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| | Amoxicillin trihydrate Basic information |
| Product Name: | Amoxicillin trihydrate | | Synonyms: | AmoxycillinTrihydrateBp98;AmoxicillineTrihydrate;AMOXICILLINE 3-HYDRATE;6-(D-[-]-α-Amino-p-hydroxyphenylacetamido) penicillanic acid trihydrate;4-Thia-1-azabicyclo3.2.0heptane-2-carboxylic acid, 6-(2R)-amino(4-hydroxyphenyl)acetylamino-3,3-dimethyl-7-oxo-, trihydrate, (2S,5R,6R)-;AMOXICILLINTRIHYDRATE,USP;amoxicillin soluble powder70%;4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-((amino(4-hydroxyphenyl)acetyl)amino)-3,3-dimethyl-7-oxo-, trihydrate (2S-(2alpha,5alpha,6beta(S*)))- | | CAS: | 61336-70-7 | | MF: | C16H21N3O6S | | MW: | 383.42 | | EINECS: | 999-999-2 | | Product Categories: | raw material;Pyridines;veterinary medicine,soluble powder;AMOXIL;Antibacterial spectrum;API;Antibiotics for Research and Experimental Use;beta-Lactams (Antibiotics for Research and Experimental Use);Biochemistry;Pharma;Chiral Reagents;Intermediates & Fine Chemicals;Pharmaceuticals;Sulfur & Selenium Compounds;Antibiotic Explorer;beta-Lactam Structure;A;Alphabetic;AM to AQAntibiotics;BactericidalAntibiotics;Chemical Structure;Principle | | Mol File: | 61336-70-7.mol |  |
| | Amoxicillin trihydrate Chemical Properties |
| Melting point | >200°C (dec.) | | alpha | D20 +246° (c = 0.1) | | refractive index | 302 ° (C=0.1, H2O) | | storage temp. | Inert atmosphere,2-8°C | | solubility | Slightly soluble in water, very slightly soluble in ethanol (96 per cent), practically insoluble in fatty oils. It dissolves in dilute acids and dilute solutions of alkali hydroxides. | | form | neat | | color | White to Off-White | | Water Solubility | Soluble in water at 3.4mg/ml. | | JECFA Number | 85 | | Merck | 14,577 | | BRN | 7507120 | | CAS DataBase Reference | 61336-70-7(CAS DataBase Reference) | | EPA Substance Registry System | Amoxicillin trihydrate (61336-70-7) |
| Hazard Codes | Xn,Xi | | Risk Statements | 42/43 | | Safety Statements | 36-36/37-22 | | WGK Germany | 2 | | RTECS | XH8300000 | | HS Code | 29411000 | | Toxicity | LD50 ipr-rat: 2870 mg/kg KSRNAM 7,3040,73 |
| | Amoxicillin trihydrate Usage And Synthesis |
| Chemical Properties | White to Off-White Solid | | Originator | Arnoxil,Bencard,UK,1972 | | Uses | Semi-synthetic antibiotic related to Penicillin. Antibacterial. | | Uses | Amoxicillin trihydratesemi-synthetic antibiotic related to Penicillin which has antibacterial poperties. It is used for treatment of a variety of bacterial infections. It is used as a pharmaceutical product as a antibiotic agent, anti-infective drug raw materials. | | Definition | ChEBI: A hydrate that is the trihydrate form of amoxicillin; a semisynthetic antibiotic, used either alone or in combination with potassium clavulanate (under the trade name Augmentin) for treatment of a variety of bacterial infections. | | Manufacturing Process | Ethyl chlorocarbonate (2.2 ml) was added to an ice cold solution of O,N-dibenzyloxycarbonyl-p-oxy-dl-α-aminophenylacetic acid (10 grams) and
triethylamine (3.85 ml) in dry acetone (193 ml). The mixture was stirred at
0°C for 5 minutes during which triethylamine hydrochloride precipitated. The
suspension was cooled to -30°C and stirred vigorously while adding as rapidly
as possible an ice cold solution of 6-aminopenicillanic acid (5.85 grams) in 3%
aqueous sodium bicarbonate (193 ml), the temperature of the mixture never
being allowed to rise above 0°C. The resulting clear solution was stirred for 30
minutes at 0°C, and then for a further 30 minutes, without external cooling,
and finally extracted with diethyl ether (3 x 200 ml) only the aqueous phase
being retained.
This aqueous solution was brought to pH 2 by the addition of hydrochloric acid
and the 6-(O,N-dibenzyloxycarbonyl-p-oxy-dl-α-
aminophenylacetamido)penicillanic acid so liberated was extracted into diethyl
ether (50 ml and 2 portions of 30 ml). The ether phase was washed with
water (3 x 5 ml) and the water washings were discarded.
Finally, the penicillin was converted to the sodium salt by shaking the ether
solution with sufficient 3% sodium bicarbonate to give a neutral aqueous
phase, separating the latter and evaporating it at low pressure and
temperature below 20°C. The product was finally dried over phosphorus
pentoxide in vacuo to give sodium 6-(O,N-dibenzyloxycarbonyl-p-oxy-dl-α-
aminophenylacetamido)-penicillanate (9.2 grams).
A suspension of palladium on calcium carbonate (36 grams of 5%) in water
(150 ml) was shaken in an atmosphere of hydrogen at room temperature and
atmospheric pressure for 1 hour. A neutral solution of sodium 6-(O,Ndibenzyloxycarbonyl-
p-oxy-dl-α-aminophenylacetamido)penicillanate (9
grams) in water (100 ml) was then added and shaking in hydrogen was
resumed for one hour. The suspension was then filtered and the collected
catalyst was washed well with water without being allowed to suck dry
between washings. The combined filtrate and washings were then brought to
pH 6.5 with dilute hydrochloric acid and evaporated to dryness at reduced
pressure and temperatures below 20°C. The product was finally dried over
phosphorus pentoxide in vacuo to give a solid (5.4 grams) containing 6-(phydroxy-
dl-α-aminophenylacetamido)penicillanic acid. | | Brand name | Amoxil (GlaxoSmithKline);
Dispermox (Ranbaxy); Larotid (GlaxoSmithKline);
Trimox (Apothecon) [Name previously used:
Amoxycillin.]. | | Therapeutic Function | Antibacterial | | Contact allergens | Amoxicillin is both a topical and a systemic sensitizer.
Topical sensitization occurs in health care workers.
Systemic drug reactions are frequent, such as urticaria,
maculo-papular rashes, baboon syndrome, acute generalized
exanthematous pustulosis, or even toxic epidermal
necrosis. Cross-reactivity is common with
ampicillin, and can occur with other penicillins. | | Safety Profile | Moderately toxic. An
experimental teratogen. Other experimental
reproductive effects. When heated to
decomposition it emits toxic fumes of SOx
and NOx. |
| | Amoxicillin trihydrate Preparation Products And Raw materials |
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