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66-28-4

66-28-4 structure
66-28-4 structure
  • Name: Card-20(22)-enolide,3,5,14-trihydroxy-19-oxo-, (3b,5b)-
  • Chemical Name: strophanthidin
  • CAS Number: 66-28-4
  • Molecular Formula: C23H32O6
  • Molecular Weight: 404.49700
  • Catalog: Research Areas Cardiovascular Disease
  • Create Date: 2018-06-23 13:08:39
  • Modify Date: 2024-01-08 18:25:18
  • Strophanthidin is a naturally available cardiac glycoside[1]. Strophanthidin 0.1 and 1 nmol/L increases and 1~100 µmol/L inhibits the Na+/K+-ATPase activities, but Strophanthidin 10 and 100 nmol/L does not affect Na+/K+-ATPase activities in cardiac sarcolemmal[2]. Strophanthidin increases both diastolic and systolic intracellular Ca2+ concentration[3].
Name strophanthidin
Synonyms Convallatoxigenin
Corchorgenin
Corchsularin
Strophanthidin K
MFCD00046266
EINECS 200-626-6
(3S,5S,8R,9S,10S,13R,14S,17R)-3,5,14-trihydroxy-13-methyl-17-(5-oxo-2H-furan-3-yl)-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-10-carbaldehyde
k-Strophanthidin
Strophanthidine
Erysimupicrone
Corchorin
Corchoside A aglycon
Description Strophanthidin is a naturally available cardiac glycoside[1]. Strophanthidin 0.1 and 1 nmol/L increases and 1~100 µmol/L inhibits the Na+/K+-ATPase activities, but Strophanthidin 10 and 100 nmol/L does not affect Na+/K+-ATPase activities in cardiac sarcolemmal[2]. Strophanthidin increases both diastolic and systolic intracellular Ca2+ concentration[3].
Related Catalog
Target

Na+/K+-ATPase[2]
In Vitro Strophanthidin (0~10 μM; 24 hours; MCF-7, A549, and HepG2 cells) is effective at suppressing the growth of cancer cells and has no toxicity in normal cells[1]. Strophanthidin (0.5 to 500 µM; PBMCs) does not show significant cytotoxicity in PBMCs. Strophanthidin (2 µM; MCF-7 cells) can arrest cell cycle at the G2/M phase[1]. Strophanthidin (MCF-7, A549, and HepG2 cells) is effective at suppressing the growth of cancer cells and has no toxicity in normal cells. Strophanthidin (MCF-7, A549, and HepG2 cells) inhibits the expression of checkpoint and cyclin-dependent kinases in three cancer cells compared to untreated controls. Strophanthidin can modulate the protein localization from the nucleus to the membrane as well as to the cytoplasm. Strophanthidin is a monosaccharide cardiac glycoside with one aglycone portion and without any sugar unit. Strophanthidin induces apoptosis by the attenuation of multiple biochemical signaling pathways and by arresting cell cycle at the G2/M phase through p53-dependent and p53-independent mechanisms[1]. Cell Viability Assay[1] Cell Line: MCF-7, A549, and HepG2 cells Concentration: 0~10 μM Incubation Time: 24 hours Result: Inhibited the proliferation in three different cancer cells.
References

[1]. Reddy D, et al. Strophanthidin Attenuates MAPK, PI3K/AKT/mTOR, and Wnt/β-Catenin Signaling Pathways in Human Cancers. Front Oncol. 2020;9:1469. Published 2020 Jan 17.

[2]. Su SW, et al. Relationship between cardiotonic effects and inhibition on cardiac sarcolemmal Na+,K+-ATPase of strophan-thidin at low concentrations. Acta Pharmacol Sin. 2003;24(11):1103-1107.

[3]. Bennett DL, et al. Strophanthidin-induced gain of Ca2+ occurs during diastole and not systole in guinea-pig ventricular myocytes. Pflugers Arch. 1999;437(5):731-736.
Density 1.432 g/cm3
Boiling Point 620.7ºC at 760 mmHg
Melting Point 169ºC
Molecular Formula C23H32O6
Molecular Weight 404.49700
Flash Point 214.9ºC
Exact Mass 404.22000
PSA 104.06000
LogP 1.89820
Index of Refraction 1.674

CHEMICAL IDENTIFICATION

RTECS NUMBER :
FH5425000
CHEMICAL NAME :
5-beta-Card-20(22)-enolide, 3-beta,5,14-trihydroxy-19-oxo-
CAS REGISTRY NUMBER :
66-28-4
BEILSTEIN REFERENCE NO. :
0097859
LAST UPDATED :
199612
DATA ITEMS CITED :
8
MOLECULAR FORMULA :
C23-H32-O6
MOLECULAR WEIGHT :
404.55
WISWESSER LINE NOTATION :
L E5 B666TJ AVH E1 IQ MQ OQ F- DT5OV EHJ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
330 ug/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
85GDA2 "CRC Handbook of Antibiotic Compounds," Vols.1- , Berdy, J., Boca Raton, FL, CRC Press, 1980- Volume(issue)/page/year: 8(2),224,1982
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intracerebral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
63 ug/kg
TOXIC EFFECTS :
Behavioral - convulsions or effect on seizure threshold
REFERENCE :
ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 11,908,1961
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Mammal - cat
DOSE/DURATION :
224 ug/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
JPETAB Journal of Pharmacology and Experimental Therapeutics. (Williams & Wilkins Co., 428 E. Preston St., Baltimore, MD 21202) V.1- 1909/10- Volume(issue)/page/year: 103,420,1951
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Unreported
SPECIES OBSERVED :
Mammal - cat
DOSE/DURATION :
260 ug/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
AIPTAK Archives Internationales de Pharmacodynamie et de Therapie. (Heymans Institute of Pharmacology, De Pintelaan 185, B-9000 Ghent, Belgium) V.4- 1898- Volume(issue)/page/year: 148,471,1964
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rabbit
DOSE/DURATION :
110 ug/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
AEPPAE Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. (Berlin, Ger.) V.110-253, 1925-66. For publisher information, see NSAPCC. Volume(issue)/page/year: 185,329,1937
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - guinea pig
DOSE/DURATION :
240 ug/kg
TOXIC EFFECTS :
Cardiac - cardiomyopathy including infarction Lungs, Thorax, or Respiration - dyspnea
REFERENCE :
AIPTAK Archives Internationales de Pharmacodynamie et de Therapie. (Heymans Institute of Pharmacology, De Pintelaan 185, B-9000 Ghent, Belgium) V.4- 1898- Volume(issue)/page/year: 155,251,1965
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Mammal - species unspecified
DOSE/DURATION :
526 ug/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
APJUA8 Acta Pharmaceutica Jugoslavica. (FDH, Masarykova 2, 41000 Zagreb, Yugoslavia) V.1-41, 1951-1991. Volume(issue)/page/year: 24,179,1974 *** REVIEWS *** TOXICOLOGY REVIEW CHIMAD Chimia. (Postfach 2027, CH-4001 Basel, Switzerland) V.1- 1947- Volume(issue)/page/year: 5,93,1951
Symbol GHS06
GHS06
Signal Word Danger
Hazard Statements H300-H310-H330
Precautionary Statements P260-P264-P280-P284-P302 + P350-P310
Personal Protective Equipment Eyeshields;Faceshields;full-face particle respirator type N100 (US);Gloves;respirator cartridge type N100 (US);type P1 (EN143) respirator filter;type P3 (EN 143) respirator cartridges
Hazard Codes T+: Very toxic;
Risk Phrases R26/27/28
Safety Phrases S22;S36/S37/S39;S45
RIDADR UN 2811 6
RTECS FH5425000
508-77-0 structure

508-77-0

~82%

66-28-4 structure

66-28-4
Literature: Makarevich, I. F.; Tishchenko, A. A.; Terno, I. S. Chemistry of Natural Compounds, 1991 , vol. 27, # 1 p. 53 - 55 Khimiya Prirodnykh Soedinenii, 1991 , # 1 p. 62 - 64
83841-55-8 structure

83841-55-8

~%

2280-44-6 structure

2280-44-6
73-34-7 structure

73-34-7
546-04-3 structure

546-04-3
Detail
Literature: Chemistry of Natural Compounds, , vol. 22, # 2 p. 186 - 189 Khimiya Prirodnykh Soedinenii, , vol. 22, # 2 p. 201 - 204
84453-54-3 structure

84453-54-3

~%

5995-99-3 structure

5995-99-3
66-28-4 structure

66-28-4
Literature: Gazzetta Chimica Italiana, , vol. 112, # 9/10 p. 349 - 352

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