Fangchinoline

Modify Date: 2024-01-01 19:29:46

Fangchinoline Structure
Fangchinoline structure
Common Name Fangchinoline
CAS Number 436-77-1 Molecular Weight 608.723
Density 1.2±0.1 g/cm3 Boiling Point 709.7±60.0 °C at 760 mmHg
Molecular Formula C37H40N2O6 Melting Point N/A
MSDS N/A Flash Point 383.0±32.9 °C

 Use of Fangchinoline


Fangchinoline is isolated from Stephania tetrandra with extensive biological activities, such as enhancing immunity, anti-inflammatory sterilization and anti-atherosclerosis. Fangchinoline, a novel HIV-1 inhibitor, inhibits HIV-1 replication by impairing gp160 proteolytic processing[1]. Fangchinoline targets Focal adhesion kinase (FAK) and suppresses FAK-mediated signaling pathway in tumor cells which highly expressed FAK[2]. Fangchinoline induces apoptosis and adaptive autophagy in bladder cancer[3].

 Names

Name Fangchinoline
Synonym More Synonyms

 Fangchinoline Biological Activity

Description Fangchinoline is isolated from Stephania tetrandra with extensive biological activities, such as enhancing immunity, anti-inflammatory sterilization and anti-atherosclerosis. Fangchinoline, a novel HIV-1 inhibitor, inhibits HIV-1 replication by impairing gp160 proteolytic processing[1]. Fangchinoline targets Focal adhesion kinase (FAK) and suppresses FAK-mediated signaling pathway in tumor cells which highly expressed FAK[2]. Fangchinoline induces apoptosis and adaptive autophagy in bladder cancer[3].
Related Catalog
Target

HIV-1 replication[1]; Focal adhesion kinase (FAK)[2]; apoptosis; autophagy[3]

In Vitro Fangchinoline (2.5-40 µM; 24-96 hours) inhibits both T24 and 5637 cells in dose-dependent manner, the IC50 values of Fangchinoline in T24 cells are 19.0 µM (24 h), 12.0 µM (48 h) and 7.57 µM (72 h), and 11.9 µM (24 h), 9.92 µM (48 h) and 7.13 µM (72 h) in 5637 cells[1]. Fangchinoline (5 µM; 24 hours) induces a significant increase in the LC3-II/LC3-I ratio and a decrease in p62 in both T24 and 5637 cells, and causes a significant increase in the cleavage of caspase-3[1]. Cell Viability Assay[3] Cell Line: T24 and 5637 cells Concentration: 2.5 µM; 5 µM; 10 µM; 20 µM; 30 µM; 40 µM Incubation Time: 24 hours; 48 hours; 96 hours Result: Inhibited both T24 and 5637 cells proliferation. Western Blot Analysis[3] Cell Line: T24 and 5637 cells Concentration: 5 µM Incubation Time: 24 hours Result: Incresed LC3-II/LC3-I ratio and the cleavage of caspase-3.
References

[1]. Wan Z, et al. Fangchinoline inhibits human immunodeficiency virus type 1 replication by interfering with gp160 proteolytic processing. PLoS One. 2012;7(6):e39225.

[2]. Guo B, et al. Fangchinoline as a kinase inhibitor targets FAK and suppresses FAK-mediated signaling pathway in A549. J Drug Target. 2015 Apr;23(3):266-74.

[3]. Fan B, et al. Fangchinoline Induces Apoptosis, Autophagy and Energetic Impairment in Bladder Cancer. Cell Physiol Biochem. 2017;43(3):1003-1011.

 Chemical & Physical Properties

Density 1.2±0.1 g/cm3
Boiling Point 709.7±60.0 °C at 760 mmHg
Molecular Formula C37H40N2O6
Molecular Weight 608.723
Flash Point 383.0±32.9 °C
Exact Mass 608.288635
PSA 72.86000
LogP 3.78
Vapour Pressure 0.0±2.3 mmHg at 25°C
Index of Refraction 1.602
Storage condition 2-8C

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
DR9280000
CHEMICAL NAME :
Berbaman-7-ol, 2,2'-dimethyl-6,6',12-trimethoxy-, (1-beta)-
CAS REGISTRY NUMBER :
436-77-1
LAST UPDATED :
199709
DATA ITEMS CITED :
1
MOLECULAR FORMULA :
C37-H40-N2-O6
MOLECULAR WEIGHT :
608.79

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
>50 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
CPBTAL Chemical and Pharmaceutical Bulletin. (Japan Pub. Trading Co., USA, 1255 Howard St., San Francisco, CA 94103) V.6- 1958- Volume(issue)/page/year: 24,2413,1976

 Synthetic Route

~36%

Detail
Literature: Pachaly; Praest Archiv der Pharmazie, 1982 , vol. 315, # 7 p. 589 - 597

~36%

Detail
Literature: Pachaly; Praest Archiv der Pharmazie, 1982 , vol. 315, # 7 p. 589 - 597

~32%

Fangchinoline Structure

Fangchinoline

CAS#:436-77-1

Literature: Kunitomo, Jun-ichi; Oshikata, Megumi; Akasu, Michinori; Ishii, Hisashi Heterocycles, 1992 , vol. 34, # 5 p. 937 - 942

~35%

Detail
Literature: Pachaly; Praest Archiv der Pharmazie, 1982 , vol. 315, # 7 p. 589 - 597

 Synonyms

Berbaman-7-ol, 6,6',12-trimethoxy-2,2'-dimethyl-
Fangquinoline
FF-0018
d,l-Fangchinolin
(S,S)-(+)-tetrandine
12-O-MethylatherosperMoline
(1β)-6,6',12-Trimethoxy-2,2'-dimethylberbaman-7-ol
Tetrandrine B
6,6',12-Trimethoxy-2,2'-dimethylberbaman-7-ol
Hanfangichin B
N1799
I06-1344
THALRUGOSINE
Fangchinoline
7-o-demethyltetrandrine
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