ENMD-1198
ENMD-1198 is a potent, orally-active, antimitotic agent that induces cell cycle arrest and apoptosis in tumor cells. ENMD-1198 has shown pronounced antitumor activity as well as substantial synergistic effects in combination with standard of care chemotherapeutic agents in numerous preclinical models. ENMD-1198 does not exhibit sensitivity to multi-drug resistance mechanisms in preclinical studies. ENMD-1198 also has shown preclinical activity towards taxane and vinca alkaloid resistant tumor cells. Additionally, ENMD-1198 decreases the activity of three oncogenic proteins (HIF-1α, NF-κB and STAT3) that are known to promote tumor growth and progression. ENMD-1198 has been evaluated in a Phase 1 clinical trial for safety, tolerability, pharmacokinetics, and clinical benefit in advanced cancer patients. (Source
1: Pasquier E, Sinnappan S, Munoz MA, Kavallaris M. ENMD-1198, a new analogue of 2-methoxyestradiol, displays both antiangiogenic and vascular-disrupting properties. Mol Cancer Ther. 2010 May;9(5):1408-18. Epub 2010 May 4. PubMed PMID: 20442304.
2: Zhou Q, Gustafson D, Nallapareddy S, Diab S, Leong S, Lewis K, Gore L, Messersmith WA, Treston AM, Eckhardt SG, Sidor C, Camidge DR. A phase I dose-escalation, safety and pharmacokinetic study of the 2-methoxyestradiol analog ENMD-1198 administered orally to patients with advanced cancer. Invest New Drugs. 2010 Jan 19. [Epub ahead of print] PubMed PMID: 20084425.
3: Agoston GE, Shah JH, Suwandi L, Hanson AD, Zhan X, LaVallee TM, Pribluda V, Treston AM. Synthesis, antiproliferative, and pharmacokinetic properties of 3- and 17-double-modified analogs of 2-methoxyestradiol. Bioorg Med Chem Lett. 2009 Nov 1;19(21):6241-4. Epub 2009 Aug 8. PubMed PMID: 19782564.
4: Moser C, Lang SA, Mori A, Hellerbrand C, Schlitt HJ, Geissler EK, Fogler WE, Stoeltzing O. ENMD-1198, a novel tubulin-binding agent reduces HIF-1alpha and STAT3 activity in human hepatocellular carcinoma(HCC) cells, and inhibits growth and vascularization in vivo. BMC Cancer. 2008 Jul 23;8:206. PubMed PMID: 18651980; PubMed Central PMCID: PMC2496914.
5: Foster PA, Stengel C, Ali T, Leese MP, Potter BV, Reed MJ, Purohit A, Newman SP. A comparison of two orally bioavailable anti-cancer agents, IRC-110160 and STX140. Anticancer Res. 2008 May-Jun;28(3A):1483-91. PubMed PMID: 18630502.
6: LaVallee TM, Burke PA, Swartz GM, Hamel E, Agoston GE, Shah J, Suwandi L, Hanson AD, Fogler WE, Sidor CF, Treston AM. Significant antitumor activity in vivo following treatment with the microtubule agent ENMD-1198. Mol Cancer Ther. 2008 Jun;7(6):1472-82. PubMed PMID: 18566218.
2: Zhou Q, Gustafson D, Nallapareddy S, Diab S, Leong S, Lewis K, Gore L, Messersmith WA, Treston AM, Eckhardt SG, Sidor C, Camidge DR. A phase I dose-escalation, safety and pharmacokinetic study of the 2-methoxyestradiol analog ENMD-1198 administered orally to patients with advanced cancer. Invest New Drugs. 2010 Jan 19. [Epub ahead of print] PubMed PMID: 20084425.
3: Agoston GE, Shah JH, Suwandi L, Hanson AD, Zhan X, LaVallee TM, Pribluda V, Treston AM. Synthesis, antiproliferative, and pharmacokinetic properties of 3- and 17-double-modified analogs of 2-methoxyestradiol. Bioorg Med Chem Lett. 2009 Nov 1;19(21):6241-4. Epub 2009 Aug 8. PubMed PMID: 19782564.
4: Moser C, Lang SA, Mori A, Hellerbrand C, Schlitt HJ, Geissler EK, Fogler WE, Stoeltzing O. ENMD-1198, a novel tubulin-binding agent reduces HIF-1alpha and STAT3 activity in human hepatocellular carcinoma(HCC) cells, and inhibits growth and vascularization in vivo. BMC Cancer. 2008 Jul 23;8:206. PubMed PMID: 18651980; PubMed Central PMCID: PMC2496914.
5: Foster PA, Stengel C, Ali T, Leese MP, Potter BV, Reed MJ, Purohit A, Newman SP. A comparison of two orally bioavailable anti-cancer agents, IRC-110160 and STX140. Anticancer Res. 2008 May-Jun;28(3A):1483-91. PubMed PMID: 18630502.
6: LaVallee TM, Burke PA, Swartz GM, Hamel E, Agoston GE, Shah J, Suwandi L, Hanson AD, Fogler WE, Sidor CF, Treston AM. Significant antitumor activity in vivo following treatment with the microtubule agent ENMD-1198. Mol Cancer Ther. 2008 Jun;7(6):1472-82. PubMed PMID: 18566218.
| Chemical | |
|---|---|
| CAS Num | 864668-87-1 |
| Chemical Formula | C20H25NO2 |
| Molecular Weight | 311.42 |
| IUPAC Chemical Name | (13R)-2-methoxy-13-methyl-7,8,9,11,12,13,14,15-octahydro-6H-cyclopenta[a]phenanthrene-3-carboxamide |
| Exact Mass | 311.18853 |
| Elemental Analysis | C, 77.14; H, 8.09; N, 4.50; O, 10.28 |
| Synonym | ENMD 1198; ENMD1198; Estra135(10)16tetraene3carboxamide 2methoxy; 2Methoxy135(10)16estratetraene3carboxamide; IRC 110160. |
| Solubility | Soluble in DMSO, not in water |
| SMILES Code | O=C(C1=C(OC)C=C2C3CC[C@]4(C)C=CCC4C3CCC2=C1)N |
| Biological | |
| Targets and Effects | HIF pathway inhibitor |
| Pathways | Apoptosis |
| Physical | |
| 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). |
| Shelf Life | >5 years if stored properly |
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