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1477-57-2

1477-57-2 structure
1477-57-2 structure
  • Name: Win 18446
  • Chemical Name: N,N'-(Octane-1,8-diyl)bis(2,2-dichloroacetamide)
  • CAS Number: 1477-57-2
  • Molecular Formula: C12H20Cl4N2O2
  • Molecular Weight: 366.111
  • Catalog: Chemical reagent Organic reagent Amide
  • Create Date: 2018-08-20 17:26:48
  • Modify Date: 2024-01-06 14:00:14
  • 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)
Synonyms 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
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
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

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
Precursor  2

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%

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