483-17-0
Chemical Structure
Cephaeline
Synonym(s): (-)-Cephaeline; NSC 32944 free base
- CAS No.: 483-17-0
- Formula:C28H38N2O4
- Molecular Weight:466.61
IUPAC Name: (R)-1-(((2S,3R,11bS)-3-ethyl-9,10-dimethoxy-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-2-yl)methyl)-7-methoxy-1,2,3,4-tetrahydroisoquinolin-6-ol
InChIKey: DTGZHCFJNDAHEN-OZEXIGSWSA-N
SMILES: OC1=CC2=C([C@@H](C[C@@H]3[C@@H](CC)CN4CCC5=CC(OC)=C(OC)C=C5[C@]4([H])C3)NCC2)C=C1OC
Biological Activity: Cephaeline ((-)-Cephaeline; NSC 32944) is a ferroptosis inducer, with broad-spectrum anticancer and antiviral activities. Cephaeline induces ferroptosis (Ferroptosis) by upregulating p53, inhibiting NRF2, activating ULK3, downregulating the expressions of SLC7A11 and GPX4 in a p53-dependent manner, reducing GSH and mitochondrial membrane potential, and increasing lipid peroxidation and iron accumulation. Cephaeline inhibits cancer cell proliferation, migration and tumor growth. Cephaeline inhibits Ebola virus (EBOV) VLP entry and infection, with IC50 values of 3.27 μM and 22.18 μM respectively; it also inhibits Zika virus (ZIKV) NS5 RdRp activity (IC50 = 976 nM), and binds to severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2) RdRp and N protein, with Kd values of 8.9 μM and 53.8 μM respectively. Cephaeline can be used in studies related to breast cancer, lung cancer, COVID-19, EBOV and ZIKV infections[1][2][3][4][5].
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Cephaeline | 99.77% | Cephaeline ((-)-Cephaeline; NSC 32944) is a ferroptosis inducer, with broad-spectrum anticancer and antiviral activities. Cephaeline induces ferroptosis (Ferroptosis) by upregulating p53, inhibiting NRF2, activating ULK3, downregulating the expressions of SLC7A11 and GPX4 in a p53-dependent manner, reducing GSH and mitochondrial membrane potential, and increasing lipid peroxidation and iron accumulation. Cephaeline inhibits cancer cell proliferation, migration and tumor growth. Cephaeline inhibits Ebola virus (EBOV) VLP entry and infection, with IC50 values of 3.27 μM and 22.18 μM respectively; it also inhibits Zika virus (ZIKV) NS5 RdRp activity (IC50 = 976 nM), and binds to severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2) RdRp and N protein, with Kd values of 8.9 μM and 53.8 μM respectively. Cephaeline can be used in studies related to breast cancer, lung cancer, COVID-19, EBOV and ZIKV infections. | ||||||||||||||||||||
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Cephaeline (Standard) | ≥98% | Cephaeline ((-)-Cephaeline), a desmethyl analog of Emetine, is a phenolic alkaloid in Indian Ipecac roots isolated from the Cephaelis ipecacuanha. Cephaeline exhibits potent inhibition of both Zika virus (ZIKV) and Ebola virus (EBOV) infections. Cephaeline is an inductor of histone H3 acetylation and an inhibitor of mucoepidermoid carcinoma cancer stem cells (MEC), which promotes ferroptosis by inhibiting NRF2 to exert anti-lung cancer efficacy. | ||||||||||||||||||||
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References
- [1]. Chen P, et al. Cephaeline promotes ferroptosis by targeting NRF2 to exert anti-lung cancer efficacy. Pharmaceutical biology. 2024 Dec;62(1):195-206. [Content Brief]
- [2]. Li X, et al. Cephaeline promotes ferroptosis in breast cancer via p53/SLC7A11/GPX4 axis. Daru : journal of Faculty of Pharmacy, Tehran University of Medical Sciences. 2026 Jun 19;34(2):38. [Content Brief]
- [3]. Ren PX, et al. A multi-targeting drug design strategy for identifying potent anti-SARS-CoV-2 inhibitors. Acta pharmacologica Sinica. 2022 Feb;43(2):483-493. [Content Brief]
- [4]. Silva LC, et al. Cephaeline is an inductor of histone H3 acetylation and inhibitor of mucoepidermoid carcinoma cancer stem cells. Journal of oral pathology & medicine : official publication of the International Association of Oral Pathologists and the American Academy of Oral Pathology. 2022 Jul;51(6):553-562. [Content Brief]
- [5]. Yang S, et al. Emetine inhibits Zika and Ebola virus infections through two molecular mechanisms: inhibiting viral replication and decreasing viral entry. Cell Discov. 2018 Jun 5;4:31.
