Cemadotin hydrochloride

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MedKoo CAT#: 412556

CAS#: 172837-41-1 (HCl)

Description: Cemadotin hydrochloride is the salt from of Cemadotin (free base), also known as, LU103793, 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 hydrochloride
CAS# 172837-41-1 (HCl)

Theoretical Analysis

MedKoo Cat#: 412556
Name: Cemadotin hydrochloride
CAS#: 172837-41-1 (HCl)
Chemical Formula: C35H57ClN6O5
Exact Mass: 676.4079
Molecular Weight: 677.33
Elemental Analysis: C, 62.07; H, 8.48; Cl, 5.23; N, 12.41; O, 11.81

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.
Note: Price will be listed if it is available in the future.

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Related CAS #: 159776-69-9 (free base)   172837-41-1 (HCl)  

Synonym: Cemadotin hydrochloride; UNII-4LJQ1IXS6C

IUPAC/Chemical Name: (S)-N-benzyl-1-(N-dimethyl-L-valyl-L-valyl-N-methyl-L-valyl-L-prolyl)pyrrolidine-2-carboxamide hydrochloride

InChi Key: MRJQTLJSMQOFTP-JGTKTWDESA-N

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

SMILES Code: CC([C@@H](C(N([C@H](C(N1CCC[C@H]1C(N2CCC[C@H]2C(NCc3ccccc3)=O)=O)=O)C(C)C)C)=O)NC([C@@H](N(C)C)C(C)C)=O)C.Cl

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

Shelf Life: >3 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 677.33 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: Jordan MA, Walker D, de Arruda M, Barlozzari T, Panda D. Suppression of microtubule dynamics by binding of cemadotin to tubulin: possible mechanism for its antitumor action. Biochemistry. 1998 Dec 15;37(50):17571-8. doi: 10.1021/bi9817414. PMID: 9860873.

2: 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. doi: 10.1007/s002800000152. PMID: 11052630.

3: Mross K, Berdel WE, Fiebig HH, Velagapudi R, von Broen IM, Unger C. Clinical and pharmacologic phase I study of Cemadotin-HCl (LU103793), a novel antimitotic peptide, given as 24-hour infusion in patients with advanced cancer. A study of the Arbeitsgemeinschaft Internistische Onkologie (AIO) Phase I Group and Arbeitsgruppe Pharmakologie in der Onkologie und Haematologie (APOH) Group of the German Cancer Society. Ann Oncol. 1998 Dec;9(12):1323-30. doi: 10.1023/a:1008430515881. PMID: 9932163.

4: Jayakumar J, Anishetty S. Molecular Dynamics simulations of Inhibitor of Apoptosis Proteins and identification of potential small molecule inhibitors. Bioorg Med Chem Lett. 2014 May 1;24(9):2098-104. doi: 10.1016/j.bmcl.2014.03.046. Epub 2014 Mar 26. PMID: 24717152.

5: Bernardes GJ, Steiner M, Hartmann I, Neri D, Casi G. Site-specific chemical modification of antibody fragments using traceless cleavable linkers. Nat Protoc. 2013 Nov;8(11):2079-89. doi: 10.1038/nprot.2013.121. Epub 2013 Oct 3. PMID: 24091555.

6: 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. doi: 10.1046/j.1432-1033.2003.03776.x. PMID: 12950266.

7: 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. PMID: 18927208; PMCID: PMC2635573.

8: Lansiaux A, Bailly C. Les dolastatines [Dolastatins]. Bull Cancer. 1999 Nov;86(11):897-901. French. PMID: 10586105.

9: 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. doi: 10.1021/ja053663v. PMID: 16351096.

10: 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. doi: 10.2174/187152006774755519. PMID: 16475925.