Opaganib
| Code | Size | Price |
|---|
| AG-CR1-3749-M005 | 5 mg | £100.00 |
Quantity:
| AG-CR1-3749-M025 | 25 mg | £370.00 |
Quantity:
| AG-CR1-3749-M100 | 100 mg | £860.00 |
Quantity:
Prices exclude any Taxes / VAT
Overview
Regulatory Status: RUO
Shipping:
AMBIENT
Storage:
Short Term: +4°C, Long Term: -20°C
Documents
Further Information
Alternate Names/Synonyms:
3-(4-Chlorophenyl)-adamantane-1-carboxylic acid (pyridin-4-ylmethyl)amide; ABC294640; Yeliva
Appearance:
White to off-white solid.
CAS:
915385-81-8
EClass:
32160000
Form (Short):
liquid
GHS Symbol:
GHS07
Handling Advice:
Keep cool and dry.
Hazards:
H302, H315, H319, H335
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)/t17-,18+,22+,23-
InChiKey:
CAOTVXGYTWCKQE-BRNYJPRKSA-N
Long Description:
Chemical. CAS: 915385-81-8. Formula: C23H25ClN2O. MW: 380.9. Opaganib is a selective inhibitor of sphingosine kinase 2 (SPHK2; Ki = 9.8 µM), a lipid kinase that catalyzes formation of the lipid signaling molecule sphingosine 1-phosphate (S1P). S1P promotes cancer growth, and proliferation and pathological inflammation, including TNF-α signaling and other inflammatory cytokine production. By inhibiting the SK2 enzyme, opaganib blocks the synthesis of S1P which regulates fundamental biological processes such as cell proliferation, migration, immune cell trafficking and angiogenesis, and is also involved in immune-modulation and suppression of innate immune responses from T cells. Opaganip has similar potency toward sphingosine kinase (SK2) and dihydroceramide desaturase (DES1). Inhibition of SK2 activity causes downregulation of the expression of myeloid cell leukemia 1 (Mcl-1) and c-Myc and suppresses the activation of nuclear factor-kappa B (NF-kB), thereby promoting apoptosis and inhibiting proliferation and inflammation. In parallel, inhibition of DES1 promotes autophagy and promotes Rb phosphorylation resulting in suppression of proliferation. Opaganib 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 also has been used in vivo to reduce tumor growth in a mouse syngeneic model of mammary adenocarcinoma and to reduce colonic inflammation in mouse and rat models of Crohn?s disease. Opaganib shows anticancer, anti-inflammatory and antiviral activities. Opaganib is an investigational drug targeting several potential oncology, inflammatory and gastrointestinal indications and it is also under development as a potential therapy for COVID-19.
MDL:
MFCD22666355
Molecular Formula:
C23H25ClN2O
Molecular Weight:
380.9
Package Type:
Vial
Precautions:
P261, P271, P280, P312
Product Description:
Opaganib is a selective inhibitor of sphingosine kinase 2 (SPHK2; Ki = 9.8 µM), a lipid kinase that catalyzes formation of the lipid signaling molecule sphingosine 1-phosphate (S1P). S1P promotes cancer growth, and proliferation and pathological inflammation, including TNF-alpha signaling and other inflammatory cytokine production. By inhibiting the SK2 enzyme, opaganib blocks the synthesis of S1P which regulates fundamental biological processes such as cell proliferation, migration, immune cell trafficking and angiogenesis, and is also involved in immune-modulation and suppression of innate immune responses from T cells. Opaganip has similar potency toward sphingosine kinase (SK2) and dihydroceramide desaturase (DES1). Inhibition of SK2 activity causes downregulation of the expression of myeloid cell leukemia 1 (Mcl-1) and c-Myc and suppresses the activation of nuclear factor-kappa B (NF-kB), thereby promoting apoptosis and inhibiting proliferation and inflammation. In parallel, inhibition of DES1 promotes autophagy and promotes Rb phosphorylation resulting in suppression of proliferation. Opaganib 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 also has been used in vivo to reduce tumor growth in a mouse syngeneic model of mammary adenocarcinoma and to reduce colonic inflammation in mouse and rat models of Crohn?s disease. Opaganib shows anticancer, anti-inflammatory and antiviral activities. Opaganib is an investigational drug targeting several potential oncology, inflammatory and gastrointestinal indications and it is also under development as a potential therapy for COVID-19.
Purity:
>98% (HPLC)
Signal word:
Warning
SMILES:
O=C(NCC1=CC=NC=C1)[C@]23C[C@](C[C@H](C4)C3)(C5=CC=C(Cl)C=C5)C[C@@H]4C2
Solubility Chemicals:
Soluble in DMSO (10mg/ml) or DMF (20mg/ml). Insoluble in water.
Transportation:
Non-hazardous
UNSPSC Category:
Protein Kinase Modulators
UNSPSC Number:
12352200
Use & Stability:
Stable for at least 2 years after receipt when stored at -20°C.
References
Pharmacology and antitumor activity of ABC294640, a selective inhibitor of sphingosine kinase-2: K.J. French, et al.; J. Pharmacol. Exp. Ther. 333, 129 (2010) | Efficacy of a novel sphingosine kinase inhibitor in experimental Crohn?s disease: L.W. Maines, et al.; Inflammopharmacol. 18, 73 (2010) | Combined anticancer effects of sphingosine kinase inhibitors and sorafenib: V. Beljanski, et al.; Invest. New Drugs 29, 1132 (2011) | Inhibition of sphingosine kinase-2 suppresses inflammation and attenuates graft injury after liver transplantation in rats: Q. Liu, et al.; PLoS One 7, e41834 (2012) | Proteasomal degradation of sphingosine kinase 1 and inhibition of dihydroceramide desaturase by the sphingosine kinase inhibitors, SKi or ABC294640, induces growth arrest in androgen-independent LNCaP-AI prostate cancer cells: M. McNaughton, et al.; Oncotarget 7, 16663 (2016) | ABC294640, A Novel Sphingosine Kinase 2 Inhibitor, Induces Oncogenic Virus-Infected Cell Autophagic Death and Represses Tumor Growth: L Dai, et al.; Mol. Cancer Ther. 16, 2724 (2017) | The sphingosine kinase 2 inhibitor ABC294640 displays anti-non-small cell lung cancer activities in vitro and in vivo: L. Dai, et al.; Int. J. Cancer 142, 2153 (2018) | Targeting Sphingosine Kinases for the Treatment of Cancer: C.S. Lewis, et al.; Adv. Cancer Res. 140, 295 (2018) (Review) | Transient inhibition of sphingosine kinases confers protection to influenza A virus infected mice: C. Xia, et al.; Antiviral Res. 158, 171 (2018) | In vitro and in vivo roles of sphingosine kinase 2 during dengue virus infection: W.H. Al-Shujairi, et al.; J. Gen. Virol. 100, 629 (2019) | Sphingosine kinase 2 inhibitor ABC294640 displays anti-epithelial ovarian cancer activities in vitro and in vivo: K. Song, et al.; Onco. Targets Ther. 12, 4437 (2019)