CAS 66-28-4|Card-20(22)-enolide,3,5,14-trihydroxy-19-oxo-, (3b,5b)-

Introduction：Basic information about CAS 66-28-4|Card-20(22)-enolide,3,5,14-trihydroxy-19-oxo-, (3b,5b)-, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Table of Contents

1. Names
2. BiologicalActivity
3. Chemical & Physical Properties
4. Toxicological Information
CHEMICAL IDENTIFICATION
HEALTH HAZARD DATA
ACUTE TOXICITY DATA
5. Safety Information
6. Articles27
7. Synonyms

Common Name	Card-20(22)-enolide,3,5,14-trihydroxy-19-oxo-, (3b,5b)-
CAS Number	66-28-4	Molecular Weight	404.49700
Density	1.432 g/cm3	Boiling Point	620.7ºC at 760 mmHg
Molecular Formula	C₂₃H₃₂O₆	Melting Point	169ºC
MSDS	ChineseUSA	Flash Point	214.9ºC
Symbol	GHS06	Signal Word	Danger

Names

Name	strophanthidin
Synonym	More Synonyms

BiologicalActivity

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	Research Areas >>Cardiovascular Disease
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.

Chemical & Physical Properties

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
InChIKey	ODJLBQGVINUMMR-HZXDTFASSA-N
SMILES	CC12CCC3C(CCC4(O)CC(O)CCC34C=O)C1(O)CCC2C1=CC(=O)OC1

Toxicological Information

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

Safety Information

Symbol	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

Articles27

Determination of strophanthidin in ingesta and plant material by LC-MS/MS.

J. Agric. Food Chem. 52 , 2174-8, (2004)

An LC-MS/MS method was developed for the semiquantitative determination of strophanthidin glycosides in ingesta from animals. Strophanthidin glycosides were simultaneously extracted and hydrolyzed to ...

Mechanistic insight into the functional and toxic effects of Strophanthidin in the failing human myocardium.

Eur. J. Heart Fail. 9(11) , 1086-94, (2007)

Cardiac glycosides are characterized by a narrow therapeutic range with Ca2+-overload and arrhythmias occurring at higher concentrations. Data on cardiac glycosides in isolated failing human myocardiu...

Summer pheasant's eye (Adonis aestivalis) poisoning in three horses.

Vet. Pathol. 41(3) , 215-20, (2004)

Three horses died as a result of eating grass hay containing summer pheasant's eye (Adonis aestivalis L.), a plant containing cardenolides similar to oleander and foxglove. A 9-year-old thoroughbred g...

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

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