MedKoo Cat#: 201071 | Name: E6201

Description:

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

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.

Chemical Structure

E6201
E6201
CAS#603987-35-5

Theoretical Analysis

MedKoo Cat#: 201071

Name: E6201

CAS#: 603987-35-5

Chemical Formula: C21H27NO6

Exact Mass: 389.1838

Molecular Weight: 389.44

Elemental Analysis: C, 64.77; H, 6.99; N, 3.60; O, 24.65

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 #
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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][1]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
More Info
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).        

Preparing Stock Solutions

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.

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: 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.