MedKoo Cat#: 407308 | Name: Dimethylenastron
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Description:

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

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

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: 302.39

Elemental Analysis: C, 63.55; H, 6.00; N, 9.26; O, 10.58; S, 10.60

Price and Availability

Size Price Availability Quantity
25mg USD 250.00 2 Weeks
50mg USD 400.00 2 Weeks
100mg USD 650.00 2 Weeks
200mg USD 950.00 2 Weeks
500mg USD 1,950.00 2 Weeks
1g USD 2,950.00 2 Weeks
2g USD 3,950.00 2 Weeks
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Related CAS #
No Data
Synonym
Dimethylenastron; Eg5 Inhibitor III; 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
More Info
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/
Solvent mg/mL mM comments
Solubility
DMF 10.0 33.07
DMSO 31.8 104.99
Ethanol 5.9 19.42
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 302.39 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.