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42971-09-5 (Vinpocetine)

1

Identification

Vinpocetine Vinpocetine
Name Vinpocetine
Formula C22H26N2O2
MW 350.45
CAS No. 42971-09-5
EINECS 256-028-0
Smiles CC[[email protected]@]1(CCC2)[[email protected]@](N2CC3)([H])C4=C3C5=C(C=CC=C5)N4C(C(OCC)=O)=C1
Synonyms Ethyl (3alpha,16alpha)-eburnamenine-14-carboxylate; (41S,13aS)-ethyl 13a-ethyl-2,3,41,5,6,13a-hexahydro-1H-indolo[3,2,1-de]pyrido[3,2,1-ij][1,5]naphthyridine-12-carboxylate
InChI InChI=1S/C22H26N2O2/c1-3-22-11-7-12-23-13-10-16-15-8-5-6-9-17(15)24(19(16)20(22)23)18(14-22)21(25)26-4-2/h5-6,8-9,14,20H,3-4,7,10-13H2,1-2H3/t20-,22+/m1/s1
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Introduction

Vinpocetine(Cavinton; Ethyl apovincaminate) is a selective for PDE1 (IC50 = 21 μM).

Background Information

Vinpocetine is a selective inhibitor of voltage-sensitive sodium channel for the treatment of stroke, vascular dementia and Alzheimer's disease. ......by AbMole BioScience
Selective Ca2+-calmodulin dependent cGMP-phosphodiesterase (PDE1) inhibitor. Shows vasorelaxant activity. Neuroprotective agent. Selectively inhibits voltage-sensitive Na2+ channels Potent anti-inflammatory agent. Inhibitor of NF-κB-dependent inflammatory responses by directly targeting IKK. Shown to inhibit the NLRP3 inflammasome. Antioxidant. Free radical scavenger. Anticancer compound. Anticonvulsant. Attenuates osteoblastic differentiation of vascular smooth muscle cells. ......by Adipogen Corporation
Vinpocetine is a Ca2+-calmodulin-dependent phosphodiesterase I (PDE1) inhibitor. ......by AdooQ BioScience, LLC
Vinpocetine, isolated from the lesser periwinkle plant, is a derivative of the vinca alkaloid vincamine with an effect of cerebral blood-flow enhancing and neuroprotection. Vinpocetine was approved for the treatment of cerebrovascular disorders and age-re ......by BOC Sciences
Vinpocetine, also known as AY-27,255 and RGH-4405, is a synthetic derivative of the vinca alkaloid vincamine (sometimes described as "a synthetic ethyl ester of apovincamine"), an extract from the lesser periwinkle plant. Vinpocetine has been reported to have cerebral blood-flow enhancing and neuroprotective effects, and has been used as a drug in Eastern Europe for the treatment of cerebrovascular disorders and age-related memory impairment. Vinpocetine acts as a phosphodiesterase (PDE) type-1 inhibitor in isolated rabbit aorta, Independent of vinpocetine's action on PDE, vinpocetine inhibits IKK preventing IκB degradation and the following translocation of NF-κB to the cell nucleus. ......by MedKoo Biosciences, Inc.
Vinpocetine (Ethyl apovincaminate) is a synthetic derivative of the vinca alkaloid vincamine, selectively inhibits PDE1 in isolated rabbit aorta with IC50 of 21 uM; inhibits IKK preventing IκB degradation and the following translocation of NF-κB to the cell nucleus, potently inhibits TNF-alpha- or LPS-induced up-regulation of proinflammatory mediators, including TNF-alpha, IL-1beta, and macrophage inflammatory protein-2, and decreases interstitial infiltration of polymorphonuclear leukocytes in mouse model of lung inflammation; demonstrates cerebral blood-flow enhancing and neuroprotective effects in vivo. ......by ProbeChem
Vinpocetine is a selective inhibitor of voltage-sensitive sodium channel for the treatment of stroke, vascular dementia and Alzheimer's disease. ......by Selleck Chemicals LLC
Vinpocetine is a selective inhibitor of cyclic GMP phosphodiesterase (PDE). ......by Target Molecule Corp.
Phosphodiesterase inhibitor, selective for PDE1 (IC50 = 21 μM). Also blocks voltage-gated Na+ channels. ......by Tocris Bioscience Inc.
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Protocol(Only for Reference)

Cell Experiment

Animal Experiment

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Physical and Chemical Properties

Appearance:White to off-white Solid EBNumber:EB000028621

Storage condition

Store at RT by Tocris Bioscience Inc.

Solubility

DMSO by MedChemexpress Co., Ltd.
(25°C) * In vitro DMSO <1 mg/mL (<1 mM); Water<1 mg/mL (<1 mM); Ethanol<! mg/mL <! by Selleck Chemicals LLC
Soluble to 50 mM in ethanol and to 10 mM in DMSO with gentle warming by Tocris Bioscience Inc.
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Mechanism and Indication

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Clinical Information

Product Name Sponsor & Collaborators Indications Start Date End Date Phase
Vinpocetine - Launched
Vinpocetine Noscira SA Progressive supranuclear palsy 2009/12/31 2011/11/30 Phase 2 Clinical
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Safety Data of Vinpocetine

Hazard Symbols : Xn
Risk Statements : R22
Safety Statements : S36
RTECS : JW4792000
WGKGermany : 3
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Spectral Information

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Suppliers List

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Related Products

Other Forms of 42971-09-5

Name CAS No Formula MW

Recommended Compounds in Phosphodiesterase (PDE) Sodium Channel

Name CAS No Formula MW
(R)-(-)-Rolipram 85416-75-7 C16H21NO3 275.34
Mirodenafil (dihydrochloride) 862189-96-6 C26H39Cl2N5O5S 604.59
Vardenafil (hydrochloride) 224785-91-5 C23H33ClN6O4S 525.06
Ibudilast 50847-11-5 C14H18N2O 230.31
Pentoxifylline 6493-05-6 C13H18N4O3 278.31
Anagrelide (hydrochloride) 58579-51-4 C10H8Cl3N3O 292.55
Vardenafil 224785-90-4 C23H32N6O4S 488.6
(S)-(+)-Rolipram 85416-73-5 C16H21NO3 275.34
Irsogladine (maleate) 84504-69-8 C13H11Cl2N5O4 372.16
Irsogladine 57381-26-7 C9H7Cl2N5 256.09
Dipyridamole (hydrochloride)(1:x) 35763-39-4 C24H41ClN8O4 541.09
Dipyridamole 58-32-2 C24H40N8O4 504.63
Pimobendan (hydrochloride) 77469-98-8 C19H19ClN4O2 370.83
Pimobendan 74150-27-9 C19H18N4O2 334.37
Aminophylline 317-34-0 C16H24N10O4 420.43
Diphylline 479-18-5 C10H14N4O4 254.24
Cilostazol 73963-72-1 C20H27N5O2 369.46
Deltarasin (hydrochloride) 1440898-82-7 C40H38ClN5O 640.22
Rolipram 61413-54-5 C16H21NO3 275.34
Deltarasin 1440898-61-2 C40H37N5O 603.75

Recommended Compounds in Same Indication

Name CAS No Formula MW
Tideglusib 865854-05-3 C19H14N2O2S 334.39
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Route of Synthesis

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References

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More Information

Vinpocetine

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