NAV

Fosmidomycin

Identification

Generic Name
Fosmidomycin
DrugBank Accession Number
DB02948
Background

Not Available

Type
Small Molecule
Groups
Experimental, Investigational
Structure
3D
Similar Structures
Weight
Average: 183.0997
Monoisotopic: 183.029658947
Chemical Formula
C4H10NO5P
Synonyms
  • Fosmidomycin
  • Fosmidomycina
  • Fosmidomycine
  • Fosmidomycinum
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
U1-deoxy-D-xylulose 5-phosphate reductoisomeraseNot AvailableEscherichia coli (strain K12)
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
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AcenocoumarolThe risk or severity of bleeding can be increased when Fosmidomycin is combined with Acenocoumarol.
AmbroxolThe risk or severity of methemoglobinemia can be increased when Fosmidomycin is combined with Ambroxol.
ArticaineThe risk or severity of methemoglobinemia can be increased when Fosmidomycin is combined with Articaine.
BCG vaccineThe therapeutic efficacy of BCG vaccine can be decreased when used in combination with Fosmidomycin.
BenzocaineThe risk or severity of methemoglobinemia can be increased when Fosmidomycin is combined with Benzocaine.
Food Interactions
Not Available

Products

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Product Ingredients
IngredientUNIICASInChI Key
Fosmidomycin sodiumIYI1EW66CX66508-37-0ZZPUYRHMTGOTEU-UHFFFAOYSA-M

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as organic phosphonic acids. These are organic compounds containing phosphonic acid.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Organic phosphonic acids and derivatives
Sub Class
Organic phosphonic acids
Direct Parent
Organic phosphonic acids
Alternative Parents
Hydroxamic acids / Organopnictogen compounds / Organophosphorus compounds / Organonitrogen compounds / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
Substituents
Aliphatic acyclic compound / Carbonyl group / Carboxylic acid derivative / Hydrocarbon derivative / Hydroxamic acid / Organic nitrogen compound / Organic oxide / Organic oxygen compound / Organonitrogen compound / Organooxygen compound
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
phosphonic acids, hydroxamic acid (CHEBI:443725)
Affected organisms
Not Available

Chemical Identifiers

UNII
5829E3D9I9
CAS number
66508-53-0
InChI Key
GJXWDTUCERCKIX-UHFFFAOYSA-N
InChI
InChI=1S/C4H10NO5P/c6-4-5(7)2-1-3-11(8,9)10/h4,7H,1-3H2,(H2,8,9,10)
IUPAC Name
[3-(N-hydroxyformamido)propyl]phosphonic acid
SMILES
ON(CCCP(O)(O)=O)C=O

References

General References
Not Available
PubChem Compound
572
PubChem Substance
46508936
ChemSpider
555
BindingDB
50153713
ChEBI
443725
ChEMBL
CHEMBL203125
ZINC
ZINC000012502867
Therapeutic Targets Database
DAP001384
PDBe Ligand
FOM
Wikipedia
Fosmidomycin
PDB Entries
1onp / 1q0h / 1q0l / 2egh / 2jcv / 2jcx / 3a06 / 3au9 / 3upy / 4aic …
show 6 more

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
3CompletedTreatmentMalaria1
2CompletedTreatmentMalaria2
2Unknown StatusTreatmentMalaria2
2Unknown StatusTreatmentOral Treatment of Acute Uncomplicated Plasmodium Falciparum Malaria1
2WithdrawnTreatmentMalaria1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility21.9 mg/mLALOGPS
logP-1.1ALOGPS
logP-2.2Chemaxon
logS-0.92ALOGPS
pKa (Strongest Acidic)1.81Chemaxon
pKa (Strongest Basic)-5.6Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area98.07 Å2Chemaxon
Rotatable Bond Count4Chemaxon
Refractivity36.83 m3·mol-1Chemaxon
Polarizability15.06 Å3Chemaxon
Number of Rings0Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.9277
Blood Brain Barrier+0.9098
Caco-2 permeable-0.6781
P-glycoprotein substrateNon-substrate0.6815
P-glycoprotein inhibitor INon-inhibitor0.9025
P-glycoprotein inhibitor IINon-inhibitor0.9359
Renal organic cation transporterNon-inhibitor0.9023
CYP450 2C9 substrateNon-substrate0.7726
CYP450 2D6 substrateNon-substrate0.8081
CYP450 3A4 substrateNon-substrate0.5727
CYP450 1A2 substrateNon-inhibitor0.7958
CYP450 2C9 inhibitorNon-inhibitor0.856
CYP450 2D6 inhibitorNon-inhibitor0.9187
CYP450 2C19 inhibitorNon-inhibitor0.8218
CYP450 3A4 inhibitorNon-inhibitor0.6376
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9611
Ames testAMES toxic0.5096
CarcinogenicityNon-carcinogens0.6785
BiodegradationNot ready biodegradable0.7712
Rat acute toxicity2.2352 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9383
hERG inhibition (predictor II)Non-inhibitor0.869
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-00fr-9500000000-efefa3a227a7b5c7f124
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-014i-1900000000-3a3053a6e32975b7750e
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-2900000000-fa168ae3caa86d3ff9b8
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-001j-9200000000-0d254c4a8e8fd0a725f6
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-003i-9800000000-24b6e8fb255dec586adc
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-9000000000-be097cff3f3d905fdb74
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-001i-9000000000-9e4a304b89d26baeca84
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-126.14544
predicted
DeepCCS 1.0 (2019)
[M+H]+129.26048
predicted
DeepCCS 1.0 (2019)
[M+Na]+138.3366
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. 1-deoxy-D-xylulose 5-phosphate reductoisomerase
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Nadph binding
Specific Function
Catalyzes the NADP-dependent rearrangement and reduction of 1-deoxy-D-xylulose-5-phosphate (DXP) to 2-C-methyl-D-erythritol 4-phosphate (MEP).
Gene Name
dxr
Uniprot ID
P45568
Uniprot Name
1-deoxy-D-xylulose 5-phosphate reductoisomerase
Molecular Weight
43387.575 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]

Drug created at June 13, 2005 13:24 / Updated at February 21, 2021 18:51