Plumbagin

Modify Date: 2025-08-21 22:05:18

Plumbagin Structure
Plumbagin structure
 Common Name Plumbagin
CAS Number 481-42-5 Molecular Weight 188.17900
Density 1.354g/cm3 Boiling Point 383.9ºC at 760 mmHg
Molecular Formula C11H8O3 Melting Point 76-78ºC(lit.)
MSDS Chinese USA Flash Point 200.2ºC
Symbol GHS05 GHS06
GHS05, GHS06		 Signal Word Danger

 Use of Plumbagin


Plumbagin (2-Methyljuglone) is a naphthoquinone isolated from Plumbago zeylanica L, exhibits anticancer and antiproliferative activities[1].

 Names

Name plumbagin
Synonym More Synonyms

 Plumbagin Biological Activity

Description Plumbagin (2-Methyljuglone) is a naphthoquinone isolated from Plumbago zeylanica L, exhibits anticancer and antiproliferative activities[1].
Related Catalog
In Vitro Plumbagin (0, 5, 10, and 15 μM) induces apoptosis of prostate cancer cell lines, such as DU145, CWR22rv1 and LNCaP, in a dose-dependent manner[1]. Plumbagin (5, 20 μM) obviously inhibits the invasion of PC3, DU145, and CWR22rv1 cells[1]. Apoptosis Analysis[1] Cell Line: DU145, CWR22rv1, LNCaP and RWPE-1 cells Concentration: 0, 5, 10, and 15 μM Incubation Time: 24 hours Result: Dose-dependently induced apoptosis of DU145, CWR22rv1 and LNCaP, but showed no effect on RWPE-1 cells at up to 20 μM.
In Vivo Plumbagin (2 mg/kg, i.p., five days a week for 11 weeks) inhibits the growth of tumor in male athymic nude mice[1]. Plumbagin (2 mg/kg, i.p., five days a week for 11 weeks) inhibits expression of PKCε, suppresses JAK-2 and Stat3 phosphorylation, and activates Stat3, PCNA, VEGF and MMP-9 in mice[1]. Animal Model: Male athymic nude mice bearing DU145 cells[1] Dosage: 2 mg/kg Administration: I.P. after 3 days post cell implantation, five days a week. Result: Delayed tumor growth by 3 weeks, and reduced tumor weight and volume in mice.
References

[1]. Aziz MH, et al. Plumbagin, a medicinal plant-derived naphthoquinone, is a novel inhibitor of the growth and invasion of hormone-refractory prostate cancer. Cancer Res. 2008 Nov 1;68(21):9024-32.

 Chemical & Physical Properties

Density 1.354g/cm3
Boiling Point 383.9ºC at 760 mmHg
Melting Point 76-78ºC(lit.)
Molecular Formula C11H8O3
Molecular Weight 188.17900
Flash Point 200.2ºC
Exact Mass 188.04700
PSA 54.37000
LogP 1.71750
Vapour Pressure 1.92E-06mmHg at 25°C
Index of Refraction 1.63
Storage condition −20°C

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
QL8500000
CHEMICAL NAME :
1,4-Naphthoquinone, 5-hydroxy-2-methyl-
CAS REGISTRY NUMBER :
481-42-5
BEILSTEIN REFERENCE NO. :
1870475
LAST UPDATED :
199709
DATA ITEMS CITED :
12
MOLECULAR FORMULA :
C11-H8-O3
MOLECULAR WEIGHT :
188.19
WISWESSER LINE NOTATION :
L66 BV EVJ C1 GQ

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 :
65 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
16 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
5 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
100 mg/kg
SEX/DURATION :
female 10 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Maternal Effects - ovaries, fallopian tubes
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
300 mg/kg
SEX/DURATION :
female 30 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Fertility - mating performance (e.g. # sperm positive females per # females mated; # copulations per # estrus cycles)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
150 mg/kg
SEX/DURATION :
female 15 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Maternal Effects - parturition
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
35 mg/kg
SEX/DURATION :
female 5-11 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - abortion
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
50 mg/kg
SEX/DURATION :
female 1-5 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - pre-implantation mortality (e.g. reduction in number of implants per female; total number of implants per corpora lutea)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
300 mg/kg
SEX/DURATION :
male 30 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Paternal Effects - testes, epididymis, sperm duct
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
10 mg/kg
SEX/DURATION :
female 1 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Fertility - other measures of fertility

MUTATION DATA

TYPE OF TEST :
Mutation in microorganisms
TEST SYSTEM :
Bacteria - Escherichia coli
DOSE/DURATION :
500 umol/L
REFERENCE :
JOBAAY Journal of Bacteriology. (American Soc. for Microbiology, 1913 I St., NW, Washington, DC 20006) V.1- 1916- Volume(issue)/page/year: 164,1309,1985

 Safety Information

Symbol GHS05 GHS06
GHS05, GHS06
Signal Word Danger
Hazard Statements H301-H314
Precautionary Statements P280-P305 + P351 + P338-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
Risk Phrases R23/24/25
Safety Phrases 22-26-36/37/39-45
RIDADR UN 2923 8/PG 2
WGK Germany 3
RTECS QL8500000
Packaging Group II
Hazard Class 6.1(a)
HS Code 2914690090

 Synthetic Route

 Customs

HS Code 2914690090
Summary 2914690090 other quinones。Supervision conditions:None。VAT:17.0%。Tax rebate rate:9.0%。MFN tariff:5.5%。General tariff:30.0%

 Articles61

More Articles
Antitumorigenic effect of plumbagin by induction of SH2-containing protein tyrosine phosphatase 1 in human gastric cancer cells.

Int. J. Oncol. 46 , 2380-8, (2015)

A recent study reported that plumbagin downregulated the activity of Janus kinase 2 (JAK2)-signal transducer and activator of transcription 3 (STAT3) pathway to show various antitumor effects in multi...

Binding and Anticancer Properties of Plumbagin with Human Serum Albumin.

Chem. Biol. Drug Des. 86 , 362-9, (2015)

Plumbagin has received extensive attention as a promising anticancer drug. Therefore, we investigated the binding and anticancer properties of plumbagin with human serum albumin. Fluorescence results ...

Inhibition of ANO1/TMEM16A Chloride Channel by Idebenone and Its Cytotoxicity to Cancer Cell Lines.

PLoS ONE 10 , e0133656, (2015)

The expression levels of anoctamin 1 (ANO1, TMEM16A), a calcium-activated chloride channel (CaCC), are significantly increased in several tumors, and inhibition of ANO1 is known to reduce cell prolife...

 Synonyms

2-Methyljuglone
5-hydroxy-2-methyl-[1,4]naphthoquinone
2-methyl-5-hydroxy-1,4-naphthalenedione
Plumbagine
EINECS 207-569-6
Plumbagin from Plumbago indica
2-Methyl-5-hydroxy-1,4-naphthoquinone
Plumbagin
5-hydroxy-2-methyl-1,4-NQ
Plumbagone
Plumbaein
5-hydroxy-2-methylnaphthalene-1,4-dione
MFCD00001682
5-hydroxy-2-methyl-1,4-naphthalenedione
5-Hydroxy-2-methyl-1,4-naphthoquinone
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