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Merck
CN

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:
1477-57-2
Molecular Weight:
366.11
UNSPSC Code:
12352200
NACRES:
NA.77
MDL number:
MFCD00000841

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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)

SMILES string

O=C(NCCCCCCCCNC(C(Cl)Cl)=O)C(Cl)Cl

InChI key

FAOMZVDZARKPFJ-UHFFFAOYSA-N

assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

−20°C

Quality Level

100

Related Categories

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

pictograms

Health hazardExclamation mark
GHS08,GHS07

signalword

Warning

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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Certificates of Analysis (COA)

Lot/Batch Number
0000430801
0000430801
0000421049
0000421049
0000138672

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