| Identification | Back Directory | [Name]
Cinobufagin | [CAS]
470-37-1 | [Synonyms]
FEMA 2288
AKOS 233-01
CINOBUFAGIN
16-beta)-bet
cinobufagine
AKOS B004228
CINOBUFAGIN(P)
Cinobufagin std.
CINOBUFAGIN95%,99%
RARECHEM BK HC T302
3-STYRYLACRYLIC ACID
3-PHENYLACRYLIC ACID
CINNAMIC ACID, TRANS-
TRANS-CINNAMYLIC ACID
cinobufagin venom toad
BETA-PHENYLACRYLIC ACID
Cinobufogenin，Cinobufagin
TRANS-3-PHENYLPROPENOIC ACID
TRANS-3-BENZENEPROPENOIC ACID
2-PROPENOIC ACID, 3-PHENYL-, (2E)-
16β-Acetoxy-14,15β-epoxy-3β-hydroxy-5β-bufa-20,22-dienolide
5b,20(22)-Bufadienolide-3b,16b-diol-14,15b-epoxy 16-acetate
5β,20(22)-Bufadienolide-3β,16β-diol-14,15β-epoxy 16-acetate
16β-Acetyloxy-14,15β-epoxy-3β-hydroxy-5β-bufa-20,22-dienolide
14,15β-Epoxy-3β,16β-dihydroxy-5β,20(22)-bufadienolide 16-acetate
5BETA,20[22]-BUFADIENOLIDE-3BETA,16BETA-DIOL-14,15BETA-EPOXY 16-ACETATE
22-dienolide,16-(acetyloxy)-14,15-epoxy-3-hydroxy-,(3-beta,5-beta,15-bufa-2
14,15BETA-EPOXY-3BETA,16BETA-DIHYDROXY-5BETA,20[22]-BUFADIENOLIDE 16-ACETATE
5β,20(22)-Bufadienolide-3β,16β-diol-14,15β-epoxy 16-acetate, 14,15β-Epoxy-3β,16β-dihydroxy-5β,20(22)-bufadienolide 16-acetate
5-((1R,2R,2aR,3aS,3bR,5aR,7S,9aS,9bS,11aR)-2-Acetyl-7-hydroxy-9a,11a-diMethylhexadecahydronaphtho[1',2':6,7]indeno[1,7a-b]oxiren-1-yl)-2H-pyran-2-one | [EINECS(EC#)]
205-398-1 | [Molecular Formula]
C26H34O6 | [MDL Number]
MFCD00004369 | [MOL File]
470-37-1.mol | [Molecular Weight]
442.55 |
| Chemical Properties | Back Directory | [Melting point ]
133 °C(lit.)
| [Boiling point ]
300 °C(lit.)
| [density ]
1.261 g/cm3 | [Fp ]
>230 °F
| [storage temp. ]
2-8°C
| [solubility ]
DMF: 10 mg/ml; DMSO: 10 mg/ml; DMSO:PBS (pH 7.2) (1:2): 0.33 mg/ml | [form ]
powder to crystal | [pka]
15.10±0.70(Predicted) | [color ]
White to Light yellow | [InChIKey]
SCULJPGYOQQXTK-QZXYOKJUNA-N | [SMILES]
C[C@]12CC[C@]3([H])[C@]4(CC[C@H](O)C[C@@]4([H])CC[C@@]3([H])[C@@]31O[C@@H]3[C@H](OC(=O)C)[C@@H]2C1=COC(=O)C=C1)C |&1:1,4,6,9,12,16,18,20,21,26,r| |
| Hazard Information | Back Directory | [Uses]
Cinobufagine is a major component of cinobufacini (huachansu), is an important cardenolidal steroid. Cinobufagine was shown to exhibit potent anti-cancer effects. | [Definition]
ChEBI: Cinobufagin is a steroid lactone. It is functionally related to a bufanolide. | [in vivo]
Cinobufagin (5 mg/kg for i.p., once a day for 10 days) inhibits xenograft growth by inducing cell apoptosis in tumor xenograft mice model[1].
Cinobufagin (5 mg/kg for i.p., once a day for 10 days) suppresses tumor growth in both subcutaneous and intracranial U87MG-EGFR xenograft mouse models and increases the median survival of nude mice bearing intracranial U87MGEGFR tumors[2].
| Animal Model: | OCM1 cells tumor xenograft in Nu/Nu nude mice [1] | | Dosage: | 5 mg/kg | | Administration: | Intraperitoneal injection (i.p.), once a day for 10 days | | Result: | Made the tumors grew more slowly than those treated with intraperitoneal injection of saline or untreated.
Increased the expression of caspase-3 and PARP in tumor tissues and decreased Bcl-2 and Bcl-xl expression in mouse tumor tissues and increased expression of Bad and Bax.
|
| Animal Model: | U87MG-EGFR subcutaneous and intracranial xenograft model[2] | | Dosage: | 5 mg/kg | | Administration: | Intraperitoneal injection (i.p.), once a day for 10 days | | Result: | Decreased the luminescence intensity of brain tumor about 70%.
Decreased p-EGFR, p-STAT3, and p-Akt levels in the intracranial tumors as compared with the vehicles.
Decreased Ki67 and active caspase-3 immunostaining of intracranial tumors.
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| Questions And Answer | Back Directory | [Description]
Cinobufagin is a cardiotoxic bufanolide steroid secreted by the Asiatic toad Bufo gargarizans, having similar effects to digitalis and used in traditional Chinese medicine. It has potential antineoplastic activity and now is widely used in clinical practice, especially in anti-liver cancer. It has benn found to suppress cancer cell proliferation and cause apoptosis in cancer cells via a sequence of apoptotic modulators, including mitochondrial Bax and cytosolic chromosome c, and caspases 3, 8, and 9.
| [References]
1. https://en.wikipedia.org/wiki/Cinobufagin
2. https://www.cancer.gov/publications/dictionaries/cancer-drug?cdrid=689412
3. http://www.yourdictionary.com/cinobufagin
4. https://www.medchemexpress.com/cinobufagin.html
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