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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 of BUTYLPHTHALIDE

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 ( + / - )

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

2001
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
[Effects of NBP on ATPase and anti-oxidant enzymes activities and lipid peroxidation in transient focal cerebral ischemic rats].
2002 Feb
Effects of chiral 3-n-butylphthalide on apoptosis induced by transient focal cerebral ischemia in rats.
2003 Aug
Simultaneous analysis of seventeen chemical ingredients of Ligusticum chuanxiong by on-line high performance liquid chromatography-diode array detector-mass spectrometry.
2003 May
Determination of 3-n-butylphthalide in rabbit plasma by HPLC with fluorescence detection and its application in pharmacokinetic study.
2003 Sep
Antiplatelet and antithrombotic activity of L-3-n-butylphthalide in rats.
2004 Jun
[Preparation of covalently bonded cellulose tris (4-methylbenzoate) derivative chiral stationary phases through a polymerization reaction].
2004 Nov
HPLC-coupled spectroscopic techniques (UV, MS, NMR) for the structure elucidation of phthalides in Ligusticum chuanxiong.
2005
Development of high-performance liquid chromatographic fingerprints for distinguishing Chinese Angelica from related umbelliferae herbs.
2005 May 6
2-(1-Hydroxypentyl)-benzoate increases cerebral blood flow and reduces infarct volume in rats model of transient focal cerebral ischemia.
2006 Jun
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
[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
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
Simultaneous quantification of active components in the herbs and products of Si-Wu-Tang by high performance liquid chromatography-mass spectrometry.
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
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
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 Fri Dec 15 18:34:30 GMT 2023
Edited
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on Fri Dec 15 18:34:30 GMT 2023
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
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
FHFI  
Common Name English
Classification Tree Code System Code
JECFA EVALUATION 3-N-BUTYLPHTHALIDE
Created by admin on Fri Dec 15 18:34:30 GMT 2023 , Edited by admin on Fri Dec 15 18:34:30 GMT 2023
DSLD 2881 (Number of products:2)
Created by admin on Fri Dec 15 18:34:30 GMT 2023 , Edited by admin on Fri Dec 15 18:34:30 GMT 2023
FDA ORPHAN DRUG 623217
Created by admin on Fri Dec 15 18:34:30 GMT 2023 , Edited by admin on Fri Dec 15 18:34:30 GMT 2023
Code System Code Type Description
DRUG CENTRAL
5257
Created by admin on Fri Dec 15 18:34:30 GMT 2023 , Edited by admin on Fri Dec 15 18:34:30 GMT 2023
PRIMARY
DRUG BANK
DB12749
Created by admin on Fri Dec 15 18:34:30 GMT 2023 , Edited by admin on Fri Dec 15 18:34:30 GMT 2023
PRIMARY
EPA CompTox
DTXSID50863687
Created by admin on Fri Dec 15 18:34:30 GMT 2023 , Edited by admin on Fri Dec 15 18:34:30 GMT 2023
PRIMARY
WIKIPEDIA
BUTYLPHTHALIDE
Created by admin on Fri Dec 15 18:34:30 GMT 2023 , Edited by admin on Fri Dec 15 18:34:30 GMT 2023
PRIMARY
JECFA MONOGRAPH
1160
Created by admin on Fri Dec 15 18:34:30 GMT 2023 , Edited by admin on Fri Dec 15 18:34:30 GMT 2023
PRIMARY
CAS
6066-49-5
Created by admin on Fri Dec 15 18:34:30 GMT 2023 , Edited by admin on Fri Dec 15 18:34:30 GMT 2023
PRIMARY
ECHA (EC/EINECS)
228-000-8
Created by admin on Fri Dec 15 18:34:30 GMT 2023 , Edited by admin on Fri Dec 15 18:34:30 GMT 2023
PRIMARY
RXCUI
1484499
Created by admin on Fri Dec 15 18:34:30 GMT 2023 , Edited by admin on Fri Dec 15 18:34:30 GMT 2023
PRIMARY RxNorm
FDA UNII
822Q956KGM
Created by admin on Fri Dec 15 18:34:30 GMT 2023 , Edited by admin on Fri Dec 15 18:34:30 GMT 2023
PRIMARY
NCI_THESAURUS
C171720
Created by admin on Fri Dec 15 18:34:30 GMT 2023 , Edited by admin on Fri Dec 15 18:34:30 GMT 2023
PRIMARY
DAILYMED
822Q956KGM
Created by admin on Fri Dec 15 18:34:30 GMT 2023 , Edited by admin on Fri Dec 15 18:34:30 GMT 2023
PRIMARY
SMS_ID
100000124420
Created by admin on Fri Dec 15 18:34:30 GMT 2023 , Edited by admin on Fri Dec 15 18:34:30 GMT 2023
PRIMARY
EVMPD
SUB32225
Created by admin on Fri Dec 15 18:34:30 GMT 2023 , Edited by admin on Fri Dec 15 18:34:30 GMT 2023
PRIMARY
MESH
C027125
Created by admin on Fri Dec 15 18:34:30 GMT 2023 , Edited by admin on Fri Dec 15 18:34:30 GMT 2023
PRIMARY
PUBCHEM
61361
Created by admin on Fri Dec 15 18:34:30 GMT 2023 , Edited by admin on Fri Dec 15 18:34:30 GMT 2023
PRIMARY
INN
9914
Created by admin on Fri Dec 15 18:34:30 GMT 2023 , Edited by admin on Fri Dec 15 18:34:30 GMT 2023
PRIMARY
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