3,4,3',4'-tetrachloroazobenzene

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

3,4,3',4'-tetrachloroazobenzene is an organochlorine compound with the formula C12H6Cl4N2. It is a yellow solid that is insoluble in water but soluble in organic solvents. It is synthesized by the reaction of 3,4-dichloroaniline with sodium nitrite in the presence of hydrochloric acid. This compound has been studied extensively for its toxicological effects, particularly its carcinogenic potential. It has been shown to be a potent mutagen and has been linked to liver cancer in animal studies. 3,4,3',4'-tetrachloroazobenzene is also a known environmental contaminant and has been detected in soil, water, and air. It is believed to be released into the environment from industrial processes, such as the manufacture of pesticides and dyes. The environmental persistence and potential toxicity of 3,4,3',4'-tetrachloroazobenzene make it a compound of concern, leading to research efforts to understand its fate and effects in the environment.'
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3,4,3',4'-tetrachloroazobenzene: unwanted contaminant found in commercial synthesis of dichloroaniline or herbicides made from dichloroaniline; implicated in outbreak of acne in chemical workers; RN given refers to parent cpd; structure [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID Source	ID
PubMed CID	26423
SCHEMBL ID	8759349
MeSH ID	M0060908

Synonyms (30)

Synonym
tcab
azobenzene, 3,3',4,4'-tetrachloro-
3,4,3',4'-tetrachloroazobenzene
diazene, bis(3,4-dichlorophenyl)-
ccris 1273
brn 4871675
bis(3,4-dichlorophenyl)diazene
14047-09-7
3,3',4,4'-tetrachloroazobenzene
3,4,3',4'-tetrachloroazobenzene, (z)-isomer
unii-pgg7w94gs9
pgg7w94gs9 ,
hsdb 8053
diazene,1,2-bis(3,4-dichlorophenyl)-
diazene, bis(3,4-dichlorophenyl)-, (z)-
64275-11-2
SCHEMBL8759349
SOBGIMQKWDUEPY-ISLYRVAYSA-N
(e)-1,2-bis(3,4-dichlorophenyl)diazene #
DTXSID6026086
3,3',4,4'-tetrachloro-azobenzene
bis(3,4-dichlorophenyl)-diazene
bis(3,4-dichlorophenyl)-(z)-diazene
diazene, bis(3,4-dichlorophenyl)- (9ci)
bis(3,4-dichlorophenyl)diazene, 9ci
3,3',4,4'-tetrachloroazobenzene 100 microg/ml in acetonitrile
tetrachloroazobenzene, 3,3',4,4'-
3,3',4,4'-tetrachloroazobenzene [iarc]
diazene, 1,2-bis(3,4-dichlorophenyl)-
DTXSID80860129

Research Excerpts

Toxicity

Excerpt	Reference	Relevance
" Both TCAB and TCAOB were more toxic than all other chemicals that have been tested in the chick embryo with the exception of 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD)."	( Embryotoxicity of 3,3',4,4'-tetrachloroazobenzene and 3,3',4,4'-tetrachloroazoxybenzene in the chick embryo. Hsia, MT; Kreamer, BL; Schrankel, KR, 1982)	0.26

Bioavailability

Excerpt	Reference	Relevance
" The absolute oral bioavailability was determined to be 30%."	( 3,3',4,4'-tetrachloroazobenzene absorption, disposition, and metabolism in male Fischer 344 rats. Kattnig, MJ; Liebler, DC; Mayersohn, M; McClure, T; Pillai, UA; Sipes, IG; Wang, DX; Ziegler, TL, 1996)	0.29

Dosage Studied

Excerpt	Relevance	Reference
" In 2 groups of weanling rats the same dosage of TCAOB was able to reduce the relative thymus weight to 31% and 38% of the comparable control animals."	( Thymic atrophy induced by acute exposure of 3,3',4,4'-tetrachloroazobenzene and 3,3',4,4'-tetrachloroazoxybenzene in rats. Burant, CF; Hsia, MT; Kreamer, BL; Schrankel, KR, 1982)	0.26
"2 and 32 mg/kg), 39-45% of the dosed radioactivity was excreted into the urine and 53-56% was recovered in the feces within 48 hr."	( 3,3',4,4'-tetrachloroazobenzene absorption, disposition, and metabolism in male Fischer 344 rats. Kattnig, MJ; Liebler, DC; Mayersohn, M; McClure, T; Pillai, UA; Sipes, IG; Wang, DX; Ziegler, TL, 1996)	0.29
" Mean body weight gains of all dosed groups of females were significantly less than those of the vehicle controls."	( Toxicology and carcinogenesis studies of 3,3',4,4'-tetrachloroazobenzene (TCAB) (CAS No. 14047-09-7) in Harlan Sprague-Dawley rats and B6C3F1 mice (gavage studies). , 2010)	0.36

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

Research

Studies (33)

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	17 (51.52)	18.7374
1990's	8 (24.24)	18.2507
2000's	2 (6.06)	29.6817
2010's	6 (18.18)	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]

Market Indicators

Research Demand Index: 17.44

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

Metric	This Compound (vs All)
Research Demand Index	17.44 (24.57)
Research Supply Index	3.58 (2.92)
Research Growth Index	4.39 (4.65)
Search Engine Demand Index	10.37 (26.88)
Search Engine Supply Index	2.00 (0.95)

This Compound (17.44)

All Compounds (24.57)

Study Types

Publication Type	This drug (%)	All Drugs (%)
Trials	0 (0.00%)	5.53%
Reviews	1 (2.86%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	34 (97.14%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Classes	Roles
eflornithine Eflornithine: An inhibitor of ORNITHINE DECARBOXYLASE, the rate limiting enzyme of the polyamine biosynthetic pathway.. eflornithine : A fluoroamino acid that is ornithine substituted by a difluoromethyl group at position 2.	1.97	1	alpha-amino acid; fluoroamino acid	trypanocidal drug
diuron Diuron: A pre-emergent herbicide.. diuron : A member of the class of 3-(3,4-substituted-phenyl)-1,1-dimethylureas that is urea in which both of the hydrogens attached to one nitrogen are substituted by methyl groups, and one of the hydrogens attached to the other nitrogen is substituted by a 3,4-dichlorophenyl group.	1.96	1	3-(3,4-substituted-phenyl)-1,1-dimethylurea; dichlorobenzene	environmental contaminant; mitochondrial respiratory-chain inhibitor; photosystem-II inhibitor; urea herbicide; xenobiotic
methyl methanesulfonate [no description available]	1.95	1	methanesulfonate ester	alkylating agent; apoptosis inducer; carcinogenic agent; genotoxin; mutagen
phenobarbital Phenobarbital: A barbituric acid derivative that acts as a nonselective central nervous system depressant. It potentiates GAMMA-AMINOBUTYRIC ACID action on GABA-A RECEPTORS, and modulates chloride currents through receptor channels. It also inhibits glutamate induced depolarizations.. phenobarbital : A member of the class of barbiturates, the structure of which is that of barbituric acid substituted at C-5 by ethyl and phenyl groups.	2.38	2	barbiturates	anticonvulsant; drug allergen; excitatory amino acid antagonist; sedative
propanil Propanil: A chlorinated anilide that is used as an herbicide.. propanil : An anilide resulting from the formal condensation of the carboxy group of propanoic acid with the amino group of 3,4-dichloroaniline. It is a herbicide used for the treatment of numerous grasses and broad-leaved weeds in rice, potatoes, and wheat.	8.23	6	anilide; dichlorobenzene	herbicide
3,4-dichloroaniline 3,4-dichloroaniline : A dichloroaniline having the two chloro-substituents at the 3- and 4-positions.	7.68	3	dichloroaniline	epitope; xenobiotic
hexachlorobenzene Hexachlorobenzene: An agricultural fungicide and seed treatment agent.. hexachlorobenzene : A member of the class of chlorobenzenes that is benzene in which all of the hydrogens are replaced by chlorines. An agricultural fungicide introduced in the mid-1940s and formerly used as a seed treatment, its use has been banned since 1984 under the Stockholm Convention on Persistent Organic Pollutants.	1.97	1	aromatic fungicide; chlorobenzenes	antifungal agrochemical; carcinogenic agent; persistent organic pollutant
linuron Linuron: A selective pre- and post-emergence herbicide. (From Merck Index, 11th ed). linuron : A member of the class of phenylureas that is N-methyl urea substituted by a methoxy group at position 1 and a 3,4-dichlorophenyl group at position 3.	1.96	1	dichlorobenzene; phenylureas	agrochemical; environmental contaminant; herbicide; xenobiotic
neburon neburon: structure in Merck Index, 9th ed, #6264	1.96	1	ureas
3,4,3',4'-tetrachloroazoxybenzene 3,4,3',4'-tetrachloroazoxybenzene: unwanted contaminant found in commercial synthesis of dichloroaniline or herbicides made from dichloroaniline; implicated in outbreak of acne in chemical workers	3.75	11
2-amino-3-methylimidazo(4,5-f)quinoline 2-amino-3-methylimidazo(4,5-f)quinoline: mutagen found in broiled food; RN given refers to parent cpd; structure given in first source; frequently abbreviated as IQ in the literature. 3-methyl-3H-imidazo[4,5-f]quinolin-2-amine : An imidazoquinoline that is 3H-imidazo[4,5-f]quinoline substituted by a methyl group at position 3 and an amino group at position 2.	1.96	1	imidazoquinoline	carcinogenic agent
nadp [no description available]	1.96	1
cyclin d1 Cyclin D1: Protein encoded by the bcl-1 gene which plays a critical role in regulating the cell cycle. Overexpression of cyclin D1 is the result of bcl-1 rearrangement, a t(11;14) translocation, and is implicated in various neoplasms.	2.07	1

Condition	Relationship Strength	Studies
Cancer of Lung [description not available]	2.1	1
Cancer of the Urethra [description not available]	2.48	2
Lung Neoplasms Tumors or cancer of the LUNG.	2.1	1
Urethral Neoplasms Cancer or tumors of the URETHRA. Benign epithelial tumors of the urethra usually consist of squamous and transitional cells. Primary urethral carcinomas are rare and typically of squamous cells. Urethral carcinoma is the only urological malignancy that is more common in females than in males.	2.48	2
Contact Dermatitis [description not available]	2.05	1
Chloracne ACNE-like skin eruptions caused by exposure to CHLORINE-containing compounds. Exposure can be by inhalation, ingestion, or through the skin. Chloracne is often seen in people who have occupational contact with chlorinated pesticides, wood preservatives, and sealants.	2.05	1
Dermatitis, Contact A type of acute or chronic skin reaction in which sensitivity is manifested by reactivity to materials or substances coming in contact with the skin. It may involve allergic or non-allergic mechanisms.	2.05	1
Bladder Cancer [description not available]	2.05	1
Urethral Diseases Pathological processes involving the URETHRA.	2.05	1
Cancer of the Ureter [description not available]	2.05	1
Urinary Bladder Neoplasms Tumors or cancer of the URINARY BLADDER.	2.05	1
Carcinoma, Transitional Cell A malignant neoplasm derived from TRANSITIONAL EPITHELIAL CELLS, occurring chiefly in the URINARY BLADDER; URETERS; or RENAL PELVIS.	2.05	1
Hyperplasia An increase in the number of cells in a tissue or organ without tumor formation. It differs from HYPERTROPHY, which is an increase in bulk without an increase in the number of cells.	2.47	2
Kidney Diseases Pathological processes of the KIDNEY or its component tissues.	2.05	1
Ureteral Neoplasms Cancer or tumors of the URETER which may cause obstruction leading to hydroureter, HYDRONEPHROSIS, and PYELONEPHRITIS. HEMATURIA is a common symptom.	2.05	1
Body Weight The mass or quantity of heaviness of an individual. It is expressed by units of pounds or kilograms.	2.9	4
Experimental Neoplasms [description not available]	2.05	1
Carcinoma, Epidermoid [description not available]	2.07	1
Congenital Epulides [description not available]	2.07	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)	2.07	1
Acne [description not available]	2.36	2
Dermatitis, Occupational A recurrent contact dermatitis caused by substances found in the work place.	2.36	2
Acne Vulgaris A chronic disorder of the pilosebaceous apparatus associated with an increase in sebum secretion. It is characterized by open comedones (blackheads), closed comedones (whiteheads), and pustular nodules. The cause is unknown, but heredity and age are predisposing factors.	2.36	2
Experimental Leukemia [description not available]	1.96	1
Atrophy Decrease in the size of a cell, tissue, organ, or multiple organs, associated with a variety of pathological conditions such as abnormal cellular changes, ischemia, malnutrition, or hormonal changes.	1.96	1
Chromosome-Defective Micronuclei [description not available]	2	1
Cleft Palate, Isolated [description not available]	1.97	1
Fetal Death Death of the developing young in utero. BIRTH of a dead FETUS is STILLBIRTH.	1.97	1
Cleft Palate Congenital fissure of the soft and/or hard palate, due to faulty fusion.	1.97	1
Pregnancy The status during which female mammals carry their developing young (EMBRYOS or FETUSES) in utero before birth, beginning from FERTILIZATION to BIRTH.	1.97	1

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