E6201

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

MedKoo CAT#: 201071

CAS#: 603987-35-5

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.

Chemical Structure

E6201

CAS# 603987-35-5

Handing Instruction

Theoretical Analysis

MedKoo Cat#: 201071
Name: E6201
CAS#: 603987-35-5
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

Size	Price	Shipping out time	Quantity
Inquire bulk and customized quantity Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Pricing updated 2021-03-07. Prices are subject to change without notice.

E6201 is not in stock, but may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.

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

Handling Instructions:

View handling instruction

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.

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

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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.

Your view history

E6201

Additional Information

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).