Cemadotin (free base)

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MedKoo CAT#: 200710

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

Description: Cemadotin (free base), 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.


Chemical Structure

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

Theoretical Analysis

MedKoo Cat#: 200710
Name: Cemadotin (free base)
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

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
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Related CAS #: 159776-69-9 (free base)   172837-41-1 (HCl)  

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

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

Preparing Stock Solutions

The following data is based on the product molecular weight 640.86 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

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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.



Additional Information

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