In a dose-dependent manner, amoxicillin (Amoxycillin) (1-100 µM; 24 hours; L. acidophilus) reduces living cells and increases the degree of cell wall rupture[1].

Rat survival rates are increased when rats are given amoxicillin (Amoxycillin) at a dose of 7 mg/kg (i.h.; female ICR/Swiss mice) and strain numbers are inhibited[2].
Swiss albino mice given amoxicillin (also known as amoxycillin) (1.6–9.5 mg/kg; p.o.; daily, for 7 or 14 days) are protected against chlamydia trachomatis infection[3].

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.

Absorption, Distribution and Excretion
Amoxicillin is approximately 60% bioavailable. A 250mg dose of oral amoxicillin reaches a Cmax 3.93±1.13mg/L with a Tmax 1.31±0.33h and an AUC of 27.29±4.72mg\*h/L. A 875mg dose of oral amoxicillin reaches a Cmax 11.21±3.42mg/L with a Tmax 1.52±0.40h and an AUC of 55.04±12.68mg\*h/L.
125mg to 1g doses of amoxicillin are 70-78% eliminated in the urine after 6 hours.
The central volume of distribution of amoxicillin is 27.7L.
The mean clearance of amoxicillin is 21.3L/h.
... A 48 year-old woman was admitted because of pneumococcal meningitis. After 4 days on high-dose amoxicillin (320 mg/kg/day), she developed acute oliguric renal failure and amoxicillin crystallization was documented by infrared spectrometry. The outcome was favorable after amoxicillin dosage tapering, together with one single hemodialysis session and further hydratation. Amoxicillin is mainly excreted in the urine in its unchanged form.
Amoxicillin diffuses readily into most body tissues and fluids, with the exception of brain and spinal fluid, except when meninges are inflamed. In blood serum, amoxicillin is approximately 20% protein-bound. Following a 1 gram dose and utilizing a special skin window technique to determine levels of the antibiotic, it was noted that therapeutic levels were found in the interstitial fluid.
Although presence of food in the GI tract reportedly results in lower and delayed peak serum concentrations of amoxicillin, the total amount of drug absorbed does not appear to be affected.
Amoxicillin was studied in normal subjects after intravenous, oral, and intramuscular administration of 250-, 500-, and 1,000-mg doses. Serum drug levels were analyzed using a two-compartment open model, as well as area under the curve (AUC) and urinary recovery. The variations of these pharmacokinetic parameters were then examined using the three-way analysis of variance and linear regression equations. These results confirmed nearly complete oral absorption: AUC was 93% of intravenous absorption, and urinary recovery was 86%. The intramuscular administration of amoxicillin results in complete and reliable absorption with peak drug levels, AUCs, and urinary recovery equivalent to oral dosage. The absorption of lyophilized amoxicillin after intramuscular injection resulted in an AUC that was 92% of intravenous absorption and urinary recovery of 91%. The peak serum levels, time to peak, and other pharmacokinetic parameters for intramuscular injection were nearly identical to those for oral administration. Kinetics of both intramuscular and oral administration exhibited dose-dependent absorption (absorption rate constant, 1.3/hr for 250 mg and 0.7/hr for 1,000 mg). This resulted in relatively later and lower peak serum levels for increasing dose. Total absorption, however, showed no dose dependence, as indicated by urinary recovery and AUC, which changed by less than 10%.
For more Absorption, Distribution and Excretion (Complete) data for AMOXICILLIN (10 total), please visit the HSDB record page.

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Metabolism / Metabolites
Incubation with human liver microsomes has lead to the detection of 7 metabolites. The M1 metabolite has undergone hydroxylation, M2 has undergone oxidative deamination, M3 to M5 have undergone oxidation of the aliphatic chain, M6 has undergone decarboxylation, and M7 has undergone glucuronidation.

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Biological Half-Life
The half life of amoxicillin is 61.3 minutes.
The half-life of amoxicillin is 61.3 minutes.

Hepatotoxicity
Rare instances of idiosyncratic liver injury have been reported in persons receiving the aminopenicillins including amoxicillin. Cases are characterized by a short latency period of a few days to as long as two weeks. The onset of liver injury can occur after the antibiotic is stopped. The serum enzyme pattern associated with aminopenicillin liver injury has included a hepatocellular pattern with marked elevations in ALT and AST, and minimal elevations in alkaline phosphatase and rapid recovery after withdrawal. In addition, cholestatic forms of hepatic injury with marked alkaline phosphatase elevations (as also seen with penicillin-induced liver injury) have also been described, some of which have been associated with prolonged cholestasis (Case 1). The onset of hepatic injury may be accompanied by signs or symptoms of hypersensitivity such as eosinophilia, rash and arthralgias, and in some cases is accompanied by toxic epidermal necrolysis or Stevens Johnson syndrome.
Much more common than liver injury from amoxicillin alone is the typically cholestatic hepatitis that occurs after treatment with the combination of amoxicillin and clavulanate. Indeed, this combination is currently the most common cause of idiosyncratic acute liver injury in the United States, Europe and Australia. The injury, however, is usually attributed to the clavulanate rather than amoxicillin. The clinical features are similar but perhaps not completely the same. In cases of liver injury seeming due to amoxicillin, an extra effort should be made to make sure that it was not amoxicillin-clavulanate [Augmentin] that was taken.
Likelihood score: B (highly likely but rare cause of clinically apparent liver injury).

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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.

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Protein Binding
Amoxicillin is 17% protein bound in serum.

[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 Chemother. 1998 Sep;42(9):2375-9.

[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]. Amoxicillin, a new penicillin antibiotic. Antimicrob Agents Chemother. 1973 Feb;3(2):262-5.

[5]. Introduction: historical perspective and development of amoxicillin/clavulanate. Int J Antimicrob Agents. 2007 Dec;30 Suppl 2:S109-12.

Amoxicillin is a penicillin in which the substituent at position 6 of the penam ring is a 2-amino-2-(4-hydroxyphenyl)acetamido group. It has a role as an antibacterial drug. It is a penicillin and a penicillin allergen. It is a conjugate acid of an amoxicillin(1-).
Amoxicillin is an antibacterial prescription medicine approved by the U.S. Food and Drug Administration (FDA) for the treatment of certain bacterial infections, such as community-acquired pneumonia; infections of the ear, nose and throat; infections of the genitourinary tract and infections of the skin and respiratory tract.
Community-acquired pneumonia, a bacterial respiratory disease, can be an opportunistic infection (OI) of HIV.
Amoxicillin, or BRL-2333, is a penicillin G derivative first described in the literature in 1972. Amoxicillin has similar activity to [penicillin] and [ampicillin], but leads to higher serum concentrations than ampicillin. Amoxicillin was granted FDA approval on 18 January 1974.
Amoxicillin anhydrous is a Penicillin-class Antibacterial.
Amoxicillin has been reported in Arundo donax and Apis cerana with data available.
Amoxicillin is a broad-spectrum, semisynthetic aminopenicillin antibiotic with bactericidal activity. Amoxicillin binds to and inactivates penicillin-binding protein (PBP) 1A 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.
Amoxicillin Anhydrous is the anhydrous 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.

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Drug Indication
Amoxicillin alone is indicated to treat susceptible bacterial infections of the ear, nose, throat, genitourinary tract, skin, skin structure, and lower respiratory tract. Amoxicillin is given with calvulanic acid to treat acute bacterial sinusitis, community acquired pneumonia, lower respiratory tract infections, acute bacterial otitis media, skin and skin structure infections, and urinary tract infections. Amoxicillin is given with omeprazole in the treatment of _Helicobacter pylori_ (_H. pylori_) infection. Amoxicillin is used in combination with [vonoprazan] and [clarithromycin] as co-packaged triple therapy or in combination with [vonoprazan] as co-packaged dual therapy to treat _H. pylori_ infection in adults.
FDA Label
Treatment of Helicobacter spp. infections
Treatment of Helicobacter spp. infections

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Mechanism of Action
Amoxicillin competitively inhibits penicillin-binding protein 1 and other high molecular weight penicillin binding proteins. Penicillin bind proteins are responsible for glycosyltransferase and transpeptidase reactions that lead to cross-linking of D-alanine and D-aspartic acid in bacterial cell walls. Without the action of penicillin binding proteins, bacteria upregulate autolytic enzymes and are unable to build and repair the cell wall, leading to bacteriocidal action.
The penicillins and their metabolites are potent immunogens because of their ability to combine with proteins and act as haptens for acute antibody-mediated reactions. The most frequent (about 95 percent) or "major" determinant of penicillin allergy is the penicilloyl determinant produced by opening the beta-lactam ring of the penicillin. This allows linkage of the penicillin to protein at the amide group. "Minor" determinants (less frequent) are the other metabolites formed, including native penicillin and penicilloic acids. /Penicillins/
Amoxicillin is similar to penicillin in its bactericidal action against susceptible bacteria during the stage of active multiplication. It acts through the inhibition of cell wall biosynthesis that leads to the death of the bacteria.

C16H25N3O8S

419.44

419.136

C, 45.82; H, 6.01; N, 10.02; O, 30.51; S, 7.64

61336-70-7

Amoxicillin sodium;34642-77-8;Amoxicillin;26787-78-0;Amoxicillin-d4;2673270-36-3;Amoxicillin trihydrate mixture with potassium clavulanate (4:1);Amoxicillin arginine;59261-05-1

33613

Crystals from water

1.54g/cm3

743.2ºC at 760 mmHg Vapour

>200ºC (dec.)

403.3ºC

302 ° (C=0.1, H2O)

0.859

4

7

4

25

590

4

S1C(C([H])([H])[H])(C([H])([H])[H])[C@]([H])(C(=O)O[H])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.O([H])[H].O([H])[H].O([H])[H]

MQXQVCLAUDMCEF-CWLIKTDRSA-N

InChI=1S/C16H19N3O5S.3H2O/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)3*1H2/t9-,10-,11+,14-/m1.../s1

(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 trihydrate

Larotid Amoxil Amoxipen Moxaline AmodexAmoxicillin Trihydrate Amoxicillin 3H2OAmoxicillin Trihydrate; Amoxicillin 3H2O; Larotid; Amoxil; Amoxipen; Moxaline; Amodex;

2934.99.9001

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

DMSO : ~10 mg/mL (~23.84 mM)
H2O : ~2 mg/mL (~4.77 mM)

Solubility in Formulation 1: ≥ 2.08 mg/mL (4.96 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 20.8 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.

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Solubility in Formulation 2: ≥ 2.08 mg/mL (4.96 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 20.8 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.

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Solubility in Formulation 3: ≥ 1 mg/mL (2.38 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 10.0 mg/mL clear DMSO stock solution to 400 μL of PEG300 and mix evenly; then add 50 μL of Tween-80 to the above solution and mix evenly; then add 450 μL of 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.

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Solubility in Formulation 4: 10% DMSO+90% (20% SBE-β-CD in Saline): ≥ 2.08 mg/mL (4.96 mM)

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 (Please use freshly prepared in vivo formulations for optimal results.)