BUTYLPHTHALIDE

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

Structure Search

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

HIDE SMILES / InChI

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 48 Target ID: GO:0006915 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28053983	Inhibitor 8297
Oxidative Stress 160 Target ID: WP408 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28053983	Inhibitor 8297
neurogenesis 3 Target ID: GO:0022008 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28053983	Activator 1430

Conditions

Condition	Modality	Highest Phase	Product
Stroke 144 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 8429	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 2001
Parkinson's disease 226 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 272 Sources: https://www.karger.com/Article/Pdf/362633 https://www.ncbi.nlm.nih.gov/pubmed/28053983	Primary	Not Provided 504	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Synthesis of phthalides and 3,4-dihydroisocoumarins using the palladium-catalyzed intramolecular benzannulation strategy.	2002 Apr 19	11950312
[Effects of NBP on ATPase and anti-oxidant enzymes activities and lipid peroxidation in transient focal cerebral ischemic rats].	2002 Feb	12905849
Characterization of interaction property of multicomponents in Chinese Herb with protein by microdialysis combined with HPLC.	2006 Jan 18	17723347
Live cell extraction and HPLC-MS analysis for predicting bioactive components of traditional Chinese medicines.	2006 May 3	16488100
Novozyme 435-catalyzed efficient acylation of 3-n-butylphthalide in organic medium.	2008	18800300
[Effects of butylphthalide on the apoptosis of PC-12 cells under the induction of β-amyloid peptide].	2010 Dec 7	21223776
[Effect of butylphthalide on the expression of GFAP and VEGF in the hippocampus of rats with Alzheimer's disease].	2010 Feb	20197608
[IR and Raman spectroscopic studies on the derivatives of butylphthalide].	2010 Jan	20302088
Synthesis and biological activity of n-butylphthalide derivatives.	2010 May	20133025
Free radical scavenging activities of Cnidium officinale Makino and Ligusticum chuanxiong Hort. methanolic extracts.	2010 Oct	21120037
Protective effect of 3-butyl-6-bromo-1(3H)-isobenzofuranone on hydrogen peroxide-induced damage in PC12 cells.	2010 Oct 28	20732309

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.

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

1(3H)-ISOBENZOFURANONE, 3-BUTYL-

Systematic Name

English

3-BUTYL-1(3H)-ISOBENZOFURANONE

Systematic Name

English

Butylphthalide [WHO-DD]

Common Name

English

3-N-BUTYLPHTHALIDE

Common Name

English

Classification Tree Code System Code

JECFA EVALUATION

3-N-BUTYLPHTHALIDE