Structure of Vinpocetine
CAS No.: 42971-09-5
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
Vinpocetine is a selective inhibitor for PDE1 with IC50 of 21 μM, it also blocks voltage-gated Na+ channels. It's a natural product isolated and purified from the herbs of Catharanthus roseus (L.) G. Don.
Synonyms: Ethyl apovincaminate; Apovincaminic Acid ethyl ester; AY 27255
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CAS No. : | 42971-09-5 |
Formula : | C22H26N2O2 |
M.W : | 350.45 |
SMILES Code : | O=C(OCC)C1=C[C@@](CCC2)(CC)[C@@](N2CC3)([H])C4=C3C5=CC=CC=C5N41 |
Synonyms : |
Ethyl apovincaminate; Apovincaminic Acid ethyl ester; AY 27255
|
MDL No. : | MFCD00211233 |
InChI Key : | DDNCQMVWWZOMLN-IRLDBZIGSA-N |
Pubchem ID : | 443955 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302 |
Precautionary Statements: | P280-P305+P351+P338 |
Target |
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In Vitro:
Cell Line
|
Concentration | Treated Time | Description | References |
Primary rat astrocytes | 30 µM | 12 hours hypoxia/6 hours reoxygenation | Vinpocetine ameliorated oxygen-glucose deprivation/reoxygenation (OGD/R)-induced astrocytic injury via the PI3K/AKT signaling pathway, improving cell viability, reducing LDH release, and decreasing oxidative stress and inflammatory responses. | Front Neurosci. 2020 Apr 2;14:223 |
Vascular smooth muscle cells (SMCs) | 10, 20, 30, 50 µM | 16 hours | Vinpocetine dose-dependently inhibited PDGF-stimulated vascular smooth muscle cell migration, as confirmed by two-dimensional migration assays and three-dimensional aortic medial explant invasive assay. | J Pharmacol Exp Ther. 2012 Nov;343(2):479-88 |
Adult mouse cardiac fibroblasts | 10 µM | 24 hours | Vinpocetine suppressed TGFβ-induced fibroblast activation and extracellular matrix gene expression | Cardiovasc Drugs Ther. 2017 Apr;31(2):157-166 |
Vascular smooth muscle cells (SMCs) | 25, 50, 75 µM | 24 hours | Vinpocetine dose-dependently inhibited vascular smooth muscle cell proliferation, causing G1-phase cell cycle arrest, associated with a decrease in cyclin D1 and an increase in p27Kip1 levels. | J Pharmacol Exp Ther. 2012 Nov;343(2):479-88 |
BV2 cells | 20 µM | 24 hours | Vinpocetine inhibits OGD-induced M1 phenotype and promotes M2 phenotype in BV2 cells | Front Cell Dev Biol. 2021 Feb 4;8:616590 |
MRC-5 cell line | 100, 50, 25, 12.5, 6.25 mcg/mL | 24-48 hours | To assess the cytotoxicity of vinpocetine on the MRC-5 cell line, results showed that vinpocetine exhibited low cytotoxicity against MRC-5 cells with an IC50 of 289.2 µg/ml. | Sci Rep. 2024 May 15;14(1):11131 |
Mouse resident peritoneal macrophages | 30 µM | 30 minutes or 6 hours | Vinpocetine suppressed TNF-α-induced p65 nuclear translocation and proinflammatory mediator expression | Clin Sci (Lond). 2020 Nov 27;134(22):2959-2976 |
MRC-5 cell line | 100 µg/mL | 48 hours | Vinpocetine significantly reduced the expression of fibrotic genes (fibronectin, vimentin, α-SMA, and Smad2/3) induced by TGF-β1, indicating its anti-fibrotic effect by interfering with the TGF-β1/Smad signaling pathway. | Sci Rep. 2024 May 15;14(1):11131 |
Human middle ear epithelial cells (HMEEC) | 10 µM | 6 hours | Vinpocetine inhibited S. pneumoniae-induced upregulation of pro-inflammatory mediators (IL-1β, IL-6, IL-8, and TNF-α) mRNA expression | J Immunol. 2020 Feb 15;204(4):933-942 |
Macrophage RAW264.7 cells | 50 µM | 60 min pretreatment followed by 6 hours | Vinpocetine potently inhibited TNF-α–induced NF-κB–dependent transcriptional activity | Proc Natl Acad Sci U S A. 2010 May 25;107(21):9795-800 |
Human lung epithelial A549 cells | 50 µM | 60 min pretreatment followed by 6 hours | Vinpocetine potently inhibited TNF-α–induced NF-κB–dependent transcriptional activity | Proc Natl Acad Sci U S A. 2010 May 25;107(21):9795-800 |
Human umbilical vein endothelial cells (HUVECs) | 50 µM | 60 min pretreatment followed by 6 hours | Vinpocetine potently inhibited TNF-α–induced NF-κB–dependent transcriptional activity | Proc Natl Acad Sci U S A. 2010 May 25;107(21):9795-800 |
Vascular smooth muscle cells (VSMCs) | 50 µM | 60 min pretreatment followed by 6 hours | Vinpocetine potently inhibited TNF-α–induced NF-κB–dependent transcriptional activity | Proc Natl Acad Sci U S A. 2010 May 25;107(21):9795-800 |
Adult mouse cardiomyocytes | 10-40 µM | 72 hours | Vinpocetine dose-dependently suppressed Ang II-stimulated myocyte hypertrophic growth | Cardiovasc Drugs Ther. 2017 Apr;31(2):157-166 |
ARPE19/NF-κB-luciferase reporter cells | 50 µM | 8 hours | To evaluate the inhibitory effect of vinpocetine on Aβ-induced NF-κB activation. Results showed that vinpocetine significantly suppressed Aβ-induced NF-κB activation, reducing it to a level comparable to the control group. | Exp Eye Res. 2014 Oct;127:49-58 |
In Vivo:
Species
|
Animal Model
|
Administration | Dosage | Frequency | Description | References |
Wistar rats | High-fructose diet-induced metabolic syndrome model | Tube feeding | 1 mg/kg | From the ninth week, lasting for 12 weeks | To investigate the ameliorative effect of Vinpocetine on metabolic syndrome-associated bladder overactivity, results showed that Vinpocetine restored the contraction and relaxation responses of bladder detrusor muscle and exerted anti-inflammatory effects. | Biomedicines. 2022 Oct 26;10(11):2716 |
Sprague Dawley rats | High-fat diet (HFD) and diabetes-induced fatty liver model | Oral | 10 and 20 mg/kg/day | Once daily for 8 weeks | Vinpo dose-dependently mitigated the HFD-induced rise in serum ALT, AST, and ALP activities and improved the hepatic architecture of steatotic rats, especially at a dose of 20 mg/kg. The findings elucidated the mechanisms behind Vinpo's beneficial effects, including insulin sensitivity improvement, attenuation of oxidative stress, and dampening of the sterile inflammatory response. The concomitant administration of Lactobacillus spp. probiotics with Vinpo significantly enhanced these effects. | AMB Express. 2024 Aug 2;14(1):89 |
Wistar rats | Middle cerebral artery occlusion (MCAO) model | Intraperitoneal injection | 10 mg/kg | Single dose, 30 min before MCAO | Vinpocetine activated the PI3K/AKT signaling pathway to enhance phosphorylation of astrocytic connexin 43 (Cx43), thereby attenuating cerebral ischemia/reperfusion injury, reducing cerebral infarction volume and edema, and decreasing oxidative stress, inflammation, and apoptosis. | Front Neurosci. 2020 Apr 2;14:223 |
Mice (C57BL/6) | S. pneumoniae-induced otitis media model | Intraperitoneal injection | 10 mg/kg | Post-infection treatment at 2 hours, continued for 3 days | Vinpocetine significantly suppressed S. pneumoniae-induced middle ear inflammation, including upregulation of inflammatory mediators, mucosal thickening, and neutrophil infiltration | J Immunol. 2020 Feb 15;204(4):933-942 |
Female Wistar albino rats | Estradiol-benzoate induced cervical hyperkeratosis model | Oral | 10 mg/kg/day | Once daily for 4 weeks | Vinpocetine significantly alleviated all biochemical and histopathological abnormalities induced by EB, mitigating cervical hyperkeratosis via NLRP3-induced pyroptosis and activation of the SIRT1/Nrf2 signaling pathway. | Sci Rep. 2024 Aug 19;14(1):19171 |
Adult Long-Evans rats | Aβ-induced retinal inflammation model | Intraperitoneal injection | 15 mg/kg | Once daily for four days | To evaluate the inhibitory effect of vinpocetine on Aβ-induced NF-κB nuclear translocation and inflammatory responses. Results showed that vinpocetine significantly inhibited NF-κB nuclear translocation and reduced the expression and activation of NLRP3, caspase-1, IL-1β, IL-18, and TNF-α. | Exp Eye Res. 2014 Oct;127:49-58 |
Mice | LPS- or TNF-α-induced lung inflammation model | Intraperitoneal injection | 2.5, 5, 10 mg/kg | Single dose, lasting 6 h | Vinpocetine dose-dependently inhibited LPS- or TNF-α-induced inflammatory mediator expression and neutrophil infiltration | Proc Natl Acad Sci U S A. 2010 May 25;107(21):9795-800 |
Male albino rats | Aluminum-induced Alzheimer's disease model | Oral | 20 mg/kg | Daily for five weeks | Vinpocetine in combination with cocoa significantly improved cognitive function and behavioral performance in the aluminum-induced Alzheimer's disease model, reduced oxidative stress and inflammation, and modulated the Wnt/β-catenin/GSK-3β/Nrf2/HO-1 and PERK/CHOP/Bcl-2 pathways. | Pharmaceutics. 2023 Jul 31;15(8):2063 |
BALB/c male mice | Bleomycin-induced pulmonary fibrosis model | Oral | 20 mg/kg/day | Once daily from day 7 of induction till the end of the experiment (day 21) | Vinpocetine significantly alleviated bleomycin-induced fibrotic endpoints, including reduced expression of fibrotic-related proteins, oxidative stress, and inflammatory mediators, and exerted anti-fibrotic effects by upregulating Nrf2 and PPAR-γ expression and downregulating the NLRP3/NF-κB pathway. | Sci Rep. 2024 May 15;14(1):11131 |
Wistar rats | Adenine-induced chronic kidney disease model | Oral | 20 mg/kg/day | Daily administration for 4 weeks | Vinpocetine ameliorated adenine-induced renal fibrosis and epithelial-mesenchymal transition by targeting the DNMT1/Klotho/β-catenin/Snail1 and MMP-7 pathways | Naunyn Schmiedebergs Arch Pharmacol. 2025 Mar;398(3):2769-2781 |
C57BL/6J male mice | Ang II-induced cardiac hypertrophy and fibrosis model | Intraperitoneal injection | 5 mg/kg/day | Once daily for 17 days (3 days prior and 14 days during Ang II infusion) | Vinpocetine significantly attenuated Ang II-induced cardiac hypertrophy and fibrosis | Cardiovasc Drugs Ther. 2017 Apr;31(2):157-166 |
FVB/NJ mice | Carotid artery ligation injury model | Intraperitoneal injection | 5 mg/kg/day | Once daily for 14 days | Vinpocetine significantly reduced neointimal formation after carotid artery ligation injury and decreased spontaneous remodeling of human saphenous vein explants. | J Pharmacol Exp Ther. 2012 Nov;343(2):479-88 |
C57BL/6J mice | Abdominal aortic aneurysm model | Intraperitoneal injection | 5mg/kg | Daily for 28 days | Vinpocetine remarkably attenuated aneurysmal dilation, improved elastin degradation, smooth muscle cell depletion, collagen fibers remodeling and macrophage infiltration | Clin Sci (Lond). 2020 Nov 27;134(22):2959-2976 |
Clinical Trial:
NCT Number | Conditions | Phases | Recruitment | Completion Date | Locations |
NCT00719953 | - | Completed | - | - | |
NCT00719953 | Elderly Memor... More >>y Impairment Less << | Phase 4 | Completed | - | Israel ... More >> Suorasky Medical Center Tel-Aviv, Israel Less << |
NCT01515839 | Traumatic Brain Injury | Not Applicable | Completed | - | United States, California ... More >> Amen Clinics, Inc. Newport Beach, California, United States, 92660 Less << |
NCT02857829 | Biomedical Enhancement | Not Applicable | Completed | - | Netherlands ... More >> Maastricht University Maastricht, Netherlands Less << |
NCT02011971 | Epilepsy | PHASE1|PHASE2 | SUSPENDED | 2025-12-26 | Stanford University, Palo Alto... More >>, California, 94304, United States Less << |
NCT01400035 | - | Completed | - | China ... More >> Weiwei Zhang Beijing, China, 100700 Less << | |
NCT02878772 | Stroke Immuno... More >>regulation Inflammation Vinpocetine Less << | Phase 2 Phase 3 | Completed | - | - |
NCT06635746 | Fetal Alcohol Spectrum Disorde... More >>rs Less << | PHASE1 | NOT_YET_RECRUITING | 2026-06-01 | - |
Tags: Vinpocetine | Ethyl apovincaminate | Sodium Channel | Phosphodiesterase (PDE) | Na channels | Na+ channels | IκB kinase | I kappa B kinase | 42971-09-5 |
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H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
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