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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
149124
Targets

Targets

Primary TargetPharmacologyConditionPotency
Antagonist
2849
 9.7 µM [Kd]
Agonist
2752
 1.1 µM [EC50]
Agonist
2752
 18.6 µM [EC50]
Antagonist
2849
 1.4 µM [IC50]
Antagonist
2849
 41.0 µM [IC50]
Antagonist
2849
 3.3 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Pharmacokinetics and dosimetry of the antiandrogen vinclozolin after oral administration in the rat.
2008-11
Steroid receptor profiling of vinclozolin and its primary metabolites.
2006-10-01
Mode of action: inhibition of androgen receptor function--vinclozolin-induced malformations in reproductive development.
2006-01-19
Liquid chromatography determination of the anti-androgen vinclozolin and its metabolites in rat serum.
2004-09-25
Response-surface modeling of the effect of 5alpha-dihydrotestosterone and androgen receptor levels on the response to the androgen antagonist vinclozolin.
2002-10
A novel cell line, MDA-kb2, that stably expresses an androgen- and glucocorticoid-responsive reporter for the detection of hormone receptor agonists and antagonists.
2002-03
Environmental xenoestrogens, antiandrogens and disorders of male sexual differentiation.
2001-06-10
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.
1999-04-03

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 Mon Mar 31 23:21:09 GMT 2025
Edited
by admin
on Mon Mar 31 23:21:09 GMT 2025
Record UNII
U6Y06GAX2T
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
J592.614I
Preferred Name English
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
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 Mon Mar 31 23:21:09 GMT 2025 , Edited by admin on Mon Mar 31 23:21:09 GMT 2025
PRIMARY
EPA CompTox
DTXSID9039789
Created by admin on Mon Mar 31 23:21:09 GMT 2025 , Edited by admin on Mon Mar 31 23:21:09 GMT 2025
PRIMARY
CAS
83792-61-4
Created by admin on Mon Mar 31 23:21:09 GMT 2025 , Edited by admin on Mon Mar 31 23:21:09 GMT 2025
PRIMARY
PUBCHEM
115209
Created by admin on Mon Mar 31 23:21:09 GMT 2025 , Edited by admin on Mon Mar 31 23:21:09 GMT 2025
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
NCATS
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