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69-53-4

69-53-4 Structure

69-53-4 Structure
IdentificationMore
[Name]

(2S,5R,6R)-6-[(R)-2-Amino-2-phenylacetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
[CAS]

69-53-4
[Synonyms]

6-[D-ALPHA-AMINOPHENYLACETAMIDO]PENICILLANIC ACID TRIHYDRATE
ALPHA-AMINOBENZYLPENICILLIN, TRIHYDRATE
AMPICILLIN TRIHYDRATE
D(-)-ALPHA-AMINOBENZYLPENICILLIN
D(-)-ALPHA-AMINOBENZYLPENICILLIN TRIHYDRATE
(aminophenylmethyl)-penicilli
[2s-[2alpha,5alpha,6beta(s)]]-o]-3-dimethyl-7-oxo
4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylicacid,6-[(aminophenylacetyl)amin
6-(d(-)-alpha-aminophenylacetamido)penicillanicacid
6-[d(-)-alpha-aminophenylacetamido]penicillanicacid
6-[d-(2-amino-2-phenylacetamido)]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0
ab-pc
adobacillin
amblosin
amfipen
aminobenzylpenicillin
amipenixs
ampi-bol
ampicillina
ampicillinacid
[EINECS(EC#)]

200-709-7
[Molecular Formula]

C16H25N3O7S
[MDL Number]

MFCD00072036
[Molecular Weight]

403.45
[MOL File]

69-53-4.mol
Chemical PropertiesBack Directory
[Appearance]

Ampicillin in anhydrous form occurs as crystals.
[Appearance]

Crystalline Solid
[Melting point ]

198-200 °C (dec.)(lit.)
[mp ]

198-200 °C (dec.)(lit.)
[Boiling point ]

201.8°C (rough estimate)
[alpha ]

D23 +287.9° (c = 1 in water)
[density ]

1.2794 (rough estimate)
[refractive index ]

1.6320 (estimate)
[storage temp. ]

2-8°C
[solubility ]

NH4OH 1 M: 50 mg/mL, clear, colorless
[Stability:]

Stable, but may be moisture sensitive. Incopmpatible with strong oxidizing agents.
[pka]

2.5 (COOH)(at 25℃)
[Usage]

Orally active, semi-synthetic antibiotic; structurally related to penicillin. Antibacterial.
[Merck ]

13,591
[Contact allergens]

Ampicillin caused contact dermatitis in a nurse also sensitized to amoxicillin (with tolerance to oral phenoxymethylpenicillin) and in a pharmaceutical factory worker. Systemic drug reactions are common. Crossreactivity is regular with ampicillin and can occur with other penicillins.
[CAS DataBase Reference]

69-53-4(CAS DataBase Reference)
[EPA Substance Registry System]

69-53-4(EPA Substance)
Hazard InformationBack Directory
[Description]

Ampicillin is an antibacterial antibiotic from the α-aminobenzyl penicillin group, which differs from penicillin by the presence of an amino group that facilitates penetration through the outer membrane of some gram-negative bacteria.
Ampicillin is Semi-synthetic derivative of penicillin that functions as an orally active broad-spectrum antibiotic. Ampicillin acts by interfering directly with the biosynthesis of peptidoglycan, which constitutes the major component of the bacterial cell wall, leading to structural instability and death of bacteria.
Ampicillin is a β-lactam antibiotic within the penicillin family. As a member of this family, Ampicillin is susceptible to β-lactamase, which hydrolyzes the β-lactam ring. This broad spectrum antibiotic is effective against gram-positive, gram-negative bacteria and anaerobic bacteria. Ampicillin is widely used in cell culture as a selective agent. As an antibiotic, Ampicillin binds to penicillin binding proteins (PBPs) on a susceptible organism and Inhibits bacterial cell-wall synthesis by inactivating transpeptidases on the inner surface of the bacterial cell membrane. After binding to the PBPs, Ampicilin acts as a structural analogue of acyl-D-alanyl-D-alanine, acylates the transpeptidase enzyme and thereby prevents the cross-linking of the peptidoglycan of the cell wall necessary for the growth of the bacterium.
Ampicillin sodium can be used as a selective agent in several types of isolation media. Ampicillin sodium is routinely used to select for cells containing the pcDNA3.1 and pEAK10 resistance plasmids in cell line A904L at an effective concentration of 50 μg/ml.
[Chemical Properties]

Crystalline Solid
[Uses]

Labelled Ampicillin. Orally active, semi-synthetic antibiotic; structurally related to penicillin. Antibacterial.
[Uses]

β-lactam antibiotics
[Definition]

ChEBI: A penicillin in which the substituent at position 6 of the penam ring is a 2-amino-2-phenylacetamido group.
[Potential Exposure]

Used as an antibiotic.
[First aid]

If this chemical gets into the eyes, remove any contact lenses at once and irrigate immediately for at least 15 minutes, occasionally lifting upper and lower lids. Seek medical attention immediately. If this chemical contacts the skin, remove contaminated clothing and wash immediately with soap and water. Seek medical attention immediately. If this chemical has been inhaled, remove from exposure, begin rescue breathing (using universal precautions, including resuscitation mask) if breathing has stopped and CPR if heart action has stopped. Transfer promptly to a medical facility. When this chemical has been swallowed, get medical attention. Give large quantities of water and induce vomiting. Do not make an unconscious person vomit.
[Shipping]

UN3077 Environmentally hazardous substances, solid, n.o.s., Hazard class: 9; Labels: 9-Miscellaneous hazardous material, Technical Name Required.
[Incompatibilities]

May be incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides.
[Waste Disposal]

It is inappropriate and possibly dangerous to the environment to dispose of expired or waste pharmaceuticals by flushing them down the toilet or discarding them to the trash. Household quantities of expired or waste pharmaceuticals may be mixed with wet cat litter or coffee grounds, double-bagged in plastic, discard in trash. Larger quantities shall carefully take into consideration applicable DEA, EPA, and FDA regulations. If possible return the pharmaceutical to the manufacturer for proper disposal being careful to properly label and securely package the material. Alternatively, the waste pharmaceutical shall be labeled, securely packaged and transported by a state licensed medical waste contractor to dispose by burial in a licensed hazardous or toxic waste landfill or incinerator.
Safety DataBack Directory
[Hazard Codes ]

Xn
[Risk Statements ]

R36/37/38:Irritating to eyes, respiratory system and skin .
R42/43:May cause sensitization by inhalation and skin contact .
[Safety Statements ]

S22:Do not breathe dust .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37:Wear suitable protective clothing and gloves .
[WGK Germany ]

2
[RTECS ]

XH8425000
[F ]

10-23
[HS Code ]

29212900
[Safety Profile]

Poison by intracerebral route. Moderately toxic by intraperitoneal route. Human systemic effects by ingestion: fever, agranulocytosis, and other blood effects. An experimental teratogen. Mutation data reported. Questionable carcinogen. When heated to decomposition it emits very toxic fumes of NO, and SOx,.
[Hazardous Substances Data]

69-53-4(Hazardous Substances Data)
Raw materials And Preparation ProductsBack Directory
[Raw materials]

Sodium hydroxide-->Hydrochloric acid-->Potassium carbonate-->Triethylamine-->Potassium chloride -->Potassium fluoride-->Barium chloride dihydrate-->Pivaloyl chloride-->4-Aminobenzoic acid-->Penicillin G-->D-2-Phenylglycine-->ALPHA-AMINOBENZENEACETYL CHLORIDE
[Preparation Products]

Potassium permanganate-->Potassium chloride -->Potassium dichromate-->Potassium dihydrogen phosphate-->Potassium fluoride-->Potassium bromide-->Potassium bromate -->Potassium tetrafluoroborate-->6-Aminopenicillanic acid-->Potassium hydrogen fluoride-->Potassium peroxymonosulfate-->Potassium chromate -->Potassium hexafluorotitanate-->Dipotassium hydrogenphosphate-->Potassium hexafluorozirconate-->Sulfur hexafluoride
Material Safety Data Sheet(MSDS)Back Directory
[msds information]

(2S,5R,6R)-6-[(R)-2-Amino-2-phenylacetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid(69-53-4).msds
Questions And AnswerBack Directory
[Brand Name(s)]

Human forms include Omnipen, Principen, Totacillin, Polycillin. Injectable forms include Omnipen-N, Polycillin-N, TotacillinN.
Veterinary forms include Amp-Equine, and Ampicillin trihydrate (Polyflex).
Spectrum DetailBack Directory
[Spectrum Detail]

Ampicillin(69-53-4) IR1
Well-known Reagent Company Product InformationBack Directory
[Sigma Aldrich]

69-53-4(sigmaaldrich)
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