BUTYLPHTHALIDE

Possibly Marketed Outside US

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 Search

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	( + / - )

Description
Sources: https://www.karger.com/Article/Pdf/362633 | https://www.ncbi.nlm.nih.gov/pubmed/28053983

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.

CNS Activity

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
apoptotic process 23 Target ID: GO:0006915 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28053983	Inhibitor 3315
Oxidative Stress 57 Target ID: WP408 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28053983	Inhibitor 3315
neurogenesis Target ID: GO:0022008 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28053983	Activator 560

Conditions

Condition	Modality	Highest Phase	Product
Stroke 49 Sources: https://www.karger.com/Article/Pdf/362633 https://www.ncbi.nlm.nih.gov/pubmed/28053983 https://www.ncbi.nlm.nih.gov/pubmed/28145815 https://www.ncbi.nlm.nih.gov/pubmed/28746179 https://www.ncbi.nlm.nih.gov/pubmed/28053983	Primary	Approved 4033	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
Parkinson's disease 83 Sources: https://www.karger.com/Article/Pdf/362633 https://www.ncbi.nlm.nih.gov/pubmed/28053983	Primary	Preclinical	Unknown Approved Use Unknown
Alzheimer’s disease 107 Sources: https://www.karger.com/Article/Pdf/362633 https://www.ncbi.nlm.nih.gov/pubmed/28053983	Primary	Not Provided 208	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
[Effects of 3-n-butylphthalide on thrombosis formation and platelet function in rats].	2001 May	12584852
Potent odorants characterize the aroma quality of leaves and stalks in raw and boiled celery.	2006 Apr	16636464
Characterization of interaction property of multicomponents in Chinese Herb with protein by microdialysis combined with HPLC.	2006 Jan 18	17723347
[The effect of butylphthalide on expression of NGF and BDNF in ischemia stroke tissue of rat cerebrum].	2007 Jun	17593816
l-3-n-Butylphthalide improves cognitive impairment induced by chronic cerebral hypoperfusion in rats.	2007 Jun	17374747
Synthesis, resolution, and antiplatelet activity of 3-substituted 1(3H)-isobenzofuranone.	2007 Sep 15	17632002
dl-3n-butylphthalide prevents stroke via improvement of cerebral microvessels in RHRSP.	2007 Sep 15	17553527
[Effects of dl-3-n-butylphthalide on expression of VEGF and bFGF in rat brain with permanent focal cerebral ischemia].	2008 Jan	18390208
l-3-n-Butylphthalide ameliorates beta-amyloid-induced neuronal toxicity in cultured neuronal cells.	2008 Mar 28	18328624
Novozyme 435-catalyzed asymmetric acylation of (R, S)-3-n- butylphthalide in hexane.	2009	19431043
[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	19726301
[Effect of butylphthalide on the expression of S100 and glial fibrillary acidic protein in a rat model of Alzheimer disease].	2009 Jun	19726345
[Effects of dl-3n-butylphthalide on the expression of VEGF and bFGF in transient middle cerebral artery occlusion rats].	2009 May	19626991
L-3-n-butylphthalide improves cognitive impairment induced by intracerebroventricular infusion of amyloid-beta peptide in rats.	2009 Oct 25	19737553
Enhanced angiogenesis with dl-3n-butylphthalide treatment after focal cerebral ischemia in RHRSP.	2009 Sep 15	19524555
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	19616517
Simultaneous quantification of active components in the herbs and products of Si-Wu-Tang by high performance liquid chromatography-mass spectrometry.	2009 Sep 8	19423264
An efficient system for the asymmetric acylation of (R,S)-3-n-butylphthalide catalyzed by novozyme 435.	2010	21108139
[Effects of butylphthalide on the apoptosis of PC-12 cells under the induction of β-amyloid peptide].	2010 Dec 7	21223776
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	20110895
Synthesis of chiral 3-substituted phthalides by a sequential organocatalytic enantioselective aldol-lactonization reaction. Three-step synthesis of (S)-(-)-3-butylphthalide.	2010 Jan 15	20000698
L-3-n-butylphthalide improves cognitive impairment and reduces amyloid-beta in a transgenic model of Alzheimer's disease.	2010 Jun 16	20554868
3-n-Butylphthalide (NBP) reduces apoptosis and enhances vascular endothelial growth factor (VEGF) up-regulation in diabetic rats.	2010 May	20483006
[Simultaneous determination of five effective components in Rhizoma Chuanxiong by RP-HPLC].	2010 Oct	21246821
Free radical scavenging activities of Cnidium officinale Makino and Ligusticum chuanxiong Hort. methanolic extracts.	2010 Oct	21120037
Dl-3-n-butylphthalide, a natural antioxidant, protects dopamine neurons in rotenone models for Parkinson's disease.	2012 Aug	21524431

Patents

Sample Use Guides

In Vivo Use Guide

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

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

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

Common Name

English

Classification Tree Code System Code

JECFA EVALUATION

3-N-BUTYLPHTHALIDE