diphenylarsinic acid profile

Diphenylarsinic acid, also known as phenylarsonic acid, is an organoarsenic compound. It is a white crystalline solid that is sparingly soluble in water but soluble in organic solvents. It is a potent antibacterial agent and was historically used in the treatment of syphilis, but its use has been largely discontinued due to its toxicity. Diphenylarsinic acid is synthesized by the reaction of phenylarsonic acid with phenylmagnesium bromide. Its importance lies in its historical significance as a pharmaceutical and its use as an analytical reagent for the detection of certain metal ions. Research on this compound continues in areas such as the development of new therapeutic agents and the study of its environmental impact.'

diphenylarsinic acid: a degradation product of diphenylcyanoarsine or diphenylchloroarsine, both of which were developed as chemical warfare agents; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

ID Source	ID
PubMed CID	20770
SCHEMBL ID	159450
MeSH ID	M0475640

Synonym
brn 2937755
arsinic acid, diphenyl-
arsine oxide, hydroxydiphenyl-
nsc 41374
kyselina difenylarsinita [czech]
diphenylarsinic acid
nsc-41374
4656-80-8
antineoplastic-41374
nsc41374
kyselina difenylarsinita
tj4e9ch5gh ,
unii-tj4e9ch5gh
4-16-00-01178 (beilstein handbook reference)
SCHEMBL159450
DTXSID80196874
as,as-diphenylarsinic acid
arsinic acid, as,as-diphenyl-

Research Excerpts

Overview

Diphenylarsinic acid (DPAA) is a non-natural pentavalent organic arsenic and was detected in well water in Kamisu, Ibaraki, Japan in 2003. It is an emerging phenylarsenic compound derived from chemical warfare agents.

Excerpt	Reference	Relevance
"Diphenylarsinic acid (DPAA) is a non-natural pentavalent organic arsenic and was detected in well water in Kamisu, Ibaraki, Japan in 2003. "	( Diphenylarsinic acid induced activation of MAP kinases, transcription factors, and oxidative stress-responsive factors and hypersecretion of cytokines in cultured normal human cerebellar astrocytes. Negishi, T; Sasaki, S; Tsuzuki, T; Yukawa, K, 2022)	3.61
"Diphenylarsinic acid (DPAA) is an emerging phenylarsenic compound derived from chemical warfare agents. "	( Contrasting effects of iron reduction on thionation of diphenylarsinic acid in a biostimulated Acrisol. Cheng, N; Christie, P; Luo, Y; Yang, R; Zhang, J; Zhang, M; Zhu, M, 2020)	2.25
"Diphenylarsinic acid (DPAA) is a toxic phenylarsenical compound often found around sites contaminated with phenylarsenic chemical warfare agents, diphenylcyanoarsine or diphenylchloroarsine, which were buried in soil after the World Wars. "	( Formation of diphenylthioarsinic acid from diphenylarsinic acid under anaerobic sulfate-reducing soil conditions. Fujii, K; Guan, L; Harada, N; Hisatomi, S; Nakajima, M; Nonaka, M, 2013)	2.1
"Diphenylarsinic acid (DPAA) is a major organic arsenic (As) compound derived from abandoned chemical weapons. "	( Solid-solution partitioning and thionation of diphenylarsinic acid in a flooded soil under the impact of sulfate and iron reduction. Christie, P; Hu, X; Li, Y; Luo, Y; Tu, C; Wei, J; Zhang, H; Zhang, L; Zhu, M, 2016)	2.14
"Diphenylarsinic acid (DPAA) is an organic arsenic compound used for the synthesis of chemical weapons. "	( Long-term accumulation of diphenylarsinic acid in the central nervous system of cynomolgus monkeys. Hosoya, T; Ishii, K; Iwasaki, N; Masuda, T; Nakayama, T; Seto, Y; Shibata, Y; Tamaoka, A; Tanaka, R, 2017)	2.2
"Diphenylarsinic acid (DPAA) is an environmental degradation product of diphenylarsine chloride or diphenylarsine cyanide, which were chemical warfare agents produced by Japan during the World War II. "	( Systemic distribution and speciation of diphenylarsinic acid fed to rats. Le, XC; McKnight-Whitford, T; Naranmandura, H; Ogra, Y; Suzuki, KT; Suzuki, N; Takano, J, 2009)	2.06
"Diphenylarsinic acid (DPAA(V)) is a chemical precursor as well as a degradation product of arsenic-containing chemical weapons such as Clark 1 (diphenylarsine chloride) and Clark 2 (diphenylarsine cyanide). "	( The role of glutathione in the metabolism of diphenylarsinic acid in rats. Hirano, S; Kobayashi, Y, 2013)	2.09
"Diphenylarsinic acid (DPAsV) is a degradation product of chemical warfare agents, over which there has been a public outcry in the Kamisu Area of Ibaraki Prefecture in Japan. "	( Activation of the Nrf2 pathway, but decreased gamma-glutamylcysteine synthetase heavy subunit chain levels and caspase-3-dependent apoptosis during exposure of primary mouse hepatocytes to diphenylarsinic acid. Kumagai, Y; Manji, A; Shinkai, Y; Sumi, D; Toyama, T, 2007)	1.97

Toxicity

Excerpt	Reference	Relevance
" By contrast, when the cytotoxic potential of DPA-GS was compared with that of DPAA, DPA-GS was about 1,000 times more toxic than DPAA, suggesting that enhancement of DPAA toxicity by SH compounds might be due to the formation of adducts in the culture medium."	( The role of glutathione on the cytotoxic effects and cellular uptake of diphenylarsinic acid, a degradation product of chemical warfare agents. Kaise, T; Kinoshita, K; Miyazaki, K; Noguchi, A; Ochi, T; Suzuki, T, 2006)	0.57
" These results suggest that DPAA is toxic to the bile duct epithelium in rats."	( A chronic toxicity study of diphenylarsinic acid in F344 rats in drinking water for 52 weeks. Doi, K; Fujioka, M; Gi, M; Ishii, N; Kakehashi, A; Kawachi, S; Tatsumi, K; Wanibuchi, H; Yamaguchi, T; Yamano, S, 2017)	0.75

Dosage Studied

Excerpt	Relevance	Reference
"2mg/kg/day, suggesting the absence of a linear dose-response relationship between the dose and deposition of DPAA(V)."	( High-sensitivity quantitative analysis reveals the non-linear relationship between the dose and deposition of diphenylarsinic acid in the rat central nervous system following its subchronic exposure. Ishii, K; Iwasaki, N; Masuda, T; Nakayama, T; Shibata, Y; Tamaoka, A, )	0.34
" The effect on DA level changed slowly after DPAA administration, with a bell-shaped dose-response relationship."	( Toxicokinetic characteristics and effects of diphenylarsinic acid on dopamine in the striatum of free-moving mice. Shibata, Y; Umezu, T, 2021)	0.88

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

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	1 (1.96)	18.7374
1990's	0 (0.00)	18.2507
2000's	19 (37.25)	29.6817
2010's	27 (52.94)	24.3611
2020's	4 (7.84)	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 (1.82%)	6.00%
Case Studies	2 (3.64%)	4.05%
Observational	0 (0.00%)	0.25%
Other	52 (94.55%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Classes	Roles
arsenic acid arsenic acid: RN given refers to orthoarsenic acid(H3AsO4); see also sodium arsenate. arsenic acid : An arsenic oxoacid comprising one oxo group and three hydroxy groups attached to a central arsenic atom.	7.05	1	arsenic oxoacid	Escherichia coli metabolite
cacodylic acid dimethylarsinic acid : The organoarsenic compound that is arsenic acid substituted on the central arsenic atom with two methyl groups.	2.03	1	organoarsenic compound	xenobiotic metabolite
oxophenylarsine oxophenylarsine: inhibits protein-tyrosine-phosphatase. phenylarsine oxide : An arsine oxide derived from phenylarsine.	2.02	1	arsine oxides	antineoplastic agent; apoptosis inducer; EC 3.1.3.48 (protein-tyrosine-phosphatase) inhibitor
diethylnitrosamine Diethylnitrosamine: A nitrosamine derivative with alkylating, carcinogenic, and mutagenic properties.. N-nitrosodiethylamine : A nitrosamine that is N-ethylethanamine substituted by a nitroso group at the N-atom.	2.08	1	nitrosamine	carcinogenic agent; hepatotoxic agent; mutagen
benzenearsonic acid benzenearsonic acid: RN given refers to parent cpd; structure	2.96	4	arsonic acids; organoarsonic acid
malondialdehyde Malondialdehyde: The dialdehyde of malonic acid.. malonaldehyde : A dialdehyde that is propane substituted by two oxo groups at the terminal carbon atoms respectively. A biomarker of oxidative damage to lipids caused by smoking, it exists in vivo mainly in the enol form.	2.03	1	dialdehyde	biomarker
titanium Titanium: A dark-gray, metallic element of widespread distribution but occurring in small amounts with atomic number, 22, atomic weight, 47.867 and symbol, Ti; specific gravity, 4.5; used for fixation of fractures.	7.52	2	titanium group element atom
titanium dioxide titanium dioxide: used medically as protectant against externally caused irritation & sunlight; high concentrations of dust may cause irritation to respiratory tract; RN given refers to titanium oxide (TiO2); structure. titanium dioxide : A titanium oxide with the formula TiO2. A naturally occurring oxide sourced from ilmenite, rutile and anatase, it has a wide range of applications.	7.52	2	titanium oxides	food colouring
dimethylarsinous acid dimethylarsinous acid: a reactive organic intermediate of dimethylarsinic acid involved in toxicity	2.03	1	methylarsinous acid
nadp [no description available]	2.03	1
arsenic Arsenic: A shiny gray element with atomic symbol As, atomic number 33, and atomic weight 75. It occurs throughout the universe, mostly in the form of metallic arsenides. Most forms are toxic. According to the Fourth Annual Report on Carcinogens (NTP 85-002, 1985), arsenic and certain arsenic compounds have been listed as known carcinogens. (From Merck Index, 11th ed)	6.42	51	metalloid atom; pnictogen	micronutrient
ferrihydrite ferric oxyhydroxide: an antiferromagnetic material; constitutes the core of natural ferritin; mol form 5Fe2O3.9H2O	2.1	1
glutaminase [no description available]	2.74	3

Condition	Relationship Strength	Studies
Body Weight The mass or quantity of heaviness of an individual. It is expressed by units of pounds or kilograms.	2.79	3
Cancer of Liver [description not available]	2.78	3
Liver Neoplasms Tumors or cancer of the LIVER.	2.78	3
Acute Liver Injury, Drug-Induced [description not available]	2.17	1
Liver Dysfunction [description not available]	2.17	1
Liver Diseases Pathological processes of the LIVER.	2.17	1
Chemical and Drug Induced Liver Injury A spectrum of clinical liver diseases ranging from mild biochemical abnormalities to ACUTE LIVER FAILURE, caused by drugs, drug metabolites, herbal and dietary supplements and chemicals from the environment.	2.17	1
Arsenic Encephalopathy [description not available]	4.47	8
Carcinogenesis The origin, production or development of cancer through genotypic and phenotypic changes which upset the normal balance between cell proliferation and cell death. Carcinogenesis generally requires a constellation of steps, which may occur quickly or over a period of many years.	7.08	1
Pregnancy The status during which female mammals carry their developing young (EMBRYOS or FETUSES) in utero before birth, beginning from FERTILIZATION to BIRTH.	2.74	3
Abortion, Tubal [description not available]	2.1	1
Abortion, Spontaneous Expulsion of the product of FERTILIZATION before completing the term of GESTATION and without deliberate interference.	2.1	1
Brain Disorders [description not available]	3.37	2
Brain Diseases Pathologic conditions affecting the BRAIN, which is composed of the intracranial components of the CENTRAL NERVOUS SYSTEM. This includes (but is not limited to) the CEREBRAL CORTEX; intracranial white matter; BASAL GANGLIA; THALAMUS; HYPOTHALAMUS; BRAIN STEM; and CEREBELLUM.	3.37	2
Chronic Illness [description not available]	2.15	1
Chronic Disease Diseases which have one or more of the following characteristics: they are permanent, leave residual disability, are caused by nonreversible pathological alteration, require special training of the patient for rehabilitation, or may be expected to require a long period of supervision, observation, or care (Dictionary of Health Services Management, 2d ed). For epidemiological studies chronic disease often includes HEART DISEASES; STROKE; CANCER; and diabetes (DIABETES MELLITUS, TYPE 2).	2.15	1
Hepatocellular Carcinoma [description not available]	2.95	4
Carcinoma, Hepatocellular A primary malignant neoplasm of epithelial liver cells. It ranges from a well-differentiated tumor with EPITHELIAL CELLS indistinguishable from normal HEPATOCYTES to a poorly differentiated neoplasm. The cells may be uniform or markedly pleomorphic, or form GIANT CELLS. Several classification schemes have been suggested.	2.95	4
Deficiency, Mental [description not available]	2.02	1
Intellectual Disability Subnormal intellectual functioning which originates during the developmental period. This has multiple potential etiologies, including genetic defects and perinatal insults. Intelligence quotient (IQ) scores are commonly used to determine whether an individual has an intellectual disability. IQ scores between 70 and 79 are in the borderline range. Scores below 67 are in the disabled range. (from Joynt, Clinical Neurology, 1992, Ch55, p28)	2.02	1
Conjugate Nystagmus [description not available]	2.03	1
Nervous System Disorders [description not available]	2.03	1
Nervous System Diseases Diseases of the central and peripheral nervous system. This includes disorders of the brain, spinal cord, cranial nerves, peripheral nerves, nerve roots, autonomic nervous system, neuromuscular junction, and muscle.	2.03	1
Poisoning Used with drugs, chemicals, and industrial materials for human or animal poisoning, acute or chronic, whether the poisoning is accidental, occupational, suicidal, by medication error, or by environmental exposure.	2.03	1
Encephalopathy, Toxic [description not available]	2.03	1
Cerebellar Diseases Diseases that affect the structure or function of the cerebellum. Cardinal manifestations of cerebellar dysfunction include dysmetria, GAIT ATAXIA, and MUSCLE HYPOTONIA.	2.03	1
Anxiety Neuroses [description not available]	2.03	1
Dyskinesia Syndromes [description not available]	2.03	1
Developmental Psychomotor Disorders [description not available]	2.03	1
Anxiety Disorders Persistent and disabling ANXIETY.	2.03	1
Movement Disorders Syndromes which feature DYSKINESIAS as a cardinal manifestation of the disease process. Included in this category are degenerative, hereditary, post-infectious, medication-induced, post-inflammatory, and post-traumatic conditions.	2.03	1

diphenylarsinic acid

Description

Cross-References

Synonyms (18)

Research Excerpts

Overview

Toxicity

Dosage Studied

Research

Studies (51)

Market Indicators

Research Demand Index: 15.59

Study Types

diphenylarsinic acid

Description

Cross-References

Synonyms (18)

Research Excerpts

Overview

Toxicity

Dosage Studied

Research

Studies (51)

Market Indicators

Research Demand Index: 15.59

Study Types

Related Drugs (13)

Related Conditions (31)