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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

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

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

Clark, T.
1
Sources: DOI: 10.1016/0045-6535(83)90141-8

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Antagonist
2778
 9.7 µM [Kd]
Agonist
2678
 1.1 µM [EC50]
Agonist
2678
 18.6 µM [EC50]
Antagonist
2778
 1.4 µM [IC50]
Antagonist
2778
 41.0 µM [IC50]
Antagonist
2778
 3.3 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
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
Environmental xenoestrogens, antiandrogens and disorders of male sexual differentiation.
2001 Jun 10
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
Response-surface modeling of the effect of 5alpha-dihydrotestosterone and androgen receptor levels on the response to the androgen antagonist vinclozolin.
2002 Oct
Liquid chromatography determination of the anti-androgen vinclozolin and its metabolites in rat serum.
2004 Sep 25
Mode of action: inhibition of androgen receptor function--vinclozolin-induced malformations in reproductive development.
2005 Oct-Nov
Steroid receptor profiling of vinclozolin and its primary metabolites.
2006 Oct 1
Pharmacokinetics and dosimetry of the antiandrogen vinclozolin after oral administration in the rat.
2008 Nov

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
  • Download
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
Structure of VINCLOZOLIN
PARENT -> DEGRADENT
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.
CHROMATOGRAPHIC PURITY (TLC)
Scientific Literature
Related Record Type Details
Structure of VINCLOZOLIN
PARENT -> METABOLITE INACTIVE
By rat liver microsomes
IN-VITRO
Scientific Literature
Structure of VINCLOZOLIN
PARENT -> METABOLITE INACTIVE
Inactive against Botrytis cinerea
IN-VITRO
Scientific Literature
NIH
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