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Fosfomycin tromethamine
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Name

Fosfomycin tromethamine

 EINECS 279-018-8
CAS No. 78964-85-9 Density N/A
PSA 166.58000 LogP -1.73000
Solubility N/A Melting Point N/A
Formula C4H11NO3.C3H7O4P Boiling Point 357 °C at 760 mmHg
Molecular Weight 259.196 Flash Point 169.7 °C
Transport Information N/A Appearance white or off-white powder
Safety Risk Codes N/A
Molecular Structure Molecular Structure of 78964-85-9 (Fosfomycin tromethamine) Hazard Symbols N/A
Synonyms

Monurol (TN);Phosphonic acid, (3-methyloxiranyl)-, (2R-cis)-, compd. with 2-amino-2-(hydroxymethyl)-1,3-propanediol (1:1);Fosfomycin tromethamine (USAN);(1R,2S)-(1,2-Epoxypropyl)phosphonic acid, compound with 2-amino-2-(hydroxymethyl)-1,3-propanediol (1:1);Monurol;Fosfomycin compd. with trometamol;Z 1282;(2R-cis)-(3-Methyloxiranyl)phosphonic acid, compound with 2-amino-2-(hydroxymethyl)propane-1,3-diol (1:1);Tromethamine-fosfomycin;

Article Data 5

Fosfomycin tromethamine Synthetic route

fosfomycin bis tromethamine

78964-85-9

fosfomycin trometamol

Conditions
ConditionsYield
With acetic anhydride In methanol at 20 - 30℃; for 1.33333h;95.1%

fosfomycin bis-tromethamine

78964-85-9

fosfomycin trometamol

Conditions
ConditionsYield
Stage #1: fosfomycin bis-tromethamine In methanol at 20℃; for 0.25h;
Stage #2: With Cyclohexyl isocyanate In methanol at 20℃; for 0.633333h; Reagent/catalyst;		90.5%

(1R,2S)-(-)-cis-1,2-epoxypropyl phosphoric acid-R-(+)-α-phenethylamine salt

77-86-1

2-amino-2-hydroxymethyl-1,3-propanediol

78964-85-9

fosfomycin trometamol

Conditions
ConditionsYield
Stage #1: (1R,2S)-(-)-cis-1,2-epoxypropyl phosphoric acid-R-(+)-α-phenethylamine salt; 2-amino-2-hydroxymethyl-1,3-propanediol In methanol at 20℃; for 0.25h;
Stage #2: With Cyclohexyl isocyanate In methanol at 20 - 33℃; for 0.633333h; Reagent/catalyst;		86.2%

C3H7O4P*C8H11N*C4H11NO3

78964-85-9

fosfomycin trometamol

Conditions
ConditionsYield
With methanesulfonic acid In ethanol at 48 - 50℃; for 0.833333h; Reagent/catalyst; Temperature;72.3%
With methanesulfonic acid In ethanol at 48 - 50℃; for 0.833333h; Temperature;
855392-18-6

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

26016-99-9

phosphomycin disodium salt

78964-85-9

fosfomycin trometamol

Conditions
ConditionsYield
In methanol at 20 - 65℃; for 3 - 4h;

Fosfomycin tromethamine Standards and Recommendations

Purity: EP4
EP: Assay: 98.0%-102.0%
Impurities A,B: not more than 0.3%
Impurities C,D: not more than 0.1%
Any other impurity: not more than 0.1%
Total impurities: not more than 0.5%

Fosfomycin tromethamine Specification

The IUPAC name of Fosfomycin trometamol is 2-amino-2-(hydroxymethyl)propane-1,3-diol; [(2R,3S)-3-methyloxiran-2-yl]phosphonic acid. With the CAS registry number 78964-85-9, it is also named as Fosfomycin tromethamine. The product's classification codes are Anti-Infective Agents; Antibacterial; Drug / Therapeutic Agent. Besides, it is an antibiotic produced by Streptomyces fradiae. In addition, its molecular formula is C4H11NO3.C3H7O4P and molecular weight is 259.19.

The other characteristics of Fosfomycin trometamol can be summarized as: (1)EINECS: 279-018-8; (2)ACD/LogP: -1.38; (3)# of Rule of 5 Violations: 1; (4)ACD/LogD (pH 5.5): -4.43; (5)ACD/LogD (pH 7.4): -3.51; (6)ACD/BCF (pH 5.5): 1; (7)ACD/BCF (pH 7.4): 1; (8)ACD/KOC (pH 5.5): 1; (9)ACD/KOC (pH 7.4): 1; (10)#H bond acceptors: 4; (11)#H bond donors: 5; (12)#Freely Rotating Bonds: 7; (13)Polar Surface Area: 27.69 Å2; (14)Flash Point: 169.7 °C; (15)Enthalpy of Vaporization: 69.73 kJ/mol; (16)Boiling Point: 357 °C at 760 mmHg; (17)Vapour Pressure: 1.57E-06 mmHg at 25 °C.

People can use the following data to convert to the molecule structure.
(1)SMILES: [O-]P(=O)(O)[C@H]1O[C@H]1C.OCC([NH3+])(CO)CO
(2)InChI: InChI=1/C4H11NO3.C3H7O4P/c5-4(1-6,2-7)3-8;1-2-3(7-2)8(4,5)6/h6-8H,1-3,5H2;2-3H,1H3,(H2,4,5,6)/t;2-,3+/m.0/s1
(3)InChIKey: QZJIMDIBFFHQDW-LMLSDSMGBH

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 unreported > 10gm/kg (10000mg/kg)   Drugs of the Future. Vol. 13, Pg. 77, 1988.
rat LD50 unreported > 10gm/kg (10000mg/kg)   Drugs of the Future. Vol. 13, Pg. 77, 1988.

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