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[ CAS No. 13010-47-4 ] {[proInfo.proName]}

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Chemical Structure| 13010-47-4
Chemical Structure| 13010-47-4
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Product Citations

Product Citations

Ingraham, Charles H. IV ; Stalinska, Joanna ; Carson, Sean C. , et al. DOI: PubMed ID:

Abstract: Glioblastomas are highly aggressive brain tumors for which therapeutic options are very limited. In a quest for new anti-glioblastoma drugs, we focused on specific structural modifications to the benzoyl-phenoxy-acetamide (BPA) structure present in a common lipid-lowering drug, fenofibrate, and in our first prototype glioblastoma drug, PP1. Here, we propose extensive computational analyses to improve the selection of the most effective glioblastoma drug candidates. Initially, over 100 structural BPA variations were analyzed and their physicochemical properties, such as water solubility (- logS), calculated partition coefficient (ClogP), probability for BBB crossing (BBB_SCORE), probability for CNS penetration (CNS-MPO) and calculated cardiotoxicity (hERG), were evaluated. This integrated approach allowed us to select pyridine variants of BPA that show improved BBB penetration, water solubility, and low cardiotoxicity. Herein the top 24 compounds were synthesized and analyzed in cell culture. Six of them demonstrated glioblastoma toxicity with IC50 ranging from 0.59 to 3.24 μM. Importantly, one of the compounds, HR68, accumulated in the brain tumor tissue at 3.7 ± 0.5 μM, which exceeds its glioblastoma IC50 (1.17 μM) by over threefold.

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Product Details of [ 13010-47-4 ]

CAS No. :13010-47-4 MDL No. :MFCD00012392
Formula : C9H16ClN3O2 Boiling Point : -
Linear Structure Formula :- InChI Key :GQYIWUVLTXOXAJ-UHFFFAOYSA-N
M.W : 233.70 Pubchem ID :3950
Synonyms :
CCNU;NSC 79037;WR139017.;Prava. CCNU. Acronym: CCNU. RB1509;Lucostine;Lucostin;Lomeblastin;Citostal;Cecenu;Belustine;Belustin;Lomustinume. CeeNU;NCI C04740;CeeNU;Gleostine
Chemical Name :1-(2-Chloroethyl)-3-cyclohexyl-1-nitrosourea

Calculated chemistry of [ 13010-47-4 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 15
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.89
Num. rotatable bonds : 6
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 59.08
TPSA : 61.77 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.72 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.36
Log Po/w (XLOGP3) : 2.83
Log Po/w (WLOGP) : 2.25
Log Po/w (MLOGP) : 1.55
Log Po/w (SILICOS-IT) : 1.04
Consensus Log Po/w : 2.01

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.68
Solubility : 0.493 mg/ml ; 0.00211 mol/l
Class : Soluble
Log S (Ali) : -3.79
Solubility : 0.0383 mg/ml ; 0.000164 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.04
Solubility : 2.14 mg/ml ; 0.00914 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.41

Safety of [ 13010-47-4 ]

Signal Word:Danger Class:6.1
Precautionary Statements:P501-P260-P270-P202-P201-P264-P280-P308+P311-P301+P310+P330-P405 UN#:2811
Hazard Statements:H301-H360-H371-H340-H350 Packing Group:Ⅲ
GHS Pictogram:
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Technical Information

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