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Amoxicillin ( CASNO:26787-78-0 )

Identification and Related Records
Name:
Amoxicillin
CAS Registry number:
26787-78-0
Synonyms:
4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylicacid, 6-[2-amino-2-(p-hydroxyphenyl)acetamido]-3,3-dimethyl-7-oxo-, D- (8CI)
Eupensol
Excillin
Farconcil
Fisamox
Foxolin
Fullcilina
Gemox
Gimalxina
Gomcillin
Gramidil
Grunamox
Hiconcil
Hipen
Histocillin
Hosboral
Imacillin
Imaxilin
Imox
Imoxil
Intermox
Jerramcil
4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid,6-[[amino(4-hydroxyphenyl)acetyl]amino]-3,3-dimethyl-7-oxo-, [2S-[2a,5a,6b(S*)]]-
6-[D-(-)-p-Hydroxy-a-aminobenzyl]penicillin
6-[D-a-Amino-a-(4-hydroxyphenyl)acetamido]penicillanicacid
A-Gram
Actimoxi
Agerpen
Alfamox
Almodan
Alphamox
Amagesen Solutab
Amodex
Amoflux
Amopenixin
Amoxa
Amoxal
Amoxapen
Amoxaren
Amoxi
Amoxi-Mast
Amoxicilina
Amoxidal
Amoxiden
Amoxil
Amoxin
Amoxipen
Amoxtrex
Amoxy
Amoxypen
Ampidroxyl
Ampy-Penyl
Anemol
Anemolin
Apitart
Apo-Amoxi
Ardine
Aspenil
Audumic
BLP1410
BRL 2333
Bactox
Betamox
Bimox
Biomox
Bioxidona
Bioxyllin
Cabermox
Cilamox
Clamox
Clamoxyl
Coamoxin
Comoxyl
D-(-)-a-Amino-p-hydroxybenzyl penicillin
D-2-Amino-2-(4-hydroxyphenyl)acetamidopenicillanic acid
D-Amoxicillin
Delacillin
Efpenix
Efpinex
Eupen
EINECS(EC#):
248-003-8
Molecular Formula:
C16H19N3O5S
Molecular Weight:
365.4
Inchi:
InChI=1/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
Canonical SMILES:
CC1(C(N2C(S1)C(C2=O)NC(=O)C(C3=CC=C(C=C3)O)N)C(=O)O)C
Isomers smiles:
CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)[C@@H](C3=CC=C(C=C3)O)N)C(=O)O)C
Chemical and Physical Properties
Appearance:
solid
Density:
1.54g/cm3
Boiling Point:
743.2 °C at 760 mmHg
Vapour:
3.39E-23mmHg at 25°C
Flash Point:
403.3 °C
Solubilities:
1 g soluble in about 370 ml
Stability:
Stable. Incompatible with strong oxidizing agents.
Storage temp:
2-8°C
Spectral properties:
SPECIFIC OPTICAL ROTATION: +248 DEG TO +268 DEG
Computed Properties:
Molecular Weight:365.40416 [g/mol]
Molecular Formula:C16H19N3O5S
XLogP3:-2
H-Bond Donor:4
H-Bond Acceptor:7
Rotatable Bond Count:4
Tautomer Count:8
Exact Mass:365.104541
MonoIsotopic Mass:365.104541
Topological Polar Surface Area:158
Heavy Atom Count:25
Formal Charge:0
Complexity:590
Isotope Atom Count:0
Defined Atom Stereocenter Count:4
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Feature 3D Acceptor Count:4
Feature 3D Donor Count:3
Feature 3D Anion Count:1
Feature 3D Cation Count:1
Feature 3D Hydrophobe Count:1
Feature 3D Ring Count:2
Effective Rotor Count:5.8
Conformer Sampling RMSD:0.8
CID Conformer Count:29
Safety and Handling
Hazard Codes:
Xn:Harmful
Risk Statements:
R42/43
Safety Statements:
S22;S36/37
Safety:
Hazard Codes :?HarmfulXn,IrritantXi
Risk Statements : 42/43?
R42/43:May cause sensitization by inhalation and skin contact.
Safety Statements : 22-36/37?
S22:Do not breathe dust.?
S36/37:Wear suitable protective clothing and gloves.
WGK Germany : 2
RTECS : XH8300000
Formulations/Preparations:
AMOXICILLIN (AMOXIL, LAROTID) IS AVAILABLE FOR ORAL USE IN CAPSULES (250 OR 500 MG), AS ORAL SUSPENSION (125 OR 250 MG/5 ML), & AS PEDIATRIC DROPS (50 MG/ML).
Exposure Standards and Regulations:
Manufacturers, packers, and distributors of drug and drug products for human use are responsible for complying with the labeling, certification, and usage requirements as prescribed by the Federal Food, Drug, and Cosmetic Act, as amended (secs 201-902, 52 Stat. 1040 et seq., as amended; 21 U.S.C. 321-392).
Specification:
? Amoxicillin ,?its cas register number is 26787-78-0. It also can be called?6-(D-(-)-alpha-Amino-p-hydroxyphenylacetamido)penicillanic acid ; 6-(D-(-)-p-Hydroxy-alpha-aminobenzyl)penicillin ; 6-(p-Hydroxy-alpha-aminophenylacetamido)penicillanic acid?; Amoclen ; Amolin ; Amopenixin ; Amoxi ; Amoxi-Mast ;Amoxicaps ; Amoxicilina ; Amoxicillin pediatric ; Amoxicilline ; Amoxicillinum Amoxiden ; Amoxil ; Amoxivet ; D-(-)-alpha-Amino-p-hydroxybenzylpenicillin ; D-2-Amino-2-(4-hydroxyphenyl)acetamidopenicillanic acid ; D-Amoxicillin ; Delacillin ; DisperMox ; Hiconcil ; Histocillin ; Ibiamox ; Imacillin ; Larotid ; Metafarma capsules ; Metifarma capsules ; Moxacin ; Moxal ; Wymox ; alpha-Amino-p-hydroxybenzylpenicillin ; p-Hydroxyampicillin .
Disposal Methods:
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
Use and Manufacturing
Use and Manufacturing:
Methods of Manufacturing

BY ACETYLATING 6-AMINOPENICILLANIC ACID WITH D-(-)-2-(P-HYDROXYPHENYL)-GLYCINE.
Usage:
Medication.
Biomedical Effects and Toxicity
Pharmacological Action:
- Substances that reduce the growth or reproduction of BACTERIA.
Therapeutic Uses:
Penicillins
ANTIMICROBIAL SPECTRUM OF AMOXICILLIN IS ESSENTIALLY IDENTICAL TO THAT OF AMPICILLIN, WITH IMPORTANT EXCEPTION THAT AMOXICILLIN APPEARS TO BE LESS EFFECTIVE THAN AMPICILLIN FOR SHIGELLOSIS.
RECOMMENDED DOSE OF AMOXICILLIN IS SIMILAR TO THAT OF AMPICILLIN ... EXCEPT THAT IT IS GIVEN 3 INSTEAD OF 4 TIMES A DAY.
Amoxicillin /is/ indicated in the treatment of acute otitis media caused by susceptible organisms. /Included in US product labeling/
Amoxicillin /is/ indicated in the treatment of bacterial pharyngitis caused by susceptible organisms. /Included in US product labeling/
Amoxicillin /is/ indicated in the treatment of bacterial pneumonia caused by susceptible organisms. /Included in US product labeling/
Amoxicillin /is/ indicated in the treatment of sinusitis caused by susceptible organisms. /Included in US product labeling/
Amoxicillin, in combination with probenecid, and (penicillin G parenteral (NOT included in US product labeling)) are indicated in the treatment of gonorrhea caused by susceptible strains of Neisseria gonorrhoea. However, because of resistance to penicillin, other agents, such as ceftiraxone, cefixime, or ciprofloxacin, are considered to be first-line agents. /Included in US product labeling/
Amoxicillin /is/ indicated in the treatment of bacterial urinary tract infections caused by susceptible organisms. /Included in US product labeling/
Amoxicillin /is/ indicated in the treatment of chlamydia infections in pregnant women who cannot tolerate erythromycin. /NOT included in US product labeling; Not included in Canadian product labeling/
Amoxicillin and penicillin V are used in the treatment of early Lyme disease, caused by Borrelia burgdorferi. Amoxicillin in combination with probenecid, and penicillin G (parenteral) are used to treat more advanced stages of Lyme disease, including mild neurological manifestations, cardiac manifestations, and arthritis. /NOT included in US product labeling; Not included in Canadian product labeling/
Amoxicillin is used, in combination with metronidazole and bismuth subsalicylate, in the treatment of gastritis and peptic ulcer disease caused by Helicobacter pylori. /Included in US product labeling/
Amoxicillin /is/ used in the treatment of typhoid fever caused by Salmonella typhi. /NOT included in US product labeling; Not included in Canadian product labeling/
Amoxicillin ... /is/ indicated in the treatment of bronchitis caused by susceptible organisms. /Included in US product labeling/
Amoxicillin /is/ indicated in the prophylaxis of bacterial endocarditis caused by susceptible organisms. /Included in US product labeling; Not included in Canadian product labeling/
Amoxicillin is used, in combination with metronidazole and bismuth subsalicylate, in the treatment of gastritis and peptic ulcer disease caused by Helicobacter pylori. /NOT included in US product labeling; Not included in Canadian product labeling/
Biomedical Effects and Toxicity:
AMOXICILLIN IS MORE RAPIDLY & COMPLETELY ABSORBED FROM GI TRACT THAN IS AMPICILLIN... PEAK PLASMA CONCN ARE REACHED @ 2 HR & AVG ABOUT 4 UG/ML WHEN 250 MG IS ADMIN. ... ABOUT 20%...IS PROTEIN BOUND IN PLASMA... APPROX 60% OF DOSE...IS EXCRETED IN ACTIVE FORM IN URINE.
FOOD HAS NEGLIGIBLE EFFECT ON GI ABSORPTION OF AMOXICILLIN.
ORAL & IM ABSORPTION OF AMOXICILLIN IN HUMANS WAS 93% & 91% OF IV UTILIZATION. PEAK SERUM LEVLES (12 UG/ML APPROX) & TIME TO PEAK LEVELS (1.2 HR) ARE NEARLY IDENTICAL FOR BOTH ROUTES. SLIGHT DELAY & DECR IN PEAK SERUM LEVELS WHEN DOSAGE INCR. [SPYKER ET AL; ANTIMICROB AGENTS CHEMOTHER 11: 132-41 (1977)] PubMed Abstract
CSF LEVELS IN 3 CHILDREN TREATED FOR BACTERIAL MENINGITIS GREATER THAN 1 UG/ML WERE NOT PREDICTABLE & APPEARED TO DEMAND BLOOD LEVELS OF 50 UG/ML. MONITORING OF CSF LEVELS MAY BE NECESSARY TO ENSURE SATISFACTORY OUTCOME.
Amoxicillin is generally stable in the presence of acidic gastric secretions, and 74-92% of a single oral dose of the drug is absorbed from the GI tract. Amoxicillin is more completely absorbed from the GI tract than is ampicillin, and peak serum concn of amoxicillin are generally 2-2.5 times higher than those attained with an equivalent oral dose of ampicillin. As oral dosage of amoxicillin is increased, the fraction of the dose absorbed from the GI tract decreases only slightly and peak serum concn and areas under the serum concn-time curves (AUCs) increase linearly with increasing dosage.
Peak serum concn are usually reached 1-2 hr after oral administration of amoxicillin capsules, tablets, or oral suspension in fasting and non-fasting adults. Following oral administration of a single 250- or 500-mg dose of amoxicillin, peak serum concn range from 3.5-5 or 5.5-11 ug/ml, respectively. In one study in healthy, fasting adults who received a single 500-mg oral dose of amoxicillin, serum concn of the drug averaged 3.3, 6.7, 9.3, 5.8, and 0.6 ug/ml @ 30 min, 1 hr, 2 hr, 3 hr, and 4 hr, respectively, after the dose.
In one study in children 4-45 mo of age receiving amoxicillin oral suspension in a dosage of 15 mg/kg daily, serum amoxicillin concn ranged from 2.4-8.5, 1.9-11.3, 1.7-6.4, 0.17-1.9, and 0.14-3.3 ug/ml @ 30 min, 1 hr, 2 hr, 4 hr, and 6 hr, respectively, after a dose.
Although presence of food in the GI tract reportedly results in lower and delayed peak serum concn of amoxicillin, the total amt of drug absorbed does not appear to be affected.
Pregnant women with GBS colonisation and/or with epidemiologic risk factors received intraparturn antibiotic infusion at the beginning of the labor (l g amoxicillin every 6 hours until the delivery). At delivery, cord blood and gastric fluid were taken infusion. Concentrations were measured in triplicate with a microbilogical method using Bacillus subtillus ATCC 6633 as test strain. In cord blood amoxicillin appeared as early as the first half hour. Concentrations were from 5 to 7 mg/l between 1 hour and 4 hours after the beginning of the infusion and from 3 to 4 mg/l after 4 hours. In gastric fluid, concentrations obtained were over 1 mg/l after 1.5 hour and over 3 mg/l after 2.5 hours, with good efficiency even after the sixth hour. The protocol using a slow intrapartum amoxicillin infusion (1 g) gave concentrations in gastric fluid and cord blood over S. agalactiae MIC. [Delcleve S et al; Pathol Biol (Paris) 42 (5): 516-9 (1994)] PubMed Abstract
Amoxicillin was given as single doses of 375, 700, 1500, 3000, and 6000 mg an oral suspension to four volunteers with an ileostomy and with no active intestinal disease after an overnight fast. The excretion of amoxicillin and its penicilloic acid was followed in samples taken from the ileostomy and in urine produced over 6 hr. Beta-lactanase activity was measured in ileal fluid and none was found. The percentage of the dose recovered from the ileostomy increased successively from 8% at the lowest dose to 77% at the highest dose. A complementary excretion pattern of amoxicillin was found in the urine amounting to 70% recovery at the lowest dose to 23% at the highest dose. The results confirm the dose-dependence of the absorption of amoxicillin which could at least in part be due to specialised absorption of this drug in humans. [Sjovall J et al; Eur J Clin Pharmacol 43 (3): 277-81 (1992)] PubMed Abstract
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