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
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
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
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: GO:0006915 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28053983 |
|||
Target ID: WP408 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28053983 |
|||
Target ID: GO:0022008 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28053983 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | 3-n-Butylphthalide (NBP) Approved Use3-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 Date2001 |
|||
Primary | Unknown Approved UseUnknown |
|||
Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
---|---|---|
Synthesis of phthalides and 3,4-dihydroisocoumarins using the palladium-catalyzed intramolecular benzannulation strategy. | 2002 Apr 19 |
|
New drugs derived from medicinal plants. | 2002 Mar-Apr |
|
Simultaneous analysis of seventeen chemical ingredients of Ligusticum chuanxiong by on-line high performance liquid chromatography-diode array detector-mass spectrometry. | 2003 May |
|
l-3-n-Butylphthalide improves cognitive impairment induced by chronic cerebral hypoperfusion in rats. | 2007 Jun |
|
Novozyme 435-catalyzed efficient acylation of 3-n-butylphthalide in organic medium. | 2008 |
|
GC-MS fingerprints for discrimination of Ligusticum chuanxiong from Angelica. | 2008 Oct |
|
[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 |
|
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 |
|
[Effect of butylphthalide on the expression of GFAP and VEGF in the hippocampus of rats with Alzheimer's disease]. | 2010 Feb |
|
Dl-3-n-butylphthalide, a natural antioxidant, protects dopamine neurons in rotenone models for Parkinson's disease. | 2012 Aug |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/28746179
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/20800583
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
Edited
Fri Dec 15 18:34:30 GMT 2023
by
admin
on
Fri Dec 15 18:34:30 GMT 2023
|
Record UNII |
822Q956KGM
|
Record Status |
Validated (UNII)
|
Record Version |
|
-
Download
Name | Type | Language | ||
---|---|---|---|---|
|
Official Name | English | ||
|
Preferred Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Code | English | ||
|
Systematic Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
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 | ||
---|---|---|---|---|---|
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | ||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 |
Related Record | Type | Details | ||
---|---|---|---|---|
|
METABOLIC ENZYME -> SUBSTRATE | |||
|
METABOLIC ENZYME -> SUBSTRATE | |||
|
PARENT -> CONSTITUENT ALWAYS PRESENT | |||
|
ENANTIOMER -> RACEMATE | |||
|
METABOLIC ENZYME -> SUBSTRATE |
|
||
|
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.
|
||
|
ENANTIOMER -> RACEMATE |
Related Record | Type | Details | ||
---|---|---|---|---|
|
METABOLITE -> PARENT |
MAJOR
PLASMA
|
||
|
METABOLITE -> PARENT |
MINOR
URINE
|
||
|
METABOLITE -> PARENT |
PLASMA; URINE
|
||
|
METABOLITE -> PARENT |
URINE
|
||
|
METABOLITE -> PARENT |
URINE
|
||
|
METABOLITE -> PARENT |
MAJOR
PLASMA
|
||
|
METABOLITE -> PARENT |
PLASMA; URINE
|
||
|
METABOLITE -> PARENT |
MAJOR
PLASMA; URINE
|
||
|
METABOLITE -> PARENT |
MAJOR
PLASMA
|
||
|
METABOLITE -> PARENT |
URINE
|
||
|
METABOLITE -> PARENT |
MAJOR
URINE
|
||
|
METABOLITE -> PARENT |
PLASMA; URINE
|
Related Record | Type | Details | ||
---|---|---|---|---|
|
ACTIVE MOIETY |
|
Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
---|---|---|---|---|---|---|
Biological Half-life | PHARMACOKINETIC |
|
SINGLE DOSE ADMINISTRATION |
|
||
Tmax | PHARMACOKINETIC |
|
SINGLE DOSE ADMINISTRATION |
|
||