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MedKoo Cat#: 585339 | Name: Piriprost

Description:

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

Piriprost is a leukotriene inhibitor attenuates the smoke-induced increase in alveolar-capillary barrier permeability and decrease in plasminogen activator activity and causes a swelling of type I alveolar epithelium.

Chemical Structure

Piriprost
Piriprost
CAS#79672-88-1 (free base)

Theoretical Analysis

MedKoo Cat#: 585339

Name: Piriprost

CAS#: 79672-88-1 (free base)

Chemical Formula: C26H35NO4

Exact Mass: 425.2566

Molecular Weight: 425.57

Elemental Analysis: C, 73.38; H, 8.29; N, 3.29; O, 15.04

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.
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Related CAS #
88851-62-1 (K); 79672-88-1 (free base)
Synonym
Piriprost; U-60,257; U60,257; U 60,257
IUPAC/Chemical Name
5-[(4R,5R)-5-hydroxy-4-[(E,3S)-3-hydroxyoct-1-enyl]-1-phenyl-5,6-dihydro-4H-cyclopenta[b]pyrrol-2-yl]pentanoic acid
InChi Key
CZIIGGQJILPHEU-HCHVXQBBSA-N
InChi Code
InChI=1S/C26H35NO4/c1-2-3-5-13-21(28)15-16-22-23-17-20(12-8-9-14-26(30)31)27(24(23)18-25(22)29)19-10-6-4-7-11-19/h4,6-7,10-11,15-17,21-22,25,28-29H,2-3,5,8-9,12-14,18H2,1H3,(H,30,31)/b16-15+/t21-,22+,25+/m0/s1
SMILES Code
O=C(O)CCCCC1=CC([C@@H](/C=C/[C@@H](O)CCCCC)[C@H](O)C2)=C2N1C3=CC=CC=C3
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

Preparing Stock Solutions

The following data is based on the product molecular weight 425.57 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: Tew KD, Bomber AM, Hoffman SJ. Ethacrynic acid and piriprost as enhancers of cytotoxicity in drug resistant and sensitive cell lines. Cancer Res. 1988 Jul 1;48(13):3622-5. PubMed PMID: 3288331. 2: Mann JS, Robinson C, Sheridan AQ, Clement P, Bach MK, Holgate ST. Effect of inhaled piriprost (U-60, 257) a novel leukotriene inhibitor, on allergen and exercise induced bronchoconstriction in asthma. Thorax. 1986 Oct;41(10):746-52. PubMed PMID: 3538476; PubMed Central PMCID: PMC460468. 3: Cejic SS, Kennedy TG. Examination of the effects of piriprost (U-60,257B) on alkaline phosphatase activity of rat endometrial stromal cells in vitro. Prostaglandins. 1991 Aug;42(2):179-89. PubMed PMID: 1775638. 4: Witten ML, Grad R, Quan SF, Sobonya RE, Hubbard AK, Lantz RC, Lentz LA, Devine LC, Lemen RJ. Piriprost pretreatment attenuates the smoke-induced increase in 99mTcDTPA lung clearance. Exp Lung Res. 1990 Jul-Aug;16(4):339-53. PubMed PMID: 2118452. 5: Johnson HG, Stout BK, Ruppel PL. Inhibition of the 5-lipoxygenase pathway with piriprost (U-60,257) protects normal primates from ozone-induced methacholine hyperresponsive small airways. Prostaglandins. 1988 Mar;35(3):459-66. PubMed PMID: 3287458. 6: Cejic SS, Kennedy TG. Effects of piriprost (U-60, 257B) and leukotrienes on alkaline phosphatase activity of rat endometrial stromal cells in vitro. Prostaglandins. 1991 Aug;42(2):163-79. PubMed PMID: 1663640. 7: Bach MK, Brashler JR. Inhibition of the leukotriene synthetase of rat basophil leukemia cells by diethylcarbamazine, and synergism between diethylcarbamazine and piriprost, a 5-lipoxygenase inhibitor. Biochem Pharmacol. 1986 Feb 1;35(3):425-33. PubMed PMID: 3004501. 8: Bach MK, Brashler JR, White GJ, Galli SJ. Experiments on the mode of action of piriprost (U-60,257), an inhibitor of leukotriene formation in cloned mouse mast cells and in rat basophil leukemia cells. Biochem Pharmacol. 1987 May 1;36(9):1461-6. PubMed PMID: 3107573. 9: Bach MK, O'Brien J, Brashler JR, Johnson MA, Morton DR Jr. Inhibition of rat liver glutathione S-transferases by piriprost: kinetics of the inhibition and preliminary evidence that piriprost may be a poor alternative substrate for these enzymes. Res Commun Chem Pathol Pharmacol. 1985 Sep;49(3):361-86. PubMed PMID: 3903894. 10: Flament J, Schandene L, Boeynaems JM. Effect of the 5-lipoxygenase inhibitor piriprost on superoxide production by human neutrophils. Prostaglandins Leukot Essent Fatty Acids. 1988 Dec;34(3):175-80. PubMed PMID: 2851839. 11: Mehta JL, Mehta P, Ward MB, Lawson D. Inhibition of human platelet and neutrophil function by piriprost (U-60,257). Prostaglandins Leukot Med. 1987 Oct;29(2-3):259-67. PubMed PMID: 3124134. 12: Keane WF, Gekker G, Schlievert PM, Peterson PK. Enhancement of endotoxin-induced isolated renal tubular cell injury by toxic shock syndrome toxin 1. Am J Pathol. 1986 Jan;122(1):169-76. PubMed PMID: 3079956; PubMed Central PMCID: PMC1888123. 13: Arenas G, Del Buono R, Oyarzún MJ, Donoso P, Quijada D. Pulmonary response to free fatty acid intravenous infusion in the rabbit: role of leukotrienes and the effect of prostacyclin. Arch Biol Med Exp (Santiago). 1989 Dec;22(4):379-85. PubMed PMID: 2488536. 14: Lawson CF, Smith HW, Fitzpatrick FA. Effect of Piriprost, a 5-lipoxygenase inhibitor, on leukocyte accumulation during thioglycollate-induced acute inflammation. Wien Klin Wochenschr. 1986 Feb 21;98(4):110-3. PubMed PMID: 3085355. 15: Bach MK, Griffin RL, Richards IM. Inhibition of the presumably leukotriene-dependent component of antigen-induced bronchoconstriction in the guinea pig by piriprost (U-60,257). Int Arch Allergy Appl Immunol. 1985;77(1-2):264-6. PubMed PMID: 3924840. 16: Lebidois J, Soifer SJ, Clyman RI, Heymann MA. Piriprost: a putative leukotriene synthesis inhibitor increases pulmonary blood flow in fetal lambs. Pediatr Res. 1987 Sep;22(3):350-4. PubMed PMID: 3309861. 17: Snider BG, Theis DL, Plaisted SM. Stability studies on piriprost and piriprost potassium using high-performance liquid chromatography. J Chromatogr. 1986 Sep 26;367(1):254-9. PubMed PMID: 3536978. 18: Bach MK, Bowman BJ, Brashler JR, Fitzpatrick FA, Griffin RL, Johnson HG, Major NJ, McGuire JC, McNee ML, Richards IM, et al. Piriprost: a selective inhibitor of leukotriene synthesis. Adv Prostaglandin Thromboxane Leukot Res. 1985;15:225-7. PubMed PMID: 2936098. 19: Burka JF. Pharmacological modulation of responses of guinea-pig airways contracted with antigen and calcium ionophore A23187. Br J Pharmacol. 1985 Jun;85(2):411-20. PubMed PMID: 3928008; PubMed Central PMCID: PMC1916616. 20: Smith RJ, Bowman BJ, Speziale SC. Interleukin-1 stimulates granule exocytosis from human neutrophils. Int J Immunopharmacol. 1986;8(1):33-40. PubMed PMID: 2420732.

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