159/000247114. PMID: 8136537. 9: Kobayashi K, Hiroi J, Kishi S, Sawase K, Hirayama Y, Chihara S, Imai T, Shigi Y, Shimomura K, Kohsaka M. Effects of quinotolast, a new orally active antiallergic drug, on experimental allergic models. Jpn J Pharmacol. 1993 Sep;63(1):73-81. doi: 10.1254/jjp.63.73. PMID: 7505860. 10: Yamada N, Ohgaki M, Muramatsu M. Repirinast inhibits antigen-induced early and late pulmonary responses and airway hyperresponsiveness in guinea pigs. Int Arch Allergy Immunol. 1993;100(4):367-72. doi: 10.1159/000236440. PMID: 8386963. 11: Schaefer HG, Beermann D, Horstmann R, Wargenau M, Heibel BA, Kuhlmann J. Effect of food on the pharmacokinetics of the active metabolite of the prodrug repirinast. J Pharm Sci. 1993 Jan;82(1):107-9. doi: 10.1002/jps.2600820123. PMID: 8381486. 12: Patel PC, Rutherford BC, Lux J, Cockcroft DW. The effect of repirinast on airway responsiveness to methacholine and allergen. J Allergy Clin Immunol. 1992 Nov;90(5):782-8. doi: 10.1016/0091-6749(92)90102-8. PMID: 1331217. 13: Yamada N, Kadowaki S, Takahashi K, Umezu K. MY-1250, a major metabolite of the anti-allergic drug repirinast, induces phosphorylation of a 78-kDa protein in rat mast cells. Biochem Pharmacol. 1992 Sep 25;44(6):1211-3. doi: 10.1016/0006-2952(92)90387-x. PMID: 1358073. 14: Umeki S. Effects of anti-allergic drugs on human neutrophil superoxide- generating NADPH oxidase. Biochem Pharmacol. 1992 Mar 3;43(5):1109-17. doi: 10.1016/0006-2952(92)90619-t. PMID: 1372806. 15: Takei M, Endo K, Takahashi K. Mechanism of action of MY-1250, an active metabolite of Repirinast, in inhibiting histamine release from rat mast cells. Br J Pharmacol. 1992 Mar;105(3):587-90. doi: 10.1111/j.1476-5381.1992.tb09023.x. PMID: 1378339; PMCID: PMC1908474. 16: Beermann D, Schaefer HG, Wargenau M, Heibel B, Sturm Y, Kuhlmann J. Pharmacokinetics of the active metabolite of the prodrug repirinast in healthy Caucasian volunteers after a single oral dose. Eur J Clin Pharmacol. 1992;42(3):307-12. doi: 10.1007/BF00266353. PMID: 1315685. 17: Hoshino K, Kawasaki A, Mizushima Y, Yano S. Effect of antiallergic agents and bronchial hypersensitivity in short-term bronchial asthma. Chest. 1991 Jul;100(1):57-62. doi: 10.1378/chest.100.1.57. PMID: 1711952. 18: Nagata M, Tabe K, Houya I, Kiuchi H, Sakamoto Y, Yamamoto K, Dohi Y. [The influence of repirinast, an anti-allergic drug, on theophylline pharmacokinetics in patients with bronchial asthma]. Nihon Kyobu Shikkan Gakkai Zasshi. 1991 Apr;29(4):413-9. Japanese. PMID: 1650860. 19: Upton RA. Pharmacokinetic interactions between theophylline and other medication (Part I). Clin Pharmacokinet. 1991 Jan;20(1):66-80. doi: 10.2165/00003088-199120010-00005. PMID: 1674242. 20: Taniguchi K, Masuda Y, Takanaka K. Action sites of antiallergic drugs on human neutrophils. Jpn J Pharmacol. 1990 Jan;52(1):101-8. doi: 10.1254/jjp.52.101. PMID: 2155337.