SML3187
WIN 18446
≥98% (HPLC)
Synonym(s):
Bis-diamine, Bisdiamine, Fertilysin, N,N′-1,8-Octanediylbis[2,2-dichloro-acetamide; N,N′-Bis(dischloroacetyl)-1,8-octamethylenediamine, NSC 59354, NSC59354, WIN 18,446
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About This Item
Empirical Formula (Hill Notation):
C12H20Cl4N2O2
CAS Number:
Molecular Weight:
366.11
UNSPSC Code:
12352200
NACRES:
NA.77
MDL number:
Quality Level
assay
≥98% (HPLC)
form
powder
color
white to beige
solubility
DMSO: 2 mg/mL, clear
storage temp.
−20°C
SMILES string
O=C(NCCCCCCCCNC(C(Cl)Cl)=O)C(Cl)Cl
InChI
1S/C12H20Cl4N2O2/c13-9(14)11(19)17-7-5-3-1-2-4-6-8-18-12(20)10(15)16/h9-10H,1-8H2,(H,17,19)(H,18,20)
InChI key
FAOMZVDZARKPFJ-UHFFFAOYSA-N
Biochem/physiol Actions
WIN 18,446 is an orally available bisdichloroacetyldiamine that potently inhibits aldehyde dehydrogenase family 1 (ALDH1) members-catalyzed all-trans retinoic acid (atRA) production (IC50 = 88 nM/human testicular S10 fraction, 102 nM/ALDH1A1, 187 nM/ALDH1A3) via retinal oxidation, efficiently inhibits ALDH1A2 enzymatic activity in a time-dependent manner (kinact = 22.0/h, Ki = 1026 nM). The inhibitory activity of WIN 18,446 against atRA production forms the basis of its in vivo efficacy as a male contraceptive in inhibiting spermatogenesis among mulitple mammalian species and zebrafish.
orally available ALDH1A1/ALDH1A2/ALDH1A3 inhibitor with in vivo male contraceptive efficacy by inhibiting spermatogenesis
signalword
Warning
hcodes
Hazard Classifications
Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Carc. 2
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
Regulatory Information
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Global Trade Item Number
| SKU | GTIN |
|---|---|
| SML3187-50MG | 04065267212968 |