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Amoxicillin trihydrate structure
Amoxicillin trihydrate structure

Amoxicillin trihydrate

Iupac Name:(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
CAS No.: 61336-70-7
Molecular Weight:419.449
Modify Date.: 2022-04-19 02:41
Introduction: Semi-synthetic antibiotic related to Penicillin. Antibacterial. View more+
1. Names and Identifiers
1.1 Name
Amoxicillin trihydrate
1.2 Synonyms

(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 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*)))- 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-[[(2R)-2-amino-2-(4-hydroxyphenyl)acetyl]amino]-3,3-dimethyl-7-oxo-, (2S,5R,6R)-, hydrate (1:3) 4-Thia-1-azabicyclo3.2.0heptane-2-carboxylic acid, 6-(2R)-amino(4-hydroxyphenyl)acetylamino-3,3-dimethyl-7-oxo-, trihydrate, (2S,5R,6R)- 6-(D-[-]-α-Amino-p-hydroxyphenylacetamido) penicillanic acid trihydrate Amoxicillin (trihydrate) AMOXICILLINE 3-HYDRATE AmoxicillineTrihydrate AmoxicillinTrihydrate AMOXICILLINTRIHYDRATE,USP Amoxycillin trihydrate AmoxycillinTrihydrateBp98 MFCD00072029

1.3 CAS No.
61336-70-7
1.4 CID
62883
1.5 EINECS(EC#)
612-127-4
1.6 Molecular Formula
C16H25N3O8S (isomer)
1.7 Inchi
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
1.8 InChkey
MQXQVCLAUDMCEF-CWLIKTDRSA-N
1.9 Canonical Smiles
CC1(C(N2C(S1)C(C2=O)NC(=O)C(C3=CC=C(C=C3)O)N)C(=O)O)C.O.O.O
1.10 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.O.O.O
2. Properties
3.1 Density
1.54
3.1 Melting point
>200°C (dec.)
3.1 Boiling point
743.2 °C at 760 mmHg Vapour
3.1 Refractive index
302 ° (C=0.1, H2O)
3.1 Flash Point
403.3 °C
3.1 Precise Quality
419.13600
3.1 PSA
185.95000
3.1 logP
0.85990
3.1 Appearance
A White CRYSTALLINE powder
3.2 Storage
Keep Cold.
3.3 Chemical Properties
White to Off-White Solid
3.4 Color/Form
Powder
3.5 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 generalizedexanthematous pustulosis, or even toxic epidermalnecrosis. Cross-reactivity is common withampicillin, and can occur with other penicillins.
3.6 Water Solubility
1 G SOL IN ABOUT 370 ML WATER, ABOUT 2000 ML ALC, ABOUT 290 ML PHOSPHATE BUFFER (1%, PH 7), ABOUT 330 ML METHANOL
3.7 Spectral Properties
SPECIFIC OPTICAL ROTATION: +248 DEG TO +268 DEG
3.8 StorageTemp
Inert atmosphere,2-8°C
3. Use and Manufacturing
4.1 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.
4.2 GHS Classification
Signal: Danger
GHS Hazard Statements
The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

H334 (100%): May cause allergy or asthma symptoms or breathing difficulties if inhaled [Danger Sensitization, respiratory]

Precautionary Statement Codes
P261, P285, P304+P341, P342+P311, and P501
4.3 Usage
Semi-synthetic antibiotic related to Penicillin. Antibacterial.
4. Safety and Handling
5.1 Symbol
GHS08
5.1 Hazard Codes
Xn
5.1 Signal Word
Danger
5.1 Risk Statements
R42/43
5.1 Safety Statements
S36
5.1 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).
5.2 Hazard Declaration
H317-H334
5.2 DisposalMethods
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.
5.3 RIDADR
NONH for all modes of transport
5.3 Safety Profile
Moderately toxic. Anexperimental teratogen. Other experimentalreproductive effects. When heated todecomposition it emits toxic fumes of SOxand NOx. Amoxicillin trihydrate Preparation Products And Raw materials Preparation Products
5.4 Caution Statement
P261-P280-P342 + P311
5.4 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).
5.5 WGK Germany
2
5.5 RTECS
XH8300000
5.5 Safety

Hazard Codes of Amoxycillin trihydrate (CAS NO.61336-70-7):?HarmfulXn,IrritantXi
Risk Statements: 42/43
42/43: May cause sensitization by inhalation and skin contact??
Safety Statements: 36-36/37-22
36:Wear suitable protective clothing
36/37: Wear suitable protective clothing and gloves
22: Do not breathe dust???
RTECS: XH8300000

5.6 Specification

?Amoxycillin trihydrate , its cas register number is 61336-70-7. It also can be called 4-Acetamido-2-ethoxybenzoesaeuremethylester ; and 6-[2-Amino-2-(4-hydroxyphenyl)-acetyl]amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid trihydrate .

5.7 Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 3590mg/kg (3590mg/kg) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)
BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Kiso to Rinsho. Clinical Report. Vol. 7, Pg. 3040, 1973.
mouse LD50 oral > 25gm/kg (25000mg/kg) ? Kiso to Rinsho. Clinical Report. Vol. 7, Pg. 3040, 1973.
mouse LD50 subcutaneous > 20gm/kg (20000mg/kg) ? Kiso to Rinsho. Clinical Report. Vol. 7, Pg. 3040, 1973.
rabbit LD50 oral > 12500mg/kg (12500mg/kg) ? Kiso to Rinsho. Clinical Report. Vol. 7, Pg. 3040, 1973.
rat LD50 intraperitoneal 2870mg/kg (2870mg/kg) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)
BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Kiso to Rinsho. Clinical Report. Vol. 7, Pg. 3040, 1973.
rat LD50 oral > 15gm/kg (15000mg/kg) ? Kiso to Rinsho. Clinical Report. Vol. 7, Pg. 3040, 1973.
rat LD50 subcutaneous > 8gm/kg (8000mg/kg) ? Kiso to Rinsho. Clinical Report. Vol. 7, Pg. 3040, 1973.

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Skin sensitization, Category 1

Respiratory sensitization, Category 1

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word

Danger

Hazard statement(s)

H317 May cause an allergic skin reaction

H334 May cause allergy or asthma symptoms or breathing difficulties if inhaled

Precautionary statement(s)
Prevention

P261 Avoid breathing dust/fume/gas/mist/vapours/spray.

P272 Contaminated work clothing should not be allowed out of the workplace.

P280 Wear protective gloves/protective clothing/eye protection/face protection.

P284 [In case of inadequate ventilation] wear respiratory protection.

Response

P302+P352 IF ON SKIN: Wash with plenty of water/...

P333+P313 If skin irritation or rash occurs: Get medical advice/attention.

P321 Specific treatment (see ... on this label).

P362+P364 Take off contaminated clothing and wash it before reuse.

P304+P340 IF INHALED: Remove person to fresh air and keep comfortable for breathing.

P342+P311 If experiencing respiratory symptoms: Call a POISON CENTER/doctor/...

Storage

none

Disposal

P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

6. Other Information
6.0 Usage
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.
6.1 Merck
14,577
6.2 BRN
7507120
6.3 Chemical Properties
White to Off-White Solid
6.4 Originator
Arnoxil,Bencard,UK,1972
6.5 Uses
Semi-synthetic antibiotic related to Penicillin. Antibacterial.
6.6 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.
6.7 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.
6.8 Brand name
Amoxil (GlaxoSmithKline); Dispermox (Ranbaxy); Larotid (GlaxoSmithKline); Trimox (Apothecon) [Name previously used: Amoxycillin.].
6.9 Therapeutic Function
Antibacterial
6.10 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.
6.11 Safety Profile
Moderately toxic. An experimental teratogen. Other experimental reproductive effects. When heated to decomposition it emits toxic fumes of SOx and NOx.
7. Computational chemical data
  • Molecular Weight: 419.449g/mol
  • Molecular Formula: C16H25N3O8S
  • Compound Is Canonicalized: True
  • XLogP3-AA: null
  • Exact Mass: 419.13623594
  • Monoisotopic Mass: 419.13623594
  • Complexity: 590
  • Rotatable Bond Count: 4
  • Hydrogen Bond Donor Count: 7
  • Hydrogen Bond Acceptor Count: 10
  • Topological Polar Surface Area: 161
  • Heavy Atom Count: 28
  • Defined Atom Stereocenter Count: 4
  • Undefined Atom Stereocenter Count: 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Isotope Atom Count: 0
  • Covalently-Bonded Unit Count: 4
  • CACTVS Substructure Key Fingerprint: AAADceB7PABAAAAAAAAAAAAAAABYAWAAAAAwAAAABYAAAAABAAAAHgQQCAAADCzF2ASyDoPAAgiIAiHSGACCAABgIBAIiIGODIgKZjqilTOUcABk1hG4mAeY2IGOIAAAAAAAAABAAAAAAAAAAAAAAAAAAA==
9. Realated Product Infomation