Structure via PubChem · Public domain (PubChem)
فوسمیدومایسین
Sign in to saveAlso known as 3-(N-hydroxyformamido)propylphosphonic acid
Fosmidomycin is an antibiotic that was originally isolated from culture broths of bacteria of the genus Streptomyces. It specifically inhibits DXP reductoisomerase, a key enzyme in the non-mevalonate pathway of isoprenoid biosynthesis. It is a structural analogue of 2-C-methyl-D-erythrose 4-phosphate. It inhibits the E. coli enzyme with a KI value of 38 nM (4), MTB at 80 nM, and the Francisella enzyme at 99 nM. Several mutations in the E. coli DXP reductoisomerase were found to confer resistance to fosmidomycin.
Chemical data
- Formula
- C4H10NO5P
- Molecular weight
- 183.1 g/mol
- IUPAC name
- 3-[formyl(hydroxy)amino]propylphosphonic acid
- SMILES
- C(CN(C=O)O)CP(=O)(O)O
- InChIKey
- GJXWDTUCERCKIX-UHFFFAOYSA-N
- XLogP
- -2.2
- Polar surface area
- 98.1 Ų
- H-bond donors
- 3
- H-bond acceptors
- 5
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Phase 3
- Molecule type
- Small molecule
- Indications
- malaria, Plasmodium falciparum malaria
via ChEMBL · EBI
Research
420 papers- Fosmidomycin as an antimalarial drug: a meta-analysis of clinical trials.Future microbiology · 2015
- Fosmidomycin for the treatment of malaria.Parasitology research · 2003
- Over 40 Years of Fosmidomycin Drug Research: A Comprehensive Review and Future Opportunities.Pharmaceuticals (Basel, Switzerland) · 2022
- Fosmidomycin for malaria.Lancet (London, England) · 2002
- Fosmidomycin biosynthesis diverges from related phosphonate natural products.Nature chemical biology · 2019
via PubMed
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 183.03
Show 6 more facts
- chemical formula
- C₄H₁₀NO₅P
- canonical SMILES
- C(CN(C=O)O)CP(=O)(O)O
- World Health Organisation international non-proprietary name
- fosmidomycin
- different from
- fosfomycin
- found in taxon
- Arabidopsis thaliana
- Commons category
- Fosmidomycin
via Wikidata · CC0