Group F-6

Group F-6 化学構造　(Chemical Structure)

● Fthalide 　（ラブサイド）
　　　CAS： 27355-22-2 　Pesticide 　MW: 271.92

REC B. subtilis Max ( 0.2 mg/disk) □ 1)

AM Sal. Max ( 1.0 mg/ml, ±S9) □ 1)

CA CHL/IU Max ( 8.0 10^-5M, ±S9) □ 1)

HMA Max(?) Max (?) □ 1)

1) Kureha Chemical Co. Ltd., J. Pesticide Sci., 15, 311-314 (1990)

● Fuchsin basic
　　　632-99-5 　Food 　 338

AM Sal./E.. coli Max ( 5.0 mg/ml, ±S9) □ 1)

1) Ministry of Labor, Japan, Mutagenicity Test Data of Exist. Chem. Subst., JETOC (Ed.) (1996) (Tables in English)

● Fumaric acid （フマル酸）
　　　110-17-8 　Food 　 116.07

AM Sal. Max ( 5.0 mg/ml, ±S9) □ 1)

CA CHL/IU Max ( 0.5 mg/ml, -S9), 24, 48h　(No deta for +S9) □ 2)

1 Ishidate MJr. (Ed.), Data Book of Mutagenicity Tests on Chemicals in Bacteria, LIC/Tokyo (1991) (Tebles in English)
2) Sofuni T. (Ed.): Data Book of Chromosomal Aberration Test In Vitro LIC, Tokyo (1998)

● Furazolidone （フラゾリドン）
　　　 67-45-8 　Medicine　 225.16

DNA B. subtilis Min(?) ○ 1)

AM E. coli Min(?) ○ 1)

CA Human LY Min ( 2.0 μg/ml, -S9) ○ 2)

SCE Human LY Min ( 0.2 μg/ml, -S9) ○ 2)

1) Tajima Y: Mutation Res., 32, 55-80 (1975)
2) Cohen MM & Sagi M: Mutation Res., 59, 139-142 (1979)

● Furfural （フルフラール）(2-Furaldehyde)
　　 98-01-1　Industry/soluvent　 96.08

AM Sal. Max (?) △ 1)

SLRL Drosophila Min(?) ○ 2)

CA CHO Min(?) ○ 3)

SCE CHO Min(?) ○ 3)

1) Mortelmans K, et al,: Environ. Mutagen., 8 (Suppl.7), 1-119,(1986)
2) Woodruff RC, et al,: Environ. Mutagen., 7, 677-702 (1985)　
3) NTP Technical Report N. 382, US (1990)

US-NTP Genotoxicity Screening:
○ Ames Test: □
○ Resiprocal Translocation Test with Drosophila: □
○ MLA: ○

【Note】　(Cited from CICADs Documents 21, 2000)

Experiments in cell-free systems have demonstrated that 2-furaldehyde causes DNA damage (Hadi & Rehman, 1989). Although bacterial mutation studies with 2-furaldehyde have been largely negative, they have in general been inadequately reported (Zdzienicka & Tudek, 1978; McMahon et al., 1979; Loquet et al., 1981; Soska et al., 1981; Marnett et al., 1985; Mortelmans et al., 1986; Shinohara & Omura, 1986; Kim et al., 1987, 1988; Nakamura et al., 1987; Shane et al., 1988; Kato et al., 1989). However, 2-furaldehyde is clearly genotoxic in vitro in mammalian cell test systems, producing chromosomal aberrations, gene mutations, and sister chromatid exchanges (Stich et al., 1981; Gomez-Arroyo & Souza, 1985; McGregor et al., 1988; Nishi et al., 1989; NTP, 1990). In addition, one positive result and one negative result were obtained in Drosophila tests (Woodruff et al., 1985; Rodriguez-Arnaiz et al., 1992). The genotoxic potential of 2-furaldehyde in vivo is less certain, with positive results being claimed in a briefly reported cytogenetics study and negative results being reported in another cytogenetics study and a sister chromatid exchange study (Subramanyam et al., 1989; NTP, 1990). Further details of these studies are provided in the source document to this CICAD (Gregg et al., 1997). Overall, no firm conclusions can be drawn from these reports. Point mutations in K-ras and H-ras genes were seen in the 2-furaldehyde-treated mouse livers taken from the NTP carcinogenicity assay, demonstrating genotoxicity (possibly direct) at the tumour site (Reynolds et al., 1987).

References
・Gomez-Arroyo S, Souza V (1985) In vitro and occupational induction of SCE in human lymphocytes with furfuryl alcohol and furfural. Mutation research, 156:233-238.
・Gregg C, Rajan R, Cocker J, Groves J (1997) 2-Furaldehyde. Sudbury, Suffolk, UK, HSE Books (Risk Assessment Document EH72/6; ISBN 0-7176-1358-5).
・Hadi S, Rehman S (1989) Specificity of the interaction of furfural with DNA. Mutation research, 225:101-106.
・Kato F, Araki A, Nozaki K, Matsushima T (1989) Mutagenicity of aldehydes and diketones. Mutation research, 216:366-367.
・Kim et al., 1987,
・Kim S, Hayase F, Kato H (1987) Desmutagenic effect of alpha-dicarbonyl and alpha-hydroxycarbonyl compounds against mutagenic heterocyclic amines. Mutation research, 177:9-15.
・Kim S, Kim I, Yeum D, Park Y (1988) Desmutagenic action of sugar degradation products. Korean journal of food science and technology, 20 (1):119-124.
・Marnett L, Hurd H, Hollstein M, Levin D, Esterbauer H, Ames B (1985) Naturally occurring carbonyl compounds are mutagens in Salmonella tester strain TA 104. Mutation research, 148:25-34.
・McGregor D, Brown A, Cattanach P, Edwards I, McBride D, Caspary W (1988) Responses of the L5l78Y tk⁺/tk^- mouse lymphoma cell forward mutation assay II: 18 coded chemicals. Environmental molecularmutagenesis, 11:91-118.
・McMahon R, Cline J, Thompson C (1979) Assay of 855 test chemicals in ten tester strains using a new modification of the Ames test for bacterial mutagens. Cancer research, 39:682-693.
・Mortelmans K, Haworth S, Lawlor T, Speck W, Tainer B, Zeiger E (1986) Salmonella mutagenicity tests 11: Results from the testing of 270 chemicals. Environmental mutagenesis, 8 (Suppl. 7):1-119.
・Nakamura S, Oda Y, Shimada T, Oki I, Sugimoto K (1987) SOS-inducing activity of chemical carcinogens and mutagens in Salmonellatyphimurium TA 1535/pSK1002. Examination of 151 chemicals. Mutationresearch, 192:239-246.
・Nishi Y, Miyakama Y, Kato K (1989) Chromosome aberrations induced by pyrolysates of carbohydrates in Chinese hamster V79 cells. Mutation research, 227:117-123.
・NTP (1990) Toxicology and carcinogenesis studies of furfural in F344/N rats and B6C3F1 mice (gavage studies). Research Triangle Park, NC, US Department of Health and Human Services, Public Health Service, National Institutes of Health, National Toxicology Program (Technical Report Series No. 382; NIH Publication No. 90-2837).
・Reynolds S, Stower S, Patterson R, Maronpot R, Aaronson S, Anderson M (1987) Activated oncogenes in B6C3F₁ mouse liver tumours: implications for risk assessment. Science, 237:1309-1316.
・Rodriguez-Arnaiz R, Morales P, Zimmering S (1992) Evaluation in Drosophila melanogaster of the mutagenic potential of furfural in the mei-9^a test for chromosome loss in germ-line cells and the wing spot test for mutational activity in somatic cells. Mutation research, 280:75-80.
・Shane B, Troxclair A, McMillin D, Henry C (1988) Comparative mutagenicity of 9 brands of coffee to Salmonella typhimurium TA100, TA102, TA104. Environmental molecular mutagenesis, 11:195-206.
・Shinohara K, Omura H (1986) Furans as mutagens formed by amino-carbonyl reactions. Developmental food science, 3:353-362.
・Soska J, Koukalova B, Ebringer L (1981) Mutagenic activities of simple nitrofuran derivatives. Comparison of related compounds in the phage inductest, chloroplast-bleaching and bacterial-repair and mutagenicity tests. Mutation research, 81:21-26.
・Stich H, Rosin M, Wu C, Powrie W (1981) Clastogenicity of furans found in food. Cancer letters, 13:89-95.
・Subramanyam S, Sailaja D, Rathnaprabha D (1989) Genotoxic assay of two dietary furans by some in vivo cytogenetic parameters. Environmental molecular mutagenesis, 14 (Suppl. 15):239. ;
・Zdzienicka M, Tudek B (1978) Mutagenic activity of furfural in Salmonella typhimurium TA 100. Mutation research, 58:205-209. Zh

● Furosemide　（フロセミド）
　　　 54-31-9　Medicine　 330.74

AM Sal Max (?) □ 1)

CA CHL/IU Min ( 3.0 mg/ml, -S9）, 24, 48h　D20= 3.6; TR= 0.50; (Very weak) ○ 2)

1) Natl. Inst. Hygien. Sci., Tokyo　(?)
2) Sofuni T. (Ed.): Data Book of Chromosomal Aberration Test In Vitro LIC, Tokyo (1998)

● Furfuryl alcohol （フルフリルアルコール）
　　　98-00-0　Industry /Solvent/ Flavoring 　 98.10

AM Sal. Max(?)　 □ 1)

1) Zeiger E, et al,: Environ. Mol. Mutagen, 19 (Suppl. 21), 2-141(1992)

US-NTP Genotoxicity Screening:
○ Ames test: □
○ CA with CHO cells: △
○ SCE with CHO cells: ○

● Furylfuramide (AF-2) 　（フリルフラマイド）
　　 3688-53-7　 Laboratory　　248.19

DNA E. coli/ B. subtilis Min (?) ○ 1)

REC B. subtilis Min (?) ○ 2)

AM Sal. Min ( 0.02 μg/plate, -S9) ○ 3)

AM Sal./TA100 Min ( 0.05 μg/plate, -S9); 　spa= 7 x 10⁷ rev./mg ◎ 4)

MB (?) (Fluctuation Test) Min(?) ○ 5)

MB N. crassa
(アカパンカビ） Min ( 5 μg/ml, -S9) ○ 6)

CA Human LY Min (?) ○ 7)

CA CHL/IU Min ( 0.005mg/ml, -S9), 24, 48h　D20= 0.0074;
TR= 4100 ◎ 8)

SM V79/8AG Min ( 2 x 10^-6M, -S9) ◎ 9)

MLA L5178Y Min (15μg/ml, ±S9) ○ 10)

CT SH/Fb Min ( 0.25μg/ml, -S9) ○ 11)

CT SH /embryo Min ( 20 mg/kg, Transplacental) ○ 12)

CAv Rats/BM Min ( 15 mg/kg, ip; 20 mg/kg, po) ○ 13)

DLv Mice Max ( 450 mg/kg, po) □ 14)

1) Tagima Y: Mutation Res., 32, 55-80 (1975)
2) Kada T: Jap. J. Genet., 48. 301-305 (1973)
3) Ames BN, et al,: Mutation Res., 31, 347-364 (1971)
4) Ishidate MJr (Ed): Data Book of Mutagenicity Tests on Chemicals in Bacteria, LIC/Tokyo (1991) (Tebles in English)
5) Green MHL, et al,: Mutation Res., 44, 139-143 (1977)
6) Ong T & Shahin MM: Science, 184, 1086-1087 (1974)
7) Tonomura A & Sasaki MS: Jap. J. Genet. , 48, 301-305 (1973)
8) Ishidate MJr(Ed): Data Book, Chromosomal Aberration Tests In Vitro, LIC/Tokyo,,
　 Elsevier/ Amsterdam (1988)
9) Wild D: Mutation Res., 31, 197-199 (1975)
10) Clive D, et al,: Mutation Res., 59, 61-108 (1979)
11) Pienta RJ, et al,: Cancer Letter, 5, 245-251 (1978)
12) Inui N, et al,: Mutation Res., 58, 331-338 (1978)
13) Sugiyama T, et al,: Mutation Res., 13, 241-246 (1975)
14) Soares ER & Sheridan W: Mutation Res., 31, 235-240 (1975)

【Note】
This agent had been used as a food additive in Tofu in Japan; Banned in 1975.
　（本剤は食品添加物として豆腐の保存剤に使用されいたが、発がん性が分かり、禁止となった。）

● Fusarenon-X
　　 23255-69-8　　Ntural Product　　 345.37

SM FM3A cells Max (?) □ 1)

1) Umeda M, et al,: Gann(Jap. J. Cancer Res.), 619-625 (1977)

●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）

REC	B. subtilis	Max ( 0.2 mg/disk)	□	1)
AM	Sal.	Max ( 1.0 mg/ml, ±S9)	□	1)
CA	CHL/IU	Max ( 8.0 10^-5M, ±S9)	□	1)
HMA	Max(?)	Max (?)	□	1)

AM	Sal.	Max ( 5.0 mg/ml, ±S9)	□	1)
CA	CHL/IU	Max ( 0.5 mg/ml, -S9), 24, 48h　(No deta for +S9)	□	2)

DNA	B. subtilis	Min(?)	○	1)
AM	E. coli	Min(?)	○	1)
CA	Human LY	Min ( 2.0 μg/ml, -S9)	○	2)
SCE	Human LY	Min ( 0.2 μg/ml, -S9)	○	2)

AM	Sal.	Max (?)	△	1)
SLRL	Drosophila	Min(?)	○	2)
CA	CHO	Min(?)	○	3)
SCE	CHO	Min(?)	○	3)

AM	Sal	Max (?)	□	1)
CA	CHL/IU	Min ( 3.0 mg/ml, -S9）, 24, 48h　D20= 3.6; TR= 0.50; (Very weak)	○	2)

DNA	E. coli/ B. subtilis	Min (?)	○	1)
REC	B. subtilis	Min (?)	○	2)
AM	Sal.	Min ( 0.02 μg/plate, -S9)	○	3)
AM	Sal./TA100	Min ( 0.05 μg/plate, -S9); 　spa= 7 x 10⁷ rev./mg	◎	4)
MB	(?)	(Fluctuation Test) Min(?)	○	5)
MB	N. crassa (アカパンカビ）	Min ( 5 μg/ml, -S9)	○	6)
CA	Human LY	Min (?)	○	7)
CA	CHL/IU	Min ( 0.005mg/ml, -S9), 24, 48h　D20= 0.0074; TR= 4100	◎	8)
SM	V79/8AG	Min ( 2 x 10^-6M, -S9)	◎	9)
MLA	L5178Y	Min (15μg/ml, ±S9)	○	10)
CT	SH/Fb	Min ( 0.25μg/ml, -S9)	○	11)
CT	SH /embryo	Min ( 20 mg/kg, Transplacental)	○	12)
CAv	Rats/BM	Min ( 15 mg/kg, ip; 20 mg/kg, po)	○	13)
DLv	Mice	Max ( 450 mg/kg, po)	□	14)