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
• Empirical Formula (Hill Notation): C₁₂H₂₀Cl₄N₂O₂
• CAS Number: 1477-57-2
• Molecular Weight: 366.11
• MDL number: MFCD00000841
• UNSPSC Code: 12352200
• NACRES: NA.77

Properties

• Quality Level: 100
• 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

Description

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.

Safety Information

• pictograms: GHS08,GHS07
• signalword: Warning
• hcodes: H312 + H332,H351
• pcodes: P202 - P261 - P280 - P302 + P352 + P312 - P304 + P340 + P312 - P308 + P313
• Hazard Classifications: Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Carc. 2
• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable