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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

1.0097568E12
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
[Effects of 3-n-butylphthalide on thrombosis formation and platelet function in rats].
2001 May
Synthesis of phthalides and 3,4-dihydroisocoumarins using the palladium-catalyzed intramolecular benzannulation strategy.
2002 Apr 19
[Effects of NBP on ATPase and anti-oxidant enzymes activities and lipid peroxidation in transient focal cerebral ischemic rats].
2002 Feb
Separation and identification of the phthalic anhydride derivatives of Liqusticum Chuanxiong Hort by GC-MS, TLC, HPLC-DAD, and HPLC-MS.
2002 Mar
New drugs derived from medicinal plants.
2002 Mar-Apr
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
Development of high-performance liquid chromatographic fingerprints for distinguishing Chinese Angelica from related umbelliferae herbs.
2005 May 6
Live cell extraction and HPLC-MS analysis for predicting bioactive components of traditional Chinese medicines.
2006 May 3
[The effect of butylphthalide on expression of NGF and BDNF in ischemia stroke tissue of rat cerebrum].
2007 Jun
[Mechanism of action of butylphalide against the injury following oxygen glucose deprivation/reoxygenation in rat cortical neurons].
2008 Apr
Novozyme 435-catalyzed asymmetric acylation of (R, S)-3-n- butylphthalide in hexane.
2009
[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
Long-term treatment of l-3-n-butylphthalide attenuated neurodegenerative changes in aged rats.
2009 Jun
[Effects of dl-3n-butylphthalide on the expression of VEGF and bFGF in transient middle cerebral artery occlusion rats].
2009 May
Enhanced angiogenesis with dl-3n-butylphthalide treatment after focal cerebral ischemia in RHRSP.
2009 Sep 15
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
Simultaneous quantification of active components in the herbs and products of Si-Wu-Tang by high performance liquid chromatography-mass spectrometry.
2009 Sep 8
Identification and determination of the major constituents in Traditional Chinese Medicinal formula Danggui-Shaoyao-San by HPLC-DAD-ESI-MS/MS.
2009 Sep 8
[IR and Raman spectroscopic studies on the derivatives of butylphthalide].
2010 Jan
L-3-n-butylphthalide improves cognitive impairment and reduces amyloid-beta in a transgenic model of Alzheimer's disease.
2010 Jun 16
3-n-Butylphthalide (NBP) reduces apoptosis and enhances vascular endothelial growth factor (VEGF) up-regulation in diabetic rats.
2010 May
DL-3-n-butylphthalide prevents neuronal cell death after focal cerebral ischemia in mice via the JNK pathway.
2010 Nov 4
Protective effect of 3-butyl-6-bromo-1(3H)-isobenzofuranone on hydrogen peroxide-induced damage in PC12 cells.
2010 Oct 28
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 Thu Jul 06 01:47:04 UTC 2023
Edited
by admin
on Thu Jul 06 01:47:04 UTC 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 Thu Jul 06 01:47:04 UTC 2023 , Edited by admin on Thu Jul 06 01:47:04 UTC 2023
DSLD 2881 (Number of products:2)
Created by admin on Thu Jul 06 01:47:04 UTC 2023 , Edited by admin on Thu Jul 06 01:47:04 UTC 2023
FDA ORPHAN DRUG 623217
Created by admin on Thu Jul 06 01:47:04 UTC 2023 , Edited by admin on Thu Jul 06 01:47:04 UTC 2023
Code System Code Type Description
DRUG CENTRAL
5257
Created by admin on Thu Jul 06 01:47:04 UTC 2023 , Edited by admin on Thu Jul 06 01:47:04 UTC 2023
PRIMARY
DRUG BANK
DB12749
Created by admin on Thu Jul 06 01:47:04 UTC 2023 , Edited by admin on Thu Jul 06 01:47:04 UTC 2023
PRIMARY
EPA CompTox
DTXSID50863687
Created by admin on Thu Jul 06 01:47:04 UTC 2023 , Edited by admin on Thu Jul 06 01:47:04 UTC 2023
PRIMARY
WIKIPEDIA
BUTYLPHTHALIDE
Created by admin on Thu Jul 06 01:47:04 UTC 2023 , Edited by admin on Thu Jul 06 01:47:04 UTC 2023
PRIMARY
CAS
6066-49-5
Created by admin on Thu Jul 06 01:47:04 UTC 2023 , Edited by admin on Thu Jul 06 01:47:04 UTC 2023
PRIMARY
ECHA (EC/EINECS)
228-000-8
Created by admin on Thu Jul 06 01:47:04 UTC 2023 , Edited by admin on Thu Jul 06 01:47:04 UTC 2023
PRIMARY
RXCUI
1484499
Created by admin on Thu Jul 06 01:47:04 UTC 2023 , Edited by admin on Thu Jul 06 01:47:04 UTC 2023
PRIMARY RxNorm
FDA UNII
822Q956KGM
Created by admin on Thu Jul 06 01:47:04 UTC 2023 , Edited by admin on Thu Jul 06 01:47:04 UTC 2023
PRIMARY
NCI_THESAURUS
C171720
Created by admin on Thu Jul 06 01:47:04 UTC 2023 , Edited by admin on Thu Jul 06 01:47:04 UTC 2023
PRIMARY
DAILYMED
822Q956KGM
Created by admin on Thu Jul 06 01:47:04 UTC 2023 , Edited by admin on Thu Jul 06 01:47:04 UTC 2023
PRIMARY
SMS_ID
100000124420
Created by admin on Thu Jul 06 01:47:04 UTC 2023 , Edited by admin on Thu Jul 06 01:47:04 UTC 2023
PRIMARY
EVMPD
SUB32225
Created by admin on Thu Jul 06 01:47:04 UTC 2023 , Edited by admin on Thu Jul 06 01:47:04 UTC 2023
PRIMARY
MESH
C027125
Created by admin on Thu Jul 06 01:47:04 UTC 2023 , Edited by admin on Thu Jul 06 01:47:04 UTC 2023
PRIMARY
PUBCHEM
61361
Created by admin on Thu Jul 06 01:47:04 UTC 2023 , Edited by admin on Thu Jul 06 01:47:04 UTC 2023
PRIMARY
INN
9914
Created by admin on Thu Jul 06 01:47:04 UTC 2023 , Edited by admin on Thu Jul 06 01:47:04 UTC 2023
PRIMARY
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