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Amoxicillin Sodium (Amoxycillin), a potent, moderate-spectrum, bacteriolytic, orally bioactive β-lactam antibiotic of the penicillin class, is widely used to treat various bacterial infections, including bronchitis, pneumonia, and infections of the ear, nose, throat, skin, and urinary tract. Though it can be highly effective in treating bacterial infections, it also comes with a list of potential side effects. It inhibits bacterial cell wall biosynthesis by preventing peptidoglycan cross-linking. Shows bacteriocidal effects against gram-positive and gram-negative species in vivo. Amoxicillin is often times combined with Clavulanic acid is a β-lactam drug that functions as a mechanism-based β-Lactamase inhibitor.
Physicochemical Properties
| Molecular Formula | C16H18N3O5S.NA |
| Molecular Weight | 387.39 |
| Exact Mass | 387.086 |
| Elemental Analysis | C, 49.61; H, 4.68; N, 10.85; Na, 5.93; O, 20.65; S, 8.28 |
| CAS # | 34642-77-8 |
| Related CAS # | Amoxicillin;26787-78-0;Amoxicillin trihydrate;61336-70-7;Amoxicillin-d4;2673270-36-3;Amoxicillin trihydrate mixture with potassium clavulanate (4:1);Amoxicillin arginine;59261-05-1 |
| PubChem CID | 23663126 |
| Appearance | White to light yellow solid powder |
| Boiling Point | 743.2ºC at 760 mmHg |
| Hydrogen Bond Donor Count | 3 |
| Hydrogen Bond Acceptor Count | 7 |
| Rotatable Bond Count | 4 |
| Heavy Atom Count | 26 |
| Complexity | 596 |
| Defined Atom Stereocenter Count | 4 |
| SMILES | S1C(C([H])([H])[H])(C([H])([H])[H])[C@]([H])(C(=O)[O-])N2C([C@@]([H])([C@@]12[H])N([H])C(C([H])(C1C([H])=C([H])C(=C([H])C=1[H])O[H])N([H])[H])=O)=O.[Na+] |
| InChi Key | BYHDFCISJXIVBV-GJUCOGTPSA-M |
| InChi Code | InChI=1S/C16H19N3O5S.Na/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);/q;+1/p-1/t9?,10-,11+,14-;/m1./s1 |
| Chemical Name | sodium (2S,5R,6R)-6-(2-amino-2-(4-hydroxyphenyl)acetamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate |
| Synonyms | Amoxicillin sodium; Lamoxy; Penamox; BRL-2333AB-B; Moxacin; |
| HS Tariff Code | 2934.99.03.00 |
| Storage |
Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: Please store this product in a sealed and protected environment, avoid exposure to moisture. |
| Shipping Condition | Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs) |
Biological Activity
| ln Vitro | In a dose-dependent manner, amoxicillin (Amoxycillin) sodium (1-100 µM; 24 hours; L. acidophilus) reduces living cells and increases the degree of cell wall rupture[1]. |
| ln Vivo |
Rats in 1 mg/L or less have a higher survival rate when given amoxicillin (amoxycillin) sodium (7 mg/kg; i.h.; female ICR/Swiss mice). It also inhibits the number of strains.[2] Chlamydia trachomatis infection in mice can be prevented by amoxicillin (Amoxycillin) sodium (1.6-9.5 mg/kg; p.o. ; daily, for 7 or 14 days; Swiss albino mice)[3]. |
| Animal Protocol |
Animal Model: Female ICR/Swiss mice[2] Dosage: 7 mg/kg Administration: Subcutaneous injection: every eight hours for a full day Result: exhibited a dose-dependent inhibition on the number of bacteria. |
| Toxicity/Toxicokinetics |
Effects During Pregnancy and Lactation ◉ Summary of Use during Lactation Limited information indicates that amoxicillin produces low levels in milk that are not expected to cause adverse effects in breastfed infants. Occasionally, rash and disruption of the infant's gastrointestinal flora, resulting in diarrhea or thrush, have been reported, but these effects have not been adequately evaluated. Amoxicillin is acceptable in nursing mothers. Amoxicillin powder for suspension reconstituted with breastmilk is absorbed as well as the powder reconstituted with water. ◉ Effects in Breastfed Infants In a telephone follow-up study, 25 nursing mothers reported taking amoxicillin (dosage unspecified). Three mothers reported diarrhea in their infants. No rashes or candidiasis were reported among the exposed infants. In contrast, a small, controlled, prospective study had mothers monitor their infants for signs of adverse effects (furring of the tongue, feeding difficulties, changes in stool frequency and consistency, diaper rash, and skin rash). Weight change and the development of jaundice were also recorded. No statistical differences in these parameters were found between the infants of the control mothers and those of mothers taking the related antibiotics, ampicillin or ampicillin-clavulanate. A prospective, controlled study asked mothers who called an information service about adverse reactions experienced by their breastfed infants. Of 40 infants exposed to amoxicillin in breastmilk, 2 developed diarrhea and 1 developed a rash. A study compared the breastfed infants of mothers taking amoxicillin to those taking a macrolide antibiotic. Adverse reactions occurred in 8.3% of the infants exposed to amoxicillin, which was similar to the rate in macrolide-exposed infants. Reactions included rash and somnolence. A 2-month-old infant breastfed since birth. His mother had taken many medications during pregnancy, but she did not recall their identity. She developed mastitis and was treated with amoxicillin/clavulanic acid 1 gram orally every 12 hours and gentamicin 160 mg intramuscularly once daily. The infant was breastfed for 10 minutes starting 15 minutes after the first dose of both drugs. About 20 minutes later, the infant developed a generalized urticaria which disappeared after 30 minutes. A few hours later, the infant breastfed again and the urticaria reappeared after 15 minutes and disappeared after an hour. After switching to formula feeding and no further infant exposure to penicillins, the reaction did not reappear with follow-up to 16 months of age. The adverse reaction was probably caused by the antibiotics in breastmilk. The drug that caused the reaction cannot be determined, but it was most likely the amoxicillin/clavulanic acid. ◉ Effects on Lactation and Breastmilk Relevant published information was not found as of the revision date. |
| References |
[1]. Metabolic response of Lactobacillus acidophilus exposed to amoxicillin. J Antibiot (Tokyo). 2022 May;75(5):268-281. [2]. In vivo activities of amoxicillin and amoxicillin-clavulanate against Streptococcus pneumoniae: application to breakpoint determinations. Antimicrob Agents. [3]. Activity of oral amoxicillin, ampicillin, and oxytetracycline against infection with chlamydia trachomatis in mice. J Infect Dis. 1979 Jun;139(6):717-9. [4]. J Oral Maxillofac Surg.2014 Feb;72(2):305.e1-5. [4]. BMC Complement Altern Med.2013 May 30;13:119. |
| Additional Infomation |
Amoxicillin sodium is an organic sodium salt that is the monosodium salt of amoxicillin. It contains an amoxicillin(1-). Amoxicillin Sodium is the sodium salt form of a broad-spectrum, semisynthetic aminopenicillin antibiotic with bactericidal activity. Amoxicillin binds to and inactivates penicillin-binding proteins (PBPs) located on the inner membrane of the bacterial cell wall. Inactivation of PBPs interferes with the cross-linkage of peptidoglycan chains necessary for bacterial cell wall strength and rigidity. This interrupts bacterial cell wall synthesis and results in the weakening of the bacterial cell wall and causes cell lysis. A broad-spectrum semisynthetic antibiotic similar to AMPICILLIN except that its resistance to gastric acid permits higher serum levels with oral administration. |
Solubility Data
| Solubility (In Vitro) |
DMSO : 78~100 mg/mL ( 201.34~258.14 mM ) Water : 78~100 mg/mL(~258.14 mM) |
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.08 mg/mL (5.37 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 1 mg/mL (2.58 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 10.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Solubility in Formulation 3: ≥ 1 mg/mL (2.58 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 10.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. Solubility in Formulation 4: 10% DMSO+40% PEG300+5% Tween-80+45% Saline: ≥ 2.08 mg/mL (5.37 mM) Solubility in Formulation 5: 100 mg/mL (258.14 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with ultrasonication. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.5814 mL | 12.9069 mL | 25.8138 mL | |
| 5 mM | 0.5163 mL | 2.5814 mL | 5.1628 mL | |
| 10 mM | 0.2581 mL | 1.2907 mL | 2.5814 mL |