Disodium phosphonomycin

Names

[ Name ]:
Disodium phosphonomycin

[Synonym ]:
(−)-(1R,2S)-(1,2-Epoxypropyl)phosphonic acid,Fosfomycin,Phosphomycin disodium salt
(1R,2S)-1,2-Epoxypropylphosphonic Acid Disodium Salt
Phosphonic acid, [(2R,3S)-3-methyloxiranyl]-, sodium salt (1:2)
Disodium fosfomycin
FosfomycinDisodiumSalt
Fosfomycin Sodium
Disodium (1R,2S)-1,2-Epoxypropylphosphonate
fosfomycin disodium
Disodium [(2R,3S)-3-methyloxiran-2-yl]phosphonate
MFCD00056853
EINECS 247-409-2
Phosphomycin Disodium Salt
Disodium [(2R,3S)-3-methyl-2-oxiranyl]phosphonate
Fosfomycin sodium salt
Sodium,(2S,3R)-3-methyloxiran-2-yl)phosphonate
Disodium phosphonomycin
Fosfomycin Disodium Salt

Biological Activity

[Description]:

Fosfomycin sodium (MK-0955 sodium) is a blood-brain barrier penetrating, broad-spectrum antibiotic by irreversibly inhibiting an early stage in cell wall synthesis. Fosfomycin sodium shows both in vivo and in vitro activity against a wide range of bacteria, including multidrug-resistant (MDR), extensively drug-resistant (XDR), and pan-drug-resistant (PDR) bacteria[1].

[Related Catalog]:

Research Areas >> Infection

Signaling Pathways >> Anti-infection >> Bacterial

[References]

[1]. Dijkmans AC, et al. Fosfomycin: Pharmacological, Clinical and Future Perspectives. Antibiotics (Basel). 2017 Oct 31;6(4). pii: E24.

Chemical & Physical Properties

[ Boiling Point ]:
342.7ºC at 760 mmHg

[ Melting Point ]:
>300°C

[ Molecular Formula ]:
C₃H₅Na₂O₄P

[ Molecular Weight ]:
182.023

[ Exact Mass ]:
181.972092

[ PSA ]:
85.53000

[ LogP ]:
0.78530

[ Vapour Pressure ]:
1.34E-05mmHg at 25°C

[ Storage condition ]:
2-8°C

[ Water Solubility ]:
H2O: 50 mg/mL, clear, colorless

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: SZ7902000

CHEMICAL NAME :: Phosphonic acid, (1,2-epoxypropyl)-, disodium salt (1R,2S) (-)-

CAS REGISTRY NUMBER :: 26016-99-9

LAST UPDATED :: 199606

DATA ITEMS CITED :: 19

MOLECULAR FORMULA :: C3-H5-O4-P.2Na

MOLECULAR WEIGHT :: 182.03

WISWESSER LINE NOTATION :: T3OTJ BPWO C1 &-NA- 2

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 4550 mg/kg

TOXIC EFFECTS :: Sense Organs and Special Senses (Eye) - lacrimation Sense Organs and Special Senses (Eye) - effect, not otherwise specified Behavioral - muscle weakness

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 2 gm/kg

TOXIC EFFECTS :: Behavioral - altered sleep time (including change in righting reflex) Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - other changes

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 4320 mg/kg

TOXIC EFFECTS :: Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - other changes Nutritional and Gross Metabolic - body temperature decrease

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 1560 mg/kg

TOXIC EFFECTS :: Sense Organs and Special Senses (Eye) - increased intraocular pressure Lungs, Thorax, or Respiration - other changes

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intramuscular

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 2460 mg/kg

TOXIC EFFECTS :: Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - other changes

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 7300 mg/kg

TOXIC EFFECTS :: Sense Organs and Special Senses (Eye) - lacrimation Sense Organs and Special Senses (Eye) - effect, not otherwise specified Lungs, Thorax, or Respiration - other changes

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 2175 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 5100 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1225 mg/kg

TOXIC EFFECTS :: Sense Organs and Special Senses (Eye) - increased intraocular pressure Behavioral - muscle contraction or spasticity Behavioral - irritability

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intramuscular

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 2625 mg/kg

TOXIC EFFECTS :: Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - other changes Nutritional and Gross Metabolic - body temperature decrease

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 15 gm/kg/35D-I

TOXIC EFFECTS :: Blood - pigmented or nucleated red blood cells Blood - changes in serum composition (e.g. TP, bilirubin, cholesterol) Nutritional and Gross Metabolic - changes in chlorine

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 78 gm/kg/26W-I

TOXIC EFFECTS :: Liver - other changes Endocrine - changes in adrenal weight Blood - changes in serum composition (e.g. TP, bilirubin, cholesterol)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 78 gm/kg/26W-I

TOXIC EFFECTS :: Liver - other changes Kidney, Ureter, Bladder - changes in tubules (including acute renal failure, acute tubular necrosis)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 22500 mg/kg

SEX/DURATION :: female 14-22 day(s) after conception lactating female 21 day(s) post-birth

TOXIC EFFECTS :: Reproductive - Effects on Newborn - live birth index (measured after birth)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 11 gm/kg

SEX/DURATION :: male 63 day(s) pre-mating female 14 day(s) pre-mating - 7 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - musculoskeletal system

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 1375 mg/kg

SEX/DURATION :: female 7-17 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Effects on Embryo or Fetus - fetal death

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 1375 mg/kg

SEX/DURATION :: female 7-17 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Newborn - growth statistics (e.g.%, reduced weight gain) Reproductive - Effects on Newborn - physical

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intravenous

DOSE :: 10400 mg/kg

SEX/DURATION :: female 6-18 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)

MUTATION DATA

TYPE OF TEST :: Mutation in microorganisms

TEST SYSTEM :: Bacteria - Klebsiella pneumoniae

DOSE/DURATION :: 20 umol/L

REFERENCE :: MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 89,269,1981

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Hazard Codes ]:
F: Flammable;C: Corrosive;

[ Risk Phrases ]:
R11

[ Safety Phrases ]:
16-26-36/37/39-45

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
2

[ RTECS ]:
SZ7902000

Precursor & DownStream

Precursor

DownStream

Articles

In vitro activity of fosfomycin against blaKPC-containing Klebsiella pneumoniae isolates, including those nonsusceptible to tigecycline and/or colistin.

Antimicrob. Agents Chemother. 54 , 526-529, (2010)

In vitro activity of fosfomycin was evaluated against 68 bla(KPC)-possessing Klebsiella pneumoniae (KpKPC) isolates, including 23 tigecycline- and/or colistin-nonsusceptible strains. By agar dilution,...

In vitro susceptibility testing procedures for fosfomycin tromethamine.

Antimicrob. Agents Chemother. 35 , 1235-1238, (1991)

Fosfomycin tromethamine (previously fosfomycin trometamol) is an orally administered fosfomycin which may be used for single-dose therapy of uncomplicated urinary tract infections. Fosfomycin trometha...