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 |
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| 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 Date2001 |
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| Primary | Unknown Approved UseUnknown |
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| Primary | Unknown Approved UseUnknown |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
514 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23169608/ |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
BUTYLPHTHALIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
864 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23169608/ |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
BUTYLPHTHALIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
5.33 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23169608/ |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
BUTYLPHTHALIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Dl-3-n-butylphthalide, a natural antioxidant, protects dopamine neurons in rotenone models for Parkinson's disease. | 2012-08 |
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| [Effects of butylphthalide on the apoptosis of PC-12 cells under the induction of β-amyloid peptide]. | 2010-12-07 |
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| DL-3-n-butylphthalide prevents neuronal cell death after focal cerebral ischemia in mice via the JNK pathway. | 2010-11-04 |
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| Protective effect of 3-butyl-6-bromo-1(3H)-isobenzofuranone on hydrogen peroxide-induced damage in PC12 cells. | 2010-10-28 |
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| [Simultaneous determination of five effective components in Rhizoma Chuanxiong by RP-HPLC]. | 2010-10 |
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| Free radical scavenging activities of Cnidium officinale Makino and Ligusticum chuanxiong Hort. methanolic extracts. | 2010-10 |
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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]. | 2010-09 |
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| L-3-n-butylphthalide improves cognitive impairment and reduces amyloid-beta in a transgenic model of Alzheimer's disease. | 2010-06-16 |
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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. | 2010-05-14 |
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| 3-n-Butylphthalide (NBP) reduces apoptosis and enhances vascular endothelial growth factor (VEGF) up-regulation in diabetic rats. | 2010-05 |
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| Synthesis and biological activity of n-butylphthalide derivatives. | 2010-05 |
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| [Effect of butylphthalide on the expression of GFAP and VEGF in the hippocampus of rats with Alzheimer's disease]. | 2010-02 |
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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. | 2010-01-15 |
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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. | 2010-01-15 |
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| [IR and Raman spectroscopic studies on the derivatives of butylphthalide]. | 2010-01 |
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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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| L-3-n-butylphthalide improves cognitive impairment induced by intracerebroventricular infusion of amyloid-beta peptide in rats. | 2009-10-25 |
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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. | 2009-09-22 |
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| Enhanced angiogenesis with dl-3n-butylphthalide treatment after focal cerebral ischemia in RHRSP. | 2009-09-15 |
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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. | 2009-09-08 |
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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. | 2009-09-08 |
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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]. | 2009-08 |
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| [Effect of butylphthalide on the expression of S100 and glial fibrillary acidic protein in a rat model of Alzheimer disease]. | 2009-06 |
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| Long-term treatment of l-3-n-butylphthalide attenuated neurodegenerative changes in aged rats. | 2009-06 |
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| [Effects of dl-3n-butylphthalide on the expression of VEGF and bFGF in transient middle cerebral artery occlusion rats]. | 2009-05 |
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| Novozyme 435-catalyzed asymmetric acylation of (R, S)-3-n- butylphthalide in hexane. | 2009 |
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| GC-MS fingerprints for discrimination of Ligusticum chuanxiong from Angelica. | 2008-10 |
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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. | 2008-07-01 |
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| [Mechanism of action of butylphalide against the injury following oxygen glucose deprivation/reoxygenation in rat cortical neurons]. | 2008-04 |
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| l-3-n-Butylphthalide ameliorates beta-amyloid-induced neuronal toxicity in cultured neuronal cells. | 2008-03-28 |
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| [Effects of dl-3-n-butylphthalide on expression of VEGF and bFGF in rat brain with permanent focal cerebral ischemia]. | 2008-01 |
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| Novozyme 435-catalyzed efficient acylation of 3-n-butylphthalide in organic medium. | 2008 |
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| Synthesis, resolution, and antiplatelet activity of 3-substituted 1(3H)-isobenzofuranone. | 2007-09-15 |
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| dl-3n-butylphthalide prevents stroke via improvement of cerebral microvessels in RHRSP. | 2007-09-15 |
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| [The effect of butylphthalide on expression of NGF and BDNF in ischemia stroke tissue of rat cerebrum]. | 2007-06 |
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| l-3-n-Butylphthalide improves cognitive impairment induced by chronic cerebral hypoperfusion in rats. | 2007-06 |
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| 2-(1-Hydroxypentyl)-benzoate increases cerebral blood flow and reduces infarct volume in rats model of transient focal cerebral ischemia. | 2006-06 |
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| Live cell extraction and HPLC-MS analysis for predicting bioactive components of traditional Chinese medicines. | 2006-05-03 |
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| Potent odorants characterize the aroma quality of leaves and stalks in raw and boiled celery. | 2006-04 |
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| Characterization of interaction property of multicomponents in Chinese Herb with protein by microdialysis combined with HPLC. | 2006-01-18 |
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| Development of high-performance liquid chromatographic fingerprints for distinguishing Chinese Angelica from related umbelliferae herbs. | 2005-05-06 |
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| Synthesis of enantiopure phthalides including 3-butylphthalide, a fragrance component of celery oil, and determination of their absolute configurations. | 2005-05-05 |
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| HPLC-coupled spectroscopic techniques (UV, MS, NMR) for the structure elucidation of phthalides in Ligusticum chuanxiong. | 2005 |
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| [Preparation of covalently bonded cellulose tris (4-methylbenzoate) derivative chiral stationary phases through a polymerization reaction]. | 2004-11 |
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| Antiplatelet and antithrombotic activity of L-3-n-butylphthalide in rats. | 2004-06 |
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| Determination of 3-n-butylphthalide in rabbit plasma by HPLC with fluorescence detection and its application in pharmacokinetic study. | 2003-09 |
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| Effects of chiral 3-n-butylphthalide on apoptosis induced by transient focal cerebral ischemia in rats. | 2003-08 |
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| Simultaneous analysis of seventeen chemical ingredients of Ligusticum chuanxiong by on-line high performance liquid chromatography-diode array detector-mass spectrometry. | 2003-05 |
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| [Effects of NBP on ATPase and anti-oxidant enzymes activities and lipid peroxidation in transient focal cerebral ischemic rats]. | 2002-02 |
|
| [Effects of 3-n-butylphthalide on thrombosis formation and platelet function in rats]. | 2001-05 |
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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| 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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| 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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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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ENANTIOMER -> RACEMATE |
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METABOLITE -> PARENT |
MAJOR
PLASMA
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METABOLITE -> PARENT |
MINOR
URINE
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METABOLITE -> PARENT |
PLASMA; URINE
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METABOLITE -> PARENT |
URINE
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METABOLITE -> PARENT |
URINE
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METABOLITE -> PARENT |
MAJOR
PLASMA
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METABOLITE -> PARENT |
PLASMA; URINE
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METABOLITE -> PARENT |
MAJOR
PLASMA; URINE
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METABOLITE -> PARENT |
MAJOR
PLASMA
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METABOLITE -> PARENT |
URINE
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METABOLITE -> PARENT |
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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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SINGLE DOSE ADMINISTRATION |
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