fosmidomycin

{{Short description|Chemical compound}}

{{distinguish|Fosfomycin}}

{{Drugbox

| Verifiedfields = changed

| verifiedrevid = 461113697

| IUPAC_name = 3-[Formyl(hydroxy)amino]propylphosphonic acid

| image = Fosmidomycin_.svg

| alt = Structural formula of fosmidomycin

| image2 = Fosmidomycin 3D ball.png

| alt2 = Ball-and-stick model of the fosmidomycin molecule

| width = 240

| tradename =

| pregnancy_AU =

| pregnancy_US =

| legal_AU =

| legal_UK =

| legal_US =

| CAS_number_Ref = {{cascite|changed|??}}

| CAS_number = 66508-53-0

| ATC_prefix = none

| PubChem = 572

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| DrugBank = DB02948

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 555

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 5829E3D9I9

| ChEBI_Ref = {{ebicite|correct|EBI}}

| ChEBI = 443725

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 203125

| C=4 | H=10 | N=1 | O=5 | P=1

| smiles = O=P(O)(O)CCCN(O)C=O

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/C4H10NO5P/c6-4-5(7)2-1-3-11(8,9)10/h4,7H,1-3H2,(H2,8,9,10)

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = GJXWDTUCERCKIX-UHFFFAOYSA-N

}}

Fosmidomycin is an antibiotic that was originally isolated from culture broths of bacteria of the genus Streptomyces.{{cite journal | vauthors = Iguchi E, Okuhara M, Kohsaka M, Aoki H, Imanaka H | title = Studies on new phosphonic acid antibiotics. II. Taxonomic studies on producing organisms of the phosphonic acid and related compounds | journal = The Journal of Antibiotics | volume = 33 | issue = 1 | pages = 19–23 | date = January 1980 | pmid = 7372546 | doi = 10.7164/antibiotics.33.18 | doi-access = free }} 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.{{cite journal | vauthors = Jawaid S, Seidle H, Zhou W, Abdirahman H, Abadeer M, Hix JH, van Hoek ML, Couch RD | title = Kinetic characterization and phosphoregulation of the Francisella tularensis 1-deoxy-D-xylulose 5-phosphate reductoisomerase (MEP synthase) | journal = PLOS ONE | volume = 4 | issue = 12 | pages = e8288 | date = December 2009 | pmid = 20011597 | pmc = 2788227 | doi = 10.1371/journal.pone.0008288 | bibcode = 2009PLoSO...4.8288J | doi-access = free }} Several mutations in the E. coli DXP reductoisomerase were found to confer resistance to fosmidomycin.{{cite journal | vauthors = Armstrong CM, Meyers DJ, Imlay LS, Freel Meyers C, Odom AR | title = Resistance to the antimicrobial agent fosmidomycin and an FR900098 prodrug through mutations in the deoxyxylulose phosphate reductoisomerase gene (dxr) | journal = Antimicrobial Agents and Chemotherapy | volume = 59 | issue = 9 | pages = 5511–9 | date = September 2015 | pmid = 26124156 | pmc = 4538460 | doi = 10.1128/AAC.00602-15 }}{{cite journal | vauthors = Pines G, Oh EJ, Bassalo MC, Choudhury A, Garst AD, Fankhauser RG, Eckert CA, Gill RT | title = Genomic Deoxyxylulose Phosphate Reductoisomerase (DXR) Mutations Conferring Resistance to the Antimalarial Drug Fosmidomycin in E. coli | journal = ACS Synthetic Biology | volume = 7 | issue = 12 | pages = 2824–2832 | date = November 2018 | pmid = 30462485 | doi = 10.1021/acssynbio.8b00219 | pmc = 6928208 }}