ISOBUTYLPARABEN

Details

Stereochemistry	ACHIRAL
Molecular Formula	C11H14O3
Molecular Weight	194.2271
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(C)COC(=O)C1=CC=C(O)C=C1

InChI

InChIKey=XPJVKCRENWUEJH-UHFFFAOYSA-N

InChI=1S/C11H14O3/c1-8(2)7-14-11(13)9-3-5-10(12)6-4-9/h3-6,8,12H,7H2,1-2H3

HIDE SMILES / InChI

Molecular Formula	C11H14O3
Molecular Weight	194.2271
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Approval Year

Conditions

Condition	Modality	Targets	Highest Phase	Product
Depression 240 Sources: https://www.drugs.com/imprints/op-719-17293.html	Inactive ingredient		Approved 8583	surmontil Approved Use Surmontil is indicated for the relief of symptoms of depression. Endogenous depression is more likely to be alleviated than other depressive states. In studies with neurotic outpatients, the drug appeared to be equivalent to amitriptyline in the less-depressed patients but somewhat less effective than amitriptyline in the more severely depressed patients. In hospitalized depressed patients, trimipramine and imipramine were equally effective in relieving depression. Launch Date 1979

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2252	inhibitor 2438	inhibitor 2507	inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 2153 rCYP2C 4 CYP2C19 2057 rCYP2E1 4 rCYP3A 6 rCYP1A1 4 rCYP1A2 5 CYP19A1 429 rCYP2B 4	Human Liver S9 2 UGT 219 SULT 12 CES1 45 CES2 33	CYP1A1 151

Drug as perpetrator

Target	Modality	Activity
CYP19A1 430	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/743139#sid=144207699	inconclusive [IC50 5.0406 uM]
CYP2D6 2546	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1671196#sid=144207699	inconclusive [IC50 70.922 uM]
CYP19A1 430	activator 342 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/743083#sid=144207699	no [EC50 4.8508 uM]
CYP3A4 2633	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1671201#sid=144207699	no
rCYP2E1 6	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/27432241/	yes [IC50 10.1 uM]
CYP1A2 2333	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1671199#sid=144207699	yes [IC50 2.8235 uM]
CYP2C9 2497	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1671198#sid=144207699	yes [IC50 25.1641 uM]
CYP2C19 2141	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1671197#sid=144207699	yes [IC50 3.168 uM]
rCYP2B 9	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/27432241/	yes [IC50 36.4 uM]
rCYP2C 4	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/27432241/	yes [IC50 36.4 uM]
rCYP1A2 6	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/27432241/	yes [IC50 7.72 uM]
rCYP3A 10	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/27432241/	yes [IC50 80.6 uM]
rCYP1A1 5	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/27432241/	yes [IC50 94.6 uM]
CYP1A1 272	inducer 1966 Sources: https://cancerres.aacrjournals.org/content/77/13_Supplement/2427.short \| https://pubs.rsc.org/en/content/articlelanding/2015/ew/c5ew00047e	yes

Drug as victim

Target	Modality	Activity
Human Liver S9 2	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/33741472/	yes [Km 32.6 uM]
CES1 45	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/33188879/	yes
CES2 33	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/33188879/	yes
SULT 12	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/33188879/	yes
UGT 219	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/33188879/	yes

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1671200#sid=144207699

PubMed

Title	Date	PubMed
Comparative study on transcriptional activity of 17 parabens mediated by estrogen receptor α and β and androgen receptor.	2013-07	23567241
Additional effects of bisphenol A and paraben on the induction of calbindin-D(9K) and progesterone receptor via an estrogen receptor pathway in rat pituitary GH3 cells.	2012-10	23211298
Potential estrogenic effect(s) of parabens at the prepubertal stage of a postnatal female rat model.	2010-06	20132880
Urinary concentrations of four parabens in the U.S. population: NHANES 2005-2006.	2010-05	20056562
In vitro study of Organization for Economic Co-operation and Development (OECD) endocrine disruptor screening and testing methods- establishment of a recombinant rat androgen receptor (rrAR) binding assay.	2010-04	20371976
Mixture effects of endocrine disrupting compounds in vitro.	2010-04	20132345
Validation of an in vitro screening test for predicting the tumor promoting potential of chemicals based on gene expression.	2010-04	20025956
Maternal exposure to isobutyl-paraben impairs social recognition in adult female rats.	2010	21030791
[Determination of six p-hydroxybenzoates in fruits and jams using solid-phase extraction-high performance liquid chromatography].	2009-11	20352935
An evaluation of estrogenic activity of parabens using uterine calbindin-d9k gene in an immature rat model.	2009-11	19654335
Maternal isobutyl-paraben exposure alters anxiety and passive avoidance test performance in adult male rats.	2009-10	19560493
Maternal isobutyl-paraben exposure decreases the plasma corticosterone level in dams and sensitivity to estrogen in female offspring rats.	2009-08	19721353
Removal of estrogenic activity of iso-butylparaben and n-butylparaben by laccase in the presence of 1-hydroxybenzotriazole.	2009-07	19109757
Parabens in male infertility-is there a mitochondrial connection?	2009-01	19007877
Evaluation of estrogenic activity of parabens and their chlorinated derivatives by using the yeast two-hybrid assay and the enzyme-linked immunosorbent assay.	2009-01	18717622
Underarm antiperspirants/deodorants and breast cancer.	2009	20030880
Simultaneous determination of 21 preservatives in cosmetics by ultra performance liquid chromatography.	2008-10	18822043
Construction of simplified models to simulate estrogenic disruptions by esters of 4-hydroxy benzoic acid (parabens).	2008-09	18602735
Final amended report on the safety assessment of Methylparaben, Ethylparaben, Propylparaben, Isopropylparaben, Butylparaben, Isobutylparaben, and Benzylparaben as used in cosmetic products.	2008	19101832
[Simultaneous determination of 7 kinds of preservatives and saccharin in foods with HPLC, and identification with LC/MS/MS].	2007-12	18203501
[Simultaneous determination of nine kinds of preservatives in foods by HPLC].	2007-06	17657998
Preliminary ecological risk assessment of butylparaben and benzylparaben -2. Fate and partitioning in aquatic environments.	2007	18382418
Preliminary ecological risk assessment of butylparaben and benzylparaben -1. Removal efficiency in wastewater treatment, acute/chronic toxicity for aquatic organisms, and effects on medaka gene expression.	2007	18382416
Parabens as urinary biomarkers of exposure in humans.	2006-12	17185273
Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods.	2006-11	16497524
A review of the endocrine activity of parabens and implications for potential risks to human health.	2005-06	16097138
Uterotrophic effects of benzophenone derivatives and a p-hydroxybenzoate used in ultraviolet screens.	2005-05	15721882
Oestrogenic activity of benzylparaben.	2003-01-09	12518336
Oestrogenic activity of isobutylparaben in vitro and in vivo.	2002-09-05	12210538
ER-dependent estrogenic activity of parabens assessed by proliferation of human breast cancer MCF-7 cells and expression of ERalpha and PR.	2001-12	11696396
[Competitive binding of some alkyl p-hydroxybenzoates to human estrogen receptor alpha and beta].	2000-12	11193391

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:50:37 GMT 2025` Edited by `admin` on `Mon Mar 31 17:50:37 GMT 2025`
Record UNII	0QQJ25X58G
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ISOBUTYLPARABEN

Official Name

English

BENZOIC ACID, 4-HYDROXY-, 2-METHYLPROPYL ESTER

Preferred Name

English

ISOBUTYL 4-HYDROXYBENZOATE

Systematic Name

English

ISOBUTYL PARABEN

Common Name

English

ISOBUTYL P-HYDROXYBENZOATE

Common Name

English

ISOBUTYL PARAHYDROXYBENZOATE

Systematic Name

English

BENZOIC ACID, P-HYDROXY-, ISOBUTYL ESTER

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C92608