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Amoxicillin

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Identification
Molecular formula
C16H19N3O5S
CAS number
26787-78-0
IUPAC name
(2S,5R,6R)-6-[[(2R)-2-amino-2-(4-hydroxyphenyl)acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
State
State

Amoxicillin is a solid at room temperature. It is often encountered in the form of capsules or tablets for pharmaceutical use. As a stable compound, it withstands typical environmental conditions without significant degradation.

Melting point (Celsius)
139.00
Melting point (Kelvin)
412.15
Boiling point (Celsius)
251.80
Boiling point (Kelvin)
525.00
General information
Molecular weight
365.41g/mol
Molar mass
365.4080g/mol
Density
1.3000g/cm3
Appearence

Amoxicillin typically appears as a white to off-white crystalline powder. It is known for its solubility in water and may have a slight odor depending on its formulation.

Comment on solubility

Solubility Overview

The compound (2S,5R,6R)-6-[[(2R)-2-amino-2-(4-hydroxyphenyl)acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, known for its complex structure, exhibits interesting solubility characteristics. Understanding its solubility is crucial for applications in pharmaceuticals and biochemistry.

Solubility Factors

Several factors contribute to the solubility of this compound:

  • Polarity: The presence of functional groups such as amino (-NH2) and carboxylic acid (-COOH) enhances its ability to form hydrogen bonds, thereby increasing its solubility in polar solvents, particularly water.
  • Hydrophilicity: The hydroxyphenyl group contributes to hydrophilicity, making the compound more soluble in aqueous environments.
  • Temperature: Like many organic compounds, solubility may increase with temperature, although specific behavior should be empirically determined.

Solubility in Different Solvents

The solubility can vary widely based on the solvent:

  • In water, it is expected to be of moderate solubility due to its polar characteristics.
  • In organic solvents like ethanol or dimethyl sulfoxide (DMSO), it may show increased solubility due to the solvent's ability to solvate hydrophobic portions of the molecule.

Overall, understanding the solubility of this compound is indispensable for its effective use in various applications. As the saying goes, "Like dissolves like," and the intricate balance of polar and non-polar characteristics dictates its behavior in different environments.

Interesting facts

Interesting Facts about (2S,5R,6R)-6-[[(2R)-2-amino-2-(4-hydroxyphenyl)acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

This compound is a fascinating example of a synthetic antibiotic, belonging to the group of beta-lactam antibiotics that play a critical role in fighting bacterial infections. Its complex structure features key characteristics that enhance its medicinal properties, making it a significant subject of study in medicinal chemistry and pharmacology.

Key Highlights:

  • Mechanism of Action: This compound works by inhibiting the synthesis of bacterial cell walls, leading to cell lysis and ultimately the death of the bacteria. This process is essential for combating a wide range of bacterial infections.
  • Stereochemistry: The specificity of the stereocenters in this compound contributes to its biological activity and effectiveness. The (2S,5R,6R) configuration is vital in ensuring the correct interaction with target enzymes in bacteria.
  • Amino Acid Derivative: The incorporation of an amino acid moiety, particularly the 4-hydroxyphenyl group, enhances its pharmacological profile, offering improved binding activities and reduced side effects compared to other compounds.
  • Research Implications: Ongoing studies are exploring modifications to the compound’s structure to create derivatives with improved efficacy or reduced resistance among bacterial strains.

As with many antibiotics, one of the crucial challenges is addressing antibiotic resistance. Research continues to focus on understanding the resistance mechanisms that bacteria develop against such compounds, aiming to preserve their effectiveness in clinical settings.

Exploring compounds like this one not only enriches our understanding of chemical biology but also underscores the importance of continuous innovation in drug development to tackle emerging health challenges.

Synonyms
amoxicillin
26787-78-0
Amoxycillin
Amoxicillin anhydrous
Amoxicilline
p-Hydroxyampicillin
Amopenixin
Amoxicilina
Amolin
Moxal
D-Amoxicillin
Amoxicillinum
Amoxil
Amoxiden
Amoxivet
Anemolin
Bristamox
Delacillin
Flemoxin
Hiconcil
Histocillin
Imacillin
Unicillin
Vetramox
Amoclen
Aspenil
Cemoxin
Efpenix
Ibiamox
Moxacin
Piramox
Amoxi
Sumox
Trimox
Amoxi-Mast
Sawamox PM
Metafarma capsules
Metifarma capsules
Moxatag
Ospamox
Robamox
Utimox
Wymox
DisperMox
Amoxicillin (anhydrous)
Amoxicaps
alpha-Amino-p-hydroxybenzylpenicillin
Biomox
AMOXICILLIN PEDIATRIC
6-(p-Hydroxy-alpha-aminophenylacetamido)penicillanic acid
BRL-2333
D-(-)-alpha-Amino-p-hydroxybenzylpenicillin
Topramoxin
Amoxyke
Atoksilin
CHEBI:2676
Demoksil
Largopen
Moksilin
Promoxil
Remoxil
Damoxy
Amoxi-Inject
Amoxi-Tabs
(2S,5R,6R)-6-[[(2R)-2-amino-2-(4-hydroxyphenyl)acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
D-2-Amino-2-(4-hydroxyphenyl)acetamidopenicillanic acid
NSC-277174
6-(D-(-)-p-Hydroxy-alpha-aminobenzyl)penicillin
DTXSID3037044
Amoxicillinum trihydricum
6-(D-(-)-alpha-Amino-p-hydroxyphenylacetamido)penicillanic acid
AMOX
9EM05410Q9
Amoxicillin (as trihydrate)
(-)-6-(2-Amino-2-(P-hydroxyphenyl)acetamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo-(3.2.0)heptane-2-carboxylic acid
(2S,5R,6R)-6-{[(2R)-2-amino-2-(4-hydroxyphenyl)acetyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
DTXCID1017044
Galenamox
NSC277174
Amoxycillin sodium
BRL 2333
(2S,5R,6R)-6-[(2R)-2-amino-2-(4-hydroxyphenyl)acetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-(((2R)-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-, D-
4-Thia-1-azobicyclo(3.2.0)heptane-2-carboxylic acid, 6-((amino(4-hydroxyphenyl)acetyl)amino)-3,3-dimethyl-7-oxo-, (2S-(2alpha,5alpha,6beta(S)))-
TALICIA COMPONENT AMOXICILLIN
AUGMENTIN COMPONENT AMOXICILLIN
amoxicillina
Amoxicillan
Amoxymed
Dedoxil
Respillin
Vetremox
Amoram
Amrit
Amoxil fiztab
Flemoxin solutab
Amoxil sf
Amoxi-Drop
Clamoxyl parenteral
Clamoxyl G.A.
(2S,5R,6R)-6-(((2R)-2-amino-2-(4-hydroxyphenyl)acetyl)amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid
(2S,5R,6R)-6-((2R)-2-amino-2-(4-hydroxyphenyl)acetamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid
Amoxident 250
Amoxident 500
Zoxycil 250
Zoxycil 500
Amoxicillin 500 mg
Amoxicillin Oral Susp
RefChem:6380
Amix 125
Amix 250
Amix 500
Amoxicillin monosodium salt
amoxicillin tablet, film coated
BRL2333
J01CA04
amoxicillin powder, for suspension
Lansoprazole, Amoxicillin, Clarithromycin
(2S,5R,6R)-6-(((2R)-2-azaniumyl-2-(4-hydroxyphenyl)acetyl)amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylate
(2S,5R,6R)-6-((R)-(-)-2-AMINO-2-(P-HYDROXYPHENYL)ACETAMIDO)-3,3-DIMETHYL-7-OXO-4-THIA-1-AZABICYCLO(3.2.0)HEPTANE-2-CARBOXYLIC ACID
248-003-8
4-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(S*)))-
804826J2HU
AMPC
Larotid
Amoxicilina [INN-Spanish]
Amoxicilline [INN-French]
Amoxicillinum [INN-Latin]
Amoxycillin Trihydrate
Amoxicillin [INN]
AMOXICILLIN CRYSTALLINE
MFCD00056860
Amoxicillin (INN)
Amopen
Amoxicillin (>90%)
Apo-Amoxi
AX
amoxicillanyl
Actimoxi
(2S,5R,6R)-6-(2-Amino-2-(4-hydroxyphenyl)acetamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
BLP 1410
Amoxicillin (TN)
(2S,5R,6R)-6-((R)-2-Amino-2-(4-hydroxyphenyl)acetamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
SMR000058707
Amoxicillin (trihydrate)
Amoxycillin (trihydrate)
Amoxicillin (Amoxycillin)
Ro 10-8756
HSDB 3204
EINECS 248-003-8
BL-P 1410
NSC 277174
amoxycilin
UNII-9EM05410Q9
notoginsenoside-fe
NCGC00016797-02
NCGC00094586-01
(2S,5R,6R)-6-[(R)-2-Amino-2-(4-hydroxyphenyl)acetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid
Prestwick_713
CAS-26787-78-0
AMOXICILLIN [MI]
Prestwick0_000357
Prestwick1_000357
Prestwick2_000357
Prestwick3_000357
Epitope ID:114241
Epitope ID:116054
EC 248-003-8
SCHEMBL3427
AMOXICILLIN [MART.]
CHEMBL1082
AMOXICILLIN [WHO-DD]
BSPBio_000453
MLS000028632
MLS002222248
SPBio_002374
BPBio1_000499
orb1310072
CHEBI:53712
GTPL10895
HY-B0467A
HMS1569G15
HMS2096G15
HMS2231K23
HMS3259P17
HMS3713G15
AMOXICILLIN ANHYDROUS [HSDB]
Tox21_111302
BDBM50350464
s3015
AKOS025395540
Tox21_111302_1
CCG-220357
DB01060
DS-3835
NC00670
6beta-[(2R)-2-amino-2-(4-hydroxyphenyl)acetamido]-2,2-dimethylpenam-3alpha-carboxylic acid
NCGC00179554-01
AA182611
AC-12263
Amoxicillin, potency: >=900 mug per mg
SY111058
co-amoxiclav (amoxicillin + clavulanic acid)
C06827
D07452
EN300-118704
Q201928
SR-01000721886
SR-01000721886-2
BRD-K55044200-001-03-9
BRD-K55044200-001-14-6
BRD-K55044200-001-15-3
BRD-K55044200-236-02-3
Z1515385072
(2S,5R,6R)-6-((R)-2-Amino-2-(4-hydroxyphenyl)acetamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylicacid
4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-[[amino (4-hydroxyphenyl)acetyl]amino]-3,3-dimethyl-7-oxo-, [2S-[2.alpha.,5.alpha.,6.beta.(S*)]]-
4-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(S*)]]-