2-ACETYLAMINOFLUORENE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C15H13NO
Molecular Weight	223.2698
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(=O)NC1=CC=C2C(CC3=C2C=CC=C3)=C1

InChI

InChIKey=CZIHNRWJTSTCEX-UHFFFAOYSA-N

InChI=1S/C15H13NO/c1-10(17)16-13-6-7-15-12(9-13)8-11-4-2-3-5-14(11)15/h2-7,9H,8H2,1H3,(H,16,17)

HIDE SMILES / InChI

Molecular Formula	C15H13NO
Molecular Weight	223.2698
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Approval Year

PubMed

Title	Date	PubMed
Evidence of a "clear and consistent threshold" for bladder and liver cancer in the large ED01 carcinogenicity study.	2003-08	12730607
Uncoupling of leading- and lagging-strand DNA replication during lesion bypass in vivo.	2003-05-23	12764199
Use of HepG2 cell line for direct or indirect mutagens screening: comparative investigation between comet and micronucleus assays.	2003-04-20	12694748
Mechanistic insights into replication across from bulky DNA adducts: a mutant polymerase I allows an N-acetyl-2-aminofluorene adduct to be accommodated during DNA synthesis.	2003-04-08	12667073
Differentially expressed transcripts in neoplastic hepatic nodules and neonatal rat liver studied by cDNA microarray analysis.	2003-03-20	12569566
Suppressive effect of herbal compound 861 on chemical hepatocarcinogenesis in rats.	2003-03	12781041
Thresholds of carcinogenicity in the ED01 study.	2003-03	12604845
Different effects of the liver mitogens triiodo-thyronine and ciprofibrate on the development of rat hepatocellular carcinoma.	2003-02-25	12597455
Prevalidation of a rat liver foci bioassay (RLFB) based on results from 1600 rats: a study report.	2003-02-25	12597450
Pregnane X receptor-dependent and -independent effects of 2-acetylaminofluorene on cytochrome P450 3A23 expression and liver cell proliferation.	2003-01-10	12504080
Polychlorinated biphenyls as initiators in liver carcinogenesis: resistant hepatocyte model.	2003-01-01	12583993
Suppressive effect of Astragalus membranaceus Bunge on chemical hepatocarcinogenesis in rats.	2003-01	12497209
Mutagenic activation of arylamines by subcellular fractions of Chamaelea gallina clams exposed to environmental pollutants.	2003	12552592
Use of nucleotide excision repair-deficient mice as a model for chemically induced lung cancer.	2003	12415716
Distinction of carcinogens from mutagens by induction of liver cell foci in a model for detection of initiation activity.	2002-12-15	12406545
Mutagenic events in Escherichia coli and mammalian cells generated in response to acetylaminofluorene-derived DNA adducts positioned in the Nar I restriction enzyme site.	2002-12-03	12450390
Oxidative DNA damage by a common metabolite of carcinogenic nitrofluorene and N-acetylaminofluorene.	2002-12-01	12402298
Deacylation of N-arylformamides and N-arylacetamides by formamidase in rat liver.	2002-12	12433795
Protection by beverages, fruits, vegetables, herbs, and flavonoids against genotoxicity of 2-acetylaminofluorene and 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) in metabolically competent V79 cells.	2002-11-26	12438004
Influence of different chemicals on MDR-1 P-glycoprotein expression and activity in the HK-2 proximal tubular cell line.	2002-09-01	12387747
The Liverbeads as a tool for the comet assay.	2002-08-26	12160901
Chemical models for cytochrome P450 as a biomimetic metabolic activation system in mutation assays.	2002-08-26	12160898
Hydrocortisone affects the N-acetylation of 2-aminofluorene and DNA-2-aminofluorene adduct formation in Sprague-Dawley rats.	2002-08-10	12168848
Trapping of DNA nucleotide excision repair factors by nonrepairable carcinogen adducts.	2002-08-01	12154024
Anticarcinogenicity of monocyclic phenolic compounds.	2002-08	12570342
Embryoid-body cells derived from a mouse embryonic stem cell line show differentiation into functional hepatocytes.	2002-07	12085345
The isomerization of the UvrB-DNA preincision complex couples the UvrB and UvrC activities.	2002-06-28	12079335
[Establishment and optimization of rat models for hepatic oval cells proliferation].	2002-06	12113673
In vivo cell lineage analysis during chemical hepatocarcinogenesis in rats using retroviral-mediated gene transfer: evidence for dedifferentiation of mature hepatocytes.	2002-06	12065689
Pleiotrophin/heparin-binding growth-associated molecule as a mitogen of rat hepatocytes and its role in regeneration and development of liver.	2002-06	12057922
Alterations of the Fhit gene in hepatocellular carcinomas induced by N-nitrosodiethylamine in rats.	2002-05	12112319
The effect of paclitaxel on 2-aminofluorene-DNA adducts formation and arylamine N-acetyltransferase activity and gene expression in human lung tumor cells (A549).	2002-05	11955676
Genomic structure, gene expression, and promoter analysis of human multidrug resistance-associated protein 7.	2002-04-25	12566991
Polyetheretherketone--cytotoxicity and mutagenicity in vitro.	2002-04	11950045
The in vivo apoptotic effect of interferon alfa-2b on rat preneoplastic liver involves Bax protein.	2002-04	11915028
Acute cytotoxicity of the chemical carcinogen 2-acetylaminofluorene in cultured rat liver epithelial cells.	2002-03-28	11888708
Induction of human MDR1 gene expression by 2-acetylaminofluorene is mediated by effectors of the phosphoinositide 3-kinase pathway that activate NF-kappaB signaling.	2002-03-27	11960367
Alteration of liver cell function and proliferation: differentiation between adaptation and toxicity.	2002-03-14	11890475
32P-Postlabeling/polyacrylamide gel electrophoresis analysis: application to the detection of DNA adducts.	2002-03	11896676
Genetics of mutagenesis in E. coli: various combinations of translesion polymerases (Pol II, IV and V) deal with lesion/sequence context diversity.	2002-02-28	12509262
Germ cells microsatellite instability. The effect of different mutagens in a mismatch repair mutant of Drosophila (spel1).	2002-02-15	11815247
Lack of DNA binding in the rat nasal mucosa and other tissues of the nasal toxicants roflumilast, a phosphodiesterase 4 inhibitor, and a metabolite, 4-amino-3,5-dichloropyridine, in contrast to the nasal carcinogen 2,6-dimethylaniline.	2002-02	11850974
In vivo cell lineage analysis in cyproterone acetate-treated rat liver using genetic labeling of hepatocytes.	2002-02	11826400
Proliferation and differentiation of ductular progenitor cells and littoral cells during the regeneration of the rat liver to CCl4/2-AAF injury.	2002-01	11813887
SDF-1alpha/CXCR4: a mechanism for hepatic oval cell activation and bone marrow stem cell recruitment to the injured liver of rats.	2002	12626097
Effects of garlic components diallyl sulfide and diallyl disulfide on arylamine N-acetyltransferase activity and 2-aminofluorene-DNA adducts in human promyelocytic leukemia cells.	2002	12230020
The drug efflux pump MRP2: regulation of expression in physiopathological situations and by endogenous and exogenous compounds.	2002	12206135
Anti-mutagenic activity of Phyllanthus amarus Schum & Thonn in vitro as well as in vivo.	2002	12111712
Ellagic [correction of ellagica] acid inhibits arylamine N-acetyltransferase activity and DNA adduct formation in human bladder tumor cell lines (T24 and TSGH 8301).	2001-12	11828989
Leukemia inhibitory factor decreases the arylamine N-acetyltransferase activity in human cumulus granulosa cells.	2001-12	11808848

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:44:06 GMT 2025` Edited by `admin` on `Mon Mar 31 18:44:06 GMT 2025`
Record UNII	9M98QLJ2DL
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

2-ACETYLAMINOFLUORENE

Systematic Name

English

N-2-FLUORENYLACETAMIDE

Preferred Name

English

2-FAA

Common Name

English

ACETYLAMINOFLUORENE, 2-

Systematic Name

English

ACETAMIDE, N-9H-FLUOREN-2-YL-

Systematic Name

English

2-ACETYLAMINOFLUORENE [HSDB]

Common Name

English

N-2-FLUORENYLACETAMIDE [MI]

Common Name

English

N-ACETYL-2-AMINOFLUORENE

Systematic Name

English

C15-H13-N-O

Common Name

English

AAF

Common Name

English

NSC-12279

Code

English

N-9H-FLUOREN-2-YLACETAMIDE

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C45176

Created by admin on Mon Mar 31 18:44:07 GMT 2025 , Edited by admin on Mon Mar 31 18:44:07 GMT 2025

Code System Code Type Description

MERCK INDEX

m5459

Created by admin on Mon Mar 31 18:44:07 GMT 2025 , Edited by admin on Mon Mar 31 18:44:07 GMT 2025

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Merck Index

NSC

12279

Created by admin on Mon Mar 31 18:44:07 GMT 2025 , Edited by admin on Mon Mar 31 18:44:07 GMT 2025

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HSDB

4077

Created by admin on Mon Mar 31 18:44:07 GMT 2025 , Edited by admin on Mon Mar 31 18:44:07 GMT 2025

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PUBCHEM

5897

Created by admin on Mon Mar 31 18:44:07 GMT 2025 , Edited by admin on Mon Mar 31 18:44:07 GMT 2025

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ECHA (EC/EINECS)

200-188-6

Created by admin on Mon Mar 31 18:44:07 GMT 2025 , Edited by admin on Mon Mar 31 18:44:07 GMT 2025

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WIKIPEDIA

2-ACETYLAMINOFLUORENE

Created by admin on Mon Mar 31 18:44:07 GMT 2025 , Edited by admin on Mon Mar 31 18:44:07 GMT 2025

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MESH

D015073

Created by admin on Mon Mar 31 18:44:06 GMT 2025 , Edited by admin on Mon Mar 31 18:44:06 GMT 2025

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EPA CompTox

DTXSID0039227

Created by admin on Mon Mar 31 18:44:07 GMT 2025 , Edited by admin on Mon Mar 31 18:44:07 GMT 2025

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CHEBI

17356

Created by admin on Mon Mar 31 18:44:07 GMT 2025 , Edited by admin on Mon Mar 31 18:44:07 GMT 2025

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NCI_THESAURUS

C29791

Created by admin on Mon Mar 31 18:44:06 GMT 2025 , Edited by admin on Mon Mar 31 18:44:06 GMT 2025

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MESH

C118533

Created by admin on Mon Mar 31 18:44:06 GMT 2025 , Edited by admin on Mon Mar 31 18:44:06 GMT 2025

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FDA UNII

9M98QLJ2DL

Created by admin on Mon Mar 31 18:44:07 GMT 2025 , Edited by admin on Mon Mar 31 18:44:07 GMT 2025

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CAS

53-96-3

Created by admin on Mon Mar 31 18:44:06 GMT 2025 , Edited by admin on Mon Mar 31 18:44:06 GMT 2025

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