Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C21H18O11 |
| Molecular Weight | 446.361 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 5 / 5 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
O[C@H]1[C@H](OC2=CC3=C(C(=O)C=C(O3)C4=CC=CC=C4)C(O)=C2O)O[C@@H]([C@@H](O)[C@@H]1O)C(O)=O
InChI
InChIKey=IKIIZLYTISPENI-ZFORQUDYSA-N
InChI=1S/C21H18O11/c22-9-6-10(8-4-2-1-3-5-8)30-11-7-12(14(23)15(24)13(9)11)31-21-18(27)16(25)17(26)19(32-21)20(28)29/h1-7,16-19,21,23-27H,(H,28,29)/t16-,17-,18+,19-,21+/m0/s1
| Molecular Formula | C21H18O11 |
| Molecular Weight | 446.361 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 5 / 5 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
Baicalin is a flavonoid compound with anti-inflammatory and anti-oxidant activity extracted from Scutellarua rivularis. Limited distribution data suggest that baicalin reached several sites such as the brain, eye lens, thymus, etc. Metabolism data suggest the rapid conversion of baicalin to baicalein. Baicalin has the potential to be used in novel anti-cancer therapeutic formulations for treatment of ovarian cancer and other cancers. Baicalin markedly inhibits replication of human immunodeficiency virus type 1 (HIV-1) in a concentration-dependent manner in normal peripheral blood mononuclear cells (PBMC) stimulated with phytohemagglutinin (PHA) in vitro. The preventive medication of baicalin shows a protective effect on C57 BL mouse with Parkinson's disease induced by 1-methyl-4-phenyl-1, 2, 3, 6-tetrahydropyridine (MPTP).
CNS Activity
Approval Year
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
1847.21 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25219601 |
2800 mg single, oral dose: 2800 mg route of administration: Oral experiment type: SINGLE co-administered: |
BAICALIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
11961.53 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25219601 |
2800 mg single, oral dose: 2800 mg route of administration: Oral experiment type: SINGLE co-administered: |
BAICALIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
9.65 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25219601 |
2800 mg single, oral dose: 2800 mg route of administration: Oral experiment type: SINGLE co-administered: |
BAICALIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
Funbound
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
11% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/16708379 |
BAICALIN plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Doses
| Dose | Population | Adverse events |
|---|---|---|
800 mg 2 times / day multiple, oral Highest studied dose Dose: 800 mg, 2 times / day Route: oral Route: multiple Dose: 800 mg, 2 times / day Sources: |
healthy, 27.83 |
Disc. AE: Erythema, Hepatic function abnormal... AEs leading to discontinuation/dose reduction: Erythema (10%) Sources: Hepatic function abnormal (10%) |
500 mg 1 times / day multiple, oral Studied dose Dose: 500 mg, 1 times / day Route: oral Route: multiple Dose: 500 mg, 1 times / day Sources: |
unhealthy, 51.3 ± 4.2 Health Status: unhealthy Age Group: 51.3 ± 4.2 Sex: M+F Sources: |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Erythema | 10% Disc. AE |
800 mg 2 times / day multiple, oral Highest studied dose Dose: 800 mg, 2 times / day Route: oral Route: multiple Dose: 800 mg, 2 times / day Sources: |
healthy, 27.83 |
| Hepatic function abnormal | 10% Disc. AE |
800 mg 2 times / day multiple, oral Highest studied dose Dose: 800 mg, 2 times / day Route: oral Route: multiple Dose: 800 mg, 2 times / day Sources: |
healthy, 27.83 |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Uptake of irinotecan metabolite SN-38 by the human intestinal cell line Caco-2. | 2005-05 |
|
| In vivo and in vitro effect of baicalein on human prostate cancer cells. | 2005-01 |
|
| In vitro studies of baicalin alone or in combination with Salvia miltiorrhiza extract as a potential anti-cancer agent. | 2005-01 |
|
| Separation methods used for Scutellaria baicalensis active components. | 2004-12-05 |
|
| Separation and isolation methods for analysis of the active principles of Sho-saiko-to (SST) oriental medicine. | 2004-12-05 |
|
| Baicalin induces NAD(P)H:quinone reductase through the transactivation of AP-1 and NF-kappaB in Hepa 1c1c7 cells. | 2004-12 |
|
| High-performance liquid chromatographic method for simultaneous determination of baicalein and baicalein 7-glucuronide in rat plasma. | 2004-11-15 |
|
| Zinc coupling potentiates anti-HIV-1 activity of baicalin. | 2004-11-12 |
|
| Enteric excretion of baicalein, a flavone of Scutellariae Radix, via glucuronidation in rat: involvement of multidrug resistance-associated protein 2. | 2004-11 |
|
| Pharmacokinetics of baicalin in rats and its interactions with cyclosporin A, quinidine and SKF-525A: a microdialysis study. | 2004-11 |
|
| A metabolomic analysis of medicinal diversity in Huang-qin (Scutellaria baicalensis Georgi) genotypes: discovery of novel compounds. | 2004-11 |
|
| Study on the precipitation reaction between baicalin and berberine by HPLC. | 2004-10-15 |
|
| Pharmacological properties of traditional medicine (XXIX): effect of Hange-shashin-to and the combinations of its herbal constituents on rat experimental colitis. | 2004-10 |
|
| Metabolic activities of ginsenoside Rb1, baicalin, glycyrrhizin and geniposide to their bioactive compounds by human intestinal microflora. | 2004-10 |
|
| In vitro antileukemic, antioxidant and prooxidant activities of Antoksyd S (C/E/XXI): a comparison with baicalin and baicalein. | 2004-09-17 |
|
| [Isolation and elucidation of antioxidant constituents from acetone extract in root of Scutellaria rehderiana]. | 2004-09 |
|
| Flavonoids inhibit tumor necrosis factor-alpha-induced up-regulation of intercellular adhesion molecule-1 (ICAM-1) in respiratory epithelial cells through activator protein-1 and nuclear factor-kappaB: structure-activity relationships. | 2004-09 |
|
| Dietary polyphenols (-)-epicatechin and chrysin inhibit intestinal glucuronidation metabolism to increase drug absorption. | 2004-09 |
|
| In vitro susceptibility of 10 clinical isolates of SARS coronavirus to selected antiviral compounds. | 2004-09 |
|
| [Experimental study on prevention and treatment of bronchial asthma by compound Chinese herbal monomer recipe]. | 2004-08 |
|
| Potent Inhibitory effect of flavonoids in Scutellaria baicalensis on amyloid beta protein-induced neurotoxicity. | 2004-06-30 |
|
| The flavonoid baicalein inhibits fibrillation of alpha-synuclein and disaggregates existing fibrils. | 2004-06-25 |
|
| Determination of rhein, baicalin and berberine in traditional Chinese medicinal preparations by capillary electrophoresis with two-marker technique. | 2004-06 |
|
| [Effects of effective component from "qing kai ling" on endothelial cell of microvessel in MCAO rats]. | 2004-05 |
|
| [Effects of baicalin on the expression of pro-MMP-1 and MMP-3 in human gingival fibroblasts and periodontal ligament cells]. | 2004-05 |
|
| Effects of Sho-saiko-to extract and its components, Baicalin, baicalein, glycyrrhizin and glycyrrhetic acid, on pharmacokinetic behavior of salicylamide in carbon tetrachloride intoxicated rats. | 2004-05 |
|
| Electrochemical investigations of baicalin and DNA-baicalin interactions. | 2004-05 |
|
| [Antagonistic effect of baicalin on oxidative stress injury in neurons and astrocytes of rats]. | 2004-04 |
|
| Inhibitory effects of Scutellaria barbata D. Don on human uterine leiomyomal smooth muscle cell proliferation through cell cycle analysis. | 2004-03 |
|
| Inhibition of nitric oxide/cyclic GMP-mediated relaxation by purified flavonoids, baicalin and baicalein, in rat aortic rings. | 2004-02-15 |
|
| Antimutagenic and antiradical properties of flavones from the roots of Scutellaria baicalensis georgi. | 2004-02 |
|
| Significant decrease of cyclosporine bioavailability in rats caused by a decoction of the roots of Scutellaria baicalensis. | 2004-02 |
|
| Quality evaluation of commercial extracts of Scutellaria baicalensis. | 2004 |
|
| Proteomic analysis of mouse liver for the evaluation of effects of Scutellariae radix by liquid chromatography with tandem mass spectrometry. | 2004 |
|
| Flavonoids from Radix Scutellariae as potential stroke therapeutic agents by targeting the second postsynaptic density 95 (PSD-95)/disc large/zonula occludens-1 (PDZ) domain of PSD-95. | 2004 |
|
| Baicalin induces differential expression of cytochrome C oxidase in human lung H441 cell. | 2003-12-03 |
|
| The antiinflammatory and analgesic effects of baicalin in carrageenan-evoked thermal hyperalgesia. | 2003-12 |
|
| Phytochemical and biological analysis of skullcap (Scutellaria lateriflora L.): a medicinal plant with anxiolytic properties. | 2003-11 |
|
| Hepatoprotective effect of baicalin, a major flavone from Scutellaria radix, on acetaminophen-induced liver injury in mice. | 2003-11 |
|
| Application of high-speed counter-current chromatography to the preparative separation and purification of baicalin from the Chinese medicinal plant Scutellaria baicalensis. | 2003-10-31 |
|
| Differential effects of natural polyphenols on neuronal survival in primary cultured central neurons against glutamate- and glucose deprivation-induced neuronal death. | 2003-10-03 |
|
| Baicalein and baicalin are potent inhibitors of angiogenesis: Inhibition of endothelial cell proliferation, migration and differentiation. | 2003-09-10 |
|
| HPLC analyses and pharmacokinetic studies of baicalin and oxymatrine in rabbits. | 2003-09 |
|
| Antioxidant status and mineral contents in tissues of rutin and baicalin fed rats. | 2003-08-08 |
|
| Effects of baicalin, baicalein, and wogonin on interleukin-6 and interleukin-8 expression, and nuclear factor-kappab binding activities induced by interleukin-1beta in human retinal pigment epithelial cell line. | 2003-08 |
|
| Immunomodulatory activities of flavonoids, monoterpenoids, triterpenoids, iridoid glycosides and phenolic compounds of Plantago species. | 2003-07 |
|
| Pharmacokinetic study on the multi-constituents of Huangqin-Tang decoction in rats. | 2003-07 |
|
| Main flavonoids in the root of Scutellaria baicalensis cultivated in Europe and their comparative antiradical properties. | 2003-06 |
|
| [The study of characteristics of absorption and separation of different glycoside on macropore resins]. | 2003-03 |
|
| Assessment of the antibacterial activity of selected flavonoids and consideration of discrepancies between previous reports. | 2003 |
Sample Use Guides
200-800 mg once daily on days 1 and 10 or twice daily on days 3-9
Route of Administration:
Oral
The culture of human trabecular meshwork (hTM) cells was stressed by hydrogen peroxide. Samples that received pre- plus co-treatment with 10 or 15 uM baicalin showed significantly increased cell survival and decreased iROS production. Further studies demonstrated that pre- plus co-treatment with 15 uM baicalin significantly inhibited proinflammatory factor IL-1alpha and ELAM-1 production, decreased activities of senescence marker SA-beta-gal, and lowered carbonylated protein levels. In contrast, samples that received only pre-treatment did not show any of these protective effects.
| Substance Class |
Chemical
Created
by
admin
on
Edited
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| Record UNII |
347Q89U4M5
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| Record Status |
Validated (UNII)
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| Record Version |
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LIVERTOX |
414
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2642 (Number of products:9)
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BAICALIN
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| Related Record | Type | Details | ||
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PARENT -> CONSTITUENT ALWAYS PRESENT |
Baicalin, the flavonoids isolated from roots of Scutellaria baicalensis
Georgi, have shown multi-functional efficacies, including antibacterial, antivirus, anti-inflammation and hepatoprotective activities (9,10).
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SUBSTANCE->ACTIVE CONSTITUENT ALWAYS PRESENT |
