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MedKoo Cat#: 525436 | Name: Leupeptin HCl

Description:

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

Leupeptin is a naturally occurring protease inhibitor that can inhibit cysteine, serine and threonine peptidases. Leupeptin is an organic compound produced by actinomycetes. Leupeptin inhibits serine proteinases (trypsin (Ki=3.5 nM), plasmin (Ki= 3.4 nM), porcine kallikrein), and cysteine proteinases (papain, cathepsin B (Ki = 4.1 nM), endoproteinase Lys-C). It does not inhibit α-chymotrypsin or thrombin. Leupeptin is a competitive transition state inhibitor and its inhibition may be relieved by an excess of substrate.

Chemical Structure

Leupeptin HCl
CAS#39740-82-4 (HCl)

Theoretical Analysis

MedKoo Cat#: 525436

Name: Leupeptin HCl

CAS#: 39740-82-4 (HCl)

Chemical Formula: C20H39ClN6O4

Exact Mass: 426.2955

Molecular Weight: 463.02

Elemental Analysis: C, 51.88; H, 8.49; Cl, 7.66; N, 18.15; O, 13.82

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 #
39740-82-4 (HCl) 55123-66-5 (free base) 1082207-96-2 (hemisulfate hydrate) 103476-89-7 (hemisulfate) 24365-47-7 (free base)
Synonym
Leupeptin HCl; Leupeptin hydrochloride; Leupeptin Ac-LL; N-Acetyl-L-leucyl-L-leucyl-L-argininal; NK-381; NK 381; NK381;
IUPAC/Chemical Name
(S)-2-acetamido-N-((S)-1-(((R)-5-guanidino-1-oxopentan-2-yl)amino)-4-methyl-1-oxopentan-2-yl)-4-methylpentanamide hydrochloride
InChi Key
OQQYPQNFLLAILR-LPZNKSAJSA-N
InChi Code
InChI=1S/C20H38N6O4.ClH/c1-12(2)9-16(24-14(5)28)19(30)26-17(10-13(3)4)18(29)25-15(11-27)7-6-8-23-20(21)22;/h11-13,15-17H,6-10H2,1-5H3,(H,24,28)(H,25,29)(H,26,30)(H4,21,22,23);1H/t15-,16+,17+;/m1./s1
SMILES Code
CC(C[C@H](NC([C@@H](NC(C)=O)CC(C)C)=O)C(N[C@H](CCCNC(N)=N)C=O)=O)C.[H]Cl
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 463.02 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: Hashimoto Y. Gelatin Zymography Using Leupeptin for the Detection of Various Cathepsin L Forms. Methods Mol Biol. 2017;1594:243-254. doi: 10.1007/978-1-4939-6934-0_16. PMID: 28456988. 2: Sharma P, Rayavara K, Ito D, Basore K, Desai SA. A CLAG3 mutation in an amphipathic transmembrane domain alters malaria parasite nutrient channels and confers leupeptin resistance. Infect Immun. 2015 Jun;83(6):2566-74. doi: 10.1128/IAI.02966-14. Epub 2015 Apr 13. PMID: 25870226; PMCID: PMC4432768. 3: Childers MK, Bogan JR, Bogan DJ, Greiner H, Holder M, Grange RW, Kornegay JN. Chronic administration of a leupeptin-derived calpain inhibitor fails to ameliorate severe muscle pathology in a canine model of duchenne muscular dystrophy. Front Pharmacol. 2012 Jan 9;2:89. doi: 10.3389/fphar.2011.00089. PMID: 22291646; PMCID: PMC3253583. 4: Gavriel H, Shulman A, Stracher A, Sohmer H. Leupeptin reduces impulse noise induced hearing loss. J Occup Med Toxicol. 2011 Dec 29;6:38. doi: 10.1186/1745-6673-6-38. PMID: 22206578; PMCID: PMC3286414. 5: Hausott B, Vallant N, Hochfilzer M, Mangger S, Irschick R, Haugsten EM, Klimaschewski L. Leupeptin enhances cell surface localization of fibroblast growth factor receptor 1 in adult sensory neurons by increased recycling. Eur J Cell Biol. 2012 Feb;91(2):129-38. doi: 10.1016/j.ejcb.2011.09.009. Epub 2011 Dec 9. PMID: 22169219. 6: Haspel J, Shaik RS, Ifedigbo E, Nakahira K, Dolinay T, Englert JA, Choi AM. Characterization of macroautophagic flux in vivo using a leupeptin-based assay. Autophagy. 2011 Jun;7(6):629-42. doi: 10.4161/auto.7.6.15100. Epub 2011 Jun 1. PMID: 21460622; PMCID: PMC3127049. 7: Abaamrane L, Raffin F, Schmerber S, Sendowski I. Intracochlear perfusion of leupeptin and z-VAD-FMK: influence of antiapoptotic agents on gunshot-induced hearing loss. Eur Arch Otorhinolaryngol. 2011 Jul;268(7):987-93. doi: 10.1007/s00405-011-1487-0. Epub 2011 Jan 19. PMID: 21246210. 8: Selsby J, Pendrak K, Zadel M, Tian Z, Pham J, Carver T, Acosta P, Barton E, Sweeney HL. Leupeptin-based inhibitors do not improve the mdx phenotype. Am J Physiol Regul Integr Comp Physiol. 2010 Nov;299(5):R1192-201. doi: 10.1152/ajpregu.00586.2009. Epub 2010 Sep 15. PMID: 20844259; PMCID: PMC3774252. 9: Muscari C, Capanni C, Giordano E, Stefanelli C, Bonavita F, Stanic I, Bonafè F, Caldarera CM, Guarnieri C. Leupeptin preserves cardiac nitric oxide synthase 3 during reperfusion following long-term cardioplegia. J Surg Res. 2010 Nov;164(1):e27-35. doi: 10.1016/j.jss.2010.05.041. Epub 2010 Jun 12. PMID: 20828747. 10: Kanias T, Acker JP. G.B. Quan et al., Inhibition of high glucose-induced erythrocyte phosphatidylserine exposure by leupeptin and disaccharides, Cryobiology 56 (1) (2008) 53-61. Cryobiology. 2009 Apr;58(2):240. doi: 10.1016/j.cryobiol.2008.12.010. Epub 2009 Jan 3. PMID: 19168046. 11: Lisk G, Pain M, Gluzman IY, Kambhampati S, Furuya T, Su XZ, Fay MP, Goldberg DE, Desai SA. Changes in the plasmodial surface anion channel reduce leupeptin uptake and can confer drug resistance in Plasmodium falciparum-infected erythrocytes. Antimicrob Agents Chemother. 2008 Jul;52(7):2346-54. doi: 10.1128/AAC.00057-08. Epub 2008 Apr 28. PMID: 18443109; PMCID: PMC2443925. 12: Quan GB, Han Y, Yang C, Hu WB, Liu A, Wang JX, Wang Y, Liu MX. Inhibition of high glucose-induced erythrocyte phosphatidylserine exposure by leupeptin and disaccharides. Cryobiology. 2008 Feb;56(1):53-61. doi: 10.1016/j.cryobiol.2007.11.001. Epub 2007 Nov 17. PMID: 18093577. 13: Maes K, Testelmans D, Powers S, Decramer M, Gayan-Ramirez G. Leupeptin inhibits ventilator-induced diaphragm dysfunction in rats. Am J Respir Crit Care Med. 2007 Jun 1;175(11):1134-8. doi: 10.1164/rccm.200609-1342OC. Epub 2007 Mar 22. PMID: 17379854. 14: Momiyama J, Hashimoto T, Matsubara A, Futai K, Namba A, Shinkawa H. Leupeptin, a calpain inhibitor, protects inner ear hair cells from aminoglycoside ototoxicity. Tohoku J Exp Med. 2006 Jun;209(2):89-97. doi: 10.1620/tjem.209.89. PMID: 16707850. 15: Rohr KB, Selwood T, Marquardt U, Huber R, Schechter NM, Bode W, Than ME. X-ray structures of free and leupeptin-complexed human alphaI-tryptase mutants: indication for an alpha-->beta-tryptase transition. J Mol Biol. 2006 Mar 17;357(1):195-209. doi: 10.1016/j.jmb.2005.12.037. Epub 2005 Dec 28. PMID: 16414069. 16: Zhang HC, Karata K, Matsushita K, Takahashi S, Tong XB, Lu J, Zhu CL, Sugaya S, Suzuki T, Suzuki N. Leupeptin-sensitive proteases involved in cell survival after X-ray irradiation in human RSa cells. Cell Biol Int. 2005 Aug;29(8):662-8. doi: 10.1016/j.cellbi.2005.03.023. PMID: 15963736. 17: Nakajima T, Takauchi S, Ohara K, Kokai M, Nishii R, Maeda S, Takanaga A, Tanaka T, Takeda M, Seki M, Morita Y. Alpha-synuclein-positive structures induced in leupeptin-infused rats. Brain Res. 2005 Apr 8;1040(1-2):73-80. doi: 10.1016/j.brainres.2005.01.099. PMID: 15804428. 18: Moldoveanu T, Campbell RL, Cuerrier D, Davies PL. Crystal structures of calpain-E64 and -leupeptin inhibitor complexes reveal mobile loops gating the active site. J Mol Biol. 2004 Nov 5;343(5):1313-26. doi: 10.1016/j.jmb.2004.09.016. PMID: 15491615. 19: Kieran D, Greensmith L. Inhibition of calpains, by treatment with leupeptin, improves motoneuron survival and muscle function in models of motoneuron degeneration. Neuroscience. 2004;125(2):427-39. doi: 10.1016/j.neuroscience.2004.01.046. PMID: 15062985. 20: Rudziński T, Mussur M, Gwiazda Z, Mussur M. Protease inhibitor leupeptin attenuates myocardial stunning in rat heart. Med Sci Monit. 2004 Jan;10(1):BR4-10. PMID: 14704627.