WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 596945
CAS#: 143839-74-1
Description: L 685818 is the C18-hydroxy, C21-ethyl analog of FK-506; binds to FKBP-12; antagonizes FK-506 and rapamycin.
MedKoo Cat#: 596945
Name: L 685818
CAS#: 143839-74-1
Chemical Formula: C43H69NO13
Exact Mass: 807.4769
Molecular Weight: 808.01
Elemental Analysis: C, 63.92; H, 8.61; N, 1.73; O, 25.74
This product is not in stock, which may be available by custom synthesis.
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Synonym: L 685818; L-685818; L685818; L-685,818; L 685,818; L685,818;
IUPAC/Chemical Name: 15,19-Epoxy-3H-pyrido(2,1-c)(1,4)oxaazacyclotricosine-1,7,20,21(4H,23H)-tetrone, 8-ethyl-5,6,8,11,12,13,14,15,16,17,18,19,24,25,26,26a-hexadecahydro-5,11,19-trihydroxy-3-(2-(4-hydroxy-3-methoxycyclohexyl)-1-methylethenyl)-14,16-dimethoxy-4,10,12,18-tetramethyl-, (3S-(3R*(E(1S*,3S*,4S*)),4S*,5R*,8S*,9E,11R*,12S*,14R*,15S*,16R*,18S*,19S*,26aR*))-
InChi Key: NOQNPBXNHMZMTC-KIJDSWADSA-N
InChi Code: InChI=1S/C43H69NO13/c1-10-29-18-23(2)37(48)24(3)19-35(54-8)39-36(55-9)20-26(5)43(52,57-39)40(49)41(50)44-16-12-11-13-30(44)42(51)56-38(27(6)32(46)22-33(29)47)25(4)17-28-14-15-31(45)34(21-28)53-7/h17-18,24,26-32,34-39,45-46,48,52H,10-16,19-22H2,1-9H3/b23-18+,25-17+/t24-,26-,27-,28+,29-,30+,31?,32+,34?,35+,36+,37-,38-,39-,43-/m1/s1
SMILES Code: O=C([C@@](CCCC1)([H])N1C(C([C@@]2(O)[C@H](C)C[C@H](OC)[C@@](O2)([H])[C@@H](OC)C[C@@H](C)[C@H](O)/C(C)=C/[C@H]3CC)=O)=O)O[C@H](/C(C)=C/[C@H]4CC(OC)C(O)CC4)[C@H](C)[C@@H](O)CC3=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
The following data is based on the product molecular weight 808.01 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: Onyewu C, Blankenship JR, Del Poeta M, Heitman J. Ergosterol biosynthesis inhibitors become fungicidal when combined with calcineurin inhibitors against Candida albicans, Candida glabrata, and Candida krusei. Antimicrob Agents Chemother. 2003 Mar;47(3):956-64. PubMed PMID: 12604527; PubMed Central PMCID: PMC149324.
2: Kontoyiannis DP, Lewis RE, Osherov N, Albert ND, May GS. Combination of caspofungin with inhibitors of the calcineurin pathway attenuates growth in vitro in Aspergillus species. J Antimicrob Chemother. 2003 Feb;51(2):313-6. PubMed PMID: 12562696.
3: Oz HS, Hughes WT, Thomas EK, McClain CJ. Effects of immunomodulators on acute Trypanosoma Cruzi infection in mice. Med Sci Monit. 2002 Jun;8(6):BR208-11. PubMed PMID: 12070425.
4: Guo X, Dawson VL, Dawson TM. Neuroimmunophilin ligands exert neuroregeneration and neuroprotection in midbrain dopaminergic neurons. Eur J Neurosci. 2001 May;13(9):1683-93. PubMed PMID: 11359520.
5: Del Poeta M, Cruz MC, Cardenas ME, Perfect JR, Heitman J. Synergistic antifungal activities of bafilomycin A(1), fluconazole, and the pneumocandin MK-0991/caspofungin acetate (L-743,873) with calcineurin inhibitors FK506 and L-685,818 against Cryptococcus neoformans. Antimicrob Agents Chemother. 2000 Mar;44(3):739-46. PubMed PMID: 10681348; PubMed Central PMCID: PMC89756.
6: Allen C, Yu Y, Maysinger D, Eisenberg A. Polycaprolactone-b-poly(ethylene oxide) block copolymer micelles as a novel drug delivery vehicle for neurotrophic agents FK506 and L-685,818. Bioconjug Chem. 1998 Sep-Oct;9(5):564-72. PubMed PMID: 9736490.
7: Salowe SP, Hermes JD. Competitive and slow-binding inhibition of calcineurin by drug x immunophilin complexes. Arch Biochem Biophys. 1998 Jul 15;355(2):165-74. PubMed PMID: 9675023.
8: Bassing CH, Shou W, Muir S, Heitman J, Matzuk MM, Wang XF. FKBP12 is not required for the modulation of transforming growth factor beta receptor I signaling activity in embryonic fibroblasts and thymocytes. Cell Growth Differ. 1998 Mar;9(3):223-8. PubMed PMID: 9543388.
9: Wiederrecht G, Siekierka JJ. Yeast immunophilins: purification and assay of yeast FKBP12. Methods Enzymol. 1998;290:74-84. PubMed PMID: 9534152.
10: Steiner JP, Connolly MA, Valentine HL, Hamilton GS, Dawson TM, Hester L, Snyder SH. Neurotrophic actions of nonimmunosuppressive analogues of immunosuppressive drugs FK506, rapamycin and cyclosporin A. Nat Med. 1997 Apr;3(4):421-8. PubMed PMID: 9095176.
11: Odom A, Del Poeta M, Perfect J, Heitman J. The immunosuppressant FK506 and its nonimmunosuppressive analog L-685,818 are toxic to Cryptococcus neoformans by inhibition of a common target protein. Antimicrob Agents Chemother. 1997 Jan;41(1):156-61. PubMed PMID: 8980772; PubMed Central PMCID: PMC163677.
12: Dumont FJ, Fischer P, Sirotina A. Increased LFA-1-mediated homotypic cell adhesion is associated with the G1 growth arrest induced by rapamycin in a T cell lymphoma. Exp Cell Res. 1995 Jul;219(1):146-58. PubMed PMID: 7543051.
13: Teutsch M, Higer M, Wang D, Wortis HW. Induction of CD5 on B and T cells is suppressed by cyclosporin A, FK-520 and rapamycin. Int Immunol. 1995 Mar;7(3):381-92. PubMed PMID: 7540861.
14: Becker JW, Rotonda J, McKeever BM, Chan HK, Marcy AI, Wiederrecht G, Hermes JD, Springer JP. FK-506-binding protein: three-dimensional structure of the complex with the antagonist L-685,818. J Biol Chem. 1993 May 25;268(15):11335-9. PubMed PMID: 7684380.
15: Dumont FJ, Staruch MJ, Koprak SL, Siekierka JJ, Lin CS, Harrison R, Sewell T, Kindt VM, Beattie TR, Wyvratt M, et al. The immunosuppressive and toxic effects of FK-506 are mechanistically related: pharmacology of a novel antagonist of FK-506 and rapamycin. J Exp Med. 1992 Sep 1;176(3):751-60. PubMed PMID: 1380976; PubMed Central PMCID: PMC2119351.
