Proscillaridin A

Names

[ CAS No. ]:
466-06-8

[ Name ]:
Proscillaridin A

[Synonym ]:
Bufa-4,20,22-trienolide, 3-[(6-deoxy-α-L-mannopyranosyl)oxy]-14-hydroxy-, (3β)-
Protasin
14-Hydroxy-3b-(rhamnosyloxy)bufa-4,20,22-trienolide
(3β)-3-[(6-Deoxy-α-L-mannopyranosyl)oxy]-14-hydroxybufa-4,20,22-trienolid
Scillarenin 3β-rhamnoside
3-β-((6-Deoxy-α-L-mannopyranosyl)oxy)-14-hydroxybufa-4,20,22-trienolide
5-[(3S,8R,9S,10R,13R,14S,17R)-14-Hydroxy-10,13-dimethyl-3-{[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl]oxy}-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2H-pyran-2-on
Desgluco-transvaalin
Urgilan
Herzo proscillan
Scillarenin 3b-Rhamnoside
Scillarenin 3a-L-Rhamnopyranoside
3b-Rhamnosido-14b-hydroxy-D4,20,22-bufatrienolide
Proscillaridin
Scillacrist
Desglucotransvaaline
Coratol
Scilla "didier"
(3β)-3-[(6-Deoxy-α-L-mannopyranosyl)oxy]-14-hydroxybufa-4,20,22-trienolide
Purosin-TC
Sandoscill
Wirnesin
Caratol
(3b)-3-[(6-Deoxy-a-L-mannopyranosyl)oxy]-14-hydroxybufa-4,20,22-trienolide
3b-[(6-Deoxy-a-L-mannopyranosyl)oxy]-14-hydroxybufa-4,20,22-trienolide
Tradenal
Herzo
Bufa-4,20,22-trienolide, 3-((6-deoxy-α-L-mannopyranosyl)oxy)-14-hydroxy-, (3β)-
psc-801
Caradrin
Cardion
14-Hydroxy-3β-(rhamnosyloxy)bufa-4,20,22-trienolide
Cardiovite
Prostosin
Proslladin
Solestril
Stellarid
proszin
proscillaridin-A
Talucard
Carmazon
Simeon
Procilan
5-[(3S,8R,9S,10R,13R,14S,17R)-14-Hydroxy-10,13-dimethyl-3-{[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl]oxy}-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2H-pyran-2-one
Talusin
5-[(3S,8R,9S,10R,13R,14S,17R)-14-Hydroxy-10,13-diméthyl-3-{[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-méthyltétrahydro-2H-pyran-2-yl]oxy}-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tétradécahydro-1H-cyclopenta[a]phénanthrén-17-yl]-2H-pyran-2-one
Procardin
Caradrine
Proscillan

Biological Activity

[Description]:

Proscillaridin A is a potent poison of topoisomerase I/II activity with IC50 values of 30 nM and 100 nM, respectively[1].

[Related Catalog]:

Research Areas >> Cancer

Signaling Pathways >> Cell Cycle/DNA Damage >> Topoisomerase

[Target]

Topoisomerase I:30 nM (IC50)

Topoisomerase II:100 nM (IC50)

[In Vitro]

Proscillaridin A (0-160 nM; 48 hours) reveals the antiproliferative response in a time- as well as dose-dependent manner in MCF-7 cells[1].

[References]

[1]. Bielawski K, et al. Inhibition of DNA topoisomerases I and II, and growth inhibition of breast cancer MCF-7 cells by ouabain, digoxin and proscillaridin A.Biol Pharm Bull. 2006 Jul;29(7):1493-7.

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Boiling Point ]:
716.7±60.0 °C at 760 mmHg

[ Melting Point ]:
233ºC

[ Molecular Formula ]:
C₃₀H₄₂O₈

[ Molecular Weight ]:
530.650

[ Flash Point ]:
232.6±26.4 °C

[ Exact Mass ]:
530.287964

[ PSA ]:
129.59000

[ LogP ]:
3.90

[ Vapour Pressure ]:
0.0±5.2 mmHg at 25°C

[ Index of Refraction ]:
1.620

[ Storage condition ]:
2-8℃

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: UK6650000

CHEMICAL NAME :: Proscillaridin A

CAS REGISTRY NUMBER :: 466-06-8

LAST UPDATED :: 199109

DATA ITEMS CITED :: 14

MOLECULAR FORMULA :: C30-H42-O8

MOLECULAR WEIGHT :: 530.72

WISWESSER LINE NOTATION :: L E5 B666 MUTJ A1 E1 IQ F- ET6OVJ& O- BT6OTJ CQ DQ EQ F1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 56 mg/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Behavioral - convulsions or effect on seizure threshold Behavioral - ataxia

REFERENCE :: TXAPA9 Toxicology and Applied Pharmacology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1959- Volume(issue)/page/year: 20,599,1971

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >1 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 2,411,1968

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 9 mg/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Behavioral - convulsions or effect on seizure threshold Behavioral - ataxia

REFERENCE :: TXAPA9 Toxicology and Applied Pharmacology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1959- Volume(issue)/page/year: 20,599,1971

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 30500 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: 6,723,1982

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 4700 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 2,411,1968

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - cat

DOSE/DURATION :: 377 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: 20,1,1970

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Mammal - cat

DOSE/DURATION :: 111 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: 20,1,1970

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Parenteral

SPECIES OBSERVED :: Mammal - cat

DOSE/DURATION :: 1 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: APPHAX Acta Poloniae Pharmaceutica. For English translation, see APPFAR. (Ars Polona, POB 1001, 00-680 Warsaw 1, Poland) V.1- 1937- Volume(issue)/page/year: 34,431,1977

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraduodenal

SPECIES OBSERVED :: Mammal - cat

DOSE/DURATION :: 268 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 14,716,1964

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - guinea pig

DOSE/DURATION :: 6810 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: USXXAM United States Patent Document. (U.S. Patent Office, Box 9, Washington, DC 20231) Volume(issue)/page/year: #4230702

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - guinea pig

DOSE/DURATION :: 280 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: 20,1,1970

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Bird - domestic

DOSE/DURATION :: 373 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: NYKZAU Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. (Nippon Yakuri Gakkai, c/o Kyoto Daigaku Igakubu Yakurigaku Kyoshitsu, Konoe-cho, Yoshida, Sakyo-ku, Kyoto 606, Japan) V.40- 1944- Volume(issue)/page/year: 62(3),195S,1966

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Bird - domestic

DOSE/DURATION :: 124 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: NYKZAU Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. (Nippon Yakuri Gakkai, c/o Kyoto Daigaku Igakubu Yakurigaku Kyoshitsu, Konoe-cho, Yoshida, Sakyo-ku, Kyoto 606, Japan) V.40- 1944- Volume(issue)/page/year: 62(3),195S,1966 *** REVIEWS *** TOXICOLOGY REVIEW 85ELDJ "Die Herzwirksamen Glykoside," Baumgarten, G., and W. Forster, Leipzig, Ger. Dem. Rep., VEB Georg Thieme, 1963 Volume(issue)/page/year: -,193,1963

Safety Information

[ Symbol ]:

GHS06

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H301

[ Precautionary Statements ]:
P301 + P310

[ Personal Protective Equipment ]:
Eyeshields;Faceshields;Gloves;type P2 (EN 143) respirator cartridges

[ Hazard Codes ]:
T: Toxic;

[ Risk Phrases ]:
R25

[ Safety Phrases ]:
28-45

[ RIDADR ]:
UN 2811 6.1/PG 3

[ WGK Germany ]:
3

[ RTECS ]:
UK6650000

Articles

Pulse pressure correlates in humans with a proscillaridin A immunoreactive compound.

Hypertension 27(5) , 1073-8, (1996)

Endogenous digitalis-like factors in humans are presumably cardenolides and bufadienolides. To test whether bufadienolide-like substances may circulate in human blood, we used antibodies from rabbits ...

Cytotoxic effects of cardiac glycosides in colon cancer cells, alone and in combination with standard chemotherapeutic drugs.

J. Nat. Prod. 72 , 1969-74, (2009)

Cardiac glycosides have been reported to exhibit cytotoxic activity against several different cancer types, but studies against colorectal cancer are lacking. In a screening procedure aimed at identif...

Role of endogenous cardiac glycosides in the spontaneously hypertensive rat--antagonism by active immunization.

Am. J. Hypertens. 9(1) , 81-5, (1996)

The effects of simultaneous active immunization against two cardiac glycoside drugs, digoxin and proscillaridin, have been examined in young spontaneously hypertensive and Wistar-Kyoto rats. Control a...