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MedKoo Cat#: 529404 | Name: Pralnacasan

Description:

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

Pralnacasan is a caspase 1 (IL-1beta converting enzyme) inhibitor potentially for the treatment of osteoarthritis.

Chemical Structure

Pralnacasan
Pralnacasan
CAS#192755-52-5

Theoretical Analysis

MedKoo Cat#: 529404

Name: Pralnacasan

CAS#: 192755-52-5

Chemical Formula: C26H29N5O7

Exact Mass: 523.2067

Molecular Weight: 523.54

Elemental Analysis: C, 59.65; H, 5.58; N, 13.38; O, 21.39

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 #
No Data
Synonym
HMR-3480; VX-740; HMR3480; VX740; HMR 3480; VX 740
IUPAC/Chemical Name
(1S,9S)-N-((2R,3S)-2-ethoxy-5-oxotetrahydrofuran-3-yl)-9-(isoquinoline-1-carboxamido)-6,10-dioxooctahydro-6H-pyridazino[1,2-a][1,2]diazepine-1-carboxamide
InChi Key
CXAGHAZMQSCAKJ-WAHHBDPQSA-N
InChi Code
InChI=1S/C26H29N5O7/c1-2-37-26-18(14-21(33)38-26)29-23(34)19-8-5-13-30-20(32)10-9-17(25(36)31(19)30)28-24(35)22-16-7-4-3-6-15(16)11-12-27-22/h3-4,6-7,11-12,17-19,26H,2,5,8-10,13-14H2,1H3,(H,28,35)(H,29,34)/t17-,18-,19-,26+/m0/s1
SMILES Code
O=C([C@@H]1CCCN2N1C([C@@H](NC(C3=NC=CC4=C3C=CC=C4)=O)CCC2=O)=O)N[C@@H](C5)[C@H](OCC)OC5=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 523.54 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: Bauer C, Loher F, Dauer M, Mayer C, Lehr HA, Schönharting M, Hallwachs R, Endres S, Eigler A. The ICE inhibitor pralnacasan prevents DSS-induced colitis in C57BL/6 mice and suppresses IP-10 mRNA but not TNF-alpha mRNA expression. Dig Dis Sci. 2007 Jul;52(7):1642-52. PubMed PMID: 17393315. 2: Loher F, Bauer C, Landauer N, Schmall K, Siegmund B, Lehr HA, Dauer M, Schoenharting M, Endres S, Eigler A. The interleukin-1 beta-converting enzyme inhibitor pralnacasan reduces dextran sulfate sodium-induced murine colitis and T helper 1 T-cell activation. J Pharmacol Exp Ther. 2004 Feb;308(2):583-90. PubMed PMID: 14610233. 3: Rudolphi K, Gerwin N, Verzijl N, van der Kraan P, van den Berg W. Pralnacasan, an inhibitor of interleukin-1beta converting enzyme, reduces joint damage in two murine models of osteoarthritis. Osteoarthritis Cartilage. 2003 Oct;11(10):738-46. PubMed PMID: 13129693. 4: Siegmund B, Zeitz M. Pralnacasan (vertex pharmaceuticals). IDrugs. 2003 Feb;6(2):154-8. Review. PubMed PMID: 12789619. 5: Handy EL, Totaro KA, Lin CP, Sello JK. Efficient and regiospecific syntheses of peptides with piperazic and dehydropiperazic acids via a multicomponent reaction. Org Lett. 2014 Jul 3;16(13):3488-91. doi: 10.1021/ol501425b. PubMed PMID: 24937740. 6: Ravizza T, Lucas SM, Balosso S, Bernardino L, Ku G, Noé F, Malva J, Randle JC, Allan S, Vezzani A. Inactivation of caspase-1 in rodent brain: a novel anticonvulsive strategy. Epilepsia. 2006 Jul;47(7):1160-8. PubMed PMID: 16886979. 7: Riad A, Walther T, Yang J, Altmann C, Escher F, Westermann D, Spillmann F, Schultheiss HP, Tschöpe C. The cardiovascular influence of interleukin-1 beta on the expression of bradykinin B1 and B2 receptors. Int Immunopharmacol. 2008 Feb;8(2):222-30. doi: 10.1016/j.intimp.2007.07.027. PubMed PMID: 18182231. 8: Cornelis S, Kersse K, Festjens N, Lamkanfi M, Vandenabeele P. Inflammatory caspases: targets for novel therapies. Curr Pharm Des. 2007;13(4):367-85. Review. PubMed PMID: 17311555. 9: Timmermans K, van der Wal SE, Vaneker M, van der Laak JA, Netea MG, Pickkers P, Scheffer GJ, Joosten LA, Kox M. IL-1β processing in mechanical ventilation-induced inflammation is dependent on neutrophil factors rather than caspase-1. Intensive Care Med Exp. 2013 Dec;1(1):27. doi: 10.1186/2197-425X-1-8. PubMed PMID: 26266796; PubMed Central PMCID: PMC4797957. 10: Qian L, Zhang CJ, Wu J, Yao SQ. Fused Bicyclic Caspase-1 Inhibitors Assembled by Copper-Free Strain-Promoted Alkyne-Azide Cycloaddition (SPAAC). Chemistry. 2017 Jan 5;23(2):360-369. doi: 10.1002/chem.201603150. PubMed PMID: 27882694. 11: Bauer C, Duewell P, Mayer C, Lehr HA, Fitzgerald KA, Dauer M, Tschopp J, Endres S, Latz E, Schnurr M. Colitis induced in mice with dextran sulfate sodium (DSS) is mediated by the NLRP3 inflammasome. Gut. 2010 Sep;59(9):1192-9. doi: 10.1136/gut.2009.197822. PubMed PMID: 20442201. 12: Gotham S. Digestive Disease Week 2004. Bowel inflammation. IDrugs. 2004 Jun;7(6):516-9. PubMed PMID: 15197649. 13: Ross J, Brough D, Gibson RM, Loddick SA, Rothwell NJ. A selective, non-peptide caspase-1 inhibitor, VRT-018858, markedly reduces brain damage induced by transient ischemia in the rat. Neuropharmacology. 2007 Oct;53(5):638-42. PubMed PMID: 17845807. 14: Hauff K, Zamzow C, Law WJ, De Melo J, Kennedy K, Los M. Peptide-based approaches to treat asthma, arthritis, other autoimmune diseases and pathologies of the central nervous system. Arch Immunol Ther Exp (Warsz). 2005 Jul-Aug;53(4):308-20. Review. PubMed PMID: 16088315. 15: Linton SD. Caspase inhibitors: a pharmaceutical industry perspective. Curr Top Med Chem. 2005;5(16):1697-717. Review. PubMed PMID: 16375749. 16: Bayés M, Rabasseda X, Prous JR. Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2003 Jan-Feb;25(1):53-76. PubMed PMID: 12690708. 17: Siegmund B. Interleukin-1beta converting enzyme (caspase-1) in intestinal inflammation. Biochem Pharmacol. 2002 Jul 1;64(1):1-8. Review. PubMed PMID: 12106600. 18: Leung-Toung R, Li W, Tam TF, Karimian K. Thiol-dependent enzymes and their inhibitors: a review. Curr Med Chem. 2002 May;9(9):979-1002. Review. PubMed PMID: 11966457. 19: Randle JC, Harding MW, Ku G, Schönharting M, Kurrle R. ICE/Caspase-1 inhibitors as novel anti-inflammatory drugs. Expert Opin Investig Drugs. 2001 Jul;10(7):1207-9. Review. PubMed PMID: 11772244.