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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
Structure of BUTYLPHTHALIDE

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

HIDE SMILES / InChI

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

Targets

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
3-n-Butylphthalide (NBP)

Approved Use

3-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 Date

1.0097568E12
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Separation and identification of the phthalic anhydride derivatives of Liqusticum Chuanxiong Hort by GC-MS, TLC, HPLC-DAD, and HPLC-MS.
2002 Mar
New drugs derived from medicinal plants.
2002 Mar-Apr
Synthesis of enantiopure phthalides including 3-butylphthalide, a fragrance component of celery oil, and determination of their absolute configurations.
2005 May 5
Potent odorants characterize the aroma quality of leaves and stalks in raw and boiled celery.
2006 Apr
2-(1-Hydroxypentyl)-benzoate increases cerebral blood flow and reduces infarct volume in rats model of transient focal cerebral ischemia.
2006 Jun
l-3-n-Butylphthalide improves cognitive impairment induced by chronic cerebral hypoperfusion in rats.
2007 Jun
Novozyme 435-catalyzed efficient acylation of 3-n-butylphthalide in organic medium.
2008
[Mechanism of action of butylphalide against the injury following oxygen glucose deprivation/reoxygenation in rat cortical neurons].
2008 Apr
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
GC-MS fingerprints for discrimination of Ligusticum chuanxiong from Angelica.
2008 Oct
Novozyme 435-catalyzed asymmetric acylation of (R, S)-3-n- butylphthalide in hexane.
2009
[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
[Effect of butylphthalide on the expression of S100 and glial fibrillary acidic protein in a rat model of Alzheimer disease].
2009 Jun
Long-term treatment of l-3-n-butylphthalide attenuated neurodegenerative changes in aged rats.
2009 Jun
[Effects of dl-3n-butylphthalide on the expression of VEGF and bFGF in transient middle cerebral artery occlusion rats].
2009 May
L-3-n-butylphthalide improves cognitive impairment induced by intracerebroventricular infusion of amyloid-beta peptide in rats.
2009 Oct 25
Enhanced angiogenesis with dl-3n-butylphthalide treatment after focal cerebral ischemia in RHRSP.
2009 Sep 15
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
Simultaneous quantification of active components in the herbs and products of Si-Wu-Tang by high performance liquid chromatography-mass spectrometry.
2009 Sep 8
Identification and determination of the major constituents in Traditional Chinese Medicinal formula Danggui-Shaoyao-San by HPLC-DAD-ESI-MS/MS.
2009 Sep 8
An efficient system for the asymmetric acylation of (R,S)-3-n-butylphthalide catalyzed by novozyme 435.
2010
[Effects of butylphthalide on the apoptosis of PC-12 cells under the induction of β-amyloid peptide].
2010 Dec 7
[Effect of butylphthalide on the expression of GFAP and VEGF in the hippocampus of rats with Alzheimer's disease].
2010 Feb
[IR and Raman spectroscopic studies on the derivatives of butylphthalide].
2010 Jan
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
Synthesis of chiral 3-substituted phthalides by a sequential organocatalytic enantioselective aldol-lactonization reaction. Three-step synthesis of (S)-(-)-3-butylphthalide.
2010 Jan 15
L-3-n-butylphthalide improves cognitive impairment and reduces amyloid-beta in a transgenic model of Alzheimer's disease.
2010 Jun 16
3-n-Butylphthalide (NBP) reduces apoptosis and enhances vascular endothelial growth factor (VEGF) up-regulation in diabetic rats.
2010 May
Synthesis and biological activity of n-butylphthalide derivatives.
2010 May
dl-3-n-Butylphthalide prevents oxidative damage and reduces mitochondrial dysfunction in an MPP(+)-induced cellular model of Parkinson's disease.
2010 May 14
DL-3-n-butylphthalide prevents neuronal cell death after focal cerebral ischemia in mice via the JNK pathway.
2010 Nov 4
[Simultaneous determination of five effective components in Rhizoma Chuanxiong by RP-HPLC].
2010 Oct
Free radical scavenging activities of Cnidium officinale Makino and Ligusticum chuanxiong Hort. methanolic extracts.
2010 Oct
Protective effect of 3-butyl-6-bromo-1(3H)-isobenzofuranone on hydrogen peroxide-induced damage in PC12 cells.
2010 Oct 28
[Butylphthalide improves learning and memory abilities of rats with Alzheimer's disease possibly by enhancing protein disulfide isomerase and inhibiting P53 expressions].
2010 Sep
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
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
Created
by admin
on Sat Jun 26 11:54:59 UTC 2021
Edited
by admin
on Sat Jun 26 11:54:59 UTC 2021
Record UNII
822Q956KGM
Record Status Validated (UNII)
Record Version
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Name Type Language
BUTYLPHTHALIDE
INN   WHO-DD  
INN  
Official Name English
3-BUTYLPHTHALIDE
Preferred Name English
PHTHALIDE, 3-BUTYL-
Systematic Name English
3-N-BUTYLPHTHALIDE [FHFI]
Common Name English
(+/-)-3-BUTYLPHTHALIDE
Systematic Name English
DL-NBP
Common Name English
BUTYLPHTHALIDE [INN]
Common Name English
DL-3-N-BUTYLPHTHALIDE
Code English
FEMA NO. 3334
Code English
BUTYLPHTHALIDE [WHO-DD]
Common Name English
1(3H)-ISOBENZOFURANONE, 3-BUTYL-
Systematic Name English
3-BUTYL-1(3H)-ISOBENZOFURANONE
Systematic Name English
3-N-BUTYLPHTHALIDE
FHFI  
Common Name English
Classification Tree Code System Code
JECFA EVALUATION 3-N-BUTYLPHTHALIDE
Created by admin on Sat Jun 26 11:54:59 UTC 2021 , Edited by admin on Sat Jun 26 11:54:59 UTC 2021
DSLD 2881 (Number of products:2)
Created by admin on Sat Jun 26 11:54:59 UTC 2021 , Edited by admin on Sat Jun 26 11:54:59 UTC 2021
FDA ORPHAN DRUG 623217
Created by admin on Sat Jun 26 11:54:59 UTC 2021 , Edited by admin on Sat Jun 26 11:54:59 UTC 2021
Code System Code Type Description
DRUG CENTRAL
5257
Created by admin on Sat Jun 26 11:54:59 UTC 2021 , Edited by admin on Sat Jun 26 11:54:59 UTC 2021
PRIMARY
DRUG BANK
DB12749
Created by admin on Sat Jun 26 11:54:59 UTC 2021 , Edited by admin on Sat Jun 26 11:54:59 UTC 2021
PRIMARY
WIKIPEDIA
BUTYLPHTHALIDE
Created by admin on Sat Jun 26 11:54:59 UTC 2021 , Edited by admin on Sat Jun 26 11:54:59 UTC 2021
PRIMARY
CAS
6066-49-5
Created by admin on Sat Jun 26 11:54:59 UTC 2021 , Edited by admin on Sat Jun 26 11:54:59 UTC 2021
PRIMARY
ECHA (EC/EINECS)
228-000-8
Created by admin on Sat Jun 26 11:54:59 UTC 2021 , Edited by admin on Sat Jun 26 11:54:59 UTC 2021
PRIMARY
RXCUI
1484499
Created by admin on Sat Jun 26 11:54:59 UTC 2021 , Edited by admin on Sat Jun 26 11:54:59 UTC 2021
PRIMARY RxNorm
FDA UNII
822Q956KGM
Created by admin on Sat Jun 26 11:54:59 UTC 2021 , Edited by admin on Sat Jun 26 11:54:59 UTC 2021
PRIMARY
NCI_THESAURUS
C171720
Created by admin on Sat Jun 26 11:54:59 UTC 2021 , Edited by admin on Sat Jun 26 11:54:59 UTC 2021
PRIMARY
EVMPD
SUB32225
Created by admin on Sat Jun 26 11:54:59 UTC 2021 , Edited by admin on Sat Jun 26 11:54:59 UTC 2021
PRIMARY
MESH
C027125
Created by admin on Sat Jun 26 11:54:59 UTC 2021 , Edited by admin on Sat Jun 26 11:54:59 UTC 2021
PRIMARY
PUBCHEM
61361
Created by admin on Sat Jun 26 11:54:59 UTC 2021 , Edited by admin on Sat Jun 26 11:54:59 UTC 2021
PRIMARY
INN
9914
Created by admin on Sat Jun 26 11:54:59 UTC 2021 , Edited by admin on Sat Jun 26 11:54:59 UTC 2021
PRIMARY
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PARENT -> CONSTITUENT ALWAYS PRESENT
ENANTIOMER -> RACEMATE
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PARENT -> CONSTITUENT ALWAYS PRESENT
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ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC SINGLE DOSE ADMINISTRATION

ORAL ADMINISTRATION

Tmax PHARMACOKINETIC SINGLE DOSE ADMINISTRATION

ORAL ADMINISTRATION