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ChemicalBook--->CAS DataBase List--->915385-81-8

915385-81-8

915385-81-8 Structure

915385-81-8 Structure
IdentificationBack Directory
[Name]

ABC294640
[CAS]

915385-81-8
[Synonyms]

CS-802
ABC294640
ABC294640(Opaganib)
Opaganib (ABC294640)
3-(4-chlorophenyl)-adamantane-1-carboxylic acid (pyridin-4-ylmethyl)amide
3-(4-Chlorophenyl)-N-(4-pyridinylmethyl)tricyclo[3.3.1.1(3,7)]decane-1-carboxamide
Tricyclo[3.3.1.13,7]decane-1-carboxamide, 3-(4-chlorophenyl)-N-(4-pyridinylmethyl)
ABC294640;ABC-294640;ABC 294640;3-(4-CHLOROPHENYL)-ADAMANTANE-1-CARBOXYLIC ACID (PYRIDIN-4-YLMETHYL)AMIDE.
ABC294640; ABC-294640; ABC 294640; 3-(4-CHLOROPHENYL)-ADAMANTANE-1-CARBOXYLIC ACID (PYRIDIN-4-YLMETHYL)AMIDE;OPAGANIB
[Molecular Formula]

C23H25ClN2O
[MDL Number]

MFCD22666355
[MOL File]

915385-81-8.mol
[Molecular Weight]

380.91
Chemical PropertiesBack Directory
[storage temp. ]

Inert atmosphere,Store in freezer, under -20°C
[solubility ]

≥38.1 mg/mL in DMSO; insoluble in H2O; ≥58.9 mg/mL in EtOH
[form ]

solid
Safety DataBack Directory
[Symbol(GHS) ]


GHS07
[Signal word ]

Warning
Hazard InformationBack Directory
[Description]

ABC294640 is an inhibitor of sphingosine kinase 2 (SPHK2; Ki = 9.8 μM). It inhibits SPHK2 (IC50 = 60 μM) without affecting SPHK1 activity up to 100 μM but does reduce SPHK1 isoform a (SPHK1a) protein levels in androgen-independent LNCaP (LNCaP-AI) cells via an SPHK1-indirect, proteasomal-dependent mechanism when used at concentrations ranging from 5 to 25 μM. ABC294640 is inactive against a panel of 20 lipid-regulated kinases at 50 μM. It decreases sphingosine-1-phosphate (S1P) production in MDA-MB-231 cells in a concentration-dependent manner. ABC294640 inhibits proliferation of a variety of cancer cells, including HepG2 liver, A-498 kidney, PANC-1 pancreas, and HT-29 colon cells (IC50s = 6, 12.2, 32.8, and 48.1 μM, respectively). It reduces actin filament polymerization in, and cell migration of, A-498 cells in a scratch assay. Oral administration of ABC294640 (35 and 100 mg/kg every other day) reduces tumor growth in a mouse syngeneic model of mammary adenocarcinoma. It also reduces colonic inflammation in mouse and rat models of Crohn’s disease induced by trinitrobenzene sulfonic acid (TNBS).
[Uses]

Opaganib is used in treating iatrogenic autoimmune colitis.
[Definition]

ChEBI: 3-(4-chlorophenyl)-N-(pyridin-4-ylmethyl)-1-adamantanecarboxamide is an organochlorine compound.
[References]

[1] french k j, zhuang y, maines l w, et al. pharmacology and antitumor activity of abc294640, a selective inhibitor of sphingosine kinase-2. journal of pharmacology and experimental therapeutics, 2010, 333(1): 129-139.
[2] antoon j w, white m d, meacham w d, et al. antiestrogenic effects of the novel sphingosine kinase-2 inhibitor abc294640. endocrinology, 2010, 151(11): 5124-5135.
Spectrum DetailBack Directory
[Spectrum Detail]

ABC294640(915385-81-8)1HNMR
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