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 |
|---|---|---|---|
Target ID: GO:0006915 |
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Target ID: WP408 |
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Target ID: GO:0022008 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| 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 |
|---|---|---|
| Separation and identification of the phthalic anhydride derivatives of Liqusticum Chuanxiong Hort by GC-MS, TLC, HPLC-DAD, and HPLC-MS. | 2002 Mar |
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| New drugs derived from medicinal plants. | 2002 Mar-Apr |
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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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| Potent odorants characterize the aroma quality of leaves and stalks in raw and boiled celery. | 2006 Apr |
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| 2-(1-Hydroxypentyl)-benzoate increases cerebral blood flow and reduces infarct volume in rats model of transient focal cerebral ischemia. | 2006 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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| Novozyme 435-catalyzed efficient acylation of 3-n-butylphthalide in organic medium. | 2008 |
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| [Mechanism of action of butylphalide against the injury following oxygen glucose deprivation/reoxygenation in rat cortical neurons]. | 2008 Apr |
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| High-performance liquid chromatography for the determination of 3-n-butylphthalide in rat plasma by tandem quadrupole mass spectrometry: application to a pharmacokinetic study. | 2008 Jul 1 |
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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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| [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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| Long-term treatment of l-3-n-butylphthalide attenuated neurodegenerative changes in aged rats. | 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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| 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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| 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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| [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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| 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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| 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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| Free radical scavenging activities of Cnidium officinale Makino and Ligusticum chuanxiong Hort. methanolic extracts. | 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
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
| 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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BUTYLPHTHALIDE
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6066-49-5
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228-000-8
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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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9914
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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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METABOLIC ENZYME -> SUBSTRATE | |||
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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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METABOLITE -> PARENT |
URINE
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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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