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Details

Stereochemistry RACEMIC
Molecular Formula C12H14O2
Molecular Weight 190.2388
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BUTYLPHTHALIDE

SMILES

CCCCC1c2ccccc2C(=O)O1

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 190.2388
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
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
[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
[Effects of dl-3-n-butylphthalide on expression of VEGF and bFGF in rat brain with permanent focal cerebral ischemia].
2008 Jan
l-3-n-Butylphthalide ameliorates beta-amyloid-induced neuronal toxicity in cultured neuronal cells.
2008 Mar 28
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
[Effect of butylphthalide on the expression of S100 and glial fibrillary acidic protein in a rat model of Alzheimer disease].
2009 Jun
[Effects of dl-3n-butylphthalide on the expression of VEGF and bFGF in transient middle cerebral artery occlusion rats].
2009 May
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
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
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
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
[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
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 Sat Jun 26 11:54:59 UTC 2021
Edited
by admin
on Sat Jun 26 11:54:59 UTC 2021
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
BUTYLPHTHALIDE [WHO-DD]
Common Name English
1(3H)-ISOBENZOFURANONE, 3-BUTYL-
Systematic Name English
3-BUTYL-1(3H)-ISOBENZOFURANONE
Systematic Name English
3-N-BUTYLPHTHALIDE
FHFI  
Common Name English
Classification Tree Code System Code
JECFA EVALUATION 3-N-BUTYLPHTHALIDE
Created by admin on Sat Jun 26 11:54:59 UTC 2021 , Edited by admin on Sat Jun 26 11:54:59 UTC 2021
DSLD 2881 (Number of products:2)
Created by admin on Sat Jun 26 11:54:59 UTC 2021 , Edited by admin on Sat Jun 26 11:54:59 UTC 2021
FDA ORPHAN DRUG 623217
Created by admin on Sat Jun 26 11:54:59 UTC 2021 , Edited by admin on Sat Jun 26 11:54:59 UTC 2021
Code System Code Type Description
DRUG CENTRAL
5257
Created by admin on Sat Jun 26 11:54:59 UTC 2021 , Edited by admin on Sat Jun 26 11:54:59 UTC 2021
PRIMARY
DRUG BANK
DB12749
Created by admin on Sat Jun 26 11:54:59 UTC 2021 , Edited by admin on Sat Jun 26 11:54:59 UTC 2021
PRIMARY
WIKIPEDIA
BUTYLPHTHALIDE
Created by admin on Sat Jun 26 11:54:59 UTC 2021 , Edited by admin on Sat Jun 26 11:54:59 UTC 2021
PRIMARY
CAS
6066-49-5
Created by admin on Sat Jun 26 11:54:59 UTC 2021 , Edited by admin on Sat Jun 26 11:54:59 UTC 2021
PRIMARY
ECHA (EC/EINECS)
228-000-8
Created by admin on Sat Jun 26 11:54:59 UTC 2021 , Edited by admin on Sat Jun 26 11:54:59 UTC 2021
PRIMARY
RXCUI
1484499
Created by admin on Sat Jun 26 11:54:59 UTC 2021 , Edited by admin on Sat Jun 26 11:54:59 UTC 2021
PRIMARY RxNorm
FDA UNII
822Q956KGM
Created by admin on Sat Jun 26 11:54:59 UTC 2021 , Edited by admin on Sat Jun 26 11:54:59 UTC 2021
PRIMARY
NCI_THESAURUS
C171720
Created by admin on Sat Jun 26 11:54:59 UTC 2021 , Edited by admin on Sat Jun 26 11:54:59 UTC 2021
PRIMARY
EVMPD
SUB32225
Created by admin on Sat Jun 26 11:54:59 UTC 2021 , Edited by admin on Sat Jun 26 11:54:59 UTC 2021
PRIMARY
MESH
C027125
Created by admin on Sat Jun 26 11:54:59 UTC 2021 , Edited by admin on Sat Jun 26 11:54:59 UTC 2021
PRIMARY
PUBCHEM
61361
Created by admin on Sat Jun 26 11:54:59 UTC 2021 , Edited by admin on Sat Jun 26 11:54:59 UTC 2021
PRIMARY
INN
9914
Created by admin on Sat Jun 26 11:54:59 UTC 2021 , Edited by admin on Sat Jun 26 11:54:59 UTC 2021
PRIMARY
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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