Win 18446

Modify Date: 2024-01-06 14:00:14

Win 18446 structure	Common Name	Win 18446
	CAS Number	1477-57-2	Molecular Weight	366.111
	Density	1.3±0.1 g/cm3	Boiling Point	530.2±50.0 °C at 760 mmHg
	Molecular Formula	C₁₂H₂₀Cl₄N₂O₂	Melting Point	118-120ºC
	MSDS	N/A	Flash Point	274.5±30.1 °C

Use of Win 18446

Win 18446 is an orally active testes-specific enzyme ALDH1a2 inhibitor, with an IC50 of 0.3 μM. Win 18446 reversibly inhibits spermatogenesis in many species and inhibits Retinoic acid (HY-14649) biosynthesis from Retinol (HY-B1342) within the testes[1][2].

Name	N,N'-(Octane-1,8-diyl)bis(2,2-dichloroacetamide)
Synonym	More Synonyms

Description	Win 18446 is an orally active testes-specific enzyme ALDH1a2 inhibitor, with an IC50 of 0.3 μM. Win 18446 reversibly inhibits spermatogenesis in many species and inhibits Retinoic acid (HY-14649) biosynthesis from Retinol (HY-B1342) within the testes[1][2].
Related Catalog	Signaling Pathways >> Metabolic Enzyme/Protease >> Aldehyde Dehydrogenase (ALDH) Research Areas >> Endocrinology
In Vitro	WIN 18446 (1 μM, 24 h) is able to suppress Stra8 expression in whole-testes cultures that contained both germ and somatic cells[2]. RT-PCR[2] Cell Line: Testes were collected from 2-dpp mice. Concentration: 1 μM. Incubation Time: 24 h. Result: Results in a VAD-like phenotype in the testis. Alone or in combination with ROL significantly reduced Stra8 expression.
In Vivo	Win 18446 (200 mg/kg, Orally for 4, 8, and 16 weeks) significantly reduces intratesticular concentrations of retinoic acid, severely impaired spermatogenesis, and caused infertility[1]. Animal Model: Six-month-old male New Zealand white rabbits[1]. Dosage: 200 mg/kg. Administration: Orally for 4, 8, and 16 weeks. Result: Resulted in marked suppression of testicular weight over time. Dramatically suppressed spermatogenesis. Significantly reduces intratesticular concentrations of retinoic acid and Stra8 expression and very severely suppresses spermatogenesis and fertility.
References	[1]. John K Amory, et al. Suppression of spermatogenesis by bisdichloroacetyldiamines is mediated by inhibition of testicular retinoic acid biosynthesis. J Androl. Jan-Feb 2011;32(1):111-9. [2]. Cathryn A Hogarth, et al. Suppression of Stra8 expression in the mouse gonad by WIN 18,446. Biol Reprod. 2011 May;84(5):957-65.

Density	1.3±0.1 g/cm3
Boiling Point	530.2±50.0 °C at 760 mmHg
Melting Point	118-120ºC
Molecular Formula	C₁₂H₂₀Cl₄N₂O₂
Molecular Weight	366.111
Flash Point	274.5±30.1 °C
Exact Mass	364.027893
PSA	58.20000
LogP	1.96
Vapour Pressure	0.0±1.4 mmHg at 25°C
Index of Refraction	1.503

Win 18446 MSDS(Chinese)

CHEMICAL IDENTIFICATION

RTECS NUMBER :: AC6800000

CHEMICAL NAME :: Acetamide, N,N'-octamethylenebis(2,2-dichloro-

CAS REGISTRY NUMBER :: 1477-57-2

LAST UPDATED :: 199612

DATA ITEMS CITED :: 23

MOLECULAR FORMULA :: C12-H20-Cl4-N2-O2

MOLECULAR WEIGHT :: 366.14

WISWESSER LINE NOTATION :: GYG&VM8MVYG&G

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - man

DOSE/DURATION :: 943 mg/kg/50D

TOXIC EFFECTS :: Gastrointestinal - nausea or vomiting

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >16 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 150 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 150 mg/kg

SEX/DURATION :: male 42 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Paternal Effects - spermatogenesis (incl. genetic material, sperm morphology, motility, and count)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 2 gm/kg

SEX/DURATION :: male 70 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Paternal Effects - spermatogenesis (incl. genetic material, sperm morphology, motility, and count)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 943 mg/kg

SEX/DURATION :: male 50 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Paternal Effects - spermatogenesis (incl. genetic material, sperm morphology, motility, and count)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 2250 mg/kg

SEX/DURATION :: male 3 week(s) pre-mating

TOXIC EFFECTS :: Reproductive - Paternal Effects - spermatogenesis (incl. genetic material, sperm morphology, motility, and count)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 1313 mg/kg

SEX/DURATION :: male 21 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Paternal Effects - testes, epididymis, sperm duct

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 100 mg/kg

SEX/DURATION :: female 10-11 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - respiratory system Reproductive - Specific Developmental Abnormalities - immune and reticuloendothelial system

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 1 gm/kg

SEX/DURATION :: female 10 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - cardiovascular (circulatory) system

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 1 gm/kg

SEX/DURATION :: female 11-12 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue) Reproductive - Specific Developmental Abnormalities - body wall Reproductive - Specific Developmental Abnormalities - musculoskeletal system

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 50 mg/kg

SEX/DURATION :: female 10-11 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Effects on Newborn - stillbirth Reproductive - Effects on Newborn - viability index (e.g., # alive at day 4 per # born alive)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Unreported

DOSE :: 2 gm/kg

SEX/DURATION :: female 9-10 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue) Reproductive - Specific Developmental Abnormalities - body wall Reproductive - Specific Developmental Abnormalities - cardiovascular (circulatory) system

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Unreported

DOSE :: 2 gm/kg

SEX/DURATION :: female 9-10 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - blood and lymphatic systems (including spleen and marrow) Reproductive - Specific Developmental Abnormalities - urogenital system

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Unreported

DOSE :: 2 gm/kg

SEX/DURATION :: female 12-13 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - body wall Reproductive - Specific Developmental Abnormalities - blood and lymphatic systems (including spleen and marrow) Reproductive - Specific Developmental Abnormalities - respiratory system

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 6400 mg/kg

SEX/DURATION :: female 8-9 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - eye/ear Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue) Reproductive - Specific Developmental Abnormalities - musculoskeletal system

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 2500 mg/kg

SEX/DURATION :: female 10 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue) Reproductive - Specific Developmental Abnormalities - musculoskeletal system

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 20 gm/kg

SEX/DURATION :: female 14 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - hepatobiliary system

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 4 gm/kg

SEX/DURATION :: female 10 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue) Reproductive - Specific Developmental Abnormalities - musculoskeletal system

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 1875 mg/kg

SEX/DURATION :: male 30 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Paternal Effects - testes, epididymis, sperm duct

TYPE OF TEST :: Sperm Morphology

MUTATION DATA

TYPE OF TEST :: Micronucleus test

TEST SYSTEM :: Rodent - mouse Cells - not otherwise specified

DOSE/DURATION :: 500 mg/kg

REFERENCE :: NKEZA4 Nippon Koshu Eisei Zasshi. Japanese Journal of Public Health. (Nippon Koshu Eisei Gakkai, 1-29-8 Shinjuku, Shinjuku-ku, Tokyo 160, Japan) V.1- 1954- Volume(issue)/page/year: 33,165,1986

Hazard Codes	Xn
Risk Phrases	20/21/22-40
Safety Phrases	S24/25
HS Code	2924199090

Dichloroacetyl ...

CAS#:79-36-7

1,8-Diaminooctane

CAS#:373-44-4

Win 18446

CAS#:1477-57-2

Literature: Journal of Medicinal and Pharmaceutical Chemistry, , vol. 3, p. 419 - 425

Precursor 2
CAS#:79-36-7 Dichloroacetyl ... CAS#:373-44-4 1,8-Diaminooctane
DownStream 0

HS Code	2924199090
Summary	2924199090. other acyclic amides (including acyclic carbamates) and their derivatives; salts thereof. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:30.0%

2,2-dichloro-N-[8-[(2,2-dichloroacetyl)amino]octyl]acetamide

N,N'-Octane-1,8-diylbis(2,2-dichloroacetamide)

Fertilysin

N,N'-1,8-Octanediylbis(2,2-dichloroacetamide)

N,N'-1,8-Octanediylbis[2,2-dichloroacetamide]

N,N'-Octamethylenebis(2,2-dichloroacetamide)

Acetamide, N,N'-1,8-octanediylbis[2,2-dichloro-

N,N'-Octamethylenebis(dichloroacetamide)

EINECS 216-033-0

N,N'-Octamethylenebis(2,2-dichloro-N-ethylacetamide)

N,N'-Bis(dichloroacetyl)-1,8-octamethylenediamine

Shanghai Jizhi Biochemical Technology Co., Ltd
China
Product Name: Win 18446
Price: ￥316.0/250mg ￥776.0/1g ￥3736.0/10g ￥2346.0/5g
Purity: 95.0%
Stocking Period: 1 Day
Contact: Liu jia

DC Chemicals Limited
China
Product Name: WIN-18446
Price: $Inquiry/100mg $Inquiry/250mg $Inquiry/1g
Purity: 98.0%
Stocking Period: 3 Day
Contact: Tony Cao

Dayang Chem (Hangzhou) Co., Ltd.
China
Product Name: Acetamide,N,N'-1,8-octanediylbis[2,2-dichloro-
Price: $Inquiry/100g $Inquiry/1kg $Inquiry/100kg $Inquiry/1000kg
Purity: 98.0%
Stocking Period: Inquiry
Contact: Ms Wang

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Price: ￥1100/10 mM * 1 mL in DMSO

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Win 18446

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