Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C15H10O5 |
| Molecular Weight | 270.2369 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
OC1=CC2=C(C(=O)C=C(O2)C3=CC=CC=C3)C(O)=C1O
InChI
InChIKey=FXNFHKRTJBSTCS-UHFFFAOYSA-N
InChI=1S/C15H10O5/c16-9-6-11(8-4-2-1-3-5-8)20-12-7-10(17)14(18)15(19)13(9)12/h1-7,17-19H
| Molecular Formula | C15H10O5 |
| Molecular Weight | 270.2369 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
Baicalein is a flavonoid is a component of the traditional herbal remedy known as Chinese skullcap (or Huang Qin), possesses various biological activities. Baicalein is a neuroprotective agent, which is studied in phase I for the treatment of Parkinson’s disease. By modulating of γ-aminobutyric acid (GABA) type A receptors, baicalein promotes nonamyloidogenic processing of amyloid precursor protein (APP), thereby reducing β-amyloid (Aβ) production and improving cognitive performance in models of Alzheimer's disease. By inhibiting the NF-κB signaling pathway, baicalein suppressed cancer cells proliferation and suppressed the viability of human endometrial stromal cells, thus it may provide a novel treatment option for endometriosis. Besides, this compound was evaluated for its ability to inhibit the influenza virus. Experiments on mice have shown that baicalein showed significant effects in preventing death, increasing the mean time to death and reducing the lung virus titer in a dose-dependent manner.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL2109243 |
13.1 µM [Ki] | ||
Target ID: map04064 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
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| Primary | Unknown Approved UseUnknown |
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| Primary | Unknown Approved UseUnknown |
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| Primary | Unknown Approved UseUnknown |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
65.171 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27352310 |
800 mg 2 times / day steady-state, oral dose: 800 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
BAICALEIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
1322.5 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/34156161 |
600 mg 3 times / day steady-state, oral dose: 600 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
BAICALEIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
17.61 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27352310 |
200 mg 2 times / day steady-state, oral dose: 200 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
BAICALEIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
31.723 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27352310 |
400 mg 2 times / day steady-state, oral dose: 400 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
BAICALEIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
1508.45 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/34156161 |
600 mg 3 times / day steady-state, oral dose: 600 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
BAICALIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
598.4 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27352310 |
800 mg 2 times / day steady-state, oral dose: 800 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
BAICALEIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
12580.06 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/34156161 |
600 mg 3 times / day steady-state, oral dose: 600 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
BAICALEIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
169 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27352310 |
200 mg 2 times / day steady-state, oral dose: 200 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
BAICALEIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
332.9 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27352310 |
400 mg 2 times / day steady-state, oral dose: 400 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
BAICALEIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
10175.14 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/34156161 |
600 mg 3 times / day steady-state, oral dose: 600 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
BAICALIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
11.09 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27352310 |
800 mg 2 times / day steady-state, oral dose: 800 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
BAICALEIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
8.8 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27352310 |
200 mg 2 times / day steady-state, oral dose: 200 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
BAICALEIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
12.53 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27352310 |
400 mg 2 times / day steady-state, oral dose: 400 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
BAICALEIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Antifibrogenic therapies in chronic HCV infection. | 2001 Aug |
|
| [Studies on metabolites of baicalin in human urine]. | 2001 Nov |
|
| Evaluation of the clastogenic, DNA intercalative, and topoisomerase II-interactive properties of bioflavonoids in Chinese hamster V79 cells. | 2002 |
|
| [A novel approach to quality evaluation of root of Scutellaria baicalensis by DPPH free radical scavenging]. | 2002 Aug |
|
| Key role of P38 mitogen-activated protein kinase and the lipoxygenase pathway in angiotensin II actions in H295R adrenocortical cells. | 2002 Aug |
|
| Fatty acid synthase inhibitors from plants: isolation, structure elucidation, and SAR studies. | 2002 Dec |
|
| Inhibition of VHR dual-specificity protein tyrosine phosphatase activity by flavonoids isolated from Scutellaria baicalensis: structure-activity relationships. | 2002 Dec |
|
| Structure-activity relationships of flavonoids, isolated from Scutellaria baicalensis, binding to benzodiazepine site of GABA(A) receptor complex. | 2002 Dec |
|
| Hepatic fibrosis: from bench to bedside. | 2002 Dec |
|
| The effects of the cyclosporin A, a P-glycoprotein inhibitor, on the pharmacokinetics of baicalein in the rat: a microdialysis study. | 2002 Dec |
|
| [Determination of flavone for Scutellaria baicalensis from different areas by HPLC]. | 2002 Mar |
|
| [The Baikal scullcap (Scutellaria baicalensis Georgi)--a potential source of new drugs]. | 2002 Nov |
|
| Lipoxygenase inhibitors attenuate growth of human pancreatic cancer xenografts and induce apoptosis through the mitochondrial pathway. | 2002 Sep |
|
| Anticancer, antiradical and antioxidative actions of novel Antoksyd S and its major components, baicalin and baicalein. | 2002 Sep-Oct |
|
| Activation of the aryl hydrocarbon receptor by some vegetable constituents determined using in vitro reporter gene assay. | 2003 Apr |
|
| 12-lipoxygenase in opioid-induced delayed cardioprotection: gene array, mass spectrometric, and pharmacological analyses. | 2003 Apr 4 |
|
| Pharmacological evaluation of several major ingredients of Chinese herbal medicines in human hepatoma Hep3B cells. | 2003 Aug |
|
| 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 Aug |
|
| Comparison of metabolic pharmacokinetics of baicalin and baicalein in rats. | 2003 Feb |
|
| Lipoxygenase products regulate nitric oxide and inducible nitric oxide synthase production in interleukin-1beta stimulated vascular smooth muscle cells. | 2003 Feb |
|
| Contribution of 5- and 12-lipoxygenase products to mechanical hyperalgesia induced by prostaglandin E(2) and epinephrine in the rat. | 2003 Feb |
|
| Effects of several polyhydroxylated flavonoids on the growth of B16F10 melanoma and Melan-a melanocyte cell lines: influence of the sequential oxidation state of the flavonoid skeleton. | 2003 Feb |
|
| Norepinephrine-induced stimulation of p38 mitogen-activated protein kinase is mediated by arachidonic acid metabolites generated by activation of cytosolic phospholipase A(2) in vascular smooth muscle cells. | 2003 Feb |
|
| 12-lipoxygenase pathway increases aldosterone production, 3',5'-cyclic adenosine monophosphate response element-binding protein phosphorylation, and p38 mitogen-activated protein kinase activation in H295R human adrenocortical cells. | 2003 Feb |
|
| Synergy of epidermal growth factor and 12(S)-hydroxyeicosatetraenoate on protein kinase C activation in lens epithelial cells. | 2003 Feb 14 |
|
| Isolation and identification of four flavonoid constituents from the seeds of Oroxylum indicum by high-speed counter-current chromatography. | 2003 Feb 21 |
|
| Baicalein inhibits Raf-1-mediated phosphorylation of MEK-1 in C6 rat glioma cells. | 2003 Feb 7 |
|
| Role of downstream metabolic processing of proinflammatory fatty acids by 5-lipoxygenase in HL-60 cell apoptosis. | 2003 Jan |
|
| Inhibition of tumor-induced angiogenesis and matrix-metalloproteinase expression in confrontation cultures of embryoid bodies and tumor spheroids by plant ingredients used in traditional chinese medicine. | 2003 Jan |
|
| Urinary pharmacokinetics of baicalein, wogonin and their glycosides after oral administration of Scutellariae Radix in humans. | 2003 Jan |
|
| Immunomodulatory activities of flavonoids, monoterpenoids, triterpenoids, iridoid glycosides and phenolic compounds of Plantago species. | 2003 Jul |
|
| Pharmacokinetic study on the multi-constituents of Huangqin-Tang decoction in rats. | 2003 Jul |
|
| Overexpression of platelet-type 12-lipoxygenase promotes tumor cell survival by enhancing alpha(v)beta(3) and alpha(v)beta(5) integrin expression. | 2003 Jul 15 |
|
| Inhibition of cancer cell proliferation and prostaglandin E2 synthesis by Scutellaria baicalensis. | 2003 Jul 15 |
|
| Effects of baicalein, berberine, curcumin and hesperidin on mucin release from airway goblet cells. | 2003 Jun |
|
| Main flavonoids in the root of Scutellaria baicalensis cultivated in Europe and their comparative antiradical properties. | 2003 Jun |
|
| Nitric oxide triggers the toxicity due to glutathione depletion in midbrain cultures through 12-lipoxygenase. | 2003 Jun 13 |
|
| Novel synthesis of flavonoids of Scutellaria baicalensis Georgi. | 2003 Mar |
|
| A role for TRPV1 in bradykinin-induced excitation of vagal airway afferent nerve terminals. | 2003 Mar |
|
| Inhibition of 15-lipoxygenases by flavonoids: structure-activity relations and mode of action. | 2003 Mar 1 |
|
| Anxiolytic-like effects of baicalein and baicalin in the Vogel conflict test in mice. | 2003 Mar 19 |
|
| Mechanisms in mediating the anti-inflammatory effects of baicalin and baicalein in human leukocytes. | 2003 Mar 28 |
|
| Fatty acid release and oxidation are factors in lipoxygenase inhibitor-induced apoptosis. | 2003 Mar 3 |
|
| Degradation of flavonoid aglycones by rabbit, rat and human fecal flora. | 2003 May |
|
| Growth factor-induced proliferation in corneal epithelial cells is mediated by 12(S)-HETE. | 2003 May |
|
| Flavonoid baicalein attenuates activation-induced cell death of brain microglia. | 2003 May |
|
| Inhibition of matrix metalloproteinase-1 and -2 expression using nitric oxide synthase inhibitors in UV-irradiated human dermal fibroblasts. | 2003 May-Jun |
|
| Analysis of Scutellaria lateriflora and its adulterants Teucrium canadense and Teucrium chamaedrys by LC-UV/MS, TLC, and digital photomicroscopy. | 2003 May-Jun |
|
| Effects of topical instillation of traditional herbal medicines, herbal extracts, and their components on prostaglandin E2-induced aqueous flare elevation in pigmented rabbits. | 2003 May-Jun |
|
| Baicalein and baicalin are potent inhibitors of angiogenesis: Inhibition of endothelial cell proliferation, migration and differentiation. | 2003 Sep 10 |
Patents
Sample Use Guides
Phase I, randomized, double-blind, single-dose trial of baicalein (100-2800 mg) in 72 healthy adults. These doses were safe and well tolerated by healthy subjects.
Route of Administration:
Oral
Baicalein (200 µM) was used to treat human cervical cancer cell line C33A cells. Cell proliferation was tested by the MTT assay. Cell apoptosis was detected by the TUNEL assay and caspase 3 activity measurement. Baicalein inhibited NF κB activity by repressing nuclear translocation. Baicalein suppressed C33A proliferation and promoted cellular apoptosis by inhibiting NF κB signaling pathway.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 18:09:58 UTC 2023
by
admin
on
Fri Dec 15 18:09:58 UTC 2023
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| Record UNII |
49QAH60606
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| Record Status |
Validated (UNII)
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| Record Version |
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| Code System | Code | Type | Description | ||
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BAICALEIN
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2979
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1048357
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491-67-8
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78324
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DTXSID2022389
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m2205
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49QAH60606
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C006680
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5281605
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1592893
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