Dimethylenastron
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MedKoo CAT#: 407308

CAS#: 863774-58-7

Description: Dimethylenastron is an inhibitor of mitotic motor kinesin Eg5 (IC50 = 200 nM). Dimethylenastron suppresses human pancreatic cancer cell migration and invasion in vitro via allosteric inhibition of mitotic kinesin Eg5. The inhibition of kinesin Eg5 by small molecules such as monastrol is currently evaluated as an approach to develop a novel class of antiproliferative drugs for the treatment of malignant tumours.


Chemical Structure

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Dimethylenastron
CAS# 863774-58-7

Theoretical Analysis

MedKoo Cat#: 407308
Name: Dimethylenastron
CAS#: 863774-58-7
Chemical Formula: C16H18N2O2S
Exact Mass: 302.1089
Molecular Weight: 302.392
Elemental Analysis: C, 63.55; H, 6.00; N, 9.26; O, 10.58; S, 10.60

Price and Availability

Size Price Availability Quantity
25.0mg USD 250.0 2 weeks
50.0mg USD 450.0 2 weeks
100.0mg USD 650.0 2 weeks
200.0mg USD 950.0 2 weeks
500.0mg USD 1950.0 2 weeks
1.0g USD 2950.0 2 weeks
2.0g USD 3950.0 2 weeks
5.0g USD 5850.0 2 weeks
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Synonym: Dimethylenastron.

IUPAC/Chemical Name: 2,3,4,6,7,8-Hexahydro-4-(3-hydroxyphenyl)-7,7-dimethyl-2-thioxo-5(1H)-quinazolinone

InChi Key: RUOOPLOUUAYNPY-UHFFFAOYSA-N

InChi Code: InChI=1S/C16H18N2O2S/c1-16(2)7-11-13(12(20)8-16)14(18-15(21)17-11)9-4-3-5-10(19)6-9/h3-6,14,19H,7-8H2,1-2H3,(H2,17,18,21)

SMILES Code: O=C1C2=C(NC(NC2C3=CC=CC(O)=C3)=S)CC(C)(C)C1

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: >2 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

Product Data:

Biological target: Dimethylenastron is a potent kinesin Eg5 inhibitor, with an IC50 of 200 nM.
In vitro activity: Eg5 expression was 9-16-fold up-regulated in the 5 pancreatic cancer cell lines. Treatment of PANC1 pancreatic cancer cells with dimethylenastron (3 and 10 μmol/L) for 24 h suppressed the migratory ability of the cancer cells in a concentration-dependent manner. Dimethylenastron inhibits the migration and invasion of PANC1 pancreatic cancer cells, independent of suppressing the cell proliferation. Reference: Acta Pharmacol Sin. 2011 Dec;32(12):1543-8. https://pubmed.ncbi.nlm.nih.gov/21986572/
In vivo activity: Dimethylenastron (1.0 µmol) induced a milder scarring compared with the control rabbit group but the length of bleb survival was not significantly prolonged (p = 0.053, Kaplan-Meier log rank test). Reference: Curr Eye Res. 2010 Dec;35(12):1090-8. https://pubmed.ncbi.nlm.nih.gov/20961218/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMF 10.0 33.07
DMSO 31.75 104.99
Ethanol 5.87 19.42

Preparing Stock Solutions

The following data is based on the product molecular weight 302.392 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
Formulation protocol: 1. She ZY, Zhong N, Yu KW, Xiao Y, Wei YL, Lin Y, Li YL, Lu MH. Kinesin-5 Eg5 is essential for spindle assembly and chromosome alignment of mouse spermatocytes. Cell Div. 2020 Mar 6;15:6. doi: 10.1186/s13008-020-00063-4. PMID: 32165913; PMCID: PMC7060529. 2. Sun XD, Shi XJ, Sun XO, Luo YG, Wu XJ, Yao CF, Yu HY, Li DW, Liu M, Zhou J. Dimethylenastron suppresses human pancreatic cancer cell migration and invasion in vitro via allosteric inhibition of mitotic kinesin Eg5. Acta Pharmacol Sin. 2011 Dec;32(12):1543-8. doi: 10.1038/aps.2011.130. Epub 2011 Oct 10. PMID: 21986572; PMCID: PMC4010204. 3. Exertier P, Javerzat S, Wang B, Franco M, Herbert J, Platonova N, Winandy M, Pujol N, Nivelles O, Ormenese S, Godard V, Becker J, Bicknell R, Pineau R, Wilting J, Bikfalvi A, Hagedorn M. Impaired angiogenesis and tumor development by inhibition of the mitotic kinesin Eg5. Oncotarget. 2013 Dec;4(12):2302-16. doi: 10.18632/oncotarget.1490. PMID: 24327603; PMCID: PMC3926828. 4. Lüke J, Nassar K, Lüke M, Tura A, Merz H, Giannis A, Grisanti S. The effect of adjuvant dimethylenastron, a mitotic Kinesin Eg5 inhibitor, in experimental glaucoma filtration surgery. Curr Eye Res. 2010 Dec;35(12):1090-8. doi: 10.3109/02713683.2010.512408. Epub 2010 Oct 20. PMID: 20961218.
In vitro protocol: 1. She ZY, Zhong N, Yu KW, Xiao Y, Wei YL, Lin Y, Li YL, Lu MH. Kinesin-5 Eg5 is essential for spindle assembly and chromosome alignment of mouse spermatocytes. Cell Div. 2020 Mar 6;15:6. doi: 10.1186/s13008-020-00063-4. PMID: 32165913; PMCID: PMC7060529. 2. Sun XD, Shi XJ, Sun XO, Luo YG, Wu XJ, Yao CF, Yu HY, Li DW, Liu M, Zhou J. Dimethylenastron suppresses human pancreatic cancer cell migration and invasion in vitro via allosteric inhibition of mitotic kinesin Eg5. Acta Pharmacol Sin. 2011 Dec;32(12):1543-8. doi: 10.1038/aps.2011.130. Epub 2011 Oct 10. PMID: 21986572; PMCID: PMC4010204.
In vivo protocol: 1. Exertier P, Javerzat S, Wang B, Franco M, Herbert J, Platonova N, Winandy M, Pujol N, Nivelles O, Ormenese S, Godard V, Becker J, Bicknell R, Pineau R, Wilting J, Bikfalvi A, Hagedorn M. Impaired angiogenesis and tumor development by inhibition of the mitotic kinesin Eg5. Oncotarget. 2013 Dec;4(12):2302-16. doi: 10.18632/oncotarget.1490. PMID: 24327603; PMCID: PMC3926828. 2. Lüke J, Nassar K, Lüke M, Tura A, Merz H, Giannis A, Grisanti S. The effect of adjuvant dimethylenastron, a mitotic Kinesin Eg5 inhibitor, in experimental glaucoma filtration surgery. Curr Eye Res. 2010 Dec;35(12):1090-8. doi: 10.3109/02713683.2010.512408. Epub 2010 Oct 20. PMID: 20961218.

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