Page last updated: 2024-12-05

sulfamoxole

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

Description

Sulfamoxole is a sulfonamide antimicrobial agent. It was developed in the 1960s and was widely used to treat bacterial infections, particularly urinary tract infections. Sulfamoxole is a synthetic compound, typically prepared by reacting sulfanilamide with a substituted benzoyl chloride. Its mechanism of action involves inhibiting the synthesis of dihydrofolic acid, a key metabolite required for bacterial growth. Sulfamoxole's effectiveness against various bacteria led to its widespread use, however, it was later associated with several adverse effects such as hypersensitivity reactions and crystalluria. Due to the development of newer, broader-spectrum antibiotics with fewer side effects, Sulfamoxole's use has declined significantly in recent years. Despite its diminished clinical relevance, studies involving Sulfamoxole continue to contribute to the understanding of antimicrobial resistance and the development of novel therapeutic strategies.'

Sulfamoxole: A sulfanilamide antibacterial agent. [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

sulfamoxole : A sulfonamide antibiotic in which 4-aminobenzenesulfonic acid and 4,5-dimethyl-1,3-oxazol-2-amine have combined to form the sulfonamide bond. [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 CID12894
CHEMBL ID2105399
CHEBI ID55548
SCHEMBL ID151518
MeSH IDM0020753

Synonyms (76)

Synonym
CHEBI:55548 ,
sulfamoxol
2-(p-aminobenzolsulfonamido)-4,5-dimethyloxazol
sulfamoxolum
sulfamoxole [usan:inn:ban]
unii-hgg82xe020
hgg82xe020 ,
nsc-683535
n1-(4,5-dimethyloxazol-2-yl)-sulfanilamide
4-amino-n-(4,5-dimethyl-1,3-oxazol-2-yl)benzenesulfonamide
sulfamoxole (usan/inn)
D02516
n(1)-(4,5-dimethyl-2-oxazolyl)sulfanilamide
nsc683535
729-99-7
sulfamoxole
4-amino-n-(4,5-dimethyloxazol-2-yl)benzenesulfonamide
inchi=1/c11h13n3o3s/c1-7-8(2)17-11(13-7)14-18(15,16)10-5-3-9(12)4-6-10/h3-6h,12h2,1-2h3,(h,13,14
sulfamoxol [inn-spanish]
tardamid
sulfavigor
sulfanilamide, n(sup 1)-(4,5-dimethyl-2-oxazolyl)-
n(sup 1)-(4,5-dimethyl-2-oxazolyl)sulfanilamide
p-aminobenzenesulfonyl-2-amino-4,5-dimethyloxazole
justamil
tardamide
solfamossolo [dcit]
4,5-dimethyl-2-sulfanilamidooxazole
oxazole, 2-(p-aminophenylsulfonylamino)-4,5-dimethyl-
2-(p-aminobenzenesulfonamido)-4,5-dimethyloxazole
einecs 211-982-7
oxasulfa
sulphamoxole
sulfamoxolum [inn-latin]
benzenesulfonamide, 4-amino-n-(4,5-dimethyl-2-oxazolyl)-
sulfmidil
n1-(4,5-dimethyl-2-oxazolyl)sulfanilamide
2-(p-aminobenzolsulfonamido)-4,5-dimethyloxazol [german]
nsc 683535
sulfadimethyloxazole
sulfuno
4-amino-n-(4,5-dimethyl-2-oxazolyl)benzenesulfonamide
DB08798
sulfono
solfamossolo
FT-0632886
EPITOPE ID:122242
CHEMBL2105399
sulfamoxole [inn]
sulfamoxole [mi]
sulfamoxole [usan]
sulfamoxole [mart.]
sulfamoxole [who-dd]
AKOS022507464
SCHEMBL151518
CYFLXLSBHQBMFT-UHFFFAOYSA-N
sulfano
4-amino-n-(4,5-dimethyl-1,3-oxazol-2-yl)benzenesulfonamide #
sulfanilamide, n1-(4,5-dimethyl-2-oxazolyl)-
sulfune
DTXSID5023617
4-amino-n-(dimethyl-1,3-oxazol-2-yl)benzene-1-sulfonamide
sr-01000944561
SR-01000944561-1
sulfamoxole, vetranal(tm), analytical standard
NS-04235
4-amino-n-(4,5-dimethyl-1,3-oxazol-2-yl)benzene-1-sulfonamide
n1-(4,5-dimethyloxazol-2-yl)sulfanilamide
gtpl12744
(+/-)-bufuralolhydrochloride
sulfamoxol 100 microg/ml in acetonitrile
Q6577297
CS-0013814
mfcd00005303
HY-B1782
sulfamoxole 1000 microg/ml in acetonitrile

Research Excerpts

Effects

ExcerptReferenceRelevance
"Sulfamoxole (SDMO) has the same half-life of elimination from human plasma as sulfamethoxazole. "( Bacteriostatic and bactericidal activity of two trimethoprim-sulfonamide combinations.
Böhni, E, 1976
)
1.7

Compound-Compound Interactions

ExcerptReferenceRelevance
" Sulfamoxole (SMO), Sulfadiazine (SDZ) and Sulfadimidine (SDD) in combination with trimethoprim (TMP) were studied in 12 healthy volunteers."( Comparative pharmacokinetic study of four different sulfonamides in combination with trimethoprim in human volunteers.
Garg, SK; Ghosh, SS; Mathur, VS, 1986
)
1.18

Dosage Studied

ExcerptRelevanceReference
" We concluded that in this type of experiment the higher dosed combination showed no advantage contrary to a previous report, but in agreement with another."( Bactericidal or bacteristatic effects of two sulphonamide plus trimethoprim preparations in human urine.
Broughall, JM; Bywater, MJ; Holt, HA; Reeves, DS, 1979
)
0.26
"The clinical trial of the combination N1-(4,5-dimethyl-2-oxazolyl)-sulfanilamide (sulfamoxole) and 2,4-diamino-5-(3,4,5-trimethoxy-benzyl)-pyrimidine (trimethoprim) (CN 3123, Nevin, Supristol) showed that, when given in the ratio of 5:1 and in a suitable dosage computed from pharmacokinetic information, it exhibited antibacterial activity and had a therapeutic effect in about 90% of the patients."( [Clinical trial of the antibacterial combination sulfamoxole/trimethoprim (CN 3123). 1st communication. Efficacy activity spectrum--resistance in therapy (author's transl)].
Etzel, M; Wesenberg, W, 1976
)
0.74
"117 clinical patients with infections of the urinary tract (nequals 47) or the bronchopulmonar system (n equals 70) were treated with a Sulfamoxol-Trimethoprim-combination in low dosage for 11 days."( [The effect of a new broad-spectrum antibiotic in bronchopulmonar and urinary infections (author's transl)].
, 1976
)
0.26
" By the suitable dosage the mortality rate could be reduced considerably."( [Experimental studies on the effect of the combination sulfamoxole/trimethoprim on the Toxoplasma infection of the mouse (author's transl)].
Maier, W; Piekarski, G, 1976
)
0.5
" In dogs there was a dose-related increase in iodine uptake by the thyroid and a decrease in serum thyroxine over a period of 6 months under the highest dosage of CN 3123 administered."( [Toxicological investigations of the combination sulfamoxole/trimethoprim, a new broad-spectrum chemotherapeutic (author's transl)].
Foitzik, E; Kiel, H; Kretzschmar, R; Kuhne, J; Lagler, F; Leuschner, F; Neumann, W, 1976
)
0.51
" In this dose range the pup weights and the weight gain of the offspring of dams with continued dosing during lactation were also reduced."( [Investigations on the effect of the combination sulfamoxole/trimethoprim on fertility and fetal development in rats and rabbits (author's tranls)].
Helm, F; Kretzschmar, R; Leuschner, F; Neumann, W, 1976
)
0.51
" Investigations on blood level, concentration in plasma water and excretion via urine and bile were done on experimental animals and with therapeutic dosage (single and repeated administration) on men."( [Pharmacokinetic studies with the combination sulfamoxole/trimethoprim in animals and men (author's transl)].
Kohlmann, FW; Kuhne, J; Seydel, JK; Wempe, E, 1976
)
0.51
"A simple spectrophotometric method for the determination of 15 sulphonamides in bulk and in dosage forms is described."( Use of p-benzoquinone for the spectrophotometric determination of certain sulphonamides.
Askal, HF; Mohamed, AM; Saleh, GA, 1991
)
0.28
" The dosage schedule for TMP-SMX was 2 tablets every 12 h for nine doses, and for TMP-SMO it was 2 tablets as in the first dose, followed by 1 tablet every 12 h for eight more doses."( Plasma levels of trimethoprim and sulfonamide after administration of trimethoprim-sulfamethoxazole and trimethoprim-sulfamoxole.
Desai, NK; Gupta, KC; Paul, T; Sheth, UK, 1980
)
0.47
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (2)

RoleDescription
antimicrobial agentA substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
drug allergenAny drug which causes the onset of an allergic reaction.
[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 (3)

ClassDescription
sulfonamideAn amide of a sulfonic acid RS(=O)2NR'2.
oxazoleAn azole based on a five-membered heterocyclic aromatic skeleton containing one N and one O atom.
sulfonamide antibioticA class of sulfonamides whose members generally have bacteriostatic antibiotic properties.
[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 (19)

Assay IDTitleYearJournalArticle
AID1079940Granulomatous liver disease, proven histopathologically. Value is number of references indexed. [column 'GRAN' in source]
AID1079934Highest frequency of acute liver toxicity observed during clinical trials, expressed as a percentage. [column '% AIGUE' in source]
AID1079949Proposed mechanism(s) of liver damage. [column 'MEC' 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]
AID1079937Severe hepatitis, defined as possibly life-threatening liver failure or through clinical observations. Value is number of references indexed. [column 'MASS' 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]
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]
AID1079943Malignant tumor, proven histopathologically. Value is number of references indexed. [column 'T.MAL' in source]
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]
AID1079947Comments (NB not yet translated). [column 'COMMENTAIRES' in source]
AID1079945Animal toxicity known. [column 'TOXIC' 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]
AID1079944Benign tumor, proven histopathologically. Value is number of references indexed. [column 'T.BEN' 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
AID1079932Highest frequency of moderate liver toxicity observed during clinical trials, expressed as a percentage. [column '% BIOL' in source]
AID1079942Steatosis, proven histopathologically. Value is number of references indexed. [column 'STEAT' in source]
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]
AID1079948Times to onset, minimal and maximal, observed in the indexed observations. [column 'DELAI' in source]
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (79)

TimeframeStudies, This Drug (%)All Drugs %
pre-199073 (92.41)18.7374
1990's5 (6.33)18.2507
2000's0 (0.00)29.6817
2010's1 (1.27)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: 45.60

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

MetricThis Compound (vs All)
Research Demand Index45.60 (24.57)
Research Supply Index4.67 (2.92)
Research Growth Index4.11 (4.65)
Search Engine Demand Index68.41 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (45.60)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials18 (20.45%)5.53%
Reviews3 (3.41%)6.00%
Case Studies3 (3.41%)4.05%
Observational0 (0.00%)0.25%
Other64 (72.73%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]