Brand Name(s)
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Ampicillin

Brand Name(s)
Product Name
Ampicillin
CAS No.
69-53-4
Chemical Name
Ampicillin
Synonyms
p-50;Wymox;ab-pc;Unasyn;qidamp;Albipen;AmpiciL;amfipen;ampicin;ampimed
CBNumber
CB2247346
Molecular Formula
C16H19N3O4S
Formula Weight
349.4
MOL File
69-53-4.mol
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Ampicillin Property

Melting point:
198-200 °C (dec.)(lit.)
alpha 
D23 +287.9° (c = 1 in water)
Boiling point:
201.8°C (rough estimate)
Density 
1.2794 (rough estimate)
refractive index 
1.6320 (estimate)
storage temp. 
2-8°C
solubility 
NH4OH 1 M: 50 mg/mL, clear, colorless
form 
solid
pka
2.5 (COOH)(at 25℃)
Water Solubility 
13.9g/L(25 ºC)
Merck 
13,591
JECFA Number
85
BRN 
1090925
Stability:
Stable, but may be moisture sensitive. Incopmpatible with strong oxidizing agents.
InChIKey
AVKUERGKIZMTKX-NJBDSQKTSA-N
CAS DataBase Reference
69-53-4(CAS DataBase Reference)
IARC
3 (Vol. 50) 1990
EPA Substance Registry System
Ampicillin (69-53-4)
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Safety

Hazard Codes 
Xn,T
Risk Statements 
36/37/38-42/43-61
Safety Statements 
22-26-36/37-45-53
WGK Germany 
2
RTECS 
XH8425000
10-23
HS Code 
29212900
Hazardous Substances Data
69-53-4(Hazardous Substances Data)
Toxicity
LD50 oral in mouse: > 5gm/kg
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H315Causes skin irritation

H317May cause an allergic skin reaction

H319Causes serious eye irritation

H334May cause allergy or asthma symptoms or breathing difficulties if inhaled

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P284Wear respiratory protection.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P333+P313IF SKIN irritation or rash occurs: Get medical advice/attention.

P342+P311IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.

P405Store locked up.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
59349
Product name
Ampicillin
Purity
analytical standard
Packaging
100mg
Price
$42.3
Updated
2020/08/18
Sigma-Aldrich
Product number
A5354
Product name
Ampicillin
Purity
Ready Made Solution, 100?mg/mL, 0.2 μm filtered
Packaging
10 mL
Price
$89.1
Updated
2021/03/22
Sigma-Aldrich
Product number
A1000000
Product name
Ampicillin
Purity
anhydrous, European Pharmacopoeia (EP) Reference Standard
Price
$190
Updated
2021/03/22
Sigma-Aldrich
Product number
A1593
Product name
Ampicillin
Purity
meets USP testing specifications
Packaging
25 g
Price
$193
Updated
2021/03/22
Sigma-Aldrich
Product number
1033000
Product name
Ampicillin
Purity
United States Pharmacopeia (USP) Reference Standard
Packaging
200mg
Price
$366
Updated
2021/03/22
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Ampicillin Chemical Properties,Usage,Production

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).

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

Chemical Properties

Ampicillin in anhydrous form occurs as crystals.

Originator

Binotal,Bayer,W. Germany,1962

Uses

Ampicillin caused contact dermatitis in a nurse also sensitized to amoxicillin (with tolerance to oral phenoxymethylpenicillin), and in a pharmaceutical factory worker.

Uses

β-lactam antibiotics

Uses

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

Definition

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

Manufacturing Process

α-Carbobenzyloxyaminophenylacetic acid (0.1 mol), which is obtained by the reaction of equivalent quantities of α-aminophenylacetic acid and benzyl chlorocarbonate in aqueous sodium hydroxide, dissolved in dry acetone is stirred and cooled to approximately -5°C. To this there is added dropwise with continued cooling and stirring a solution of ethyl chlorocarbonate (0.1 mol). After approximately 10 minutes, the acylating mixture is cooled to about -5°C and then is slowly added to a stirred ice-cold mixture of 6-aminopenicillanic acid (0.1 mol), 3% sodium bicarbonate solution (0.1 mol) and acetone. This reaction mixture is allowed to attain room temperature, stirred for an additional thirty minutes at this temperature and then is extracted with ether.
The extracted aqueous solution is covered with butanol and the pH adjusted to 2 by the addition of HCl. The acidified aqueous phase is extracted with butanol, the pH of the aqueous phase being adjusted to pH 2 each time. The combined butanol solutions which contain the free acid, α- carbobenzyloxyaminobenzylpenicillin, are washed with water, and are then shaken with water to which sufficient 3% sodium bicarbonate has been added to bring the aqueous phase to pH 7. The process of washing and shaking is repeated with fresh water and bicarbonate solution. The combined aqueous solutions are washed with ether and then are evaporated under reduced pressure and low temperature. The product, the sodium salt of α- carbobenzyloxyaminobenzylpenicillin, is obtained as a yellow solid in a yield of 65%.
A suspension of palladium on barium carbonate (3.7 grams of 30%) in water (20 ml) is shaken in an atmosphere of hydrogen at room temperature. The catalyst is then filtered and washed well with water, care being taken that it does not become dry. A solution of the sodium salt of α- carbobenzyloxyaminobenzylpenicillin (4 grams) in water (20 ml) is added to the pretreated catalyst and the suspension is shaken in an atmosphere of hydrogen at room temperature and pressure for one hour. The catalyst is then filtered off, washed well with water, and the combined filtrate and washings adjusted to pH 7 with hydrochloric acid. The resulting solution is evaporated in vacuum at a temperature below 20°C to give α-aminobenzylpenicillin (2.4 grams, 74% yield), which is assayed at approximately 48% pure by the manometric method.

brand name

Amcill (Parke-Davis); Omnipen (Wyeth-Ayerst); Polycillin (Apothecon); Principen (Apothecon).

Therapeutic Function

Antibacterial

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.

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,.

Potential Exposure

Used as an antibiotic.

Veterinary Drugs and Treatments

In dogs and cats, ampicillin is not as well absorbed after oral administration as amoxicillin and its oral use has largely been supplanted by amoxicillin. It is used commonly in parenteral dosage forms when an aminopenicillin is indicated in all species.
The aminopenicillins, also called the “broad-spectrum” or ampicillin penicillins, have increased activity against many strains of gram-negative aerobes not covered by either the natural penicillins or penicillinase-resistant penicillins, including some strains of E. coli, Klebsiella, and Haemophilus.

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.

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Ampicillin Suppliers

Yueyang Tianqing Biological Technology Co., Ltd.
Tel
15173087635
Email
tq201818@163.com
Country
CHINA
ProdList
35
Advantage
58
Wuhan Zeuschem. Co. Ltd.
Tel
027-88866057- ;027-88866057-
Fax
1735832116
Email
1735832116@qq.com;info@zeuschem.cn
Country
China
ProdList
486
Advantage
58
Wuhan kemike Biomedical Technology Co., Ltd
Tel
027-87747081-
Email
1344475572@qq.com
Country
China
ProdList
4278
Advantage
58
Wuhan Huajiu Pharmaceutical Technology Co.,Ltd.
Tel
027-59225746-
Fax
027-59225746
Email
730880265@qq.com
Country
China
ProdList
3209
Advantage
58
Wuhan diesel Biotechnology Co., Ltd
Tel
Fax
13100710651
Email
1572909019@qq.com
Country
China
ProdList
30
Advantage
58
Guangzhou Belka Biological Technology Co., Ltd.
Tel
Fax
18665676617
Email
11353066@qq.com
Country
China
ProdList
9971
Advantage
58
J & K SCIENTIFIC LTD.
Tel
010-82848833- ;010-82848833-
Fax
86-10-82849933
Email
jkinfo@jkchemical.com;market6@jkchemical.com
Country
China
ProdList
96815
Advantage
76
3B Pharmachem (Wuhan) International Co.,Ltd.
Tel
821-50328103-801
Fax
86-21-50328109
Email
3bsc@sina.com
Country
China
ProdList
15877
Advantage
69
BeiJing Hwrk Chemicals Limted
Tel
0757-86329057-
Fax
0757-86311057
Email
sales.gd@hwrkchemical.com
Country
China
ProdList
17295
Advantage
55
LGM Pharma
Tel
1-(800)-881-8210
Fax
615-250-9817
Email
inquiries@lgmpharma.com
Country
United States
ProdList
1938
Advantage
70
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View Lastest Price from Ampicillin manufacturers

WUHAN CIRCLE POWDER TECHNOLOGY CO.,LTD
Product
Ampicillin 69-53-4
Price
US $0.00/KG
Min. Order
1g
Purity
99%
Supply Ability
200kg
Release date
2020-12-04
Jiangsu Monade Biological Technology Co., Ltd.
Product
Ampicillin 69-53-4
Price
US $0.00/ASSAYS
Min. Order
100ASSAYS
Purity
99.99
Supply Ability
10000
Release date
2021-09-10
Hebei Zhanyao Biotechnology Co. Ltd
Product
Ampicillin 69-53-4
Price
US $99.00/KG
Min. Order
1KG
Purity
>99%
Supply Ability
5000Kg/month
Release date
2021-03-10

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