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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 ( + / - )

Description

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

2009
330
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8146
Inhibitor
8146
Activator
1404
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8307
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
Preclinical
Unknown

Approved Use

Unknown
Primary
Not Provided
505
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
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
Antiplatelet and antithrombotic activity of L-3-n-butylphthalide in rats.
2004 Jun
Synthesis of enantiopure phthalides including 3-butylphthalide, a fragrance component of celery oil, and determination of their absolute configurations.
2005 May 5
Development of high-performance liquid chromatographic fingerprints for distinguishing Chinese Angelica from related umbelliferae herbs.
2005 May 6
Potent odorants characterize the aroma quality of leaves and stalks in raw and boiled celery.
2006 Apr
Characterization of interaction property of multicomponents in Chinese Herb with protein by microdialysis combined with HPLC.
2006 Jan 18
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
l-3-n-Butylphthalide improves cognitive impairment induced by chronic cerebral hypoperfusion in rats.
2007 Jun
Synthesis, resolution, and antiplatelet activity of 3-substituted 1(3H)-isobenzofuranone.
2007 Sep 15
dl-3n-butylphthalide prevents stroke via improvement of cerebral microvessels in RHRSP.
2007 Sep 15
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
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
Identification and determination of the major constituents in Traditional Chinese Medicinal formula Danggui-Shaoyao-San by HPLC-DAD-ESI-MS/MS.
2009 Sep 8
[Effects of butylphthalide on the apoptosis of PC-12 cells under the induction of β-amyloid peptide].
2010 Dec 7
[Effect of butylphthalide on the expression of GFAP and VEGF in the hippocampus of rats with Alzheimer's disease].
2010 Feb
[IR and Raman spectroscopic studies on the derivatives of butylphthalide].
2010 Jan
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
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
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
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

Patents

CN1257706A
1
CN1283621A
1
CN1375288A
1

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 Sat Dec 17 00:40:32 UTC 2022
Edited
by admin
on Sat Dec 17 00:40:32 UTC 2022
Record UNII
822Q956KGM
Record Status Validated (UNII)
Record Version
  • Download
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 Sat Dec 17 00:40:32 UTC 2022 , Edited by admin on Sat Dec 17 00:40:32 UTC 2022
DSLD 2881 (Number of products:2)
Created by admin on Sat Dec 17 00:40:32 UTC 2022 , Edited by admin on Sat Dec 17 00:40:32 UTC 2022
FDA ORPHAN DRUG 623217
Created by admin on Sat Dec 17 00:40:32 UTC 2022 , Edited by admin on Sat Dec 17 00:40:32 UTC 2022
Code System Code Type Description
DRUG CENTRAL
5257
Created by admin on Sat Dec 17 00:40:32 UTC 2022 , Edited by admin on Sat Dec 17 00:40:32 UTC 2022
PRIMARY
DRUG BANK
DB12749
Created by admin on Sat Dec 17 00:40:32 UTC 2022 , Edited by admin on Sat Dec 17 00:40:32 UTC 2022
PRIMARY
EPA CompTox
DTXSID50863687
Created by admin on Sat Dec 17 00:40:32 UTC 2022 , Edited by admin on Sat Dec 17 00:40:32 UTC 2022
PRIMARY
WIKIPEDIA
BUTYLPHTHALIDE
Created by admin on Sat Dec 17 00:40:32 UTC 2022 , Edited by admin on Sat Dec 17 00:40:32 UTC 2022
PRIMARY
CAS
6066-49-5
Created by admin on Sat Dec 17 00:40:32 UTC 2022 , Edited by admin on Sat Dec 17 00:40:32 UTC 2022
PRIMARY
ECHA (EC/EINECS)
228-000-8
Created by admin on Sat Dec 17 00:40:32 UTC 2022 , Edited by admin on Sat Dec 17 00:40:32 UTC 2022
PRIMARY
RXCUI
1484499
Created by admin on Sat Dec 17 00:40:32 UTC 2022 , Edited by admin on Sat Dec 17 00:40:32 UTC 2022
PRIMARY RxNorm
FDA UNII
822Q956KGM
Created by admin on Sat Dec 17 00:40:32 UTC 2022 , Edited by admin on Sat Dec 17 00:40:32 UTC 2022
PRIMARY
NCI_THESAURUS
C171720
Created by admin on Sat Dec 17 00:40:32 UTC 2022 , Edited by admin on Sat Dec 17 00:40:32 UTC 2022
PRIMARY
DAILYMED
822Q956KGM
Created by admin on Sat Dec 17 00:40:32 UTC 2022 , Edited by admin on Sat Dec 17 00:40:32 UTC 2022
PRIMARY
EVMPD
SUB32225
Created by admin on Sat Dec 17 00:40:32 UTC 2022 , Edited by admin on Sat Dec 17 00:40:32 UTC 2022
PRIMARY
MESH
C027125
Created by admin on Sat Dec 17 00:40:32 UTC 2022 , Edited by admin on Sat Dec 17 00:40:32 UTC 2022
PRIMARY
PUBCHEM
61361
Created by admin on Sat Dec 17 00:40:32 UTC 2022 , Edited by admin on Sat Dec 17 00:40:32 UTC 2022
PRIMARY
INN
9914
Created by admin on Sat Dec 17 00:40:32 UTC 2022 , Edited by admin on Sat Dec 17 00:40:32 UTC 2022
PRIMARY
Related Record Type Details
CYTOCHROME P450 1A2
METABOLIC ENZYME -> SUBSTRATE
CYTOCHROME P450 3A4
METABOLIC ENZYME -> SUBSTRATE
CELERY SEED
PARENT -> CONSTITUENT ALWAYS PRESENT
Structure of BUTYLPHTHALIDE, (S)-
ENANTIOMER -> RACEMATE
CYTOCHROME P450 2E1
METABOLIC ENZYME -> SUBSTRATE
ANGELICA SINENSIS ROOT OIL
PARENT -> CONSTITUENT ALWAYS PRESENT
Senkyunolide I, coniferyl ferulate, senkyunolide A, 3-butylphthalide, Z-butylidenephthalide and levistolide A were isolated from essential oil of Angelica sinensis.
Structure of BUTYLPHTHALIDE, (R)-
ENANTIOMER -> RACEMATE
Related Record Type Details
Structure of 1(3H)-ISOBENZOFURANONE, 3-(3-OXOBUTYL)-
METABOLITE -> PARENT
MAJOR
PLASMA
Structure of 1(3H)-ISOBENZOFURANONE, 3-BUTYL-3-(SULFOOXY)-
METABOLITE -> PARENT
MINOR
URINE
Structure of 3-(1,3-DIHYDRO-3-OXO-1-ISOBENZOFURANYL)-1-METHYLPROPYL-.BETA.-D-GLUCOPYRANOSIDURONIC ACID
METABOLITE -> PARENT
PLASMA; URINE
Structure of .BETA.-D-GLUCOPYRANOSIDURONIC ACID, 1-BUTYL-1,3-DIHYDRO-3-OXOISOBENZOFURAN-1-YL
METABOLITE -> PARENT
URINE
Structure of 2-ACETAMIDO-3-(1-BUTYL-3-OXO-ISOBENZOFURAN-1-YL)SULFANYL-PROPANOIC ACID
METABOLITE -> PARENT
URINE
Structure of 1(3H)-ISOBENZOFURANONE, 3-(3-HYDROXYBUTYL)-
METABOLITE -> PARENT
MAJOR
PLASMA
Structure of 1(3H)-ISOBENZOFURANONE, 3-(3-(SULFOOXY)BUTYL)-
METABOLITE -> PARENT
PLASMA; URINE
Structure of 1,3-DIHYDRO-3-OXO-1-ISOBENZOFURANBUTANOIC ACID
METABOLITE -> PARENT
MAJOR
PLASMA; URINE
Structure of 1(3H)-ISOBENZOFURANONE, 3-BUTYL-3-HYDROXY-
METABOLITE -> PARENT
MAJOR
PLASMA
Structure of 1,3-DIHYDRO-3-OXO-1-ISOBENZOFURANACETIC ACID
METABOLITE -> PARENT
URINE
Structure of .BETA.-D-GLUCOPYRANURONIC ACID, 1-(1,3-DIHYDRO-3-OXO-1-ISOBENZOFURANBUTANOATE)
METABOLITE -> PARENT
MAJOR
URINE
Structure of 2-(1-HYDROXYPENTYL)BENZOIC ACID
METABOLITE -> PARENT
PLASMA; URINE
Related Record Type Details
Structure of BUTYLPHTHALIDE
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC SINGLE DOSE ADMINISTRATION

ORAL ADMINISTRATION

Tmax PHARMACOKINETIC SINGLE DOSE ADMINISTRATION

ORAL ADMINISTRATION

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