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[ CAS No. 530-78-9 ] {[proInfo.proName]}

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Chemical Structure| 530-78-9
Chemical Structure| 530-78-9
Structure of 530-78-9 * Storage: {[proInfo.prStorage]}

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Product Citations

Product Citations

Tonduru, Arun Kumar ; Maljaei, Seyed Hamed ; Adla, Santosh Kumar , et al. DOI: PubMed ID:

Abstract: OATP1C1 (organic anion-transporting polypeptide 1C1) transports thyroid hormones, particularly thyroxine (T4), into human astrocytes. In this study, we investigated the potential of utilizing OATP1C1 to improve the delivery of anti-inflammatory drugs into glial cells. We designed and synthesized eight novel prodrugs by incorporating T4 and 3,5-diiodo-L-tyrosine (DIT) as promoieties to selected anti-inflammatory drugs. The prodrug uptake in OATP1C1-expressing human U-87MG glioma cells demonstrated higher accumulation with T4 promoiety compared to those with DIT promoiety or the parent drugs themselves. In silico models of OATP1C1 suggested dynamic binding for the prodrugs, wherein the pose changed from vertical to horizontal. The predicted binding energies correlated with the transport profiles, with T4 derivatives exhibiting higher binding energies when compared to prodrugs with a DIT promoiety. Interestingly, the prodrugs also showed utilization of oatp1a4/1a5/1a6 in mouse primary astrocytes, which was further supported by docking studies and a great potential for improved brain drug delivery.

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Product Details of [ 530-78-9 ]

CAS No. :530-78-9 MDL No. :MFCD00002422
Formula : C14H10F3NO2 Boiling Point : -
Linear Structure Formula :HO2CC6H4NHC6H4CF3 InChI Key :LPEPZBJOKDYZAD-UHFFFAOYSA-N
M.W : 281.23 Pubchem ID :3371
Synonyms :
Chemical Name :2-((3-(Trifluoromethyl)phenyl)amino)benzoic acid

Calculated chemistry of [ 530-78-9 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 20
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.07
Num. rotatable bonds : 4
Num. H-bond acceptors : 5.0
Num. H-bond donors : 2.0
Molar Refractivity : 67.95
TPSA : 49.33 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -4.29 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.16
Log Po/w (XLOGP3) : 5.25
Log Po/w (WLOGP) : 5.3
Log Po/w (MLOGP) : 2.61
Log Po/w (SILICOS-IT) : 3.13
Consensus Log Po/w : 3.69

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -5.07
Solubility : 0.00239 mg/ml ; 0.00000849 mol/l
Class : Moderately soluble
Log S (Ali) : -6.04
Solubility : 0.000259 mg/ml ; 0.000000922 mol/l
Class : Poorly soluble
Log S (SILICOS-IT) : -5.22
Solubility : 0.00168 mg/ml ; 0.00000598 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.06

Safety of [ 530-78-9 ]

Signal Word:Danger Class:6.1
Precautionary Statements:P264-P270-P280-P301+P310+P330-P302+P352-P305+P351+P338-P332+P313-P337+P313-P405-P501 UN#:2811
Hazard Statements:H301-H315-H319 Packing Group:Ⅲ
GHS Pictogram:

Application In Synthesis of [ 530-78-9 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 530-78-9 ]
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