Product Name

  • Name

    Disodium phosphonomycin

  • EINECS 247-409-2
  • CAS No. 26016-99-9
  • Article Data7
  • CAS DataBase
  • Density
  • Solubility water: 50 mg/mL, clear, colorless
  • Melting Point >300 °C
  • Formula C3H5Na2O4P
  • Boiling Point 342.7oC at 760 mmHg
  • Molecular Weight 182.024
  • Flash Point 161°C
  • Transport Information
  • Appearance white solid
  • Safety 16-26-36/37/39-45
  • Risk Codes 11-34
  • Molecular Structure Molecular Structure of 26016-99-9 (Disodium phosphonomycin)
  • Hazard Symbols FlammableF,CorrosiveC
  • Synonyms Disodium phosphonomycin;Disodium fosfomycin;FOM-Na;Fosfocin;Fosfomycindisodium salt;Fosmicin S;Levo-phosphonomycin disodium salt;NSC 136017;Sodium fosfomycin;Phosphonicacid, P-[(2R,3S)-3-methyl-2-oxiranyl]-, sodium salt (1:2);Fosfomycin Sodium;
  • PSA 85.53000
  • LogP 0.78530

Synthetic route

syn-(1R,2S)-1-chloro-2-hydroxypropane phosphonic acid disodium salt

syn-(1R,2S)-1-chloro-2-hydroxypropane phosphonic acid disodium salt

phosphomycin disodium salt
26016-99-9

phosphomycin disodium salt

Conditions
ConditionsYield
With sodium hydroxide for 1h;90%
dibenzyl (1R,2S)-1,2-epoxypropylphosphonate
172585-28-3

dibenzyl (1R,2S)-1,2-epoxypropylphosphonate

phosphomycin disodium salt
26016-99-9

phosphomycin disodium salt

Conditions
ConditionsYield
With Dowex 50WX8 (Na form); hydrogen; cyclohexylamine; palladium on activated charcoal In methanol76%
(1-bromo-2-hydroxypropyl)phosphonic acid
119007-50-0

(1-bromo-2-hydroxypropyl)phosphonic acid

phosphomycin disodium salt
26016-99-9

phosphomycin disodium salt

Conditions
ConditionsYield
With sodium methylate In methanol1.91 g
(1R,2S)-1-chloro-2-hydroxypropanephosphonic acid
640716-21-8

(1R,2S)-1-chloro-2-hydroxypropanephosphonic acid

phosphomycin disodium salt
26016-99-9

phosphomycin disodium salt

Conditions
ConditionsYield
With sodium hydroxide In methanol pH=9 - 10;
disodium (1S,2S)-2-hydroxy-1-methanesulphonyloxypropyl phosphonate

disodium (1S,2S)-2-hydroxy-1-methanesulphonyloxypropyl phosphonate

phosphomycin disodium salt
26016-99-9

phosphomycin disodium salt

Conditions
ConditionsYield
With sodium hydroxide In water
With sodium hydroxide In water
With sodium hydroxide In water
phosphomycin disodium salt
26016-99-9

phosphomycin disodium salt

cyclohexylamine
108-91-8

cyclohexylamine

((1R,2R)-1,2-Dihydroxy-propyl)-phosphonic acid; compound with cyclohexylamine
132125-61-2

((1R,2R)-1,2-Dihydroxy-propyl)-phosphonic acid; compound with cyclohexylamine

Conditions
ConditionsYield
With sulfuric acid at 50℃; for 48h;60%
phosphomycin disodium salt
26016-99-9

phosphomycin disodium salt

A

(1S,2S)-(+)-(1-Amino-2-hydroxypropyl)phosphonsaeure
128708-51-0

(1S,2S)-(+)-(1-Amino-2-hydroxypropyl)phosphonsaeure

B

(1R,2R)-(-)-(2-Amino-1-hydroxypropyl)phosphonsaeure
84601-12-7

(1R,2R)-(-)-(2-Amino-1-hydroxypropyl)phosphonsaeure

Conditions
ConditionsYield
With ammonia at 60℃;A 42%
B 58%
2-amino-2-hydroxymethyl-propane-1,3-diol; hydrogenoxalate
855392-18-6

2-amino-2-hydroxymethyl-propane-1,3-diol; hydrogenoxalate

phosphomycin disodium salt
26016-99-9

phosphomycin disodium salt

fosfomycin trometamol
78964-85-9

fosfomycin trometamol

Conditions
ConditionsYield
In methanol at 20 - 65℃; for 3 - 4h;
dimethyltin dichloride
753-73-1

dimethyltin dichloride

phosphomycin disodium salt
26016-99-9

phosphomycin disodium salt

Me2Sn((1R,2S)-1,2-epoxypropylphosphonate)

Me2Sn((1R,2S)-1,2-epoxypropylphosphonate)

Conditions
ConditionsYield
In methanol 1:1 mixt. stirred for 24 h at 40°C; pptd. on cooling, septd., recrystd. (benzene/chloroform=1/1), dried overP4O10 (vac.), elem. anal.;
trimethyltin(IV)chloride
1066-45-1

trimethyltin(IV)chloride

phosphomycin disodium salt
26016-99-9

phosphomycin disodium salt

(Me3Sn)2((1R,2S)-1,2-epoxypropylphosphonate)

(Me3Sn)2((1R,2S)-1,2-epoxypropylphosphonate)

Conditions
ConditionsYield
In methanol stoich. mixt. stirred for 24 h at 40°C; pptd. on cooling, septd., recrystd. (benzene/chloroform=1/1), dried overP4O10 (vac.), elem. anal.;
dibutyltin chloride
683-18-1

dibutyltin chloride

phosphomycin disodium salt
26016-99-9

phosphomycin disodium salt

Bu2Sn((1R,2S)-1,2-epoxypropylphosphonate)

Bu2Sn((1R,2S)-1,2-epoxypropylphosphonate)

Conditions
ConditionsYield
In methanol 1:1 mixt. stirred for 24 h at 40°C; pptd. on cooling, septd., recrystd. (benzene/chloroform=1/1), dried overP4O10 (vac.), elem. anal.;
phosphomycin disodium salt
26016-99-9

phosphomycin disodium salt

triphenyltin chloride
639-58-7

triphenyltin chloride

(Ph3Sn)2((1R,2S)-1,2-epoxypropylphosphonate)

(Ph3Sn)2((1R,2S)-1,2-epoxypropylphosphonate)

Conditions
ConditionsYield
In methanol stoich. mixt. stirred for 24 h at 40°C; pptd. on cooling, septd., recrystd. (benzene/chloroform=1/1), dried overP4O10 (vac.), elem. anal.;
phosphomycin disodium salt
26016-99-9

phosphomycin disodium salt

fosfomycin
23155-02-4

fosfomycin

Conditions
ConditionsYield
With Dowex 50x8, H(+) In water
phosphomycin disodium salt
26016-99-9

phosphomycin disodium salt

A

(1R,2R) (1,2-dihydroxypropyl)phosphonate

(1R,2R) (1,2-dihydroxypropyl)phosphonate

B

(1S,2S) (1,2-dihydroxypropyl)phosphonate

(1S,2S) (1,2-dihydroxypropyl)phosphonate

Conditions
ConditionsYield
With water; sodium hydroxide at 90℃; for 24h;

Disodium phosphonomycin Chemical Properties


IUPAC Name: Disodium [(2R,3S)-3-methyloxiran-2-yl]-dioxido-oxo-λ5-phosphane
Molecular Weight: 182.022701 [g/mol]
Molecular Formula: C3H5Na2O4P
H-Bond Donor: 0
H-Bond Acceptor: 4 
EINECS: 247-409-2
Product Categories: chiral; Antibiotic Explorer; Intermediates & Fine Chemicals; Pharmaceuticals; Peptide Synthesis / Antibiotics 
Storage temp.: 2-8 °C
Solubility: H2O: 50 mg/mL, clear, colorless
Appearance: White Solid
Melting Point: >300 °C
Classification Code of Disodium phosphonomycin (CAS NO.26016-99-9): Drug / Therapeutic Agent; Mutation data; Reproductive Effect 

Disodium phosphonomycin Uses

 Disodium phosphonomycin (CAS NO.26016-99-9) is used as an antibiotic.

Disodium phosphonomycin Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intramuscular 2625mg/kg (2625mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES		 Japanese Journal of Antibiotics. Vol. 32, Pg. 61, 1979.
mouse LD50 intraperitoneal 2175mg/kg (2175mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 12, Pg. 668, 1981.
mouse LD50 intravenous 1225mg/kg (1225mg/kg) SENSE ORGANS AND SPECIAL SENSES: INCREASED INTRAOCULAR PRESSURE: EYE

BEHAVIORAL: IRRITABILITY

BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)		 Japanese Journal of Antibiotics. Vol. 32, Pg. 61, 1979.
mouse LD50 oral 7300mg/kg (7300mg/kg) SENSE ORGANS AND SPECIAL SENSES: LACRIMATION: EYE

SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES		 Japanese Journal of Antibiotics. Vol. 32, Pg. 61, 1979.
mouse LD50 subcutaneous 5100mg/kg (5100mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 12, Pg. 668, 1981.
rat LD50 intramuscular 2460mg/kg (2460mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES		 Japanese Journal of Antibiotics. Vol. 32, Pg. 61, 1979.
rat LD50 intraperitoneal 2gm/kg (2000mg/kg) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES		 Japanese Journal of Antibiotics. Vol. 32, Pg. 61, 1979.
rat LD50 intravenous 1560mg/kg (1560mg/kg) SENSE ORGANS AND SPECIAL SENSES: INCREASED INTRAOCULAR PRESSURE: EYE

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES		 Japanese Journal of Antibiotics. Vol. 32, Pg. 61, 1979.
rat LD50 oral 4550mg/kg (4550mg/kg) SENSE ORGANS AND SPECIAL SENSES: LACRIMATION: EYE

SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE

BEHAVIORAL: MUSCLE WEAKNESS		 Japanese Journal of Antibiotics. Vol. 32, Pg. 61, 1979.
rat LD50 subcutaneous 4320mg/kg (4320mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES		 Japanese Journal of Antibiotics. Vol. 32, Pg. 61, 1979.
 

Disodium phosphonomycin Safety Profile

Poison by intraperitoneal and subcutaneous routes. Moderately toxic by intravenous and intramuscular routes. Mildly toxic by ingestion. Experimental teratogenic and reproductive effects. Mutation data reported. When heated to decomposition it emits toxic fumes of POx and Na2O.
Hazard Codes: F,C
Risk Statements: 11-34
11:  Highly Flammable 
34:  Causes burns 
Safety Statements: 16-26-36/37/39-45
16:  Keep away from sources of ignition - No smoking 
26:  In case of contact with eyes, rinse immediately with plenty of water and seek medical advice 
36/37/39:  Wear suitable protective clothing, gloves and eye/face protection 
45:  In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) 
WGK Germany: 2
RTECS: SZ7902000
F: 10-21
F10: Keep under argon.
F21: Sensitive to humidity.

Disodium phosphonomycin Specification

 Disodium phosphonomycin (CAS NO.26016-99-9), its Synonyms are (1R,2S)(-)-(1,2-Epoxypropyl)phosphonic acid disodium salt ; (2R-cis)-(3-Methyloxiranyl)phosphonic acid disodium salt ; Disodium fosfomycin ; Fosfocina disodium salt ; Fosfomycin disodium ; Fosfomycin disodium salt ; Fosfomycin sodium ; Fosfomycin sodium salt ; Phosphonemycin ; Phosphonomycin disodium salt ; Phosphonomycin sodium ; Priomicina ; Sodium fosfomycin ; Veramina ; Disodium (1R,2S)-(1,2-epoxypropyl)phosphonate ; Phosphonic acid, (1,2-epoxypropyl)-, disodium salt (1R,2S) (-)- ; Phosphonic acid, (3-methyloxiranyl)-, disodium salt, (2R-cis)- (9CI) .

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