Cefquinome Sulfate
Basic information
- CAS
118443-89-3- Standard SMILES
CO/N=C(\C(=O)N[C@@H]1C(=O)N2C(C(=O)[O-])=C(C[n+]3cccc4c3CCCC4)CS[C@H]12)c1csc(N)n1.O=S(=O)(O)O- InChIKey
KYOHRXSGUROPGY-OFNLCGNNSA-N- Molecular formula
- C23H26N6O9S3
- Average molar mass
- 626.7 g/mol
- Monoisotopic mass
- 626.09233995
Overview
Cefquinome Sulfate is the sulfate form of cefquinome, a semisynthetic, broad-spectrum, fourth-generation aminothiazolyl cephalosporin with antibacterial activity. Cefquinome binds to and inactivates penicillin-binding proteins (PBPs) located on the inner membrane of the bacterial cell wall. PBPs are enzymes involved in the terminal stages of assembling the bacterial cell wall and in reshaping the cell wall during growth and division. Inactivation of PBPs interferes with the cross-linkage of peptidoglycan chains necessary for bacterial cell wall strength and rigidity. This results in the weakening of the bacterial cell wall and causes cell lysis.
Names & identifiers
- Preferred name
- Cefquinome Sulfate
- IUPAC
- (6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-8-oxo-3-(5,6,7,8-tetrahydroquinolin-1-ium-1-ylmethyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate;sulfuric acid
- English name
- Cefquinome sulfate
- Molecular formula
- C23H25N6O5S2.HO4S
- Molecular weight
- 626.69
Names & synonyms
Cefquinome sulfate118443-89-3Cefquinome sulphateHR111V-SULFATEHr111v-sulphateCefquinome sulfate [USAN]HR-111V-SULFATEUNII-3858K104DQ3858K104DQCEFQUINOME SULFATE [MI]CEFQUINOME SULFATE [MART.]Cefquinome sulfate (USAN)
Show more names
1-(((6R,7R)HR 111V Sulfate[6R-[6α,7β(Z)]]-1-Cefoquiuonie sulphateCefquinoMe Sulfate DMFC11064700 CefquinomEsulfateCefquinome sulfate USP/EP/BPcefquinome Sulfate (Standard)Cefuroxime sulfate 118443-89-3
CEFQUINOME SULFATE (MART.)QUINOLINIUM, 1-((7-(((2-AMINO-4-THIAZOLYL)(METHOXYIMINO)ACETYL)AMINO)-2-CARBOXY-8-OXO-5-THIA-1-AZABICYCLO(4.2.0)OCT-2-EN-3-YL)METHYL)-5,6,7,8-TETRAHYDRO-, HYDROXIDE, INNER SALT, (6R-(6.ALPHA.,7.BETA.(Z)))-, SULFATE (1:1)QUINOLINIUM, 1-((7-(((2-AMINO-4-THIAZOLYL)(METHOXYIMINO)ACETYL)AMINO)-2-CARBOXY-8-OXO-5-THIA-1-AZABICYCLO(4.2.0)OCT-2-EN-3-YL)METHYL)-5,6,7,8-TETRAHYDRO-, HYDROXIDE, INNER SALT, (6R-(6.ALPHA.,7.BETA.(Z)))-, SULPHATE (1:1)Quinolinium, 1-((7-(((2-amino-4-thiazolyl)(methoxyimino)acetyl)amino)-2-carboxy-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-en-3-yl)methyl)-5,6,7,8-tetrahydro-, hydroxide, inner salt, (6R-(6alpha,7beta(Z)))-, sulfate (1:1)Quinolinium, 1-[[(6R,7R)-7-[[(2Z)-(2-amino-4-thiazolyl)(methoxyimino)acetyl]amino]-2-carboxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl]-5,6,7,8-tetrahydro-, sulfate (1:1)Quinolinium, 1-(((6R,7R)-7-(((2Z)-(2-amino-4-thiazolyl)(methoxyimino)acetyl)amino)-2-carboxy-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-en-3-yl)methyl)-5,6,7,8-tetrahydro-, sulfate (1:1)RefChem:124250690-053-1
Properties
Computed structural properties
- Topological polar surface area
- 290 Ų
- Hydrogen bond donors
- 4
- Hydrogen bond acceptors
- 14
- Rotatable bonds
- 6
- Heavy atoms
- 41
- Formal charge
- 0
- Complexity
- 1,050
Physicochemical properties
- Melting point
- 161 · 161-166°C
- storage temp.
- 2 · under inert gas (nitrogen or Argon) at 2–8 °C
- solubility
- DMSO (Slightly), Methanol (Slightly)
- form
- Solid
- color
- White to Off-White
- InChIKey
- KYOHRXSGUROPGY-NIZYHBPXNA-N
- SMILES
- S(O)([O-])(=O)=O.C(C1=C(CS[C@]2([H])[C@H](NC(=O)/C(/C3=CSC(N)=N3)=N\OC)C(=O)N12)C[N+]1=CC=CC2CCCCC1=2)(=O)O |&1:10,12,r|
- FDA UNII
- 3858 K104DQ · 3858K104DQ
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 302 · H302-H315-H319-H335
- Precautionary statements
- 261 · P261-P280-P301+P312-P302+P352-P305+P351+P338
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Danger
H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
P233, P260, P261, P264, P264+P265, P271, P273, P280, P284, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P342+P316, P362+P364, P391, P403, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 53 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Danger
H317 (100%): May cause an allergic skin reaction [Warning Sensitization, Skin]
Hazard information
Regulatory InformationCefquinome sulfate: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
Hazard Classes and Categories
Skin Sens. 1 (100%)
Skin Irrit. 2 (100%)
Safety data
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Hazard statements
- H302-H315-H319-H335
- Precautionary statements
- P261-P280-P301+P312-P302+P352-P305+P351+P338
Chemistry & industry
Applications
DescriptionCefquinome sulfate is a veterinary, parenteral, fourth-generation cephalosporin belonging to the class of aminothiazolyl compounds. They have high cell permeability and high stability to beta-lactamases. They have broad-spectrum antimicrobial activity against Gram-positive and Gram-negative bacteria (e.g. Pseudomonas aeruginosa and Enterobacteriaceae).
UsesCefquinome sulfate is an antibacterial used in veterinary medicine. Used in the treatment of infections caused by pathogens such as S. aureus, E. coli, Streptococcus, P. multocida and A. pleuropneumoniae. Also used to trea t mastitis in dairy cows.
UsesAn antibacterial used in veterinary medicine. Used in the treatment of infections caused by pathogens such as S. aureus, E. coli, Streptococcus, P. multocida and A. pleuropneumoniae. Also used to treat mastitis in dairy cows.
Additional notes
DefinitionNCIt: Cefquinome Sulfate is the sulfate form of cefquinome, a semisynthetic, broad-spectrum, fourth-generation aminothiazolyl cephalosporin with antibacterial activity. Cefquinome binds to and inactivates penicillin-binding proteins (PBPs) located on the inner membrane of the bacterial cell wall. PBPs are enzymes involved in the terminal stages of assembling the bacterial cell wall and in reshaping the cell wall during growth and division. Inactivation of PBPs interferes with the cross-linkage of peptidoglycan chains necessary for bacterial cell wall strength and rigidity. This results in the weakening of the bacterial cell wall and causes cell lysis.
Related reactions
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Compound notes
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