| Identification | Back 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 Properties | Back Directory | [Boiling point ]
589.5±50.0 °C(Predicted) | [density ]
1.273±0.06 g/cm3(Predicted) | [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 | [pka]
14.57±0.40(Predicted) | [color ]
White to off-white | [InChI]
InChI=1S/C23H25ClN2O/c24-20-3-1-19(2-4-20)22-10-17-9-18(11-22)13-23(12-17,15-22)21(27)26-14-16-5-7-25-8-6-16/h1-8,17-18H,9-15H2,(H,26,27) | [InChIKey]
CAOTVXGYTWCKQE-UHFFFAOYSA-N | [SMILES]
C12(C(NCC3C=CN=CC=3)=O)CC3CC(CC(C4=CC=C(Cl)C=C4)(C3)C1)C2 |
| Hazard Information | Back Directory | [Description]
ABC294640 is an inhibitor of sphingosine kinase 2 (SPHK2; Ki = 9.8 μM).1 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.2 ABC294640 is inactive against a panel of 20 lipid-regulated kinases at 50 μM.1 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).3 | [Uses]
Opaganib is used in treating iatrogenic autoimmune colitis. | [Definition]
ChEBI: 3-(4-chlorophenyl)-N-(pyridin-4-ylmethyl)-1-adamantanecarboxamide is an organochlorine compound. | [in vivo]
Opaganib induces a transient minor decrease in the hematocrit of rats. Hematology studies indicate decreases in red blood cell number and hematocrit of approximately 20% in animals given either 100 or 250 mg/kg/day; and a slight increase in neutrophils and decrease in basophils in the treated rats[1]. Mice are gavaged with Opaganib (50 mg/kg), a selective inhibitor of sphingosine kinase-2 (SK2), 1 h before surgery and subjected to 1 h-warm ischemia to ~70% of the liver followed by reperfusion. Opaganib-treatment largely prevented the increase of sphingosine-1-phosphate (S1P) after ischemia-reperfusion (IR) in vivo[2]. | [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. |
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