cefalexin HCl monohydrate
Basic information
- CAS
1820673-23-1- Standard SMILES
CC1=C(C(=O)O)N2C(=O)[C@@H](NC(=O)[C@H](N)c3ccccc3)C2SC1- InChIKey
ZAIPMKNFIOOWCQ-MHSSMOFYSA-N- Molecular formula
- C16H17N3O4S
- Average molar mass
- 347.4 g/mol
- Monoisotopic mass
- 347.09397721
Overview
(7R)-7-[[(2R)-2-amino-2-phenylacetyl]amino]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid has been reported in Streptomyces with data available.
Names & identifiers
- Preferred name
- cefalexin HCl monohydrate
- IUPAC
- (7R)-7-[[(2R)-2-amino-2-phenylacetyl]amino]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
- English name
- Cephalexin hydrate
- Molecular formula
- C16H19N3O5S
- Molecular weight
- 365.40416
Names & synonyms
1820673-23-1cefalexin HCl monohydrateSCHEMBL11985597SBB058115AKOS015962251AC-16005AC-22680C2248ST50320058(7R)-7-((2R)-2-amino-2-phenylacetylamino)-3-methyl-6-oxo-2H,7H,7aH-azetidino[2 ,1-b]1,3-thiazine-4-carboxylic acid(7R)-7-((2R)-2-amino-2-phenylacetylamino)-3-methyl-6-oxo-2H,7H-azetidino[2,1-b ]1,3-thiazine-4-carboxylic acid1212823-95-4
Database identifiers
- CAS
1820673-23-1- PubChem CID
- 62922
- EC Number
- 998-943-4
Properties
Computed structural properties
- XLogP
- 0.6
- Topological polar surface area
- 138 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 4
- Heavy atoms
- 24
- Formal charge
- 0
- Complexity
- 600
Physicochemical properties
- solubility
- Soluble in DMSO and Methanol.
- form
- Powder
- Stability
- Unstable in Solution
- InChI
- 1S/C16H17N3O4S.H2O/c1-8-7-24-15-11(14(21)19(15)12(8)16(22)23)18-13(20)10(17)9-5-3-2-4-6-9;/h2-6,10-11,15H,7,17H2,1H3,(H,18,20)(H,22,23);1H2/t10-,11-,15;/m1./s1
- InChIKey
- AVGYWQBCYZHHPN-FNOHQHCYSA-N
- SMILES
- S1C2N(C(=C(C1)C)C(=O)O)C(=O)[C@H]2NC(=O)[C@H](N)c3ccccc3.O
- UNSPSC Code
- 51282503 · 51282503
- NACRES
- 85 · NA.85
- Symbol(GHS)
- 8 · GHS08
- Signal word
- Warning
- Hazard statements
- 317 · H317-H334
- Precautionary statements
- 261 · P261-P272-P280g-P285-P302+P352-P304+P341-P333+P313-P342+P311-P363-P403-P501c
- PPE
- 95 · dust mask type N95 (US), Eyeshields, Faceshields, Gloves
- WGK Germany
- 3 · WGK 3
- Storage Class
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 (100%): 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)
The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.
Hazard information
Hazard Classes and CategoriesSkin Sens. 1 (100%)
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Faceshields, Gloves
- wgk
- WGK 3
- Signal word
- Warning
- Symbol(GHS)
- GHS08
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H317-H334
- Hazard Classifications
- Resp. Sens. 1Skin Sens. 1
- Precautionary statements
- P261-P272-P280g-P285-P302+P352-P304+P341-P333+P313-P342+P311-P363-P403-P501c
Chemistry & industry
Applications
UsesCephalexin is a cephalosporin antibiotic used to study the effect of expression, binding, and inhibition of PBP3 and other penicillin-binding proteins (PBPs) on bacterial cell wall mucopeptide synthesis. Cephalexin disrupts the synthesis of the peptidoglycan layer of bacterial cell walls which is responsible for cell wall structural integrity. Peptidoglycan synthesis is facilitated by transpeptidases known as penicillin-binding proteins (PBPs). PBPs bind to the D-Ala-D-Ala at the end of muropeptides (peptidoglycan precursors) to crosslink the peptidoglycan. Cephalexin antibiotics mimic the D-Ala-D-Ala site, thereby competitively inhibiting PBP crosslinking of peptidoglycan.
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