Details
Stereochemistry | RACEMIC |
Molecular Formula | C12H14O2 |
Molecular Weight | 190.2388 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CCCCC1c2ccccc2C(=O)O1
InChI
InChIKey=HJXMNVQARNZTEE-UHFFFAOYSA-N
InChI=1S/C12H14O2/c1-2-3-8-11-9-6-4-5-7-10(9)12(13)14-11/h4-7,11H,2-3,8H2,1H3
Molecular Formula | C12H14O2 |
Molecular Weight | 190.2388 |
Charge | 0 |
Count |
|
Stereochemistry | RACEMIC |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Optical Activity | ( + / - ) |
3-N-Butylphthalide (NBP), a family comprised of optical isomers l-3-N-butylphthalide (l-NBP) and d-3-N-butylphthalide (d-NBP), with l-NBP being an extract from seeds of Apium graveolens Linn. (celery) and dl-3-N-butylphthalide (dl-NBP), a synthetized version, has been studied for its significant neuroprotective effects. NBP showed neuroprotective effects by decreasing oxidative damage, inhibiting inflammatory responses, improving mitochondrial function, and reducing
neuronal apoptosis. NBP received approval by the State Food and Drug Administration of China for clinical use in stroke patients in 2002. It demonstrates a potential for the treatment of central nervous system diseases, including Parkinson’s disease, Alzheimer’s disease.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: GO:0006915 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28053983 |
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Target ID: WP408 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28053983 |
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Target ID: GO:0022008 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28053983 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | 3-n-Butylphthalide (NBP) Approved Use3-n-Butylphthalide (NBP), an extract from the seeds of Apium graveolens Linn (Chinese
celery), was synthesized and received approval by the State Food and Drug Administration of China for clinical use in stroke patients in 2002 Launch Date1.0097568E12 |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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[Effects of 3-n-butylphthalide on thrombosis formation and platelet function in rats]. | 2001 May |
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Potent odorants characterize the aroma quality of leaves and stalks in raw and boiled celery. | 2006 Apr |
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Characterization of interaction property of multicomponents in Chinese Herb with protein by microdialysis combined with HPLC. | 2006 Jan 18 |
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[The effect of butylphthalide on expression of NGF and BDNF in ischemia stroke tissue of rat cerebrum]. | 2007 Jun |
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l-3-n-Butylphthalide improves cognitive impairment induced by chronic cerebral hypoperfusion in rats. | 2007 Jun |
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Synthesis, resolution, and antiplatelet activity of 3-substituted 1(3H)-isobenzofuranone. | 2007 Sep 15 |
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dl-3n-butylphthalide prevents stroke via improvement of cerebral microvessels in RHRSP. | 2007 Sep 15 |
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[Effects of dl-3-n-butylphthalide on expression of VEGF and bFGF in rat brain with permanent focal cerebral ischemia]. | 2008 Jan |
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l-3-n-Butylphthalide ameliorates beta-amyloid-induced neuronal toxicity in cultured neuronal cells. | 2008 Mar 28 |
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Novozyme 435-catalyzed asymmetric acylation of (R, S)-3-n- butylphthalide in hexane. | 2009 |
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[Butylphthalide improves learning and memory abilities of rats with Alzheimer's disease possibly by inhibiting P38 mitogen-activated protein kinase and enhancing extra-cellular signal regulated kinase expressions]. | 2009 Aug |
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[Effect of butylphthalide on the expression of S100 and glial fibrillary acidic protein in a rat model of Alzheimer disease]. | 2009 Jun |
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[Effects of dl-3n-butylphthalide on the expression of VEGF and bFGF in transient middle cerebral artery occlusion rats]. | 2009 May |
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L-3-n-butylphthalide improves cognitive impairment induced by intracerebroventricular infusion of amyloid-beta peptide in rats. | 2009 Oct 25 |
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Enhanced angiogenesis with dl-3n-butylphthalide treatment after focal cerebral ischemia in RHRSP. | 2009 Sep 15 |
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DL-3-n-butylphthalide protects endothelial cells against oxidative/nitrosative stress, mitochondrial damage and subsequent cell death after oxygen glucose deprivation in vitro. | 2009 Sep 22 |
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Simultaneous quantification of active components in the herbs and products of Si-Wu-Tang by high performance liquid chromatography-mass spectrometry. | 2009 Sep 8 |
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An efficient system for the asymmetric acylation of (R,S)-3-n-butylphthalide catalyzed by novozyme 435. | 2010 |
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[Effects of butylphthalide on the apoptosis of PC-12 cells under the induction of β-amyloid peptide]. | 2010 Dec 7 |
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Identification and comparative quantification of bio-active phthalides in essential oils from si-wu-tang, fo-shou-san, radix angelica and rhizoma chuanxiong. | 2010 Jan 15 |
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Synthesis of chiral 3-substituted phthalides by a sequential organocatalytic enantioselective aldol-lactonization reaction. Three-step synthesis of (S)-(-)-3-butylphthalide. | 2010 Jan 15 |
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L-3-n-butylphthalide improves cognitive impairment and reduces amyloid-beta in a transgenic model of Alzheimer's disease. | 2010 Jun 16 |
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3-n-Butylphthalide (NBP) reduces apoptosis and enhances vascular endothelial growth factor (VEGF) up-regulation in diabetic rats. | 2010 May |
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[Simultaneous determination of five effective components in Rhizoma Chuanxiong by RP-HPLC]. | 2010 Oct |
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Free radical scavenging activities of Cnidium officinale Makino and Ligusticum chuanxiong Hort. methanolic extracts. | 2010 Oct |
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Dl-3-n-butylphthalide, a natural antioxidant, protects dopamine neurons in rotenone models for Parkinson's disease. | 2012 Aug |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/28746179
The efficacy and safety of DL-3-n-Butylphthalide (NBP) for the treatment of progressive cerebral infarction (PCI) were evaluated in a randomized, double-blind placebo-controlled study. The test group received 200 mg of NBP soft capsules orally, 15 minutes before each meal, 3 times daily. The control group received 200 mg of placebo soft capsules orally, 15 minutes before each meal, 3 times daily. Treatment was administered during 21 days.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/20800583
DL-3-n-Butylphthalide (NBP) (10 μM) attenuated serum deprivation-induced neuronal apoptosis and the production of reactive oxygen species (ROS) in cortical neuronal cultures.
Substance Class |
Chemical
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Record UNII |
822Q956KGM
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Validated (UNII)
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JECFA EVALUATION |
3-N-BUTYLPHTHALIDE
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DSLD |
2881 (Number of products:2)
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FDA ORPHAN DRUG |
623217
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5257
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DB12749
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BUTYLPHTHALIDE
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6066-49-5
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1484499
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822Q956KGM
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C171720
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SUB32225
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C027125
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61361
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Related Record | Type | Details | ||
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METABOLIC ENZYME -> SUBSTRATE | |||
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METABOLIC ENZYME -> SUBSTRATE | |||
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PARENT -> CONSTITUENT ALWAYS PRESENT | |||
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ENANTIOMER -> RACEMATE | |||
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PARENT -> CONSTITUENT ALWAYS PRESENT |
Senkyunolide I, coniferyl ferulate, senkyunolide A, 3-butylphthalide, Z-butylidenephthalide and levistolide A were isolated from essential oil of Angelica sinensis.
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ACTIVE MOIETY |
Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Biological Half-life | PHARMACOKINETIC |
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SINGLE DOSE ADMINISTRATION |
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Tmax | PHARMACOKINETIC |
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