MedKoo Cat#: 571555 | Name: Citiolone
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Description:

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

​Citiolone, chemically known as N-(2-oxothiolan-3-yl)acetamide, is a derivative of the amino acid cysteine. It appears as a white to off-white crystalline powder, exhibiting a melting point between 109-111 °C and an estimated density of 1.202 g/cm³. Structurally, citiolone features a thiolactone ring, which is believed to contribute to its hepatoprotective properties. Historically, citiolone has been utilized in liver therapy, particularly for its potential to mitigate liver damage. Additionally, its role as a hydroxyl free radical scavenger has been explored, with studies indicating protective effects on cells subjected to hypothermic conditions.

Chemical Structure

Citiolone
Citiolone
CAS#1195-16-0

Theoretical Analysis

MedKoo Cat#: 571555

Name: Citiolone

CAS#: 1195-16-0

Chemical Formula: C6H9NO2S

Exact Mass: 159.0354

Molecular Weight: 159.04

Elemental Analysis: C, 45.27; H, 5.70; N, 8.80; O, 20.10; S, 20.14

Price and Availability

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5g USD 350.00 2 Weeks
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Related CAS #
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Synonym
Citiolase; Citiolona; Citiolonum; NSC 22878; NSC22878; NSC-22878; BO 714; BO714; BO-714
IUPAC/Chemical Name
Acetamide, N-(tetrahydro-2-oxo-3-thienyl)-
InChi Key
NRFJZTXWLKPZAV-UHFFFAOYSA-N
InChi Code
InChI=1S/C6H9NO2S/c1-4(8)7-5-2-3-10-6(5)9/h5H,2-3H2,1H3,(H,7,8)
SMILES Code
CC(NC(CCS1)C1=O)=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 159.04 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: Sexton A, Mbiya W, Morakinyo MK, Simoyi RH. Kinetics and mechanism of the oxidation of N-acetyl homocysteine thiolactone with aqueous iodine and iodate. J Phys Chem A. 2013 Dec 5;117(48):12693-702. doi: 10.1021/jp408540u. Epub 2013 Nov 19. PubMed PMID: 24164347. 2: Mbiya W, Choi B, Martincigh BS, Morakinyo MK, Simoyi RH. Oxyhalogen-sulfur chemistry: kinetics and mechanism of oxidation of N-acetyl homocysteine thiolactone by acidified bromate and aqueous bromine. J Phys Chem A. 2013 Dec 12;117(49):13059-69. doi: 10.1021/jp408304e. Epub 2013 Nov 27. PubMed PMID: 24156819. 3: Qian F. [Conjugation of Plasmodium falciparum Pfs25 to Pseudomonas aeruginosa ExoProtein A with different chemical linkers]. Zhongguo Ji Sheng Chong Xue Yu Ji Sheng Chong Bing Za Zhi. 2011 Aug;29(4):254-7. Chinese. PubMed PMID: 21972597. 4: Bertani I, Venturi V. Regulation of the N-acyl homoserine lactone-dependent quorum-sensing system in rhizosphere Pseudomonas putida WCS358 and cross-talk with the stationary-phase RpoS sigma factor and the global regulator GacA. Appl Environ Microbiol. 2004 Sep;70(9):5493-502. PubMed PMID: 15345437; PubMed Central PMCID: PMC520884. 5: Papaccio G, De Luca B, Pisanti FA. Macrophages and antioxidant status in the NOD mouse pancreas. J Cell Biochem. 1998 Dec 15;71(4):479-90. PubMed PMID: 9827694. 6: Bapu C, Rao PA, Sood PP. Restoration of methylmercury inhibited adenosine triphosphatases during vitamin and monothiol therapy. J Environ Pathol Toxicol Oncol. 1998;17(1):75-80. PubMed PMID: 9490323. 7: Emonet N, Leccia MT, Favier A, Beani JC, Richard MJ. Thiols and selenium: protective effect on human skin fibroblasts exposed to UVA radiation. J Photochem Photobiol B. 1997 Aug;40(1):84-90. PubMed PMID: 9301047. 8: de Barrio M, Tornero P, Prieto A, Sainza T, Zubeldia JM, Herrero T. Recurrent fixed drug eruption caused by citiolone. J Investig Allergol Clin Immunol. 1997 May-Jun;7(3):193-4. PubMed PMID: 9252880. 9: Powers RW, Chambers C, Larsen WJ. Diabetes-mediated decreases in ovarian superoxide dismutase activity are related to blood-follicle barrier and ovulation defects. Endocrinology. 1996 Jul;137(7):3101-10. PubMed PMID: 8770936. 10: Delgado PG, Florido Lopez F, de San Pedro BS. Fixed drug eruption due to citiolone. Contact Dermatitis. 1995 Nov;33(5):352. PubMed PMID: 8565496. 11: Luque Sánchez M, Romero Ortego R, Moreno Corredor A. [Serum sickness type reaction to citiolone]. Aten Primaria. 1995 Sep 30;16(5):295-6. Spanish. PubMed PMID: 7578844. 12: Sood PP, Bapu C, Vijayalakshmi K. Vitamins and monothiols efficacy in the restoration of adenosine nucleotide degradation enzymes altered during methylmercury intoxication. J Environ Pathol Toxicol Oncol. 1995;14(2):101-5. PubMed PMID: 9372838. 13: Strålin P, Marklund SL. Effects of oxidative stress on expression of extracellular superoxide dismutase, CuZn-superoxide dismutase and Mn-superoxide dismutase in human dermal fibroblasts. Biochem J. 1994 Mar 1;298 ( Pt 2):347-52. PubMed PMID: 8135741; PubMed Central PMCID: PMC1137946. 14: Papaccio G, Frascatore S, Pisanti FA. An increase in superoxide dismutase counteracts islet vascular alterations in low-dose streptozocin-treated mice. Histochemistry. 1994 Mar;101(3):215-21. PubMed PMID: 8056621. 15: Bapu C, Vijayalakshmi K, Sood PP. Comparison of monothiols and vitamin therapy administered alone or in combinations during methylmercury poisoning. Bull Environ Contam Toxicol. 1994 Feb;52(2):182-9. PubMed PMID: 8123976. 16: Burkart V, Kolb H. Protection of islet cells from inflammatory cell death in vitro. Clin Exp Immunol. 1993 Aug;93(2):273-8. PubMed PMID: 8348756; PubMed Central PMCID: PMC1554829. 17: Kruuv J, Glofcheski DJ. Further evidence for two modes of hypothermia damage. Cryobiology. 1993 Jun;30(3):313-21. PubMed PMID: 8370318. 18: Sood PP, Vijayalakshmi K, Bapu C. Ameliorative capacities of vitamins and monothiols administered alone or in combinations in methylmercury mobilisation in nervous and non-nervous tissues of mice. Cell Mol Biol (Noisy-le-grand). 1993 Mar;39(2):213-9. PubMed PMID: 8513276. 19: Naqvi SM, Hasan M. Acetylhomocysteine thiolactone protection against phosphamidon-induced alteration of regional superoxide dismutase activity in the central nervous system and its correlation with altered lipid peroxidation. Indian J Exp Biol. 1992 Sep;30(9):850-2. PubMed PMID: 1478721. 20: Vinay SD, Raghu KG, Sood PP. Differential therapeutic responses of thiol compounds in the reversal of methylmercury inhibited acid phosphatase and cathepsin E in the central nervous system of rat. Bull Environ Contam Toxicol. 1992 Jul;49(1):78-84. PubMed PMID: 1392297.