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61336-70-7 molecular structure
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(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

ChemBase ID: 931
Molecular Formular: C16H19N3O5S
Molecular Mass: 365.40416
Monoisotopic Mass: 365.10454172
SMILES and InChIs

SMILES:
S1[C@H]2N([C@H](C1(C)C)C(=O)O)C(=O)[C@H]2NC(=O)[C@H](N)c1ccc(O)cc1
Canonical SMILES:
O=C([C@@H](c1ccc(cc1)O)N)N[C@@H]1C(=O)N2[C@@H]1SC([C@@H]2C(=O)O)(C)C
InChI:
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-/m1/s1
InChIKey:
LSQZJLSUYDQPKJ-NJBDSQKTSA-N

Cite this record

CBID:931 http://www.chembase.cn/molecule-931.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(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
IUPAC Traditional name
amoxicillin
Brand Name
Imacillin
Lamoxy
Metafarma capsules
Metifarma capsules
Moxacin
Moxal
Ospamox
Pamoxicillin
Piramox
Polymox
Robamox
Sawamox PM
Sumox
Tolodina
Trimox
Unicillin
Utimox
Vetramox
Wymox
Zimox
AMPC
Actimoxi
Amoclen
Amolin
Amopen
Amopenixin
Amoxi
Amoxi-Mast
Amoxibiotic
Amoxiden
Amoxil
Amoxivet
Anemolin
Aspenil
Biomox
Bristamox
Cemoxin
Clamoxyl
Delacillin
Dispermox
Efpenix
Flemoxin
Hiconcil
Histocillin
Ibiamox
Actimoxi, Alphamox, Amocla,Tycil, Amoxil, Trimox, among others
Synonyms
Amoxicillin
Amoxicilina [INN-Spanish]
Amoxicillin anhydrous
Amoxicillin Trihydrate
Amoxicilline [INN-French]
Amoxicillinum [INN-Latin]
AMC
Amoxycillin Trihydrate
Amoxycillin
D-Amoxicillin
p-Hydroxyampicillin
Amoxicillin
(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-d4
AMPC-d4
Amoxycillin-d4
Helvamox-d4
Pasetocin-d4
Penimox-d4
Zamocillin-d4
Amoxicillin-d4
(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
Amoxillat
Ardine
Helvamox
Pasetocin
Penimox
Zamocillin
Amoxicillin Trihydrate
AMPC
Amolin
Amoxi
(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
阿莫西林
CAS Number
61336-70-7
26787-78-0
EC Number
248-003-8
MDL Number
MFCD00056860
Beilstein Number
7507120
PubChem SID
46507578
160964394
PubChem CID
33613
CHEBI ID
2676
ATC CODE
J01CA04
QG51AA03
CHEMBL
1082
Chemspider ID
31006
DrugBank ID
DB01060
KEGG ID
D07452
Unique Ingredient Identifier
9EM05410Q9
Wikipedia Title
Amoxicillin
Medline Plus
a685001

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 3.2314606  H Acceptors
H Donor LogD (pH = 5.5) -2.3092988 
LogD (pH = 7.4) -2.5697672  Log P -2.3101761 
Molar Refractivity 89.5044 cm3 Polarizability 35.524654 Å3
Polar Surface Area 132.96 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 0.75  LOG S -2.58 
Solubility (Water) 9.58e-01 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
3430 mg/L expand Show data source
Do you have solubility information on this product that you would like to share? expand Show data source
Water expand Show data source
Apperance
Off-White to Pale Yellow Solid expand Show data source
White to Off-White Solid expand Show data source
Melting Point
>200°C (dec.) expand Show data source
209-210°C expand Show data source
Hydrophobicity(logP)
0 expand Show data source
-1.872 expand Show data source
Storage Condition
-20°C Freezer expand Show data source
-20°C Freezer, Under Inert Atmosphere expand Show data source
2-8°C expand Show data source
RTECS
XH8300000 expand Show data source
European Hazard Symbols
Harmful Harmful (Xn) expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
2 expand Show data source
Risk Statements
42/43 expand Show data source
Safety Statements
22-36/37 expand Show data source
GHS Pictograms
GHS08 expand Show data source
GHS Signal Word
Danger expand Show data source
GHS Hazard statements
H317-H334 expand Show data source
GHS Precautionary statements
P261-P280-P342 + P311 expand Show data source
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Faceshields, Gloves expand Show data source
Storage Temperature
2-8°C expand Show data source
Admin Routes
Oral, intravenous expand Show data source
Bioavailability
95% oral expand Show data source
Excretion
renal expand Show data source
Half Life
61.3 minutes expand Show data source
Metabolism
less than 30% biotransformed in liver expand Show data source
Legal Status
POM (UK) expand Show data source
Rx-only (US) expand Show data source
Pregnancy Category
A (Australia) expand Show data source
B (US) expand Show data source
Purity
≥97.0% (dried material, NT) expand Show data source
95% expand Show data source
Potency
≥900 μg per mg expand Show data source
Certificate of Analysis
Download expand Show data source
Download expand Show data source
Impurities
~15% water expand Show data source
Empirical Formula (Hill Notation)
C16H19N3O5S expand Show data source

DETAILS

DETAILS

MP Biomedicals MP Biomedicals DrugBank DrugBank Wikipedia Wikipedia Sigma Aldrich Sigma Aldrich TRC TRC
DrugBank - DB01060 external link
Item Information
Drug Groups approved
Description A broad-spectrum semisynthetic antibiotic similar to ampicillin except that its resistance to gastric acid permits higher serum levels with oral administration. Amoxicillin is commonly prescribed with clauvanic acid (a beta lactamase inhibitor) as it is susceptible to beta-lacatamase degradation. [PubChem]
Indication For the treatment of infections of the ear, nose, and throat, the genitourinary tract, the skin and skin structure, and the lower respiratory tract due to susceptible (only b-lactamase-negative) strains of Streptococcus spp. (a- and b-hemolytic strains only), S. pneumoniae, Staphylococcus spp., H. influenzae, E. coli, P. mirabilis, or E. faecalis. Also for the treatment of acute, uncomplicated gonorrhea (ano-genital and urethral infections) due to N. gonorrhoeae (males and females).
Pharmacology Amoxicillin is a moderate-spectrum antibiotic active against a wide range of Gram-positive, and a limited range of Gram-negative organisms. It is usually the drug of choice within the class because it is better absorbed, following oral administration, than other beta-lactam antibiotics. Amoxicillin is susceptible to degradation by β-lactamase-producing bacteria, and so may be given with clavulanic acid to increase its susceptability. The incidence of β-lactamase-producing resistant organisms, including E. coli, appears to be increasing. Amoxicillin is sometimes combined with clavulanic acid, a β-lactamase inhibitor, to increase the spectrum of action against Gram-negative organisms, and to overcome bacterial antibiotic resistance mediated through β-lactamase production.
Toxicity Serious toxicity is unlikely following large doses of amoxicillin. Acute ingestion of large doses of amoxicillin may cause nausea, vomiting, diarrhea and abdominal pain. Acute oliguric renal failure and hematuria may occur following large doses.
Affected Organisms
Enteric bacteria and other eubacteria
Biotransformation Hepatic metabolism accounts for less than 30% of the biotransformation of most penicillins
Absorption Rapidly absorbed after oral administration.
Half Life 61.3 minutes
Protein Binding In blood serum, amoxicillin is approximately 20% protein-bound
Elimination Most of the amoxicillin is excreted unchanged in the urine; its excretion can be delayed by concurrent administration of probenecid.
References
Drawz SM, Bonomo RA: Three decades of beta-lactamase inhibitors. Clin Microbiol Rev. 2010 Jan;23(1):160-201. [Pubmed]
External Links
Wikipedia
RxList
Drugs.com
Sigma Aldrich - A8523 external link
Application
Do you have application information on this product that you would like to share?
Amoxicillin is a moderate-spectrum, β-lactam antibiotic . Amoxicillin is one of the most common antibiotics prescribed for children. It is used to study the oxygen dependent antimicrobial systems of polymorphonuclear leukocytes (PMNLs), the risk of resistance development in Helicobacter pylor, and various dosing strategies against Streptococcus pneumoniae and Pneumococcal pneumonia 1,2,3,4. It is also used to study the synthesis of bacterial cell walls at the level of peptidoglycan polymer chain cross-linking involving bacterial transpeptidase.
Amoxicillin is used to study the synthesis of bacterial cell walls at the level of peptidoglycan polymer chain cross-linking involving bacterial transpeptidase.
Biochem/physiol Actions
Amoxicillin inhibits the synthesis of bacterial cell walls. It inhibits cross-linkage between the linear peptidoglycan polymer chains that make up a major component of the cell walls of both Gram-positive and Gram-negative bacteria.
Toronto Research Chemicals - A634238 external link
Labelled semi-synthetic antibiotic related to Penicillin. Antibacterial.
Toronto Research Chemicals - A634235 external link
Semi-synthetic antibiotic related to Penicillin. Antibacterial.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Drawz SM, Bonomo RA: Three decades of beta-lactamase inhibitors. Clin Microbiol Rev. 2010 Jan;23(1):160-201. Pubmed
  • • Brogden, R.N., et al.: Drugs, 18, 169 (1979)
  • • Bird, A.E., et al.: Anal. Profiles Drug Subs. Excip., 23, 1 (1979)
  • • Brogden, R.N., et al.: Drugs, 18, 169 (1979)
  • • Bird, A.E., et al.: Anal. Profiles Drug Subs. Excip., 23, 1 (1979)
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PATENTS

PATENTS

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INTERNET

INTERNET

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