Cefadroxil Monohydrate
Basic information
- CAS
66592-87-8- Standard SMILES
CC1=C(C(=O)O)N2C(=O)[C@@H](NC(=O)[C@H](N)c3ccc(O)cc3)[C@H]2SC1.O- InChIKey
NBFNMSULHIODTC-CYJZLJNKSA-N- Molecular formula
- C16H19N3O6S
- Average molar mass
- 381.4 g/mol
- Monoisotopic mass
- 381.09945651
Overview
Cefadroxil monohydrate is the hydrate that is the monohydrate of the cephalosporin cefadroxil. It contains a cefadroxil.
Names & identifiers
- Preferred name
- Cefadroxil Monohydrate
- IUPAC
- (6R,7R)-7-[[(2R)-2-amino-2-(4-hydroxyphenyl)acetyl]amino]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid;hydrate
- English name
- Cefadroxil
- Molecular formula
- C16H17N3O5S.H2O
- Molecular weight
- 381.41
Names & synonyms
Cefadroxil monohydrate66592-87-8Cefadroxil 1-wasser5-Thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 7-(((2R)-amino(4-hydroxyphenyl)acetyl)amino)-3-methyl-8-oxo-, monohydrate, (6R,7R)-CHEBI:53667DTXSID80904597RefChem:124195DTXCID201333721Cefadroxil (hydrate)BL-S 578MFCD01682047(6R,7R)-7-((R)-2-Amino-2-(4-hydroxyphenyl)acetamido)-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid hydrate
Show more names
AMOXYCILLINCefadroxil hydrate5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylicacid, 7-[[(2R)-2-aMino-2-(4-hydroxyphenyl)acetyl]aMino]-3-Methyl-8-oxo-,hydrate (1:1), (6R,7R)-CEFADROXILEBaxanDuracefCEFAMOXCEFADROXILCefa-Drops
BidocelHY-B1190ACCG-268421(6R,7R)-7-((R)-2-Amino-2-(p-hydroxyphenyl)acetamido)-3-methyl-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid monohydrateAS-75209Moxacef KapselnBaxan KapselnCefos Granulat
Properties
Computed structural properties
- Topological polar surface area
- 159 Ų
- Hydrogen bond donors
- 5
- Hydrogen bond acceptors
- 8
- Rotatable bonds
- 4
- Heavy atoms
- 26
- Formal charge
- 0
- Complexity
- 629
Physicochemical properties
- Melting point
- 197 °C · 197 °C
- storage temp.
- 2 · Keep in dark place,Inert atmosphere,2-8°C
- solubility
- 96 per · Slightly soluble in water, very slightly soluble in ethanol (96 per cen
- pka
- 1.38 · pKa 1.38(H2O t=20±2 N2atmosphere) (Uncertain); 7.35(H2O t=20±2 N2atmosphere) (Uncertain);10.10(H2O t=20±2 N2atmosphere) (Uncertain)
- form
- Solid
- color
- White to Off-White
- BCS Class
- 3 · 3
- InChIKey
- NBFNMSULHIODTC-CYJZLJNKSA-N
- SMILES
- N12C([C@@H](NC(=O)[C@H](N)C3=CC=C(O)C=C3)[C@@]1([H])SCC(C)=C2C(=O)O)=O.O |&1:2,6,15,r|
- CAS DataBase Reference
- 66592 · 66592-87-8(CAS DataBase Reference)
- FDA UNII
- 280111 G160 · 280111G160
- ATC code
- 1 DB05 · J01DB05
- Protein binding
- 20 % · 20%
- Excreted unchanged in urine
- 90 % · >90%
- Volume of distribution
- 0.31 · 0.31(L/kg)
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
H317 (15.2%): May cause an allergic skin reaction [Warning Sensitization, Skin]
P233, P260, P261, P271, P272, P280, P284, P302+P352, P304+P340, P321, P333+P317, P342+P316, P362+P364, P403, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 33 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory InformationCefadroxil monohydrate: 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.
Other Safety InformationIMAP assessments - 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 7-[[amino(4-hydroxyphenyl)acetyl]amino]-3-methyl-8-oxo-, monohydrate, [6R-[6.alpha.,7.beta.(R*)]]-: Environment tier I assessment
Hazard Classes and CategoriesSkin Sens. 1 (15.2%)
Safety data
- wgk
- 2
- rtecs
- XI0337000
- hs_code
- 2941906000
- risk_code
- 36/37/38-42/43
- Signal word
- Danger
- Symbol(GHS)
- GHS05
- hazard_code
- Xn,Xi
- safety_code
- 26-36-36/37
- Hazard statements
- H314
Chemistry & industry
Pharmacology
MeSH Pharmacological ClassificationSubstances that inhibit the growth or reproduction of BACTERIA.
Applications
DescriptionCefadroxil has an amoxicillin-like side chain at C-7 and is orally active. There are some indications that cefadroxil has some immunostimulant properties mediated through T-cell activation and that this is of material assistance to patients in fighting infections. The prolonged biological half-life of cefadroxil allows once-a-day dosage.
UsesCefadroxil Monohydrate is a semi-synthetic cephalosporin antibacterial. It has been used for various community-acquired infections for which oral cephalosporins are appropriate.
General DescriptionCefadroxil is a semisynthetic first-generation β-lactam cephalosporin antibiotic derived from cefalexin with antibacterial activity. It is used to treat urinary tract infections, skin and skin structure infections, pharyngitis, and tonsillitis caused by susceptible bacteria.
Additional notes
DefinitionChEBI: The hydrate that is the monohydrate of the cephalosporin cefadroxil.
Related reactions
21 records
Compound notes
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