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

Description:

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

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

Cemadotin (free base)
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: 640.4312

Molecular Weight: 640.86

Elemental Analysis: C, 65.60; H, 8.81; N, 13.11; O, 12.48

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

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
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.