Compounds > aditoprim
Page last updated: 2024-11-06

aditoprim

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

Description

aditoprim: structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID68755
CHEMBL ID293299
SCHEMBL ID2109578
MeSH IDM0146328

Synonyms (25)

Synonym
aditoprimum [latin]
2,4-diamino-5-(4-(dimethylamino)-3,5-dimethoxybenzyl)pyrimidine
aditoprim [inn]
aditoprima [spanish]
aditoprim
5-((4-(dimethylamino)-3,5-dimethoxyphenyl)methyl)-2,4-pyrimidinediamine
2,4-pyrimidinediamine, 5-((4-(dimethylamino)-3,5-dimethoxyphenyl)methyl)-
brn 0697192
CHEMBL293299
5-[[4-(dimethylamino)-3,5-dimethoxyphenyl]methyl]pyrimidine-2,4-diamine
unii-2z81wdx2zh
2z81wdx2zh ,
56066-63-8
5-25-13-00395 (beilstein handbook reference)
aditoprimum
aditoprima
bdbm50405954
SCHEMBL2109578
DTXSID90204616
Q15633946
BCP19328
5-[(4-dimethylamino-3,5-dimethoxy-phenyl)methyl]pyrimidine-2,4-diamine
5-(4-(dimethylamino)-3,5-dimethoxybenzyl)pyrimidine-2,4-diamine
CS-0255053
aditoprime

Research Excerpts

Overview

Aditoprim (ADP) is a recently developed dihydrofolate reductase inhibitor. It has shown promise for therapeutic use in veterinary medicine because of its excellent pharmacokinetic properties.

ExcerptReferenceRelevance
"Aditoprim (ADP) is a newly developed antibacterial agent in veterinary medicine. "( Metabolism and Disposition of Aditoprim in Swine, Broilers, Carp and Rats.
Ahmad, I; Chen, D; Huang, L; Klímová, B; Kuča, K; Liu, Z; Pan, Y; Tao, Y; Wan, D; Wang, L; Wu, Q; Xie, S; Yuan, Z, 2016)		2.17
"Aditoprim (ADP) is a recently developed dihydrofolate reductase inhibitor that has shown promise for therapeutic use in veterinary medicine because of its excellent pharmacokinetic properties. "( Simultaneous determination of aditoprim and its three major metabolites in pigs, broilers and carp tissues, and its application in tissue distribution and depletion studies.
Huang, L; Pan, Y; Wang, L; Wu, Q; Xie, S; Yuan, Z, 2016)		2.17
"Aditoprim (AP) is a new dihydrofolate reductase inhibitor, which is structurally related to trimethoprim (TMP). "( Some pharmacokinetic data of aditoprim and trimethoprim in healthy and tick-borne fever infected dwarf goats.
Knoppert, NW; Korstanje, C; Nijmeijer, SM; van Duin, CT; van Gogh, H; van Miert, AS, 1988)		2.01

Effects

ExcerptReferenceRelevance
"Aditoprim (ADP) has potential use as an antimicrobial agent in animals. "( The antibacterial activities of aditoprim and its efficacy in the treatment of swine streptococcosis.
Chen, D; Cheng, G; Hao, H; Huang, L; Liu, Z; Pan, Y; Wang, L; Wang, Y; Xie, S; Xu, Y; Yuan, Z; Zhu, X, 2017)		2.18

Toxicity

ExcerptReferenceRelevance
" The LD50 calculated was 1400 mg kg(-1) body weight (BW) day(-1) in rats and 1130 mg kg(-1) BW day(-1) in mice."( Safety assessment of aditoprim acute, subchronic toxicity and mutagenicity studies.
Chen, D; Cheng, G; Huang, L; Ihsan, A; Liu, Q; Liu, Z; Pan, Y; Tan, Z; Tao, Y; Wang, X; Yuan, Z, 2015)		0.74

Pharmacokinetics

Aditoprim had a longer half-life and a larger volume of distribution than trimethoprim (TMP) This suggests enhanced and prolonged antibacterial activity of ad itoprim over TMP.

ExcerptReferenceRelevance
" Pharmacokinetic characteristics of aditoprim in healthy cows were a large volume of distribution (6."( Effects of endotoxin-induced mastitis on the pharmacokinetic properties of aditoprim in dairy cows.
Graser, T; Lohuis, JA; Ludwig, B; Rehm, WF; Rohde, E; Schneider, B; Sutter, HM; van Miert, AS; van Werven, T; Wanner, M, 1992)		0.79
"Some pharmacokinetic parameters of aditoprim were determined in 3- and 6-month-old pigs."( The influence of age on the pharmacokinetics of aditoprim in pigs after intravenous and oral administration.
Müller, P; Riond, JL; Wanner, M, 1992)		0.82
" In comparison with trimethoprim (TMP), the new inhibitor of DHFR, aditoprim, had a longer half-life and a larger volume of distribution, suggesting enhanced and prolonged antibacterial activity of aditoprim over TMP."( Pharmacokinetics of aditoprim in goats using a radioassay.
Iqbal, MP; Mahboobali, N; Mahmood, MA; Niazi, SK, )		0.69
" The elimination half-life of aditoprim (6."( Pharmacokinetics of aditoprim and trimethoprim in buffalo calves.
Ashfaq, MK; Iqbal, MP; Khawaja, KN; Mahboobali, M; Niazi, SK, 1994)		0.9
" After intravenous administration to conventionally fed calves, aditoprim total body clearance increased and elimination half-life decreased with age."( Comparative pharmacokinetics of aditoprim in milk-fed and conventionally fed calves of different ages.
Riond, JL; Sutter, HM; Wanner, M, 1993)		0.81
" Consequently, mean aditoprim elimination half-life was relatively short (3."( Research note: pharmacokinetics of aditoprim in turkeys after intravenous and oral administration.
Engeli, J; Riond, JL; Wanner, M, 1993)		0.89

Bioavailability

ExcerptReferenceRelevance
" After oral administration of 5 mg/kg body weight, the mean absorption rate constant was smaller and the mean absorption half-life was longer in the older pigs."( The influence of age on the pharmacokinetics of aditoprim in pigs after intravenous and oral administration.
Müller, P; Riond, JL; Wanner, M, 1992)		0.54
"16 h; systemic bioavailability (F) was 10."( Some pharmacokinetic data of aditoprim and trimethoprim in healthy and tick-borne fever infected dwarf goats.
Knoppert, NW; Korstanje, C; Nijmeijer, SM; van Duin, CT; van Gogh, H; van Miert, AS, 1988)		0.57

Dosage Studied

Aditoprim is a broad spectrum antimicrobial agent acting as a reversible dihydrofolate reductase inhibitor. Age-related changes in the pharmacokinetics were not sufficiently pronounced to suggest the necessity of modifying the oral dosage regimen in pigs of this age range.

ExcerptRelevanceReference
" The age-related changes in the pharmacokinetics of aditoprim were not sufficiently pronounced to suggest the necessity of modifying the oral dosage regimen in pigs of this age range."( The influence of age on the pharmacokinetics of aditoprim in pigs after intravenous and oral administration.
Müller, P; Riond, JL; Wanner, M, 1992)		0.79
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (2)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Dihydrofolate reductaseGallus gallus (chicken)Ki70.79460.11220.21580.3311AID56467
Dihydrofolate reductaseLacticaseibacillus caseiKi0.35480.00001.26756.3096AID57779
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (6)

Processvia Protein(s)Taxonomy
one-carbon metabolic processDihydrofolate reductaseGallus gallus (chicken)
response to methotrexateDihydrofolate reductaseGallus gallus (chicken)
tetrahydrofolate metabolic processDihydrofolate reductaseGallus gallus (chicken)
tetrahydrofolate biosynthetic processDihydrofolate reductaseGallus gallus (chicken)
dihydrofolate metabolic processDihydrofolate reductaseGallus gallus (chicken)
folic acid metabolic processDihydrofolate reductaseGallus gallus (chicken)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (3)

Processvia Protein(s)Taxonomy
mRNA bindingDihydrofolate reductaseGallus gallus (chicken)
dihydrofolate reductase activityDihydrofolate reductaseGallus gallus (chicken)
NADP bindingDihydrofolate reductaseGallus gallus (chicken)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (1)

Processvia Protein(s)Taxonomy
mitochondrionDihydrofolate reductaseGallus gallus (chicken)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (7)

Assay IDTitleYearJournalArticle
AID57779Inhibitory activity against Lactobacillus casei dihydrofolate reductase1989Journal of medicinal chemistry, Aug, Volume: 32, Issue:8
On the structure selectivity problem in drug design. A comparative study of benzylpyrimidine inhibition of vertebrate and bacterial dihydrofolate reductase via molecular graphics and quantitative structure-activity relationships.
AID56461Inhibition of chicken liver dihydrofolate reductase1986Journal of medicinal chemistry, May, Volume: 29, Issue:5
Inhibition of chicken liver dihydrofolate reductase by 5-(substituted benzyl)-2,4-diaminopyrimidines. A quantitative structure-activity relationship and graphics analysis.
AID56467Inhibitory activity against chicken liver dihydrofolate reductase1989Journal of medicinal chemistry, Aug, Volume: 32, Issue:8
On the structure selectivity problem in drug design. A comparative study of benzylpyrimidine inhibition of vertebrate and bacterial dihydrofolate reductase via molecular graphics and quantitative structure-activity relationships.
AID57574Activity against dihydrofolate reductase of Escherichia coli strain MB 14281992Journal of medicinal chemistry, Aug-21, Volume: 35, Issue:17
Application of neural networks: quantitative structure-activity relationships of the derivatives of 2,4-diamino-5-(substituted-benzyl)pyrimidines as DHFR inhibitors.
AID23497Partition coefficient (logD) (aqueous phase 0.1 N HCl)1986Journal of medicinal chemistry, May, Volume: 29, Issue:5
Inhibition of chicken liver dihydrofolate reductase by 5-(substituted benzyl)-2,4-diaminopyrimidines. A quantitative structure-activity relationship and graphics analysis.
AID27589Partition coefficient (logD) (0.01 N NaOH)1989Journal of medicinal chemistry, Aug, Volume: 32, Issue:8
On the structure selectivity problem in drug design. A comparative study of benzylpyrimidine inhibition of vertebrate and bacterial dihydrofolate reductase via molecular graphics and quantitative structure-activity relationships.
AID57083Inhibitory activity against dihydrofolate reductase2001Journal of medicinal chemistry, Aug-16, Volume: 44, Issue:17
Adaptive neuro-fuzzy inference system: an instant and architecture-free predictor for improved QSAR studies.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (28)

TimeframeStudies, This Drug (%)All Drugs %
pre-19907 (25.00)18.7374
1990's12 (42.86)18.2507
2000's1 (3.57)29.6817
2010's7 (25.00)24.3611
2020's1 (3.57)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 19.67

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.

MetricThis Compound (vs All)
Research Demand Index19.67 (24.57)
Research Supply Index3.40 (2.92)
Research Growth Index5.44 (4.65)
Search Engine Demand Index15.26 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (19.67)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other29 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
methane
Methane: The simplest saturated hydrocarbon. It is a colorless, flammable gas, slightly soluble in water. It is one of the chief constituents of natural gas and is formed in the decomposition of organic matter. (Grant & Hackh's Chemical Dictionary, 5th ed). methane : A one-carbon compound in which the carbon is attached by single bonds to four hydrogen atoms. It is a colourless, odourless, non-toxic but flammable gas (b.p. -161degreeC).		2.3110alkane;
gas molecular entity;
mononuclear parent hydride;
one-carbon compound		bacterial metabolite;
fossil fuel;
greenhouse gas
sulfadimethoxine
Sulfadimethoxine: A sulfanilamide that is used as an anti-infective agent.. sulfadimethoxine : A sulfonamide consisting of pyrimidine having methoxy substituents at the 2- and 6-positions and a 4-aminobenzenesulfonamido group at the 4-position.		2.3920aromatic ether;
pyrimidines;
substituted aniline;
sulfonamide antibiotic;
sulfonamide		antiinfective agent;
antimicrobial agent;
drug allergen;
environmental contaminant;
xenobiotic
sulfamerazine
[no description available]		1.9710pyrimidines;
sulfonamide antibiotic;
sulfonamide		antiinfective agent;
drug allergen
sulfamethazine
Sulfamethazine: A sulfanilamide anti-infective agent. It has a spectrum of antimicrobial action similar to other sulfonamides.. sulfamethazine : A sulfonamide consisting of pyrimidine with methyl substituents at the 4- and 6-positions and a 4-aminobenzenesulfonamido group at the 2-position.		2.3820pyrimidines;
sulfonamide antibiotic;
sulfonamide		antibacterial drug;
antiinfective agent;
antimicrobial agent;
carcinogenic agent;
drug allergen;
EC 2.5.1.15 (dihydropteroate synthase) inhibitor;
environmental contaminant;
ligand;
xenobiotic
sulfamethoxazole
Sulfamethoxazole: A bacteriostatic antibacterial agent that interferes with folic acid synthesis in susceptible bacteria. Its broad spectrum of activity has been limited by the development of resistance. (From Martindale, The Extra Pharmacopoeia, 30th ed, p208). sulfamethoxazole : An isoxazole (1,2-oxazole) compound having a methyl substituent at the 5-position and a 4-aminobenzenesulfonamido group at the 3-position.		2.730isoxazoles;
substituted aniline;
sulfonamide antibiotic;
sulfonamide		antibacterial agent;
antiinfective agent;
antimicrobial agent;
drug allergen;
EC 1.1.1.153 [sepiapterin reductase (L-erythro-7,8-dihydrobiopterin forming)] inhibitor;
EC 2.5.1.15 (dihydropteroate synthase) inhibitor;
environmental contaminant;
epitope;
P450 inhibitor;
xenobiotic
trimethoprim
Trimethoprim: A pyrimidine inhibitor of dihydrofolate reductase, it is an antibacterial related to PYRIMETHAMINE. It is potentiated by SULFONAMIDES and the TRIMETHOPRIM, SULFAMETHOXAZOLE DRUG COMBINATION is the form most often used. It is sometimes used alone as an antimalarial. TRIMETHOPRIM RESISTANCE has been reported.. trimethoprim : An aminopyrimidine antibiotic whose structure consists of pyrimidine 2,4-diamine and 1,2,3-trimethoxybenzene moieties linked by a methylene bridge.		4.67280aminopyrimidine;
methoxybenzenes		antibacterial drug;
diuretic;
drug allergen;
EC 1.5.1.3 (dihydrofolate reductase) inhibitor;
environmental contaminant;
xenobiotic
adenosine diphosphate
Adenosine Diphosphate: Adenosine 5'-(trihydrogen diphosphate). An adenine nucleotide containing two phosphate groups esterified to the sugar moiety at the 5'-position.		2.1310adenosine 5'-phosphate;
purine ribonucleoside 5'-diphosphate		fundamental metabolite;
human metabolite
diaveridine
diaveridine: RN given refers to parent cpd; structure. diaveridine : An aminopyrimidine in which the pyrimidine ring carries amino substituents at C-2 and C-4 and a 3,4-dimethoxybenzyl group at C-5. A folic acid antagonist, it is used as a synergist with sulfonamides against the parasitic Eimeria species.		3.0950aminopyrimidineantiparasitic agent;
drug allergen
tetroxoprim
tetroxoprim: structure given in Negwer 5th ed, #6419		2.8940dimethoxybenzene
metioprim
[no description available]		2.8940
brodimoprim
brodimoprim: inhibits dihydrofolate reductase. brodimoprim : An aminopyrimidine that is 2,4-diaminopyrimidine in which the hydrogen at position 5 has been replaced by a 4-bromo-3,5-dimethoxybenzyl group.		2.8940aminopyrimidine;
bromobenzenes;
methoxybenzenes		antibacterial drug;
antiinfective agent;
EC 1.5.1.3 (dihydrofolate reductase) inhibitor
epiroprim
epiroprim: an analog of trimethoprim with improved antimicrobial and pharmacokinetic properties; structure given in first source		2.8940
2,4-diamino-5-benzylpyrimidine
2,4-diamino-5-benzylpyrimidine: structure given in first source		2.8940
scopolamine hydrobromide
[no description available]		2.2110
ConditionIndicatedRelationship StrengthStudiesTrials
Age-Related Memory Disorders
[description not available]		02.2110
Memory Disorders
Disturbances in registering an impression, in the retention of an acquired impression, or in the recall of an impression. Memory impairments are associated with DEMENTIA; CRANIOCEREBRAL TRAUMA; ENCEPHALITIS; ALCOHOLISM (see also ALCOHOL AMNESTIC DISORDER); SCHIZOPHRENIA; and other conditions.		02.2110
Body Weight
The mass or quantity of heaviness of an individual. It is expressed by units of pounds or kilograms.		02.1110
Abnormalities, Drug-Induced
Congenital abnormalities caused by medicinal substances or drugs of abuse given to or taken by the mother, or to which she is inadvertently exposed during the manufacture of such substances. The concept excludes abnormalities resulting from exposure to non-medicinal chemicals in the environment.		02.1110
Delayed Effects, Prenatal Exposure
[description not available]		02.1110
Pregnancy
The status during which female mammals carry their developing young (EMBRYOS or FETUSES) in utero before birth, beginning from FERTILIZATION to BIRTH.		02.4320
Swine Diseases
Diseases of domestic swine and of the wild boar of the genus Sus.		02.1510
Group A Strep Infection
[description not available]		02.1510
Streptococcal Infections
Infections with bacteria of the genus STREPTOCOCCUS.		02.1510
Bacterial Disease
[description not available]		01.9810
Disease Models, Animal
Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.		01.9810
Pyrexia
[description not available]		01.9810
Bacterial Infections
Infections by bacteria, general or unspecified.		01.9810
Fever
An abnormal elevation of body temperature, usually as a result of a pathologic process.		01.9810
Aging
The gradual irreversible changes in structure and function of an organism that occur as a result of the passage of time.		02.3820
Mastitis, Bovine
INFLAMMATION of the UDDER in cows.		01.9810
Infections, Rickettsiaceae
[description not available]		01.9710