Details
Stereochemistry | RACEMIC |
Molecular Formula | C12H14O2 |
Molecular Weight | 190.2384 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CCCCC1OC(=O)C2=C1C=CC=C2
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 | 190.2384 |
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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Synthesis of phthalides and 3,4-dihydroisocoumarins using the palladium-catalyzed intramolecular benzannulation strategy. | 2002 Apr 19 |
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[Effects of NBP on ATPase and anti-oxidant enzymes activities and lipid peroxidation in transient focal cerebral ischemic rats]. | 2002 Feb |
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New drugs derived from medicinal plants. | 2002 Mar-Apr |
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Effects of chiral 3-n-butylphthalide on apoptosis induced by transient focal cerebral ischemia in rats. | 2003 Aug |
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Antiplatelet and antithrombotic activity of L-3-n-butylphthalide in rats. | 2004 Jun |
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Synthesis of enantiopure phthalides including 3-butylphthalide, a fragrance component of celery oil, and determination of their absolute configurations. | 2005 May 5 |
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Development of high-performance liquid chromatographic fingerprints for distinguishing Chinese Angelica from related umbelliferae herbs. | 2005 May 6 |
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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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Live cell extraction and HPLC-MS analysis for predicting bioactive components of traditional Chinese medicines. | 2006 May 3 |
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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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GC-MS fingerprints for discrimination of Ligusticum chuanxiong from Angelica. | 2008 Oct |
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Novozyme 435-catalyzed asymmetric acylation of (R, S)-3-n- butylphthalide in hexane. | 2009 |
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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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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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Identification and determination of the major constituents in Traditional Chinese Medicinal formula Danggui-Shaoyao-San by HPLC-DAD-ESI-MS/MS. | 2009 Sep 8 |
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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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[Effect of butylphthalide on the expression of GFAP and VEGF in the hippocampus of rats with Alzheimer's disease]. | 2010 Feb |
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[IR and Raman spectroscopic studies on the derivatives of butylphthalide]. | 2010 Jan |
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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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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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Synthesis and biological activity of n-butylphthalide derivatives. | 2010 May |
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dl-3-n-Butylphthalide prevents oxidative damage and reduces mitochondrial dysfunction in an MPP(+)-induced cellular model of Parkinson's disease. | 2010 May 14 |
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DL-3-n-butylphthalide prevents neuronal cell death after focal cerebral ischemia in mice via the JNK pathway. | 2010 Nov 4 |
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[Simultaneous determination of five effective components in Rhizoma Chuanxiong by RP-HPLC]. | 2010 Oct |
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Protective effect of 3-butyl-6-bromo-1(3H)-isobenzofuranone on hydrogen peroxide-induced damage in PC12 cells. | 2010 Oct 28 |
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[Butylphthalide improves learning and memory abilities of rats with Alzheimer's disease possibly by enhancing protein disulfide isomerase and inhibiting P53 expressions]. | 2010 Sep |
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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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822Q956KGM
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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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DTXSID50863687
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BUTYLPHTHALIDE
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6066-49-5
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228-000-8
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C171720
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C027125
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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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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 |
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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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