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

Molecular Formula	C12H14O2
Molecular Weight	190.2384
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 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
[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
[Mechanism of action of butylphalide against the injury following oxygen glucose deprivation/reoxygenation in rat cortical neurons].	2008 Apr	18664197
Novozyme 435-catalyzed asymmetric acylation of (R, S)-3-n- butylphthalide in hexane.	2009	19431043
[Effects of dl-3n-butylphthalide on the expression of VEGF and bFGF in transient middle cerebral artery occlusion rats].	2009 May	19626991
Enhanced angiogenesis with dl-3n-butylphthalide treatment after focal cerebral ischemia in RHRSP.	2009 Sep 15	19524555
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
[IR and Raman spectroscopic studies on the derivatives of butylphthalide].	2010 Jan	20302088
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
3-n-Butylphthalide (NBP) reduces apoptosis and enhances vascular endothelial growth factor (VEGF) up-regulation in diabetic rats.	2010 May	20483006
Free radical scavenging activities of Cnidium officinale Makino and Ligusticum chuanxiong Hort. methanolic extracts.	2010 Oct	21120037

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 `Fri Dec 15 18:34:30 GMT 2023` Edited by `admin` on `Fri Dec 15 18:34:30 GMT 2023`
Record UNII	822Q956KGM
Record Status	`Validated (UNII)`
Record Version

Download

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