3',5'-DICHLORO-2-HYDROXY-2-METHYLBUT-3-ENANILIDE

Details

Stereochemistry	RACEMIC
Molecular Formula	C11H11Cl2NO2
Molecular Weight	260.117
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of 3',5'-DICHLORO-2-HYDROXY-2-METHYLBUT-3-ENANILIDE

Structure Search

SMILES

CC(O)(C=C)C(=O)NC1=CC(Cl)=CC(Cl)=C1

InChI

InChIKey=FBYYIBNYONAZCU-UHFFFAOYSA-N

InChI=1S/C11H11Cl2NO2/c1-3-11(2,16)10(15)14-9-5-7(12)4-8(13)6-9/h3-6,16H,1H2,2H3,(H,14,15)

HIDE SMILES / InChI

Molecular Formula	C11H11Cl2NO2
Molecular Weight	260.117
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/8209380 | https://www.ncbi.nlm.nih.gov/pubmed/16750840

3',5'-DICHLORO-2-HYDROXY-2-METHYLBUT-3-ENANILIDE is a metabolite of vinclozolin, a dicarboximide fungicide widely used in the United States and Europe for control of diseases caused by B. cineera, S. sclerotiorum, and Monilinia species in fruits, grapes, ornamental plants, turfgrass and vegetables. This fungicide possesses antiandrogenic activity. 3',5'-DICHLORO-2-HYDROXY-2-METHYLBUT-3-ENANILIDE has an antiandrogenic activity too. Moreover, it is an antagonist of progesterone, glucocorticoid, mineralocorticoid receptors and agonist for both estrogen receptors. This ability to act via more than one mechanism must be taken into consideration in the risk assessment process.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Androgen Receptor 167 Target ID: CHEMBL1871 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8209380 \| https://www.ncbi.nlm.nih.gov/pubmed/16750840	Antagonist 2778	9.7 µM [Kd]
Estrogen receptor alpha 127 Target ID: CHEMBL206 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16750840	Agonist 2678	1.1 µM [EC50]
Estrogen receptor beta 110 Target ID: CHEMBL242 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16750840	Agonist 2678	18.6 µM [EC50]
Mineralocorticoid receptor 53 Target ID: CHEMBL1994 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16750840	Antagonist 2778	1.4 µM [IC50]
Glucocorticoid receptor 172 Target ID: CHEMBL2034 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16750840	Antagonist 2778	41.0 µM [IC50]
Progesterone receptor 61 Target ID: CHEMBL208 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16750840	Antagonist 2778	3.3 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2578

PubMed

Title	Date	PubMed
Peripubertal exposure to the antiandrogenic fungicide, vinclozolin, delays puberty, inhibits the development of androgen-dependent tissues, and alters androgen receptor function in the male rat.	1999 Jan-Mar	10188192
A novel cell line, MDA-kb2, that stably expresses an androgen- and glucocorticoid-responsive reporter for the detection of hormone receptor agonists and antagonists.	2002 Mar	11861974
Mode of action: inhibition of androgen receptor function--vinclozolin-induced malformations in reproductive development.	2005 Oct-Nov	16417039
Steroid receptor profiling of vinclozolin and its primary metabolites.	2006 Oct 1	16750840
Pharmacokinetics and dosimetry of the antiandrogen vinclozolin after oral administration in the rat.	2008 Nov	18703562

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

3',5'-DICHLORO-2-HYDROXY-2-METHYLBUT-3-ENANILIDE was able to inhibit rat epididymal 5alpha-reductase activity by 5% at 100uM and 28% at the highest dose examined - 1.0 mM. Since serum level of this drug following in vivo administration is far less than 1 mM, it is unlikely that it acts by inhibiting the enzymatic activity of 5alpha-reductase in the male reproductive target organs.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 10:36:40 GMT 2023` Edited by `admin` on `Sat Dec 16 10:36:40 GMT 2023`
Record UNII	U6Y06GAX2T
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

3',5'-DICHLORO-2-HYDROXY-2-METHYLBUT-3-ENANILIDE

Systematic Name

English

3-BUTENAMIDE, N-(3,5-DICHLOROPHENYL)-2-HYDROXY-2-METHYL-

Systematic Name

English

J592.614I

Code

English

N-(3,5-DICHLOROPHENYL)-2-HYDROXY-2-METHYL-3-BUTENAMIDE

Systematic Name

English

Code System Code Type Description

FDA UNII

U6Y06GAX2T

Created by admin on Sat Dec 16 10:36:40 GMT 2023 , Edited by admin on Sat Dec 16 10:36:40 GMT 2023

PRIMARY

EPA CompTox

DTXSID9039789

Created by admin on Sat Dec 16 10:36:40 GMT 2023 , Edited by admin on Sat Dec 16 10:36:40 GMT 2023

PRIMARY

CAS

83792-61-4

Created by admin on Sat Dec 16 10:36:40 GMT 2023 , Edited by admin on Sat Dec 16 10:36:40 GMT 2023

PRIMARY

PUBCHEM

115209

Created by admin on Sat Dec 16 10:36:40 GMT 2023 , Edited by admin on Sat Dec 16 10:36:40 GMT 2023

PRIMARY

Related Record Type Details


					JJ258EZN1I

VINCLOZOLIN

PARENT -> DEGRADENT

Comments:

Vinclozolin (20.2 mg) was suspended in tap water (500 mL, pH 8.0), stirred for three days, and then, allowed to stand for further two weeks (20-21 centigrade degree). The suspension was filtered, extracted with diethyl ether (150 mL x 3), dried over sodium sulfate (4 hrs), and analyzed by TLC after evaporation.

Interaction Type:

CHROMATOGRAPHIC PURITY (TLC)

Qualification:

Scientific Literature

Related Record Type Details


					JJ258EZN1I

VINCLOZOLIN

PARENT -> METABOLITE INACTIVE

Comments:

By rat liver microsomes

Interaction Type:

IN-VITRO

Qualification:

Scientific Literature


					JJ258EZN1I

VINCLOZOLIN

PARENT -> METABOLITE INACTIVE

Comments:

Inactive against Botrytis cinerea

Interaction Type:

IN-VITRO

Qualification:

Scientific Literature

Details

SMILES

InChI

DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/8209380 | https://www.ncbi.nlm.nih.gov/pubmed/16750840

CNS Activity

Originator

Approval Year

Targets

Conditions

PubMed

Sample Use Guides

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/8209380 | https://www.ncbi.nlm.nih.gov/pubmed/16750840