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SML3187

Sigma-Aldrich

WIN 18446

≥98% (HPLC)

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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:
Molecular Weight:
366.11
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

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This Item
14513SML0826SML1043
WIN 18446 ≥98% (HPLC)

SML3187

WIN 18446

Sigma-Aldrich

SML0826

FH1

KC7F2 ≥98% (HPLC)

SML1043

KC7F2

assay

≥98% (HPLC)

assay

≥95% (HPLC)

assay

≥98% (HPLC)

assay

≥98% (HPLC)

Quality Level

100

Quality Level

-

Quality Level

-

Quality Level

-

storage temp.

−20°C

storage temp.

−20°C

storage temp.

2-8°C

storage temp.

−20°C

solubility

DMSO: 2 mg/mL, clear

solubility

H2O: 10 mg/mL, clear, faintly yellow

solubility

DMSO: 10 mg/mL, clear (warmed)

solubility

DMSO: 20 mg/mL, clear

color

white to beige

color

-

color

white to beige

color

white to beige

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.

pictograms

Exclamation markHealth hazard

signalword

Warning

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


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