| Identification | Back Directory | [Name]
N,N'-OCTAMETHYLENEBIS(DICHLOROACETAMIDE) | [CAS]
1477-57-2 | [Synonyms]
r-010-tk
win18441
win18446
win18,446
NSC 59354
bisdiamine
FERTILYSIN
bis-diamine
Fertilysine
N,N'-OCTAMETHYLENEBIS(DICHLOROACETAMIDE)
N,N''-OCTMETHYLENEBIS (DICHLOROACETAMIDE)
n,n-bis(dichloroacetyl)-1,8-octanediamine
n,n’-bis(dichloroacetyl)-1,8-diaminooctane
n,n’-bis(dichloroacetyl)-1,8-octanediamine
n,n’-octamethylenebis(2,2-dichloro-acetamid
n,n’-octamethylenebis(2,2-dichloroactamide)
n,n’,1,8-octanediylbis(2,2-dichloro-acetamid
N,N'-Octamethylenebis(dichloroacetamide),97%
AcetaMide,N,N'-1,8-octanediylbis[2,2-dichloro-
N,N'-OCTA-METHYLENE-BIS[2,2-DICHLOROACETAMIDE]
N,N'-(1,8-Octanediyl)bis(2,2-dichloroacetamide)
N,N'-(Octane-1,8-diyl)bis(2,2-dichloroacetaMide)
N,N'-BIS(DICHLOROACETYL)-1,8-OCTAMETHYLENEDIAMINE | [EINECS(EC#)]
216-033-0 | [Molecular Formula]
C12H20Cl4N2O2 | [MDL Number]
MFCD00000841 | [MOL File]
1477-57-2.mol | [Molecular Weight]
366.11 |
| Chemical Properties | Back Directory | [Appearance]
white crystalline powder | [Melting point ]
118-120 °C
| [Boiling point ]
530℃ | [density ]
0.726
| [refractive index ]
1.6200 (estimate) | [Fp ]
275℃ | [storage temp. ]
2-8°C | [solubility ]
Acetone (Very Slightly), DMSO (Slightly), Methanol (Sparingly, Heated, Sonicated | [form ]
Solid | [pka]
12.28±0.46(Predicted) | [color ]
White to Off-White | [CAS DataBase Reference]
1477-57-2 |
| Hazard Information | Back Directory | [Chemical Properties]
white crystalline powder | [Uses]
Win 18446 was shown to inhibit the biosynthesis of retinoic acid from retinol in neonatal and adult murine testis and in the embryonic murine gonad. | [Definition]
ChEBI: A carboxamide that is 1,8-diaminooctane in which a hydrogen attached to each of the amino groups has been replaced by a dichloroacetyl group. Inhibitor of aldehyde dehydrogenase 1a2 (ALDH1a2). Inhibits the biosynthesis of retinoic acid from retinol in neon
tal and adult murine testis. It down-regulates sex related genes in zebrafish. | [Biological Activity]
win 18446 is a bis-(dichloroacetyl)-diamine which inhibits aldehyde dehydrogenase 1a2 (aldh1a2), with ic50 value of 300 nm [1].aldh1a2, expressed almost exclusively in the testes, localizes to developing germ cells within the seminiferous tubules and strongly binds retinol, but does not recognize acetaldehyde as a substrate, suggesting that aldh1a2 functions in testicular retinoic acid biosynthesis [1].in whole testes or germ cells isolated from mice at 2 days postpartum, win 18,446 alone (1 μm) or in combination with retinol significantly reduced the expression of stra8, a marker for retinoic acid activity [2].in male rabbits, oral administration of win 18446 at 200 mg/kg for 16 weeks substantially reduced intratesticular concentrations of retinoic acid, significantly impaired spermatogenesis, and resulted in infertility. reduced concentrations of intratesticular retinoic acid became obvious after only 4 weeks of treatment and preceded the decrease in sperm counts and the loss of mature germ cells in tissue samples. sperm counts and fertility recovered after treatment was discontinued [1].[1]. amory j k, muller c h, shimshoni j a, et al. suppression of spermatogenesis by bisdichloroacetyldiamines is mediated by inhibition of testicular retinoic acid biosynthesis. journal of andrology, 2011, 32(1): 111-119.[2]. hogarth c a, evanoff r, snyder e, et al. suppression of stra8 expression in the mouse gonad by win 18,446. biology of reproduction, 2011, 84(5): 957-965. | [Safety Profile]
Poison by intraperitoneal route.Human systemic effects by ingestion: nausea andvomiting. Human reproductive effects by ingestion:changes in spermatogenesis. An experimental teratogen.Other experimental reproductive effects. Human mutationdata reporte | [storage]
Store at -20°C |
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