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479-41-4

479-41-4 structure

Name: Indirubin
Chemical Name: Indirubin
CAS Number: 479-41-4
Molecular Formula: C₁₆H₁₀N₂O₂
Molecular Weight: 262.263
Catalog: API Antineoplastic agents Natural source antineoplastic agents
Create Date: 2018-04-14 08:00:00
Modify Date: 2024-01-02 22:38:37
Indirubin(Couroupitine B) is a purple 3,2- bisindole and a stable isomer of indigo isolated from Indigo naturalis (Apiaceae); anti-inflammatory and anticancer activities.IC50 value:Target:in vitro: The activation of EGF receptor, known to be highly expressed in psoriatic lesions, was inhibited by indigo naturalis or indirubin. The cell proliferation and CDC25B expression of epidermal keratinocytes were induced by EGF alone and confirmed to be inhibited by indigo naturalis or indirubin [2]. indirubin inhibited prostate tumor growth through inhibiting tumor angiogenesis. indirubin inhibited angiogenesis in vivo. We also showed the inhibition activity of indirubin in endothelial cell migration, tube formation and cell survival in vitro [3].in vivo: Indirubin treatment suppressed skin inflammation in DNCB-exposed mice. The skin lesions were significantly thinner in the Indirubin-treated group than in untreated controls, and the hyperkeratosis disappeared. Indirubin reduced the total serum IgE level and cytokines production. In addition, it normalized NF-κB, IκB-α and MAP kinase expression [1]. Indirubin dose-dependently inhibited intersegmental vessel formation in zebrafish embryos. It also inhibited HUVEC proliferation by the induction of cellular apoptosis and cell-cycle arrest at the G0/G1 phase [4].

Name	Indirubin
Synonyms	Indirubin (3Z)-3-(3-Oxo-1,3-dihydro-2H-indol-2-ylidene)-1,3-dihydro-2H-indol-2-one Indigo Red 2-ylidene)-1,3-dihydro COUROUPITINE B [2,3'-Biindolinylidene]-2',3-dione MFCD00221745 INDIGOPURPURIN 2H-Indol-2-one, 3-(1,3-dihydro-3-oxo-2H-indol-2-ylidene)-1,3-dihydro-, (3Z)-

Description	Indirubin(Couroupitine B) is a purple 3,2- bisindole and a stable isomer of indigo isolated from Indigo naturalis (Apiaceae); anti-inflammatory and anticancer activities.IC50 value:Target:in vitro: The activation of EGF receptor, known to be highly expressed in psoriatic lesions, was inhibited by indigo naturalis or indirubin. The cell proliferation and CDC25B expression of epidermal keratinocytes were induced by EGF alone and confirmed to be inhibited by indigo naturalis or indirubin [2]. indirubin inhibited prostate tumor growth through inhibiting tumor angiogenesis. indirubin inhibited angiogenesis in vivo. We also showed the inhibition activity of indirubin in endothelial cell migration, tube formation and cell survival in vitro [3].in vivo: Indirubin treatment suppressed skin inflammation in DNCB-exposed mice. The skin lesions were significantly thinner in the Indirubin-treated group than in untreated controls, and the hyperkeratosis disappeared. Indirubin reduced the total serum IgE level and cytokines production. In addition, it normalized NF-κB, IκB-α and MAP kinase expression [1]. Indirubin dose-dependently inhibited intersegmental vessel formation in zebrafish embryos. It also inhibited HUVEC proliferation by the induction of cellular apoptosis and cell-cycle arrest at the G0/G1 phase [4].
Related Catalog	Signaling Pathways >> Others >> Others Natural Products >> Alkaloid Research Areas >> Cancer
References	[1]. Kim MH, et al. Indirubin, a purple 3,2- bisindole, inhibited allergic contact dermatitis via regulating T helper (Th)-mediated immune system in DNCB-induced model. J Ethnopharmacol. 2013 Jan 9;145(1):214-9. [2]. Hsieh WL, et al. Indirubin, an acting component of indigo naturalis, inhibits EGFR activation and EGF-induced CDC25B gene expression in epidermal keratinocytes. J Dermatol Sci. 2012 Aug;67(2):140-6. [3]. Zhang X, et al. Indirubin inhibits tumor growth by antitumor angiogenesis via blocking VEGFR2-mediated JAK/STAT3 signaling in endothelial cell. Int J Cancer. 2011 Nov 15;129(10):2502-11. [4]. Alex D, et al. Indirubin shows anti-angiogenic activity in an in vivo zebrafish model and an in vitro HUVEC model. J Ethnopharmacol. 2010 Sep 15;131(2):242-7.

Density	1.4±0.1 g/cm3
Boiling Point	496.6±45.0 °C at 760 mmHg
Melting Point	350 °C
Molecular Formula	C₁₆H₁₀N₂O₂
Molecular Weight	262.263
Flash Point	207.0±28.9 °C
Exact Mass	262.074219
PSA	58.20000
LogP	2.48
Vapour Pressure	0.0±1.3 mmHg at 25°C
Index of Refraction	1.709

CHEMICAL IDENTIFICATION

RTECS NUMBER :: DU2995000

CHEMICAL NAME :: (delta(sup 2,3')-Biindoline)-2',3-dione

CAS REGISTRY NUMBER :: 479-41-4

BEILSTEIN REFERENCE NO. :: 0088279

LAST UPDATED :: 199612

DATA ITEMS CITED :: 3

MOLECULAR FORMULA :: C16-H10-N2-O2

MOLECULAR WEIGHT :: 262.28

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 10 gm/kg

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

REFERENCE :: CTYAD8 Zhongcaoyao. Chinese Traditional and Herbal Medicine. (China International Book Trading Corp., POB 2820, Beijing, Peop. Rep. China) V.11- 1980- Volume(issue)/page/year: 13,24,1982

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1100 mg/kg

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

REFERENCE :: DRFUD4 Drugs of the Future. (J.R. Prous, S.A., Apartado de Correos 540, 08080 Barcelona, Spain) V.1- 1975/76- Volume(issue)/page/year: 9,266,1984 ** OTHER MULTIPLE DOSE TOXICITY DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 36400 mg/kg/26W-I

TOXIC EFFECTS :: Gastrointestinal - hypermotility, diarrhea Blood - changes in serum composition (e.g. TP, bilirubin, cholesterol) Related to Chronic Data - death

REFERENCE :: CTYAD8 Zhongcaoyao. Chinese Traditional and Herbal Medicine. (China International Book Trading Corp., POB 2820, Beijing, Peop. Rep. China) V.11- 1980- Volume(issue)/page/year: 12,75,1981

Hazard Codes	N
Risk Phrases	R20/21/22
Safety Phrases	S36/37
HS Code	2933990090

Precursor 10
608-08-2 91-56-5 120-72-9 24704-90-3
480-93-3 607-28-3 612-54-4 59-48-3
856068-50-3 612-42-0
DownStream 5
91-56-5 120-72-9 482-89-3 75038-06-1
80789-74-8

HS Code	2933990090
Summary	2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

479-41-4	854171-35-0
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