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Ampicillin

Brand Name(s)
Ampicillin
Ampicillin structure
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

Ampicillin Properties

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)
JECFA Number
85
Merck 
13,591
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)
FDA 21 CFR
556.40
FDA UNII
7C782967RD
NCI Drug Dictionary
Wymox
ATC code
J01CA01,J01CA51,S01AA19
IARC
3 (Vol. 50) 1990
EPA Substance Registry System
Ampicillin (69-53-4)
SAFETY
  • Risk and Safety Statements
Symbol(GHS) 
GHS08,GHS07
Signal word  Danger
Hazard statements  H315-H317-H319-H334-H335
Precautionary statements  P280a-P405-P501a-P261-P280-P284-P304+P340-P305+P351+P338-P342+P311-P333+P313
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
Toxicity LD50 oral in mouse: > 5gm/kg

Ampicillin price More Price(12)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 59349 Ampicillin analytical standard 69-53-4 100mg $42.3 2020-08-18 Buy
Sigma-Aldrich A5354 Ampicillin Ready Made Solution, 100?mg/mL, 0.2 μm filtered 69-53-4 10 mL $89.1 2021-03-22 Buy
Sigma-Aldrich A1000000 Ampicillin anhydrous, European Pharmacopoeia (EP) Reference Standard 69-53-4 $190 2021-03-22 Buy
Sigma-Aldrich A1593 Ampicillin meets USP testing specifications 69-53-4 25 g $193 2021-03-22 Buy
Sigma-Aldrich 1033000 Ampicillin United States Pharmacopeia (USP) Reference Standard 69-53-4 200mg $366 2021-03-22 Buy

Ampicillin Chemical Properties,Uses,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.

Ampicillin Preparation Products And Raw materials

Raw materials

Preparation Products


Ampicillin Suppliers

Global( 358)Suppliers
Supplier Tel Fax Email Country ProdList Advantage
Univar Solutions(China) Co., Ltd.
15902132654
86-21-61932700 Ivy.zhuang@univarsolutions.com CHINA 275 58
Henan Tianfu Chemical Co.,Ltd.
0371-55170693
0371-55170693 info@tianfuchem.com CHINA 22607 55
Hangzhou FandaChem Co.,Ltd.
008615858145714
+86-571-56059825 fandachem@gmail.com CHINA 8910 55
Guangzhou PI PI Biotech Inc
+8618371201331
020-81716319 sales@pipitech.com;87478684@qq.com China 3245 55
Hubei XinRunde Chemical Co., Ltd.
+8615102730682
02783214688 bruce@xrdchem.cn CHINA 567 55
career henan chemical co
+86-371-86658258
sales@coreychem.com CHINA 29954 58
Shaanxi Yikanglong Biotechnology Co., Ltd.
17791478691
yklbiotech@163.com CHINA 297 58
Hubei Jusheng Technology Co.,Ltd.
86-18871470254
027-59599243 linda@hubeijusheng.com CHINA 28229 58
Xiamen AmoyChem Co., Ltd
+86 592-605 1114
sales@amoychem.com CHINA 6369 58
Standardpharm Co. Ltd.
86-714-3992388
overseasales1@yongstandards.com United States 14344 58

View Lastest Price from Ampicillin manufacturers

Image Release date Product Price Min. Order Purity Supply Ability Manufacturer
2021-12-01 Ampicillin
69-53-4
US $10.50 / KG 1KG 99% 10 ton Hebei Crovell Biotech Co Ltd
2021-11-16 Ampicillin
69-53-4
US $0.00 / KG 1g 99% 200kg WUHAN CIRCLE POWDER TECHNOLOGY CO.,LTD
2021-11-15 Ampicillin
69-53-4
US $125.00 / KG 1KG 99% 200000pcs Hebei Yirun Sega Biological Technology Co. Ltd

Ampicillin Spectrum


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