Cemadotin

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

MedKoo CAT#: 200710

CAS#: 159776-69-9 (free base)

Description: Cemadotin, also known as, LU103793, is a mitosis inhibitor potentially for the treatment of solid tumours. Cemadotin is also a synthetic derivative of Dolastatin 15, an antiproliferative compound which was isolated from the mollusk Dolabella auricularia. Like Dolastatin 15, LU103793 is highly cytotoxic in vitro (IC50 = 0.1 nM). LU103793 inhibits microtubule polymerization in a concentration-dependent manner (IC50 = 7 microM). Treatment with this compound also induced depolymerization of preassembled microtubules. Cell cycle analysis of tumor cell lines treated with LU103793 indicated a block in the G2-M phase.


Price and Availability

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Cemadotin is not in stock, 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.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 200710
Name: Cemadotin
CAS#: 159776-69-9 (free base)
Chemical Formula: C35H56N6O5
Exact Mass: 640.43122
Molecular Weight: 640.86
Elemental Analysis: C, 65.60; H, 8.81; N, 13.11; O, 12.48


Synonym: LU 103793; LU-103793; LU103793; NNdimethylLvalylLvalylNmethylLvalylLprolylLprolinebenzylamide.

IUPAC/Chemical Name: (S)-1-benzyl-N-((S)-2-((S)-2-(dimethylamino)-3-methylbutanamido)-3-methylbutanoyl)-N-((S)-1-((S)-3-methyl-2-(methylamino)butanoyl)pyrrolidine-2-carbonyl)pyrrolidine-2-carboxamide

InChi Key: LSIZJZZMXCWHBR-IIZANFQQSA-N

InChi Code: InChI=1S/C35H56N6O5/c1-22(2)28(36-7)34(45)40-20-14-18-27(40)33(44)41(32(43)26-17-13-19-39(26)21-25-15-11-10-12-16-25)35(46)29(23(3)4)37-31(42)30(24(5)6)38(8)9/h10-12,15-16,22-24,26-30,36H,13-14,17-21H2,1-9H3,(H,37,42)/t26-,27-,28-,29-,30-/m0/s1

SMILES Code: O=C([C@H]1N(CC2=CC=CC=C2)CCC1)N(C([C@@H](NC([C@@H](N(C)C)C(C)C)=O)C(C)C)=O)C([C@H]3N(C([C@@H](NC)C(C)C)=O)CCC3)=O


Technical Data

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).

Harmonized System Code:
293490


Additional Information

 Related CAS#
159776-69-9 (Cemadotin free base)
172837-41-1 (Cemadotin Hydrochloride)
 


References

1: Casi G, Huguenin-Dezot N, Zuberbühler K, Scheuermann J, Neri D. Site-specific traceless coupling of potent cytotoxic drugs to recombinant antibodies for pharmacodelivery. J Am Chem Soc. 2012 Apr 4;134(13):5887-92. doi: 10.1021/ja211589m. Epub 2012 Mar 26. PubMed PMID: 22394212.

2: Bai R, Edler MC, Bonate PL, Copeland TD, Pettit GR, Ludueña RF, Hamel E. Intracellular activation and deactivation of tasidotin, an analog of dolastatin 15: correlation with cytotoxicity. Mol Pharmacol. 2009 Jan;75(1):218-26. doi: 10.1124/mol.108.051110. Epub 2008 Oct 16. PubMed PMID: 18927208; PubMed Central PMCID: PMC2635573.

3: Rawat DS, Joshi MC, Joshi P, Atheaya H. Marine peptides and related compounds in clinical trial. Anticancer Agents Med Chem. 2006 Jan;6(1):33-40. Review. PubMed PMID: 16475925.

4: Zask A, Kaplan J, Musto S, Loganzo F. Hybrids of the hemiasterlin analogue taltobulin and the dolastatins are potent antimicrotubule agents. J Am Chem Soc. 2005 Dec 21;127(50):17667-71. PubMed PMID: 16351096.

5: Cruz-Monserrate Z, Mullaney JT, Harran PG, Pettit GR, Hamel E. Dolastatin 15 binds in the vinca domain of tubulin as demonstrated by Hummel-Dreyer chromatography. Eur J Biochem. 2003 Sep;270(18):3822-8. PubMed PMID: 12950266.

6: Marks RS, Graham DL, Sloan JA, Hillman S, Fishkoff S, Krook JE, Okuno SH, Mailliard JA, Fitch TR, Addo F. A phase II study of the dolastatin 15 analogue LU 103793 in the treatment of advanced non-small-cell lung cancer. Am J Clin Oncol. 2003 Aug;26(4):336-7. PubMed PMID: 12902880.

7: Kerbrat P, Dieras V, Pavlidis N, Ravaud A, Wanders J, Fumoleau P; EORTC Early Clinical Studies Group/New Drug Development Office. Phase II study of LU 103793 (dolastatin analogue) in patients with metastatic breast cancer. Eur J Cancer. 2003 Feb;39(3):317-20. PubMed PMID: 12565983.

8: Smyth J, Boneterre ME, Schellens J, Calvert H, Greim G, Wanders J, Hanauske A; EORTC Early Clinical Studies Group. Activity of the dolastatin analogue, LU103793, in malignant melanoma. Ann Oncol. 2001 Apr;12(4):509-11. PubMed PMID: 11398885.

9: Supko JG, Lynch TJ, Clark JW, Fram R, Allen LF, Velagapudi R, Kufe DW, Eder JP Jr. A phase I clinical and pharmacokinetic study of the dolastatin analogue cemadotin administered as a 5-day continuous intravenous infusion. Cancer Chemother Pharmacol. 2000;46(4):319-28. PubMed PMID: 11052630.

10: Hu MK, Huang WS. Synthesis and cytostatic properties of structure-simplified analogs of dolastatin 15. J Pept Res. 1999 Dec;54(6):460-7. PubMed PMID: 10604591.