Amoxicillin, L-
Basic information
- CAS
26787-78-0- Standard SMILES
CC1(C)S[C@@H]2[C@H](NC(=O)[C@@H](N)c3ccc(O)cc3)C(=O)N2[C@H]1C(=O)O- InChIKey
LSQZJLSUYDQPKJ-BBGACYKPSA-N- Molecular formula
- C16H19N3O5S
- Average molar mass
- 365.4 g/mol
- Monoisotopic mass
- 365.10454189
Overview
(2S,5R,6R)-6-[[(2S)-2-amino-2-(4-hydroxyphenyl)-1-oxoethyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid is a penicillin.
Names & identifiers
- Preferred name
- Amoxicillin, L-
- IUPAC
- (2S,5R,6R)-6-[[(2S)-2-amino-2-(4-hydroxyphenyl)acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
- English name
- L-Amoxicillin
- Molecular formula
- C16H19N3O5S
- Molecular weight
- 365.4
Names & synonyms
L-Amoxicillin26889-93-0Amoxicillin, L-UNII-623M8I9SZN623M8I9SZN(2S,5R,6R)-6-[[(2S)-2-amino-2-(4-hydroxyphenyl)acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acidAmoxicillin trihydrate impurity BAmoxicillin trihydrate impurity B [EP]DTXSID301813964-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-(((2S)-amino(4-hydroxyphenyl)acetyl)amino)-3,3-dimethyl-7-oxo-, (2S,5R,6R)-4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-(2-amino-2-(p-hydroxyphenyl)acetamido)-3,3-dimethyl-7-oxo-, stereoisomer4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-((amino(4-hydroxyphenyl)acetyl)amino)-3,3-dimethyl-7-oxo-, (2S-(2alpha,5alpha,6beta(R*)))-
Show more names
AMoxicillin EP IMpurity BAmoxicillin EP Imp BAmoxicillin USP RC BAmoxicillin Sodium Impurity BAMoxicillin Related CoMpound BAmoxicillin USP Related Compound B(2S,5R,6R)-6-[[(2S)-2-Amino-2-(4-hy
Properties
Computed structural properties
- XLogP
- -2
- Topological polar surface area
- 158 Ų
- Hydrogen bond donors
- 4
- Hydrogen bond acceptors
- 7
- Rotatable bonds
- 4
- Heavy atoms
- 25
- Formal charge
- 0
- Complexity
- 590
Physicochemical properties
- Boiling point
- 743.2 · 743.2±60.0 °C(Predicted)
- Density
- 1.54 · 1.54±0.1 g/cm3(Predicted)
- storage temp.
- -20 °C · Hygroscopic, -20°C Freezer, Under inert atmosphere
- solubility
- DMSO (Slightly), Water (Slightly, Heated, Sonicated)
- pka
- 2.44 · 2.44±0.50(Predicted)
- form
- Solid
- color
- White to Off-White
- InChI
- 1S/C16H19N3O5S/c1-16(2)11(15(23)24)19-13(22)10(14(19)25-16)18-12(21)9(17)7-3-5-8(20)6-4-7/h3-6,9-11,14,20H,17H2,1-2H3,(H,18,21)(H,23,24)/t9-,10+,11-,14+/m0/s1
- InChIKey
- LSQZJLSUYDQPKJ-BBGACYKPSA-N
- SMILES
- S1[C@H]2N([C@H](C1(C)C)C(=O)[O-])C(=O)[C@H]2NC(=O)[C@@H]([N+H3])c3ccc(cc3)O
- FDA UNII
- 623 M8I9SZN · 623M8I9SZN
- UNSPSC Code
- 41116107 · 41116107
- NACRES
- 24 · NA.24
- Symbol(GHS)
- 8 · GHS08
- Signal word
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
H302 (50%): Harmful if swallowed [Warning Acute toxicity, oral]
P233, P260, P261, P264, P270, P271, P272, P280, P284, P301+P317, P302+P352, P304+P340, P321, P330, P333+P317, P342+P316, P362+P364, P403, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 2 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesSkin Sens. 1 (50%)
Safety data
- wgk
- WGK 3
- hs_code
- 2934990002
- Signal word
- Danger
- Symbol(GHS)
- GHS08
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H317-H334
- Hazard Classifications
- Resp. Sens. 1Skin Sens. 1
- Precautionary statements
- P261-P272-P280-P284-P302+P352-P333+P313
Chemistry & industry
Applications
UsesIsomer of Amoxicillin (A634235), a semi-synthetic antibiotic related to penicillin. Antibacterial.
UsesL-Amoxicillin (Amoxicillin EP Impurity B) is an isomer of Amoxicillin (A634235), a semi-synthetic antibiotic related to penicillin.
Additional notes
DefinitionChEBI: (2S,5R,6R)-6-[[(2S)-2-amino-2-(4-hydroxyphenyl)-1-oxoethyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid is a penicillin.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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