Page last updated: 2024-12-06
1,2,4-triazole-3-carboxamide
Description
1,2,4-triazole-3-carboxamide is a heterocyclic compound with a triazole ring system, and a carboxamide group attached at the 3-position. It has the following structure:
[Image of 1,2,4-triazole-3-carboxamide structure]
**Importance in Research:**
1,2,4-triazole-3-carboxamide has gained significant attention in research due to its diverse biological activities, including:
**1. Antifungal Activity:**
- This compound exhibits potent antifungal properties against a broad spectrum of fungal pathogens, including Candida albicans, Aspergillus fumigatus, and Cryptococcus neoformans.
- Its mechanism of action involves interfering with the synthesis of ergosterol, a key component of fungal cell membranes.
**2. Antibacterial Activity:**
- Some derivatives of 1,2,4-triazole-3-carboxamide have been shown to possess antibacterial activity, particularly against Gram-positive bacteria.
**3. Anticancer Activity:**
- Research suggests that 1,2,4-triazole-3-carboxamide and its analogs may have potential anticancer properties.
- Studies have demonstrated their ability to inhibit tumor cell growth and induce apoptosis (programmed cell death).
**4. Anti-inflammatory Activity:**
- This compound and its derivatives have shown anti-inflammatory activity, potentially by modulating the production of inflammatory mediators.
**5. Antiviral Activity:**
- Some studies indicate that 1,2,4-triazole-3-carboxamide derivatives may exhibit antiviral activity against certain viruses, such as HIV.
**6. Other Potential Applications:**
- 1,2,4-triazole-3-carboxamide has also been explored for its potential applications in areas such as agricultural fungicides, plant growth regulators, and agrochemicals.
**Research Focus:**
Current research focuses on:
- Developing new and more potent derivatives of 1,2,4-triazole-3-carboxamide with improved therapeutic properties.
- Understanding the detailed mechanism of action of this compound and its derivatives.
- Exploring its potential as a lead compound for the development of new drugs for treating various diseases.
In conclusion, 1,2,4-triazole-3-carboxamide is a promising research molecule with potential applications in various fields, particularly in the development of new antifungal, antibacterial, anticancer, and antiviral agents.
1,2,4-triazole-3-carboxamide : A member of the class of triazoles that is 1H-1,2,4-triazole substituted by an aminocarbonyl group at position 3. It is the major catabolite and aglycon of ribavirin. [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 Source | ID |
PubMed CID | 65125 |
CHEBI ID | 180482 |
SCHEMBL ID | 381885 |
MeSH ID | M0069121 |
Synonyms (46)
Synonym |
AC-797 |
CHEBI:180482 |
NCIOPEN2_000872 , |
1h-1,2,4-triazole-3-carboxamide |
nsc-80860 |
nsc80860 |
icn 1253 |
3641-08-5 |
STK007228 |
T2402 |
1,2,4-triazole-3-carboxamide |
1h-1,2,4-triazole-5-carboxamide |
zewjfunfeabpgl-uhfffaoysa- |
2h-1,2,4-triazole-3-carboxamide |
inchi=1/c3h4n4o/c4-2(8)3-5-1-6-7-3/h1h,(h2,4,8)(h,5,6,7) |
c405on563a , |
unii-c405on563a |
nsc 80860 |
A823234 |
1h-1,2,4-triazole-5-carboxamide;1h-1,2,4-triazole-3-carboxamide |
AKOS016001784 |
AKOS005375701 |
BP-20317 |
FT-0601192 |
PS-3438 |
AKOS017269537 |
s-triazole-3-carboxamide |
ribavirin impurity d [ep impurity] |
SCHEMBL381885 |
ZEWJFUNFEABPGL-UHFFFAOYSA-N |
1, 2, 4-triazole-3-carboxamide |
1,2,4-triazole- 3-carboxamide |
1,2,4-triazole-3-formamide |
BS-3499 |
DTXSID50189935 |
mfcd15142764 |
ribavirin imp. d (ep); ribavirin usp related compound d; ribavirin usp rc d; 1h-1,2,4-triazole-3-carboxamide; ribavirin related compound d; ribavirin impurity d |
1h-[1,2,4]triazole-3-carboxamide |
676456-95-4 |
F14916 |
CS-W021700 |
AMY38327 |
Q27275157 |
n-des-1-beta-d-ribofuranosyl ribavirin |
EN300-83457 |
4h-1,2,4-triazole-3-carboxamide |
Roles (2)
Role | Description |
human urinary metabolite | Any metabolite (endogenous or exogenous) found in human urine samples. |
drug metabolite | null |
[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)
Class | Description |
triazoles | An azole in which the five-membered heterocyclic aromatic skeleton contains three N atoms and two C atoms. |
primary carboxamide | A carboxamide resulting from the formal condensation of a carboxylic acid with ammonia; formula RC(=O)NH2. |
monocarboxylic acid amide | A carboxamide derived from a monocarboxylic acid. |
aromatic amide | An amide in which the amide linkage is bonded directly to an aromatic system. |
[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] |
Research
Studies (9)
Timeframe | Studies, This Drug (%) | All Drugs % |
pre-1990 | 3 (33.33) | 18.7374 |
1990's | 0 (0.00) | 18.2507 |
2000's | 3 (33.33) | 29.6817 |
2010's | 2 (22.22) | 24.3611 |
2020's | 1 (11.11) | 2.80 |
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] |
Market Indicators
Research Demand Index: 12.12
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.
Metric | This Compound (vs All) |
---|
Research Demand Index | 12.12 (24.57) | Research Supply Index | 2.30 (2.92) | Research Growth Index | 4.42 (4.65) | Search Engine Demand Index | 0.00 (26.88) | Search Engine Supply Index | 0.00 (0.95) |
| |
Study Types
Publication Type | This drug (%) | All Drugs (%) |
Trials | 0 (0.00%) | 5.53% |
Reviews | 0 (0.00%) | 6.00% |
Case Studies | 0 (0.00%) | 4.05% |
Observational | 0 (0.00%) | 0.25% |
Other | 9 (100.00%) | 84.16% |
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] |