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
Effects of chiral 3-n-butylphthalide on apoptosis induced by transient focal cerebral ischemia in rats.	2003 Aug	12904280
[The effect of butylphthalide on expression of NGF and BDNF in ischemia stroke tissue of rat cerebrum].	2007 Jun	17593816
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
L-3-n-butylphthalide improves cognitive impairment induced by intracerebroventricular infusion of amyloid-beta peptide in rats.	2009 Oct 25	19737553
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
3-n-Butylphthalide (NBP) reduces apoptosis and enhances vascular endothelial growth factor (VEGF) up-regulation in diabetic rats.	2010 May	20483006
[Butylphthalide improves learning and memory abilities of rats with Alzheimer's disease possibly by enhancing protein disulfide isomerase and inhibiting P53 expressions].	2010 Sep	20855262

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