Group C-12

化学構造　(Chemical Structure)

●Cyclohexanone 　（シクロヘキサノン）
　　CAS： 108-94-1　　Industrｙ/Solvent)　　MW: 98.14

AM	Sal.	Min (?)	○	1)
MB	B. subtilis	Min (?)	○	1)
DNA	Human LY	(Single strand break); Min ( 0.005 mg/L )	○	2)

1) Massoud A., et al.: Mutation Res., 74, 174 (1980)
2) Dyshlovol VD., et al.: Gig. Sanit., 5, 76-77 (1981)
　　　
  US-NTP Genotoxicity Screening：
  ○ Ames Test : □
  ○ MLA Test : □

● Cyclohexene（シクロヘキセン ）
　　110-83-8　Industrｙ　 82.15

AM

Sal

Min ( 0.625 mg/plate, -S9), spa= 83.2 (TA2637)

○w

1)

1) Ministry of Labour, Japan; Mutagen. Test Data of Exist. Chem. Subst., JETOC (Ed.), Suppl.. 3 pp. 208 (2005)  (Tables in English)

● Cyclohexene oxide（シクロヘキセン オキシド）
　　286-20-4　　Industrｙ　 98.14

AM

Sal /E. coli

Min (0.5 mg/plate, -S9); Spe= 151 (TA100)

○

1)

1) Ministry of Labour, Japan; Mutagen. Test Data of Exist. Chem. Subst., JETOC (Ed.) (1996)  (Tables in English)

● Cyclohexylamine 　（シクロヘキシラミン; Amonocyclohexane; Hexahydroaniline)
　　　108-91-8　　Industrｙ/Intermediate)　 112.56

AM	Sal.	Max ( 10 mg/plate, ±S9)	□	1)
AM	Sal.	Max ( 2.5 mg/plate, ±S9)	□	2, 3)
AM	Sal.	Max ( 0.015 mg/plate, -S9)	□	4)
AM	Sal.	Max ( 1 mM, ±S9)	□	5)
SM	CHO	Max ( 1.7  mg/ml, ±S9)	□	6)
CA	CHL/IU	Min (  0.5 mg/ml, ±S9)	○	7)
CA	CH, Fibro.	Min (  0.1 mg/ml, -S9)	○	8)
CA	Kangaroon rat / kidney	Min (  0.5 mg/ml, -S9)	○	9)
CA	Human LY	Min (  1 mM, -S9)	○	10)
CA	Human LY	Max (0.5 mg/ml, ±S9)	□	11)
DNA	Phage-induct./ E. coli	Max (?), -S9)	□	12)
DNA	E. coli	Max ( 50 μｌ),  -S9)	□	13)
UM	Sal.	Max ( 0.1. ml, ±S9)	□	14)
SCE	Human lym.	Min (  1 mM,  -S9)	○w	15)
UDS	Rat hepatocytes	Max ( 0.86. mg, -S9)	□	6)
CT	Sy. ham.	Min ( 0.5 mg/ml,  -S9)	○	16)
CT	BHK21	Max (?) (-S9)	□	17)
SLRL	Drosophila:	Max ( 5 mg,/ml, ip,/fed)	□	18-21)
SLRL	Drosophila:	Max ( 1.7 mg/ml, fed)	□	6)
SMv	Mice, spot test	Min ( 200 mg/kg), ip	○w	22)
CAv	Mice, germ cells	Max ( 100 mg/kg/d, ip), for 5d.	□	23)
CAv	Rats, germ cells/ BM	Max ( 50 mg/kg/d, ip ), for 5d.	○	24)
CAv	Rats, BM	Max ( 89 mg/kg/d, or ), for 69d.	□	25)
CAv	Rats, BM	Max ( 50 mg/kg/d, or/ip ), for 5d.	□	26)
CAv	Rats, lym.	Max ( 50 mg/kg/d, ip ), for 7w	□	27)
CAv	CH, germ cells	Max ( 50 mg/kg/d, ip/or ), for 3-7w	□	3, 28)
CAv	CH, lym.	Min  ( 200 mg/kg/d, or ), for 3d	○	29)
DLv	Mice	Max ( 150 mg/kg, or )	□	30)
DLv	Mice	Max ( 150 mg/kg/d, or ), for 5d	□	31)
DLv	Mice	Max ( 0.11 %), fed	□	32)
DLv	Mice	Max ( 25 mg/kg/d, i,p ), 1-3d	□	33)
DLv	Mice	Min ( 100 mg/kg/d x 5, ip )	○	34)
DLv	Rats	Max ( 150 mg/kg, or )	□	35)
DNAv	Mice, liver/lym.	Max ( 142 mg/kg x 2, or )	□	36)

1) Mortelmans , K., et al., Environ., Mol. Mutagen., 8, 1-119 (1986)
2) Anderson D & Styles JA., Bri. J. Cancer, 37, 924-930 (1978)
3) Herbold, BA., Mutation Res., 90, 365-372 (1981)
4) McGlinchey G., et al., J. Pharmacol. Sci., 71, 661-665 (1982)
5) Kubo T et al., J. Health Sci., 48, 545-554 (2002)
6) Brusick D., et al., environ. Mol. Mutagens, 14, 188-199 (1989)
7) Matsuoka A., et al., Environ. Mutation Res., 20, 159-165 (1998)
8) Dixon CH.., Diss. Abs. Int.. (B) Food Cosmet. Toxicol., 8, 617-623 (1972)
9) Green S., et al., Food Cosmet. Toxicol., 8, 617-623 (1970)
10) Stoltz DR., et al., Science, 167, 1501-1502 (1970)
11) Brewen JG., et al.: Nature New Biol., 230, 15-16 (1971)  
12) Mayer VW., Appl. Microbiol., 18, 697-698 (1969)
13) Fluck ER., et al., Chem. Biol. Inerract., 15, 219-231 (1976)
14) Degirmenci E., et al., Water Sci. Tech., 42, 125-131 (2000)
15) Wolff S., Ann NY. Acad. Sci., 407, 142-153 (1983)
16) Casto BC., In: Mishall., et al. (eds), Advances inMod. Env. Toxicol., Vol 1., Senate Press, Princeton, NJ., pp 241-271 (1981)
17) Styles JA.: Brit. J. Cancer, 37, 931-936 (1978)  
18) Browning LS., EMS Newsletter, 6, 18-19 (1972)
19) Knaap AG., et al.: Mutation Res., 21, 341-344 (1973)    
20) Felix R & de la Rosa ME., Dros. Inform. Serr., 47, 114-116 (1971)
21) Vogel E & Chandler JLR., Experimantation, 30, 621-623 (1974)
22) Fahrig R., Mution Res., 103, 43-47 (1982)
23) Cattanach BM & Pllard CE., Mutation Res., 12, 472-434 (1971)
24) Legator MS, et al,: Science, 165, 1139-1140 (1969)      7)
25) khera KS., et al., Toxicol. Appl., Pharm., 18, 263-268 (1971)
26) Dick CE., et al., Mutation Res., 26, 199-203 (1974)
27) Mostardi RA., et al., Ohio J. Sci.., 72, 313-318 (1972)
28) Machemer L & Lorke D., Mutation Res., 40, 243-250 (1976)
29) Van Went-de-Broes GF., et al.: Fd. Cosmet. Toxicol., 13, 415-418 (1975)  
30) Machemer L & Lorke., Mutation Res., 29, 209-214 (1975)
31) Lorke D & Machemer L., Toxicol., 2, 231-237 (1974)
32) Lorke D & Machemer L., Humangenetik, 26, 199-205 (1975)
33) Epstein SS., SS Toxicol. Appl. Pharm., 23, 288-325 (1972)
34) Petersen KW., et al.: Mutation Res., 14, 126-129 (1972)    
35) Bailey DE., et al., Toxicol. Appl. Pharm., 22, 330-331 (1972)
36) Kitehin KT., et al., Biochem. Pharm., 38, 2733-2738 (1989)

US-NTP Genotoxicity Screening：
○ Ames Test : □

【Note】　(Cited from IARC Monographs Suppl., 6, 1987)

The activity of cyclothexylamine in short-term tests has been reviewed recently (Nat. Res., Council, 49, 1985). No data were available on the genetic and related effects of this compound in humans. 　　This compound did not induce DL mutation in one study in rats, but contradictory results were obtained in mice. It gave weakly positive results in the mouse spot test. It induced CAss in lymphocytes but not in bone-marrow cells of hamsters and lambs or in spermatogonia of hamsters and mice treated in vivo. In treated rats, CAs were induced in spermatogonia but not in leucocytes, and contradictory results were obtained for bone-marrow cells. it induced SCEs in cultured human Lym., but again, conflicting results were obtained concerning the induction CAs. It enhanced virus-induced transformation of Syr. hamster embryo cells and induced CAs in cultured rat kangaroo cells. It did not induce somatic or SLRL mutations, aneuploidy or heritable translocations in Drosophila and was not mutagenic and did not induce prophage in bacteria. In host-mediated assays (HMA), it did not induce mutation in bacteria or CAs in human leucocytes. (IARC Monographs, 22, 59)

●N-Cyclohexyl-2-benzothiazolesulfenamide （N-シクロヘキシル-2-ベンゾ−チアゾールスルフェンアミド）
　　95-33-0　　Industrｙ　264.43

AM	Sal /E.coli	Max ( 5.0 mg/plate, ±S9)	□	1)
AM	E. coli	Max ( 3.0 mg/plate, ±S9)	□	2)
CA	CHL/IU	Max ( 0.08 mg/ml, ±S9)	□	1)

1) Ministry of Health, Labour & Welfare, Japan (Ed):Toxicity Testing Reports of Environ. Chemicals, Vol. 5 (1997) (Tables in English)
2)  IUCLID (Internat. Uniform Chem. Inform. Data Base ) Data Sheet, EU (1995)

● Cyclonite 　（シクロナイト）
　 　121-82-4　Explosive/Rodenticide　 222.26

AM	Sal	Max (?)	□	1)
MB	Yeast	Min (?)	□	2)
UDS	Human Fb	Min (?)	□	3)

1) Whong WZ ., et al.: Toxicol. Lett., 5, 11-17 (1980)
2) Simmon VF., et al.: Toxicol. Appl. Pharmacol., 41, 197 (1977)
3) Dilley JV., et al.: Toxicol. Appl. Pharmacol., 45, 256-257 (1978)

● Cyclophosphamide (Endoxan)（シクロホスファミド; エンドキサン）
　　　 50-18-0　Medicine/Laboratory 　261.09

AM	Sal.	Min (?) (+S9)	○	1)
SLRL	Drosophila:	Min (?)	○	2)
CA	Human LY	Min ( 0.09 mM, +S9)	○	3)
CA	CHL/IU	Min ( 0.01 mg/ml, +S9), 6-18h; D20= 0.0093 mg/ml,  TR= 4200	◎	4)
SCE	CHO	Min ( 10-3M, +S9)	○	5)
UDS	HeLa cells	Min ( 10-7 M, +S9)	○	6)
CT	C3H/T101/	Min ( 10μg/ml), +S9	○	7)
CAv	Rat/BM	Min(  5 mg/kg, ip)	○	8)
MNv	Mice/BM	Min (?)	○	9)
DLv	Mice/CD-1	Min ( 200 mg/kg/Day, ip )	○	10)
SPMv	Mice	Min ( 50 mg/kg x 5, ip )	○	11)
UDSv	Mice	Min ( 200 mg/kg), or )	○	12)

1) McCann J, et al,: Proc. Natl. Acad. Sci. (USA), 72, 3190-3193 (1975)
2) Vogel E: Mutation Res., 33, 221-228 (1975)
3) Madle S et al,: Mutation Res., 54, 95-99 (1978)
4) Sofuni T. (Ed.): Data Book of Chromosomal Aberration Test In Vitro,, LIC, Tokyo (1998)  (Tables in English)
5) Stetka DG & Wolf S: Mutation Res., 41, 343-350 (1976)
6) Martin CN, et al,: Cancer Res., 38, 2621-2627 (1978)
7) Benedict WF, et al,: Cancer Res., 37, 2202-2208 (1977)
8) Goetz P, et al, :Mutation Res., 31, 247-254 (1975)
9) Wakata A, et al,: Mutation Res., 223, 369-372 (1989)
10) Anderson D, et al,: Mutation Res., 43, 231-246 (1977)
11) Wyrobek AJ & Bruce WR: Pro. Natl. Acad. Sci. (USA), 72, 4425-4429 (1975)
12) Sotomayor RE, et al,: Mutation Res., 50, 225-240 (1978)

【Note】　(Cited from IARC Monographs Suppl., 6, 1987)

Cyclophosphamide is metabolized to an alkylatiing intermediate (IARC, 26, 165). Increased incidences of CAs and SCEs were observed in peripheral blood Lym. and, in one study, in bone-marrow cells of patients treated with this agent for a variety of malignant and nonmalignant diseases. 　　It has been tested extensively for genetic effects in a wide variety of tests in vivo and in vitro, giving consistently positive results. It bound to DNA in kidney, lung and liver of mice and induced DL mutations, CAs, MNs SCE, mutation and DNA damage in rodents treated in vivo. In human cells in vitro, it induced CAs, SCEs and DNA damage. In rodent cells in vitro, it induced transformation, cCAs, SCEs, mutation and UDS. In Drosophila, it induced aneuploidy, heritable translocation and somatic and SLRL mutations. In fungi, it induced aneuploidy, mutation, recombination, gene conversion and DNA damage. In bacteria, it induced mutation and DNA damage. In host-mediated assays, it induced CAs and SCEs in human Lym. cells, mutation and SCEs in Chinese hamster cells, gene conversion in yeast, and mutation in bacteria. Iwas active in body-fluid assays of urine from humans and rodents exposed in vivo, and in one study using serum from rats. (IARC Monographs, 9, 135; 26, 165)

REC	B. subtilis	Max ( 2 mg/disk)	□	1)
AM	Sal../E. coli	Max ( 5 mg/plate), ±S9	□	1)
CA	L5178Y	Max ( 1.25 mg/ml), ±S9	□	1)

1) Nihon Kayaku Co., Ltd.: J. Pesticide Sci., 16, 697-702 (1991)

● Cinnabarinic acid　（シンナバリニック酸）　　　　　　　　 　　
　　　606-59-7 　　　　　Laboratory 　　 285.21

CA

CHL/IU

Min (0.25 mg/ml, -S9), 48h: D20= 0.46; TR= 24)

○

1)

1) Sofuni T. (Ed.): Data Book of Chromosomal Aberration Test In Vitro,, LIC, Tokyo (1998） (Tables in English)

● Cyproconazole (ALTO)　　　 　　
　　　 94361-06-5　Pesticide　 291.78　　

REC	B. subtilis	Max ( 10 mg/disk)	□	1)
AM	Sal../E. coli	Max ( 5 mg/plate), ±S9	□	1)
CA	CHO	Max ( 0.3mg/ml), ±S9	□	1)

1) SDS Biotech K.K..: J. Pesticide Sci., 22, 263-268 (1997)

● L-Cysteine-HCl　 （L-システイン･塩酸）
　　　 52-89-1　　Food　　 175.64

AM	Sal..	Min ( 0.5 mg/plate, -S9)	○	1)
CA	CHL/IU	Min ( 2.0 mg/ml, -S9), 24-48h: D20= 2.28; TR= 6.0	○	2)
MNv	Mice/BM	Max ( 500 mg/kg x 1), ip	□	3)

1) Ishidate MJr (Ed): Data Bood for Mutagenicity Tests on Chem. in Bacteria, LIC/Yokyo (1991)   (Tables in English)
2) Sofuni T. (Ed.): Data Book of Chromosomal Aberration Test In Vitro,, LIC, Tokyo (1998）   (Tables in English)
3) Hayashi M, et al,: Fd. Chem. Toxicol., 26, 487-500 (1988)

● Cytosine arabinoside （シトシン　アラビノサイド）(Ara-C；　Cytarabine)
　　　　 147-94-4　　Medicine　 243.25

AM	Sal. /E.coli	Min (?)	○	1)
CA	CHL/IU	Min (0.001 mg/ml, -S9), 24-48h: D20= 0.001; TR= 11000	◎	2)
CA	Hum. Lym.	Min ( 0.03 μg/ml)	○	3)
SCE	Hum. Lym.	Min ( 0.003 μg/ml)	○	3)
SM	V79(8-AG)	Min ( 10-6M)	○	4)
CT	Syr.Hamster	Min (10-6M)	○	5)
MNv	Mice/ICR/BM	Min ( 1 mg/kg, iv )	○	6)
MNv	Mice/ddY/BM	Min (?)	○	7)
CTv	Mice/AB/BM	Min ( 315 mg/kg, ip )	○	8)

1) Natl Inst. Hygien. Sci., Tokyo, Japan (?)
2) Sofuni T. (Ed.): Data Book of Chromosomal Aberration Test In Vitro,, LIC, Tokyo (1998）   (Tables in English)
3) Shiraishi Y & Sandberg A: J. Natl. Cancer Inst., 62, 27-35 (1979)
4) Huberman E & Heidelberger C: Mutation Res., 14, 130-132 (1972)
5) Jones PA et al.: Eur. J. Cancer, 8, 595-599 (1972)
6) Maier P & Schmid W: Mutation Res., 40, 325-338 (1976)
7) Hayashi M, et al, Mutation Res., 127, 129-137 (1984)
8) Wobus AM et al.: Mutation Res., 58, 67-77 (1978)

●Top Page　（トップページ）

●Abbreviation 　（省略記号）

●Mutagenicity （変異原性）

●Test Systems　(試験法の種類）

●Technical Problems　（技術的問題点）

●List of　Compounds （化合物リスト）

●Evaluation of Results　（試験結果の評価）