n-hydroxy-4-aminobiphenyl profile

n-hydroxy-4-aminobiphenyl, also known as 4-amino-2-hydroxybiphenyl, is a metabolite of the industrial chemical 4-aminobiphenyl. It is formed in the body through enzymatic oxidation of 4-aminobiphenyl. This compound has been identified as a potential human bladder carcinogen. The formation of n-hydroxy-4-aminobiphenyl is thought to be an important step in the metabolic activation of 4-aminobiphenyl, which leads to its carcinogenic activity. Research on n-hydroxy-4-aminobiphenyl focuses on understanding its role in bladder cancer development and its potential as a biomarker for exposure to 4-aminobiphenyl. This compound is also investigated in relation to other types of cancers, including lung cancer and breast cancer. Studies are conducted to identify possible preventive or therapeutic strategies related to this compound and its impact on human health.'

ID Source	ID
PubMed CID	81261
CHEBI ID	16580
SCHEMBL ID	4948154
MeSH ID	M0063232

Synonym
kjc7v247mg ,
unii-kjc7v247mg
n-hydroxy-[1,1'-biphenyl]-4-amine
n-1,1'-biphenyl-4-ylhydroxylamine
4-hydroxyaminobiphenyl
n-4-biphenylylhydroxylamine
4-hydroxylaminobiphenyl
4-biphenylhydroxylamine
CHEBI:16580
6810-26-0
(1,1'-biphenyl)-4-amine, n-hydroxy-
hydroxylamine, n-4-biphenylyl-
ccris 2823
brn 2639597
n-hydroxy-4-aminobiphenyl ,
C03622
n-biphenyl-4-yl-hydroxylamine
FT-0669301
n-(4-phenylphenyl)hydroxylamine
AKOS006273145
n-(4-phenyl-phenyl)-hydroxylamine
4-(hydroxyamino)-1,1'-biphenyl
AM20041003
[1,1'-biphenyl]-4-amine,n-hydroxy-
MYVLYOJYVMLSFA-UHFFFAOYSA-N
n-(biphenyl-4-yl)hydroxylamine
SCHEMBL4948154
[1,1'-biphenyl]-4-amine, n-hydroxy-
DTXSID00218300
Q27101983
4-amino-4-hydroxybiphenyl
n-hydroxy[1,1'-biphenyl]-4-amine
hydroxy-4-aminobiphenyl, n-

Research Excerpts

Bioavailability

Excerpt	Reference	Relevance
" In addition, in view of the putative role of N-OH-ABP as a major transport form of the carcinogen to the urinary bladder and of the absence of sulfotransferase activity in this tissue, we hypothesize that sulfotransferase activation in the liver may actually decrease the bioavailability of N-OH-ABP toward extrahepatic tissues and thus serve as an important overall detoxification mechanism for the urinary bladder."	( Metabolic activation of the N-hydroxy derivative of the carcinogen 4-aminobiphenyl by human tissue sulfotransferases. Chou, HC; Kadlubar, FF; Lang, NP, 1995)	0.29

Dosage Studied

Excerpt	Relevance	Reference
" Rats dosed with nitrosobenzene (56 mumol/kg), 4-chloronitrosobenzene (53 mumol/kg), 3,4-dichloronitrosobenzene (53 mumol/kg), 4-ethoxynitrosobenzene (86 mumol/kg), 4-nitrosobiphenyl(nitroso-BP, 55 mumol/kg) or 2-nitrosofluorene (256 mumol/kg) had maximal ferrihaemoglobin (HbFe3+) concn of 69, 68, 69, 67, 55 and 42% after 15, 25, 48, 35, 80 and 115 min, respectively, indicating differences in solubility of the nitrosoarenes in body fluids."	( The metabolism of 4-aminobiphenyl in rat. IV. Ferrihaemoglobin formation by 4-aminobiphenyl metabolites. Karreth, S; Lenk, W, 1991)	0.28
" In the mutation assay analysis, as the toxicant concentration increased, there was an increase in mutation fraction, indicating a direct correlation to metabolite dosing level and mutations occurring at these two loci."	( Quantification of N-(deoxyguanosin-8-yl)-4-aminobiphenyl adducts in human lymphoblastoid TK6 cells dosed with N-hydroxy-4-acetylaminobiphenyl and their relationship to mutation, toxicity, and gene expression profiling. Fan, W; Luo, W; Ricicki, EM; Vouros, P; Zarbl, H; Zhao, LP, 2006)	0.33

[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Role	Description
human xenobiotic metabolite	Any human metabolite produced by metabolism of a xenobiotic compound in humans.
carcinogenic agent	A role played by a chemical compound which is known to induce a process of carcinogenesis by corrupting normal cellular pathways, leading to the acquistion of tumoral capabilities.
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Class	Description
N-substituted amine
aminobiphenyl	Any member of the class of biphenyls in which the biphenyl skeleton is substituted by at least one amino group.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Pathway	Proteins	Compounds
Metabolism	1496	1108
Biological oxidations	150	276
Phase I - Functionalization of compounds	69	175
Cytochrome P450 - arranged by substrate type	30	110
Xenobiotics	4	50
Aromatic amines can be N-hydroxylated or N-dealkylated by CYP1A2	1	10
Phase II - Conjugation of compounds	73	122
Cytosolic sulfonation of small molecules	17	47

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	6 (20.00)	18.7374
1990's	15 (50.00)	18.2507
2000's	8 (26.67)	29.6817
2010's	1 (3.33)	24.3611
2020's	0 (0.00)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Publication Type	This drug (%)	All Drugs (%)
Trials	0 (0.00%)	5.53%
Reviews	1 (3.23%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	30 (96.77%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Classes	Roles
cytosine [no description available]	7.01	1	aminopyrimidine; pyrimidine nucleobase; pyrimidone	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
dimethyl sulfoxide Dimethyl Sulfoxide: A highly polar organic liquid, that is used widely as a chemical solvent. Because of its ability to penetrate biological membranes, it is used as a vehicle for topical application of pharmaceuticals. It is also used to protect tissue during CRYOPRESERVATION. Dimethyl sulfoxide shows a range of pharmacological activity including analgesia and anti-inflammation.. dimethyl sulfoxide : A 2-carbon sulfoxide in which the sulfur atom has two methyl substituents.	1.98	1	sulfoxide; volatile organic compound	alkylating agent; antidote; Escherichia coli metabolite; geroprotector; MRI contrast agent; non-narcotic analgesic; polar aprotic solvent; radical scavenger
2-amino-1-methyl-6-phenylimidazo(4,5-b)pyridine 2-amino-1-methyl-6-phenylimidazo(4,5-b)pyridine: mutagen from fried ground beef; structure given in first source. PhIP : An imidazopyridine that is 1H--imidazo[4,5-b]pyridine which is substituted at positions 1, 2, and 6 by methyl, amino, and phenyl groups, respectively. It is the most abundant of the mutagenic heterocyclic amines found in cooked meat and fish.	2.03	1	imidazopyridine; primary amino compound	carcinogenic agent; mutagen
2-aminofluorene [no description available]	1.96	1
n-hydroxy-2-aminofluorene N-hydroxy-2-aminofluorene: structure	2.88	4
hydroxyacetylaminofluorene Hydroxyacetylaminofluorene: A N-hydroxylated derivative of 2-ACETYLAMINOFLUORENE that has demonstrated carcinogenic action.	2.37	2	2-acetamidofluorenes
2-naphthylamine 2-Naphthylamine: A naphthalene derivative with carcinogenic action.. 2-naphthylamine : A naphthylamine carrying the amino group at position 2.	2.67	3	naphthylamine	carcinogenic agent
4-biphenylamine 4-biphenylamine: used in detection of sulfates, & as a carcinogen in cancer research; RN given refers to parent cpd; structure. biphenyl-4-amine : An aminobiphenyl that is biphenyl substituted by an amino group at position 4.	5.23	16	aminobiphenyl	carcinogenic agent
benzidine benzidine: RN given refers to parent cpd. benzidine : A member of the class of biphenyls that is 1,1'-biphenyl in which the hydrogen at the para-position of each phenyl group has been replaced by an amino group.	3.16	1	biphenyls; substituted aniline	carcinogenic agent
paraoxon [no description available]	1.97	1	aryl dialkyl phosphate; organophosphate insecticide	EC 3.1.1.7 (acetylcholinesterase) inhibitor; mouse metabolite
4-acetylaminobiphenyl [no description available]	1.98	1	biphenyls
n-hydroxy-4-acetylaminobiphenyl N-hydroxy-4-acetylaminobiphenyl: structure. N-hydroxy-4-acetylaminobiphenyl : A hydroxamic acid that is biphenyl-4-amine bearing N-hydroxy and N-acetyl substituents.	8.08	5	hydroxamic acid
bathocuproine bathocuproine: reagent for copper; RN given refers to parent cpd	2.41	2
1,7-phenanthroline [no description available]	2.41	2	phenanthroline
n-hydroxy-2-naphthylamine [no description available]	1.96	1
n-acetoxy-4-acetylaminobiphenyl [no description available]	2.68	3
n-hydroxy-3,2'-dimethyl-4-aminobiphenyl [no description available]	2.37	2
acetyl coenzyme a Acetyl Coenzyme A: Acetyl CoA participates in the biosynthesis of fatty acids and sterols, in the oxidation of fatty acids and in the metabolism of many amino acids. It also acts as a biological acetylating agent.	2.66	3	acyl-CoA	acyl donor; coenzyme; effector; fundamental metabolite
thioguanine anhydrous Thioguanine: An antineoplastic compound which also has antimetabolite action. The drug is used in the therapy of acute leukemia.. tioguanine : A 2-aminopurine that is the 6-thiono derivative of 2-amino-1,9-dihydro-6H-purine. Incorporates into DNA and inhibits synthesis. Used in the treatment of leukaemia.	1.98	1	2-aminopurines	anticoronaviral agent; antimetabolite; antineoplastic agent
ammonium sulfate Ammonium Sulfate: Sulfuric acid diammonium salt. It is used in CHEMICAL FRACTIONATION of proteins.. ammonium sulfate : An inorganic sulfate salt obtained by reaction of sulfuric acid with two equivalents of ammonia. A high-melting (decomposes above 280degreeC) white solid which is very soluble in water (70.6 g/100 g water at 0degreeC; 103.8 g/100 g water at 100degreeC), it is widely used as a fertilizer for alkaline soils.	1.98	1	ammonium salt; inorganic sulfate salt	fertilizer
nad NAD(1-) : An anionic form of nicotinamide adenine dinucleotide arising from deprotonation of the two OH groups of the diphosphate moiety.	2	1	organophosphate oxoanion	cofactor; human metabolite; hydrogen acceptor; Saccharomyces cerevisiae metabolite
deoxyguanosine [no description available]	4.37	6	purine 2'-deoxyribonucleoside; purines 2'-deoxy-D-ribonucleoside	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
methylnitronitrosoguanidine Methylnitronitrosoguanidine: A nitrosoguanidine derivative with potent mutagenic and carcinogenic properties.. N-methyl-N'-nitro-N-nitrosoguanidine : An N-nitroguanidine compound having nitroso and methyl substituents at the N'-position	1.98	1	nitroso compound	alkylating agent
8-hydroxy-2'-deoxyguanosine 8-Hydroxy-2'-Deoxyguanosine: Common oxidized form of deoxyguanosine in which C-8 position of guanine base has a carbonyl group.. 8-hydroxy-2'-deoxyguanosine : Guanosine substituted at the purine 8-position by a hydroxy group. It is used as a biomarker of oxidative DNA damage.	3.81	3	guanosines	biomarker
phosphorus radioisotopes Phosphorus Radioisotopes: Unstable isotopes of phosphorus that decay or disintegrate emitting radiation. P atoms with atomic weights 28-34 except 31 are radioactive phosphorus isotopes.	2.69	3

Condition	Relationship Strength	Studies
Benign Neoplasms [description not available]	3.33	2
Neoplasms New abnormal growth of tissue. Malignant neoplasms show a greater degree of anaplasia and have the properties of invasion and metastasis, compared to benign neoplasms.	3.33	2
Bladder Cancer [description not available]	3.08	5
Urinary Bladder Neoplasms Tumors or cancer of the URINARY BLADDER.	3.08	5
EHS Tumor [description not available]	1.96	1
Diathesis [description not available]	1.98	1
Experimental Neoplasms [description not available]	1.98	1
Sensitivity and Specificity Binary classification measures to assess test results. Sensitivity or recall rate is the proportion of true positives. Specificity is the probability of correctly determining the absence of a condition. (From Last, Dictionary of Epidemiology, 2d ed)	1.98	1
Carcinoma, Epidermoid [description not available]	1.98	1
Cell Transformation, Neoplastic Cell changes manifested by escape from control mechanisms, increased growth potential, alterations in the cell surface, karyotypic abnormalities, morphological and biochemical deviations from the norm, and other attributes conferring the ability to invade, metastasize, and kill.	1.98	1
Carcinoma, Squamous Cell A carcinoma derived from stratified SQUAMOUS EPITHELIAL CELLS. It may also occur in sites where glandular or columnar epithelium is normally present. (From Stedman, 25th ed)	1.98	1

n-hydroxy-4-aminobiphenyl

Cross-References

Synonyms (33)

Research Excerpts

Bioavailability

Dosage Studied

Roles (2)

Drug Classes (2)

Pathways (8)

Research

Studies (30)

Market Indicators

Research Demand Index: 10.99

Study Types

n-hydroxy-4-aminobiphenyl

Cross-References

Synonyms (33)

Research Excerpts

Bioavailability

Dosage Studied

Roles (2)

Drug Classes (2)

Pathways (8)

Research

Studies (30)

Market Indicators

Research Demand Index: 10.99

Study Types

Related Drugs (25)

Related Conditions (11)