Chemical Property of Andrographolide
Chemical Property:
- Appearance/Colour:powder
- Vapor Pressure:9.64E-15mmHg at 25°C
- Melting Point:229-232 °C(lit.)
- Refractive Index:1.567
- Boiling Point:557.3 °C at 760 mmHg
- PKA:12.36±0.20(Predicted)
- Flash Point:195.5 °C
- PSA：86.99000
- Density:1.21 g/cm3
- LogP:1.96260
- Storage Temp.:+2C to +8C
- Solubility.:Soluble in DMSO (up to 25 mg/ml) or in Ethanol (up to 8 mg/ml).
- XLogP3:2.2
- Hydrogen Bond Donor Count:3
- Hydrogen Bond Acceptor Count:5
- Rotatable Bond Count:3
- Exact Mass:350.20932405
- Heavy Atom Count:25
- Complexity:597
- Purity/Quality:
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more than 98% *data from raw suppliers
Andrographolide *data from reagent suppliers
Safty Information:
- Pictogram(s):
Xn
- Hazard Codes:Xn
- Statements:
20/21/22-36/37/38
- Safety Statements:
22-24/25-36-26
- MSDS Files:
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SDS file from LookChem
Useful:
- Canonical SMILES:CC12CCC(C(C1CCC(=C)C2CC=C3C(COC3=O)O)(C)CO)O
- Isomeric SMILES:C[C@@]12CC[C@H]([C@@]([C@H]1CCC(=C)[C@H]2C/C=C/3\[C@@H](COC3=O)O)(C)CO)O
- Recent ClinicalTrials:Phase II Study of HMPL-004 in Patients With Ulcerative Colitis
- Recent EU Clinical Trials:A Phase III Double Blind, Multi-Center Placebo Controlled Maintenance Trial of HMPL-004 in Subjects with Mild to Moderate Ulcerative Colitis with Clinical Remission or Response from Induction Therapy. (NATRUL-4)
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Description
Andrographolide is the bitter principle, a colorless and neutral crystalline substance. It is the major labdane diterpenoid isolated from Andrographis paniculate. It exhibits antiviral, anti-inflammatory, and anticancer activities. The underlying mechanism is the inhibition of the mitogen-activated protein kinase/extracellular signal-regulated kinase (MAPK/ERK) signaling (specifically p38 MAPK/ERK1/2) pathway and downstream transcription factors such as nuclear factor kappa B (NF-κB) and nuclear factor of activated T cells (NFAT). Andrographolide is also confirmed with chemopreventive effects against and the inhibitory effects on cancer cell growth in breast, colon, epidermoid, gastric, liver, leukemia, myeloma, peripheral blood lymphocytes, and prostate cancers.
Andrographolide has been used for liver complaints and fever, and as an anti-inflammatory and immunostimulant. Andrographolide exerts anti-growth and pro-apoptotic effects on human rheumatoid arthritis fibroblast- like synoviocytes, the main cellular constituent of pannus, that combined with a massive infiltration of lymphocytes and macrophages, invades and destroys the local articular structure. Thereby, andrographolide is proposed to be used in Rheumatoid Arthritis and other autoimmune diseases. Andrographolide is a diterpene lactone compound extracted from Andrographis.
paniculata (Burm. F) Nees. Andrographis paniculata is also known as lanhelian,
yijianxi, zhanshecao, kucao, kudancao, etc. Since this product originates in India, it
is also known as Indian grass. This product is dry ground part of Jupiteraceae plant
Andrographis paniculata (conus) may originate in South Asia. It is commonly cultivated in China such as in Fujian, Guangdong, Hainan, Guangxi, and Yunnan and
also in Australia and was also introduced in Jiangsu and Shaanxi.Andrographis paniculata is commonly used in traditional Chinese medicine. Its
ability of relieving “snake venom, and internal injuries cough” was recorded in
“Lingnan herbal medicine records.” “Quanzhou Materia Medica” described it as
“heat-clearing and detoxifying, anti-inflammatory, detumescence and inhibition
throat inflammation, dysentery and high fever.”The above ground part of Andrographis paniculata contains andrographolide,
neo-andrographolide, 14-deoxygenated andrographolide, etc., and the root contains
mainly flavonoids.
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Uses
Andrographolide is a labdane diterpenoid. Andrographolide is the main bioactive component isolated from the medicinal plant Andrographis paniculata. It has a broad range of therapeutic applications including anti-inflammatory and anti-platelet aggregation activities and potential antineoplastic properties. Andrographolide showed significant antihepatotoxic action in P. berghei K173- induced hepatic damage in M. natalensis. Andrographolide inhibits tumor necrosis factor-α (TNF-α)-induced intercellular adhesion mol.-1 (ICAM-1) expression and adhesion of HL-60 cells onto human umbilical vein endothelial cells (HUVEC), which are associated with inflammatory diseases. These findings suggest that Andrographolide may have potential as a cardiovascular-protective agent.
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Clinical Use
This product is commonly used clinically for dysentery, leptospirosis, meningitis,
pneumonia, upper respiratory tract infection, and enhancing adrenal cortical function. In view of the requirement for clinical viral infection emergency, it is important to introduce the hydrophilic group in different lactone structure, enhance its
water solubility, and improve efficacy. There are a variety kinds of andrographolide
injection, including potassium dehydroandrograpolide succinate needle, potassium
sodium dehydroandrographolide succinate needle. Lianbizhi is the representative of
this class of drugs in current clinical application. Oral administration of andrographolide may induce bitter vomiting. Oral administration of this product and other
preparations in large doses can cause epigastric discomfort and loss of appetite. It
had been reported of drug eruption, upper abdominal pain, and anaphylactic shock
caused by intramuscular injection. Severe symptom response emerged such as chest
tightness, shortness of breath, pallor, lip bruising, cold sweats, weak pulse, decreased
blood pressure, etc. Light reactions include abdominal pain, vomiting, asthma, urticaria, pimples, dizziness, head swelling, sneezing, chest pain, etc. The reaction is
real time and also 5–20?min after injection and gradually improves 5–45?min after
rescue and individual recovered by 24?h. There are also reports of acute amniotic
fluid blockage caused by weaning lotion exchange. In addition, taking into account
the adverse effects of andrographolide on reproduction, it is recommended to be
used cautiously by fertility couples and pregnant women.
