WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 201071
Description: E6201 is a synthetic, fungal metabolite analogue inhibitor of mitogen-activated protein kinase kinase 1 (MEK-1) and mitogen-activated protein kinase kinase kinase 1 (MEKK-1) with potential antipsoriatic and antineoplastic activities. MEK-1/MEKK-1 inhibitor E6201 specifically binds to and inhibits the activities of MEK-1 and MEKK-1, which may result in the inhibition of tumor cell proliferation. MEK-1 and MEKK-1 are key components in the RAS/RAF/MEK/MAPK signaling pathway, which regulates cell proliferation and is frequently activated in human cancers.
MedKoo Cat#: 201071
Chemical Formula: C21H27NO6
Exact Mass: 389.18384
Molecular Weight: 389.44
Elemental Analysis: C, 64.77; H, 6.99; N, 3.60; O, 24.65
This product is not in stock, which may be available by custom synthesis.
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Synonym: E6201; E-6201; E 6201; ER 806201; ER806201; ER-806201; LLZ16402; LLZ-16402; LLZ 16402;
IUPAC/Chemical Name: (3S,4R,5Z,8S,9S,11E)-14-(ethylamino)-8,9,16-trihydroxy-3,4-dimethyl-3,4,9,10-tetrahydro-1H-benzo[c]oxacyclotetradecine-1,7(8H)-dione
InChi Key: MWUFVYLAWAXDHQ-HMNLTAHHSA-N
InChi Code: InChI=1S/C21H27NO6/c1-4-22-15-10-14-6-5-7-16(23)20(26)17(24)9-8-12(2)13(3)28-21(27)19(14)18(25)11-15/h5-6,8-13,16,20,22-23,25-26H,4,7H2,1-3H3/b6-5+,9-8-/t12-,13+,16+,20+/m1/s1
SMILES Code: O=C(C1=C(O)C=C(NCC)C=C1/C=C/C[C@H](O)[C@@H]2O)O[C@@H](C)[C@H](C)/C=C\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, not in water
Shelf Life: >5 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 389.44 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: Muramoto K, Goto M, Inoue Y, Ishii N, Chiba KI, Kuboi Y, Omae T, Wang YJ, Gusovsky F, Shirota H. E6201, a Novel Kinase Inhibitor of MEK-1 and MEKK-1: In Vivo Effects on Cutaneous Inflammatory Responses by Topical Administration. J Pharmacol Exp Ther. 2010 Jul 13. [Epub ahead of print] PubMed PMID: 20627998.
2: Shen Y, Boivin R, Yoneda N, Du H, Schiller S, Matsushima T, Goto M, Shirota H, Gusovsky F, Lemelin C, Jiang Y, Zhang Z, Pelletier R, Ikemori-Kawada M, Kawakami Y, Inoue A, Schnaderbeck M, Wang Y. Discovery of anti-inflammatory clinical candidate E6201, inspired from resorcylic lactone LL-Z1640-2, III. Bioorg Med Chem Lett. 2010 May 15;20(10):3155-7. Epub 2010 Mar 30. PubMed PMID: 20399648.
3: Goto M, Chow J, Muramoto K, Chiba K, Yamamoto S, Fujita M, Obaishi H, Tai K, Mizui Y, Tanaka I, Young D, Yang H, Wang YJ, Shirota H, Gusovsky F. E6201 [(3S,4R,5Z,8S,9S,11E)-14-(ethylamino)-8, 9,16-trihydroxy-3,4-dimethyl-3,4,9,19-tetrahydro-1H-2-benzoxacyclotetradecine-1,7 (8H)-dione], a novel kinase inhibitor of mitogen-activated protein kinase/extracellular signal-regulated kinase kinase (MEK)-1 and MEK kinase-1: in vitro characterization of its anti-inflammatory and antihyperproliferative activities. J Pharmacol Exp Ther. 2009 Nov;331(2):485-95. Epub 2009 Aug 14. PubMed PMID: 19684251.
4: Bischerour J, Chalmers R. Base flipping in tn10 transposition: an active flip and capture mechanism. PLoS One. 2009 Jul 10;4(7):e6201. PubMed PMID: 19593448; PubMed Central PMCID: PMC2705183.
5: Poplin E, Feng Y, Berlin J, Rothenberg ML, Hochster H, Mitchell E, Alberts S, O'Dwyer P, Haller D, Catalano P, Cella D, Benson AB 3rd. Phase III, randomized study of gemcitabine and oxaliplatin versus gemcitabine (fixed-dose rate infusion) compared with gemcitabine (30-minute infusion) in patients with pancreatic carcinoma E6201: a trial of the Eastern Cooperative Oncology Group. J Clin Oncol. 2009 Aug 10;27(23):3778-85. Epub 2009 Jul 6. Erratum in: J Clin Oncol. 2009 Dec 1;27(34):5859. PubMed PMID: 19581537; PubMed Central PMCID: PMC2727286.
Inspired by natural product, LL-Z1640-2, clinical candidate, E6201 was discovered in a medicinal chemistry effort through total synthesis. The modification on C14-position to N-alkyl substitution showed to be potent in vitro and orally active in vivo in anti-inflammatory assays. Phase I clinical trails showed that E6201 MTD of 320 mg/m2 IV once weekly for 3 out of a 4-week cycle was well tolerated in patients with advanced solid tumors. (source: http://www.asco.org/ASCOv2/Meetings/Abstracts?&vmview=abst_detail_view&confID=74&abstractID=44399).