Ac-YVAD-CMK | CAS#178603-78-6

MedKoo Cat#: 556338 | Name: Ac-YVAD-CMK

Description:

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

Ac-YVAD-CMK is a selective, irreversible inhibitor of interleukin-1β converting enzyme (ICE; Caspase-1). Ac-YVAD-CMK is neuroprotective in a rat model of cerebral ischemia.

Chemical Structure

Ac-YVAD-CMK

CAS#178603-78-6

Theoretical Analysis

MedKoo Cat#: 556338

Name: Ac-YVAD-CMK

CAS#: 178603-78-6

Chemical Formula: C24H33ClN4O8

Exact Mass: 540.1987

Molecular Weight: 541.00

Elemental Analysis: C, 53.28; H, 6.15; Cl, 6.55; N, 10.36; O, 23.66

Price and Availability

Size	Price	Availability
5mg	USD 350.00	2 Weeks
10mg	USD 650.00	2 Weeks
25mg	USD 1,250.00	2 Weeks
50mg	USD 1,950.00	2 Weeks
100mg	USD 3,250.00	2 Weeks
200mg	USD 4,250.00	2 Weeks
500mg	USD 6,950.00	2 Weeks
1g	USD 8,950.00	2 Weeks

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Related CAS #

No Data

Synonym

Ac-YVAD-CMK; N-Ac-Tyr-Val-Ala-Asp-CMK;

IUPAC/Chemical Name

(4S,7S,10S,13S)-13-(2-chloroacetyl)-4-(4-hydroxybenzyl)-7-isopropyl-10-methyl-2,5,8,11-tetraoxo-3,6,9,12-tetraazapentadecan-15-oic acid

InChi Key

UOUBHJRCKHLGFB-DGJUNBOTSA-N

InChi Code

InChI=1S/C24H33ClN4O8/c1-12(2)21(24(37)26-13(3)22(35)28-17(10-20(33)34)19(32)11-25)29-23(36)18(27-14(4)30)9-15-5-7-16(31)8-6-15/h5-8,12-13,17-18,21,31H,9-11H2,1-4H3,(H,26,37)(H,27,30)(H,28,35)(H,29,36)(H,33,34)/t13-,17-,18-,21-/m0/s1

SMILES Code

CC(N[C@@H](CC1=CC=C(O)C=C1)C(N[C@@H](C(C)C)C(N[C@@H](C)C(N[C@H](C(CCl)=O)CC(O)=O)=O)=O)=O)=O

Appearance

To be determined

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

To be determined

Shelf Life

>2 years if stored properly

Drug Formulation

To be determined

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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 541.00 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

1: Yang M, Fang JT, Zhang NS, Qin LJ, Zhuang YY, Wang WW, Zhu HP, Zhang YJ, Xia P, Zhang Y. Caspase-1-Inhibitor AC-YVAD-CMK Inhibits Pyroptosis and Ameliorates Acute Kidney Injury in a Model of Sepsis. Biomed Res Int. 2021 Jun 10;2021:6636621. doi: 10.1155/2021/6636621. PMID: 34222479; PMCID: PMC8213477. 2: Tanaka T, Warner BM, Michael DG, Nakamura H, Odani T, Yin H, Atsumi T, Noguchi M, Chiorini JA. LAMP3 inhibits autophagy and contributes to cell death by lysosomal membrane permeabilization. Autophagy. 2022 Jul;18(7):1629-1647. doi: 10.1080/15548627.2021.1995150. Epub 2021 Nov 22. PMID: 34802379; PMCID: PMC9298453. 3: Qiu Z, He Y, Ming H, Lei S, Leng Y, Xia ZY. Lipopolysaccharide (LPS) Aggravates High Glucose- and Hypoxia/Reoxygenation-Induced Injury through Activating ROS-Dependent NLRP3 Inflammasome-Mediated Pyroptosis in H9C2 Cardiomyocytes. J Diabetes Res. 2019 Feb 17;2019:8151836. doi: 10.1155/2019/8151836. PMID: 30911553; PMCID: PMC6398034. 4: Lin X, Ye H, Siaw-Debrah F, Pan S, He Z, Ni H, Xu Z, Jin K, Zhuge Q, Huang L. AC-YVAD-CMK Inhibits Pyroptosis and Improves Functional Outcome after Intracerebral Hemorrhage. Biomed Res Int. 2018 Oct 16;2018:3706047. doi: 10.1155/2018/3706047. PMID: 30410928; PMCID: PMC6206581. 5: Liang H, Sun Y, Gao A, Zhang N, Jia Y, Yang S, Na M, Liu H, Cheng X, Fang X, Ma W, Zhang X, Wang F. Ac-YVAD-cmk improves neurological function by inhibiting caspase-1-mediated inflammatory response in the intracerebral hemorrhage of rats. Int Immunopharmacol. 2019 Oct;75:105771. doi: 10.1016/j.intimp.2019.105771. Epub 2019 Jul 25. Erratum in: Int Immunopharmacol. 2023 Jun;119:110283. PMID: 31352322. 6: Zheng D, Wang H, Zhou Y, Chen Y, Chen G. Ac-YVAD-cmk ameliorated sevoflurane- induced cognitive dysfunction and revised mitophagy impairment. PLoS One. 2023 Jan 25;18(1):e0280914. doi: 10.1371/journal.pone.0280914. PMID: 36696410; PMCID: PMC9876368. 7: Pan P, Shen M, Yu Z, Ge W, Chen K, Tian M, Xiao F, Wang Z, Wang J, Jia Y, Wang W, Wan P, Zhang J, Chen W, Lei Z, Chen X, Luo Z, Zhang Q, Xu M, Li G, Li Y, Wu J. SARS-CoV-2 N protein promotes NLRP3 inflammasome activation to induce hyperinflammation. Nat Commun. 2021 Aug 2;12(1):4664. doi: 10.1038/s41467-021-25015-6. Erratum in: Nat Commun. 2021 Aug 31;12(1):5306. PMID: 34341353; PMCID: PMC8329225. 8: Zhang F, Wang L, Wang JJ, Luo PF, Wang XT, Xia ZF. The caspase-1 inhibitor AC-YVAD-CMK attenuates acute gastric injury in mice: involvement of silencing NLRP3 inflammasome activities. Sci Rep. 2016 Apr 7;6:24166. doi: 10.1038/srep24166. PMID: 27053298; PMCID: PMC4823746. 9: Wu B, Ma Q, Khatibi N, Chen W, Sozen T, Cheng O, Tang J. Ac-YVAD-CMK Decreases Blood-Brain Barrier Degradation by Inhibiting Caspase-1 Activation of Interleukin-1β in Intracerebral Hemorrhage Mouse Model. Transl Stroke Res. 2010 Mar 1;1(1):57-64. doi: 10.1007/s12975-009-0002-z. PMID: 20596246; PMCID: PMC2892994. 10: Kim H, Seo JS, Lee SY, Ha KT, Choi BT, Shin YI, Ju Yun Y, Shin HK. AIM2 inflammasome contributes to brain injury and chronic post-stroke cognitive impairment in mice. Brain Behav Immun. 2020 Jul;87:765-776. doi: 10.1016/j.bbi.2020.03.011. Epub 2020 Mar 19. PMID: 32201254. 11: Wang Z, Meng S, Cao L, Chen Y, Zuo Z, Peng S. Critical role of NLRP3-caspase-1 pathway in age-dependent isoflurane-induced microglial inflammatory response and cognitive impairment. J Neuroinflammation. 2018 Apr 17;15(1):109. doi: 10.1186/s12974-018-1137-1. PMID: 29665808; PMCID: PMC5904978. 12: Chang Y, Zhu J, Wang D, Li H, He Y, Liu K, Wang X, Peng Y, Pan S, Huang K. NLRP3 inflammasome-mediated microglial pyroptosis is critically involved in the development of post-cardiac arrest brain injury. J Neuroinflammation. 2020 Jul 23;17(1):219. doi: 10.1186/s12974-020-01879-1. PMID: 32703306; PMCID: PMC7376727. 13: Zhang L, Xing R, Huang Z, Zhang N, Zhang L, Li X, Wang P. Inhibition of Synovial Macrophage Pyroptosis Alleviates Synovitis and Fibrosis in Knee Osteoarthritis. Mediators Inflamm. 2019 Sep 8;2019:2165918. doi: 10.1155/2019/2165918. PMID: 31582897; PMCID: PMC6754937. 14: Li H, Li Y, Song C, Hu Y, Dai M, Liu B, Pan P. Neutrophil Extracellular Traps Augmented Alveolar Macrophage Pyroptosis via AIM2 Inflammasome Activation in LPS-Induced ALI/ARDS. J Inflamm Res. 2021 Sep 21;14:4839-4858. doi: 10.2147/JIR.S321513. PMID: 34588792; PMCID: PMC8473117. 15: Wang Z, Zhou L, An D, Xu W, Wu C, Sha S, Li Y, Zhu Y, Chen A, Du Y, Chen L, Chen L. TRPV4-induced inflammatory response is involved in neuronal death in pilocarpine model of temporal lobe epilepsy in mice. Cell Death Dis. 2019 May 16;10(6):386. doi: 10.1038/s41419-019-1612-3. Erratum in: Cell Death Dis. 2019 Jun 21;10(7):491. PMID: 31097691; PMCID: PMC6522539. 16: Mathiak G, Grass G, Herzmann T, Luebke T, Zetina CC, Boehm SA, Bohlen H, Neville LF, Hoelscher AH. Caspase-1-inhibitor ac-YVAD-cmk reduces LPS-lethality in rats without affecting haematology or cytokine responses. Br J Pharmacol. 2000 Oct;131(3):383-6. doi: 10.1038/sj.bjp.0703629. PMID: 11015286; PMCID: PMC1572369. 17: Liang H, Sun Y, Gao A, Zhang N, Jia Y, Yang S, Na M, Liu H, Cheng X, Fang X, Ma W, Zhang X, Wang F. Corrigendum to "Ac-YVAD-cmk improves neurological function by inhibiting caspase-1-mediated inflammatory response in the intracerebral hemorrhage of rats" [Int. Immunopharmacol. 75 (2019) 105771]. Int Immunopharmacol. 2023 Jun;119:110283. doi: 10.1016/j.intimp.2023.110283. Epub 2023 May 11. Erratum for: Int Immunopharmacol. 2019 Oct;75:105771. PMID: 37179200. 18: Fu Q, Wu J, Zhou XY, Ji MH, Mao QH, Li Q, Zong MM, Zhou ZQ, Yang JJ. NLRP3/Caspase-1 Pathway-Induced Pyroptosis Mediated Cognitive Deficits in a Mouse Model of Sepsis-Associated Encephalopathy. Inflammation. 2019 Feb;42(1):306-318. doi: 10.1007/s10753-018-0894-4. PMID: 30276509; PMCID: PMC6394578. 19: Zhang Y, Zhou X, Zhang H, Huan C, Ye Z. [Caspase-1 inhibitor AC-YVAD-CMK blocks IL-1β secretion of bone marrow-derived macrophages induced by Acinetobacter baumannii]. Xi Bao Yu Fen Zi Mian Yi Xue Za Zhi. 2017 Dec;33(12):1594-1599. Chinese. PMID: 29382416. 20: Wu X, Yao J, Hu Q, Kang H, Miao Y, Zhu L, Li C, Zhao X, Li J, Wan M, Tang W. Emodin Ameliorates Acute Pancreatitis-Associated Lung Injury Through Inhibiting the Alveolar Macrophages Pyroptosis. Front Pharmacol. 2022 Jun 2;13:873053. doi: 10.3389/fphar.2022.873053. PMID: 35721108; PMCID: PMC9201345.