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Monuril

HCID 54331
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Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
78964-85-9
Standard SMILES
C[C@@H]1O[C@@H]1P(=O)([O-])O.[NH3+]C(CO)(CO)CO
InChIKey
QZJIMDIBFFHQDW-LMLSDSMGSA-N
Molecular formula
C7H18NO7P
Average molar mass
259.19 g/mol
Monoisotopic mass
259.08208891

Overview

See also: Fosfomycin Tromethamine (preferred); Fosfomycin (has active moiety).

Names & identifiers

Preferred name
Monuril
IUPAC
[1,3-dihydroxy-2-(hydroxymethyl)propan-2-yl]azanium;hydroxy-[(2R,3S)-3-methyloxiran-2-yl]phosphinate
English name
Fosfomycin tromethamine
Molecular formula
C7H18NO7P
Molecular weight
259.19

Names & synonyms

Monuril[1,3-dihydroxy-2-(hydroxymethyl)propan-2-yl]azanium;hydroxy-[(2R,3S)-3-methyloxiran-2-yl]phosphinateFosfomycin tromethanolTromethamine-fosfomycinFosfotricinMonurol Sachet78964-85-9 (Tromethamine)EINECS 279-018-8UNII-7FXW6U30GYAKOS015896108AC-4209KS-1266
Show more names
FOSFOMYCIN TROMETAMOLFOSFOMYCIN TROMETHAMOLphosphomycin trometamolz1282Fosfomycin tramineFosfomycine Trometamolfosfomycin tromethamine
(2R-cis)-(3-Methyloxiranyl)phosphonic acid, compound with 2-amino-2-(hydroxymethyl)propane-1,3-diol (1:1)

Database identifiers

CAS
78964-85-9
PubChem CID
54331

Properties

Computed structural properties

Topological polar surface area
161 Ų
Hydrogen bond donors
5
Hydrogen bond acceptors
7
Rotatable bonds
4
Heavy atoms
16
Formal charge
0
Complexity
190

Physicochemical properties

Melting point
122 · 122-125oC
storage temp.
Hygroscopic, Refrigerator, under inert atmosphere
solubility
Very soluble in water, slightly soluble in ethanol (96 per cent) and in methanol, practically insoluble in acetone.
form
Solid
color
White to Off-White
Stability
Hygroscopic
Major Application
pharmaceutical (small molecule)
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+/s3
InChIKey
QZJIMDIBFFHQDW-LMLSDSMGSA-N
SMILES
C(N)(CO)(CO)CO.P([C@H]1O[C@H]1C)(O)(O)=O |&1:9,11,r|
FDA UNII
7 FXW6U30GY · 7FXW6U30GY
NCI Drug Dictionary
fosfomycin tromethamine
UNSPSC Code
41116107 · 41116107
NACRES
24 · NA.24
Symbol(GHS)
8 · GHS08

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

Safety data

wgk
WGK 3
hs_code
2941906000
Signal word
Danger
Symbol(GHS)
GHS08
Storage Class
11 - Combustible Solids
Hazard statements
H319-H317-H334-H315
Precautionary statements
P261-P272-P280-P302+P352-P333+P313-P321-P363-P501-P261-P285-P304+P341-P342+P311-P501-P264-P280-P305+P351+P338-P337+P313P-P264-P280-P302+P352-P321-P332+P313-P362

Chemistry & industry

Applications · 3 items

UsesPhosphonic acid derivative; antibacterial.

UsesFosfomycin Tromethamine is used as an antibiotic compound in the treatment of urinary tract infections.

General DescriptionFosfomycin tromethamine (Monurol) is a phosphonic acidepoxide derivative that was initially isolated from fermentationsof Streptomyces spp. Making the tromethamine salt greatly expanded the therapeutic utility of this antibacterial because water solubilityincreased enough to allow oral administration.Fosfomycin is a broad-spectrum, bactericidal antibacterialthat inhibits the growth of E. coli, S. aureus, andSerratia, Klebsiella, Citrobacter, Enterococcus, andEnterobacter spp. at a concentration less than 64 mg/L.Currently fosfomycin is recommended as single-dose therapyfor uncomplicated urinary tract infections. It possessesin vitro efficacy similar to that of norfloxacin and trimethoprim-sulfamethoxazole.Fosfomycin covalently inactivates the first enzyme in thebacterial cell wall biosynthesis pathway, UDP-N-acetylglucosamineenolpyruvyl transferase (MurA) by alkylation ofthe cysteine-115 residue. The inactivation reaction occursthrough nucleophilic opening of the epoxide ring. Resistanceto fosfomycin can occur through chromosomal mutationsthat result in reduced uptake or reduced MurA affinity for theinhibitor. Plasmid-mediated resistance mechanisms involveconjugative bioinactivation of the antibiotic with glutathione.The frequency of resistant mutants in in vitro studies hasbeen low, and there appears to be little cross-resistance betweenfosfomycin and other antibacterials.

Suppliers100 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
Shandong chuangyingchemical Co., Ltd.18853181302 · [email protected]
济南百隆化学有限公司[email protected] · [email protected]

Related reactions

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Signal word
Danger
Hazard statements
319 · H319-H317-H334-H315
Precautionary statements
261 · P261-P272-P280-P302+P352-P333+P313-P321-P363-P501-P261-P285-P304+P341-P342+P311-P501-P264-P280-P305+P351+P338-P337+P313P-P264-P280-P302+P352-P321-P332+P313-P362
WGK Germany
3 · WGK 3
HS Code
2941906000 · 2941906000
Storage Class
11 · 11 - Combustible Solids
武汉鹏垒生物科技有限公司
15871464247 · [email protected]
合肥翰刚医药科技有限公司+8618062405514 · [email protected]
Shanghai Yingrui Biopharma Co.,Ltd21-33585366 · [email protected]
杭州言鼎生物医药科技有限公司18989469219 · [email protected]
Baoji Guokang Healthchem co.,ltd+8615604608665 15604608665 · [email protected]
重庆康洲智通医药科技有限公司173-08362167 17308362167 · [email protected]
Dayang Chem (Hangzhou) Co.,Ltd.+86-0571-88938639 17705817739 · [email protected]
Hebei Yanxi Chemical Co., Ltd.+86-17531190177 · [email protected]
大连美仑生物技术有限公司0411-62910999 13889544652 · [email protected]
太原市瑞和丰科贸有限公司+86 351 7031519 · [email protected]
南京圣亿来化工有限公司19951936396 · [email protected]
上海柯维化学技术有限公司021-64609169 18901607656 · [email protected]
MedBio脉铂医药021-69568360 18916172912 · [email protected]
上海钰康生物科技有限公司+86-18930848214 +86-021-56762820 · [email protected]
上海瀚香生物科技有限公司177-54423994 17754423994 · [email protected]
合肥天健化工有限公司551-65418679 15856988503;15837135945 · [email protected]
武汉裕清嘉衡药业有限公司027-83850128 18207128853 · [email protected]
贵州迪大科技有限责任公司0851-8475-2296 18096062265 · [email protected]
河南多贝化工有限公司0370-2785118 17550508557 · [email protected]
深圳振强药物研发有限公司0755-66853366 13670046396 · [email protected]
武汉普洛夫生物科技有限公司17612776928 · [email protected]
南京生利德生物科技有限公司025-57798810 18652991625 · [email protected]
湖北威德利化学试剂有限公司186-02735115 18602735115 · [email protected]
上海喀露蓝科技有限公司18149758185 18149758185 · [email protected]
深圳菲斯生物科技有限公司0755-83725350 13380397412 · [email protected]
郑州鸿晟医药科技有限公司0371-0371-13526885213 15637198702 · [email protected]
南京伊鹤田科技有限公司025 86551269
上海御略医药科技有限公司021-60345187 13671753212 · [email protected]
杭州杰恒化工有限公司0571-87396432 · [email protected]
上海孚一生物科技有限公司+86 (21) 61124340
池州凯隆进出口贸易有限公司[email protected]
桦特昇生物科技(武汉)有限公司027-59207879 1972026995 18140587686 · [email protected]
安徽赛诺制药有限公司+86-18512541987 · [email protected]
TargetMol中国(陶术生物)021-021-33632979 15002134094 · [email protected]
上海皓之翔生物科技有限公司(原上海拓青化工有限公司)526763801 13301653310 · [email protected]
湖北威德利化学科技有限公司027-83989310 18627915365
湖北威德利化学试剂有限公司18327179646 · [email protected]
泰安嘉岳生物化工有限公司15318151873 · [email protected]
浙江珲达生物科技有限公司0571-89903022 18679456698 · [email protected]
上海珞珐生化科技有限公司021-51111890 15317326293 · [email protected]
BOC Sciences16314854226 · [email protected]
陕西缔都医药化工有限公司+86-29-81139210 +86-17392587031 · [email protected]
上海源叶生物科技有限公司18916372613 · [email protected]
湖南华纳大药厂股份有限公司—
湖北威德利化学试剂有限公司13429867250 13429867250
重庆华烽医药科技有限公司23-67950001 13883380852 · [email protected]

Additional notes

DefinitionChEBI: Fosfomycin tromethamine is a phosphonoacetic acid.