Page last updated: 2024-11-11

amocarzine

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

Description

amocarzine : A thiourea resulting from the formal condensation of the secondary amino group of 1-methylpiperazine and the primary amino group of N-(4-nitrophenyl)benzene-1,4-diamine with carbonothioic O,O-acid. [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]

Cross-References

ID SourceID
PubMed CID5464102
CHEMBL ID469328
CHEBI ID38946
SCHEMBL ID157806
MeSH IDM0147122

Synonyms (31)

Synonym
36590-19-9
CHEBI:38946 ,
amocarzinum
amocarzina
phenthiourezine
amocarzine
4-methyl-n-{4-[(4-nitrophenyl)amino]phenyl}piperazine-1-carbothioamide
4-methyl-n-(4-((4-nitrophenyl)amino)phenyl)-1-piperazinecarbothioamide
cgp 6140
4-methyl-n-[4-(4-nitroanilino)phenyl]piperazine-1-carbothioamide
CHEMBL469328
unii-99807u412y
99807u412y ,
amocarzina [inn-spanish]
4-methyl-4'-(p-nitroanilino)thio-1-piperazinecarboxanilide
1-piperazinecarbothioamide, 4-methyl-n-(4-((4-nitrophenyl)amino)phenyl)-
s 80016
amocarzinum [inn-latin]
amocarzine [inn]
amocarzine [who-dd]
amocarzine [mart.]
amocarzine [mi]
SCHEMBL157806
4-methyl-n-[4-[(4-nitrophenyl)amino]phenyl]-1-piperazinecarbothioamide
1-piperazinecarbothioamide,4-methyl-n-[4-[(4-nitrophenyl)amino]phenyl]-
cgp6140
Q27118042
BCP28101
cgp 6140; phenthiourezine; s 80016
4-methyl-n-(4-((4-nitrophenyl)amino)phenyl)piperazine-1-carbothioamide
DTXSID90865827

Research Excerpts

Effects

ExcerptReferenceRelevance
"Amocarzine has been reported to have onchocercacidal effects. "( Longterm follow-up of onchocerciasis patients in Latin America after treatment and retreatment with amocarzine. Preliminary results.
Guderian, R; Moran, M; Poltera, AA; Striebel, HP; Zea-Flores, G, 1991
)
1.94

Pharmacokinetics

ExcerptReferenceRelevance
" Biochemical and pharmacokinetic studies suggest that the selective toxicity of the new series of drugs towards filarial parasites is most likely preferential drug uptake by the pathogen."( Activity, mechanism of action and pharmacokinetics of 2-tert-butylbenzothiazole and CGP 6140 (amocarzine) antifilarial drugs.
Davies, KP; Köhler, P; Zahner, H, 1992
)
0.5
" The median time to Cmax was 3 h in fed and 2 h in fasting patients."( The influence of food on the pharmacokinetics of CGP 6140 (amocarzine) after oral administration of a 1200 mg single dose to patients with onchocerciasis.
Dubois, JP; Ginger, CD; Lecaillon, JB; Pichard, E; Poltera, AA; Soula, G, 1990
)
0.52

Bioavailability

A repeat low dose regimen of amocarzine (3 mg/kg twice daily post-prandially for three consecutive days) was well absorbed with predictable plasma levels, macro- and microfilaricidal with good local and systemic tolerability in patients with moderate to heavy onchocerciasis.

ExcerptReferenceRelevance
" In conclusion, a repeat low dose regimen of amocarzine (3 mg/kg twice daily post-prandially for three consecutive days) was well absorbed with predictable plasma levels, macro- and microfilaricidal with good local and systemic tolerability in patients with moderate to heavy onchocerciasis."( Amocarzine investigated as oral onchocercacidal drug in 272 adult male patients from Guatemala. Results from three dose regimens spread over three days.
Beltranena, F; de Ramirez, I; Lecaillon, JB; Lopez, M; Moran, M; Palomo, M; Poltera, AA; Zak, F; Zea-Flores, CE; Zea-Flores, G, 1991
)
1.98
" The relative improvement of bioavailability of amocarzine due to food was less prominent than previously obtained after a high dose of 1200 mg which demonstrated a bioavailability improvement of a factor of three."( Influence of food related to dose on the pharmacokinetics of amocarzine and of its N-oxide metabolite, CGP 13 231, after oral administration to 20 onchocerciasis male patients from Guatemala.
de Ramirez, I; Lecaillon, JB; Nowell de Arevalo, A; Poltera, AA; Zea-Flores, G, 1991
)
0.78
" A greater variability in plasma concentrations was apparent after the 800 and 1600 mg doses indicating a poor bioavailability of the drug administered in fasting conditions to several patients."( Pharmacokinetics of CGP 6140 (amocarzine) after oral administration of single 100-1600 mg doses to patients with onchocerciasis.
Awadzi, K; Dubois, JP; Ginger, CD; Lecaillon, JB; Poltera, AA, 1990
)
0.57
" The low solubility of CGP 6140 in aqueous solutions at neutral pH and its higher solubility at acidic pH might explain the increase in bioavailability after food intake."( The influence of food on the pharmacokinetics of CGP 6140 (amocarzine) after oral administration of a 1200 mg single dose to patients with onchocerciasis.
Dubois, JP; Ginger, CD; Lecaillon, JB; Pichard, E; Poltera, AA; Soula, G, 1990
)
0.52

Dosage Studied

Single dosing after overnight fasting proved to produce irregular absorption of amocarzine. Some microfilaricidal effect was achieved.

ExcerptRelevanceReference
"The clinical investigations with three types of a three days regimen of amocarzine permitted to adjust the fixed dosing to the body weight related dosing and subsequently the administration of amocarzine from fasting state to drug intake after food."( Amocarzine investigated as oral onchocercacidal drug in 272 adult male patients from Guatemala. Results from three dose regimens spread over three days.
Beltranena, F; de Ramirez, I; Lecaillon, JB; Lopez, M; Moran, M; Palomo, M; Poltera, AA; Zak, F; Zea-Flores, CE; Zea-Flores, G, 1991
)
1.96
" Single dosing after overnight fasting proved to produce irregular absorption of amocarzine, although some microfilaricidal effect was achieved."( Onchocercacidal effect of three drug regimens of amocarzine in 148 patients of two races and both sexes from Esmeraldas, Ecuador.
Anselmi, M; Cascante, S; Guderian, RH; Lecaillon, JB; Moran, M; Naranjo, A; Poltera, AA; Proaño, R; Zak, F, 1991
)
0.76
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
antinematodal drugA substance used in the treatment or control of nematode infestations.
[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]

Drug Classes (4)

ClassDescription
C-nitro compoundA nitro compound having the nitro group (-NO2) attached to a carbon atom.
N-methylpiperazine
thioureasCompounds of general formula RR'NC(=S)NR''R'''.
secondary amino compoundA compound formally derived from ammonia by replacing two hydrogen atoms by organyl groups.
[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]

Bioassays (21)

Assay IDTitleYearJournalArticle
AID1079931Moderate liver toxicity, defined via clinical-chemistry results: ALT or AST serum activity 6 times the normal upper limit (N) or alkaline phosphatase serum activity of 1.7 N. Value is number of references indexed. [column 'BIOL' in source]
AID1079943Malignant tumor, proven histopathologically. Value is number of references indexed. [column 'T.MAL' in source]
AID1079945Animal toxicity known. [column 'TOXIC' in source]
AID1079938Chronic liver disease either proven histopathologically, or through a chonic elevation of serum amino-transferase activity after 6 months. Value is number of references indexed. [column 'CHRON' in source]
AID1079947Comments (NB not yet translated). [column 'COMMENTAIRES' in source]
AID1079933Acute liver toxicity defined via clinical observations and clear clinical-chemistry results: serum ALT or AST activity > 6 N or serum alkaline phosphatases activity > 1.7 N. This category includes cytolytic, choleostatic and mixed liver toxicity. Value is
AID1079937Severe hepatitis, defined as possibly life-threatening liver failure or through clinical observations. Value is number of references indexed. [column 'MASS' in source]
AID1079942Steatosis, proven histopathologically. Value is number of references indexed. [column 'STEAT' in source]
AID393031Antiparasitic activity against Onchocerca gutturosa assessed as inhibition of MTT formazan formation2009Bioorganic & medicinal chemistry, Feb-15, Volume: 17, Issue:4
New potent imidazoisoquinolinone derivatives as anti-Trypanosoma cruzi agents: biological evaluation and structure-activity relationships.
AID1079940Granulomatous liver disease, proven histopathologically. Value is number of references indexed. [column 'GRAN' in source]
AID1079941Liver damage due to vascular disease: peliosis hepatitis, hepatic veno-occlusive disease, Budd-Chiari syndrome. Value is number of references indexed. [column 'VASC' in source]
AID1079948Times to onset, minimal and maximal, observed in the indexed observations. [column 'DELAI' in source]
AID1079936Choleostatic liver toxicity, either proven histopathologically or where the ratio of maximal ALT or AST activity above normal to that of Alkaline Phosphatase is < 2 (see ACUTE). Value is number of references indexed. [column 'CHOLE' in source]
AID1079934Highest frequency of acute liver toxicity observed during clinical trials, expressed as a percentage. [column '% AIGUE' in source]
AID1079932Highest frequency of moderate liver toxicity observed during clinical trials, expressed as a percentage. [column '% BIOL' in source]
AID1079944Benign tumor, proven histopathologically. Value is number of references indexed. [column 'T.BEN' in source]
AID1079939Cirrhosis, proven histopathologically. Value is number of references indexed. [column 'CIRRH' in source]
AID1079946Presence of at least one case with successful reintroduction. [column 'REINT' in source]
AID1079949Proposed mechanism(s) of liver damage. [column 'MEC' in source]
AID393030Antiparasitic activity against Onchocerca gutturosa assessed as reduction in motility after 120 hrs2009Bioorganic & medicinal chemistry, Feb-15, Volume: 17, Issue:4
New potent imidazoisoquinolinone derivatives as anti-Trypanosoma cruzi agents: biological evaluation and structure-activity relationships.
AID1079935Cytolytic liver toxicity, either proven histopathologically or where the ratio of maximal ALT or AST activity above normal to that of Alkaline Phosphatase is > 5 (see ACUTE). Value is number of references indexed. [column 'CYTOL' in source]
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (36)

TimeframeStudies, This Drug (%)All Drugs %
pre-199014 (38.89)18.7374
1990's21 (58.33)18.2507
2000's1 (2.78)29.6817
2010's0 (0.00)24.3611
2020's0 (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: 10.33

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 weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index10.33 (24.57)
Research Supply Index3.93 (2.92)
Research Growth Index4.26 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (10.33)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials12 (31.58%)5.53%
Reviews3 (7.89%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other23 (60.53%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]