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MedKoo Cat#: 591047 | Name: Cloricromen

Description:

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

Cloricromene is a platelet aggregation inhibitor. cloricromene is a coumarin derivative and exerts protective effects in models of inflammation and shock. Cloricromene treatment, which reduced tumour necrosis factor production, may be of benefit in the treatment of periodontitis. Cloricromene inhibited lipopolysaccharide-induced TNF-alpha release in a dose-dependent manner (IC(50)=5.9 +/- 0.8 microM). Cloricromene inhibited lipopolysaccharide-induced expression of TNF-alpha mRNA. Cloricromene interferes with the early signal transduction pathway triggered by lipopolysaccharide.

Chemical Structure

Cloricromen
Cloricromen
CAS#68206-94-0 (free base)

Theoretical Analysis

MedKoo Cat#: 591047

Name: Cloricromen

CAS#: 68206-94-0 (free base)

Chemical Formula: C20H26ClNO5

Exact Mass: 395.1500

Molecular Weight: 395.88

Elemental Analysis: C, 60.68; H, 6.62; Cl, 8.95; N, 3.54; O, 20.21

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 #
68206-94-0 (free base) 74697-28-2 (HCl)
Synonym
Cloricromen; Cloricromene;
IUPAC/Chemical Name
Acetic acid, ((8-chloro-3-(2-(diethylamino)ethyl)-4-methyl-2-oxo-2H-1-benzopyran-7-yl)oxy)-, ethyl ester
InChi Key
GYNNRVJJLAVVTQ-UHFFFAOYSA-N
InChi Code
InChI=1S/C20H26ClNO5/c1-5-22(6-2)11-10-15-13(4)14-8-9-16(26-12-17(23)25-7-3)18(21)19(14)27-20(15)24/h8-9H,5-7,10-12H2,1-4H3
SMILES Code
O=C(OCC)COC1=CC=C(C(O2)=C1Cl)C(C)=C(CCN(CC)CC)C2=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 395.88 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: Gao L, Wang F, Chen Y, Li F, Han B, Liu D. The antithrombotic activity of natural and synthetic coumarins. Fitoterapia. 2021 Oct;154:104947. doi: 10.1016/j.fitote.2021.104947. Epub 2021 Aug 2. PMID: 34352355. 2: Bucolo C, Ward KW, Mazzon E, Cuzzocrea S, Drago F. Protective effects of a coumarin derivative in diabetic rats. Invest Ophthalmol Vis Sci. 2009 Aug;50(8):3846-52. doi: 10.1167/iovs.08-3328. Epub 2009 Mar 11. PMID: 19279317. 3: Bucolo C, Maugeri F, Maltese A, Ward KW. Retinal and systemic pharmacokinetics of the anti-inflammatory drug cloricromene following oral administration in the rat and rabbit. J Ocul Pharmacol Ther. 2007 Jun;23(3):257-63. doi: 10.1089/jop.2006.141. PMID: 17593009. 4: Pignatello R, Maltese A, Maugeri F, Bucolo C. Enhancement of availability of cloricromene at brain level by a lipophilic prodrug. J Pharm Pharmacol. 2006 Jul;58(7):1001-5. doi: 10.1211/jpp.58.7.0017. PMID: 16805962. 5: Pignatello R, Ricupero N, Bucolo C, Maugeri F, Maltese A, Puglisi G. Preparation and characterization of eudragit retard nanosuspensions for the ocular delivery of cloricromene. AAPS PharmSciTech. 2006 Mar 24;7(1):E27. doi: 10.1208/pt070127. PMID: 16584158; PMCID: PMC2750734. 6: Muià C, Mazzon E, Zito D, Maiere D, Britti D, Crisafulli C, Oteri G, Cordasco G, Cuzzocrea S. Cloricromene, a coumarine derivative, reduced the development of periodontitis in rats. Naunyn Schmiedebergs Arch Pharmacol. 2006 Apr;373(1):51-9. doi: 10.1007/s00210-006-0048-3. Epub 2006 Mar 28. PMID: 16572308. 7: Pignatello R, Ricupero N, Bucolo C, Maugeri F, Maltese A, Puglisi G. Preparation and characterization of Eudragit Retard nanosuspensions for the ocular delivery of cloricromene. AAPS PharmSciTech. 2006 Mar;7(1):E192-E198. doi: 10.1208/pt070127. Epub 2017 Mar 8. PMID: 28290042. 8: Ragazzi E, Costa CV, Comai S, Bertazzo A, Caparrotta L, Allegri G. Cloricromene effect on the enzyme activities of the tryptophan-nicotinic acid pathway in diabetic/hyperlipidemic rabbits. Life Sci. 2006 Jan 18;78(8):785-94. doi: 10.1016/j.lfs.2005.05.077. Epub 2005 Aug 26. PMID: 16126232. 9: Ianaro A, Maffia P, Grassia G, Di Meglio P, Sorrentino R, di Villa Bianca Rd, Di Rosa M, Ialenti A. Cloricromene in endotoxemia: role of NF-kappaB. Naunyn Schmiedebergs Arch Pharmacol. 2004 Aug;370(2):140-5. doi: 10.1007/s00210-004-0956-z. Epub 2004 Jul 30. PMID: 15322736. 10: Bucolo C, Maltese A, Maugeri F, Busà B, Puglisi G, Pignatello R. Eudragit RL100 nanoparticle system for the ophthalmic delivery of cloricromene. J Pharm Pharmacol. 2004 Jul;56(7):841-6. doi: 10.1211/0022357023835. PMID: 15233861. 11: Leo E, Brina B, Forni F, Vandelli MA. In vitro evaluation of PLA nanoparticles containing a lipophilic drug in water-soluble or insoluble form. Int J Pharm. 2004 Jun 18;278(1):133-41. doi: 10.1016/j.ijpharm.2004.03.002. PMID: 15158956. 12: Fries W, Mazzon E, Sturiale S, Giofré MR, Lo Presti MA, Cuzzocrea S, Campo GM, Caputi AP, Longo G, Sturniolo GC. A protective effect of the synthetic coumarine derivative Cloricromene against DNB-colitis in the rat. Life Sci. 2004 Apr 16;74(22):2749-56. doi: 10.1016/j.lfs.2003.10.016. PMID: 15043989. 13: Bondì ML, Fontana G, Carlisi B, Giammona G. Preparation and characterization of solid lipid nanoparticles containing cloricromene. Drug Deliv. 2003 Oct- Dec;10(4):245-50. doi: 10.1080/drd_10_4_245. PMID: 14612340. 14: Bucolo C, Cuzzocrea S, Mazzon E, Caputi AP. Effects of cloricromene, a coumarin derivative, on endotoxin-induced uveitis in Lewis rats. Invest Ophthalmol Vis Sci. 2003 Mar;44(3):1178-84. doi: 10.1167/iovs.02-0559. PMID: 12601047. 15: Maltese A, Bucolo C. Simultaneous determination of cloricromene and its active metabolite in rabbit aqueous humor by high-performance liquid chromatography. J Chromatogr B Analyt Technol Biomed Life Sci. 2002 Feb 5;767(1):153-8. doi: 10.1016/s1570-0232(01)00567-0. PMID: 11863286. 16: Savastano M, Tomaselli F, Maggiori S. Intradermal injection vs. oral treatment of tinnitus. Therapie. 2001 Jul-Aug;56(4):403-7. PMID: 11677863. 17: Corsini E, Lucchi L, Binaglia M, Viviani B, Bevilacqua C, Monastra G, Marinovich M, Galli CL. Cloricromene, a semi-synthetic coumarin derivative, inhibits tumor necrosis factor-alpha production at a pre-transcriptional level. Eur J Pharmacol. 2001 Apr 27;418(3):231-7. doi: 10.1016/s0014-2999(01)00910-4. PMID: 11343695. 18: Cuzzocrea S, Mazzon E, Bevilaqua C, Costantino G, Britti D, Mazzullo G, De Sarro A, Caputi AP. Cloricromene, a coumarine derivative, protects against collagen-induced arthritis in Lewis rats. Br J Pharmacol. 2000 Dec;131(7):1399-407. doi: 10.1038/sj.bjp.0703695. PMID: 11090113; PMCID: PMC1572455. 19: Gresele P, Migliacci R, Di Sante G, Nenci GG; CRAMPS Investigator Group. Effect of cloricromene on intermittent claudication. A randomized, double-blind, placebo-controlled trial in patients treated with aspirin: effect on claudication distance and quality of life. CRAMPS Investigator Group. Cloricromene Randomized Arteriopathy Multicenter Prospective Study. Vasc Med. 2000;5(2):83-9. doi: 10.1177/1358836X0000500204. PMID: 10943584. 20: Aliev G, Ragazzi E, Smith MA, Mironov A, Perry G. Morphological features of regeneration of rabbit aortic endothelium after cryoinduced vascular damage. J Submicrosc Cytol Pathol. 1999 Oct;31(4):495-502. PMID: 10685390.