ChemicalBook
Chinese Japanese Germany Korea

Ampicillin

Description References
Ampicillin
Ampicillin structure
CAS No.
7177-48-2
Chemical Name:
Ampicillin
Synonyms
amcap;cymbi;amcill;amplin;pensyn;amperil;morepen;ro-ampen;ampinova;ampichel
CBNumber:
CB5247347
Molecular Formula:
C16H25N3O7S
Formula Weight:
403.45
MOL File:
7177-48-2.mol

Ampicillin Properties

Melting point:
208 °C (dec.)(lit.)
Boiling point:
684℃
refractive index 
265 ° (C=0.1, H2O)
Flash point:
87 °C
storage temp. 
2-8°C
solubility 
NH4OH 1 M: 50 mg/mL, clear, colorless
form 
solid
color 
white to off-white
pka
2.5 (COOH)(at 25℃)
Water Solubility 
0.1-1 g/100 mL at 21 ºC
Merck 
14,586
BRN 
5399534
InChIKey
RXDALBZNGVATNY-CWLIKTDRSA-N
CAS DataBase Reference
7177-48-2(CAS DataBase Reference)
FDA UNII
HXQ6A1N7R6
EPA Substance Registry System
Ampicillin trihydrate (7177-48-2)
SAFETY
  • Risk and Safety Statements
Symbol(GHS) 
GHS08,GHS07
Signal word  Danger
Hazard statements  H315-H317-H319-H334-H335-H362
Precautionary statements  P280a-P405-P501a-P261-P280-P305+P351+P338-P342+P311-P284-P304+P340-P201-P260-P263-P264-P270-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313-P308+P313
Hazard Codes  Xn,Xi
Risk Statements  36/37/38-42/43
Safety Statements  22-26-36/37-36-45-23
WGK Germany  2
RTECS  XH8425000
3-10
HS Code  29411020
Toxicity LD50 orl-rat: 10 g/kg ANTBAL 20,653,75

Ampicillin price More Price(13)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 31591 Ampicillin trihydrate VETRANAL 7177-48-2 250mg $43.1 2020-08-18 Buy
Sigma-Aldrich A1593 Ampicillin meets USP testing specifications 7177-48-2 25g $116 2020-08-18 Buy
TCI Chemical A2092 Ampicillin Trihydrate >98.0%(HPLC)(T) 7177-48-2 5g $25 2020-06-24 Buy
TCI Chemical A2092 Ampicillin Trihydrate >98.0%(HPLC)(T) 7177-48-2 25g $73 2020-06-24 Buy
Alfa Aesar J66514 Ampicillin trihydrate 7177-48-2 25g $59.2 2020-06-24 Buy

Ampicillin Chemical Properties,Uses,Production

Description

As a penicillin group of beta-lactam antibiotics, Ampicillin is the first broad-spectrum penicillin, which has in vitro activity against Gram-positive and Gram-negative aerobic and anaerobic bacteria, commonly used for preventing and treating bacterial infections of respiratory tract, urinary tract, middle ear, sinuses, stomach and intestines, bladder, and kidney, etc. caused by susceptible bacteria. It is also used to treat uncomplicated gonorrhea, meningitis, endocarditis salmonellosis, and other serious infections through administered by mouth, intramuscular injection or by intravenous infusion. Like all antibiotics, it is not effective for the treatment of viral infections.
Ampicillin functions by killing the bacteria or preventing their growth. After penetrating Gram-positive and Gram-negative bacteria, it acts as an irreversible inhibitor of the enzyme transpeptidase needed by bacteria to make the cell wall, which results to the inhibition of cell wall synthesis and eventually leads to cell lysis.

References

https://en.wikipedia.org/wiki/Ampicillin
https://www.drugbank.ca/drugs/DB00415
http://www.medicinenet.com/ampicillin/article.htm

Chemical Properties

White or almost white, crystalline powder.

Chemical Properties

Ampicillin in anhydrous form occurs as crystals.

Originator

Polycillin,Bristol,US,1963

Uses

Penicillin antibacterial.

Indications

Ampicillin may also be helpful in certain patients, particularly pregnant women with acne, for whom the use of tetracycline, erythromycin, and minocycline should be avoided. In resistant acne patients, culture may reveal a gram-negative bacteria responsive to ampicillin.

Manufacturing Process

The known methods for the preparation of D-(-)-α-aminobenzylpenicillin by the acylation of 6-aminopenicillanic acid result in the preparation of aqueous mixtures which contain, in addition to the desired penicillin, unreacted 6- aminopenicillanic acid, hydrolyzed acylating agent, and products of side reactions such as the products of the acylating agent reacted with itself and/or with the desired penicillin, as well as other impurities.
The D-(-)-α-aminobenzylpenicitlin may then be recovered from the aqueous reaction mixture by concentration to small volume and recovering the product by filtration. However, due to the fact that anhydrous D-(-)-α- aminobenzylpenicillinis soluble in water to the extent of about 20-25 mg/ml at 20°-25°C, it is very difficult to recover the product in high yields. Furthermore, the recovered D-(-)-α-aminobenzylpenicillin may be obtained in the form of a monohydrate. The monohydrates (as well as the dihydrates) of D-(-)-α-aminobenzylpenicillin possess poor biological stability.
The trihydrate which is obtained in high yields, is relatively insoluble in water, possesses high biological stability and can be obtained by contacting, at a temperature not above 60°C, an acid addition salt of D-(-)-α- aminobenzylpenicillin with an amine in a water immiscible solvent containing at least 3 mols of water per mol of such penicillin.
The following is an example of the conduct of such a process. To a vigorously agitated mixture of 100 ml of methyl isobutyl ketone there are added at 25° to 30°C 15 ml of water and 10 ml of a mixture of secondary amines.
To this mixture there is then added slowly over a period of 30 minutes 10 grams of D-(-)-α-aminobenzylpenicillin α-naphthalenesulfonate. The mixture is agitated for 3 hours at 25-30°C. The product, D-(-)-α-aminobenzylpenicillin trihydrate precipitates and is collected by filtration. The filter cake of the product is washed several times with methyl isobutyl ketone and is dried at 40°C. The product is obtained in about a 90% yield and has a potency of 865 mcg/mg. It is determined by Karl Fischer analysis to have a moisture content of 13.4% by weight.

brand name

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

Therapeutic Function

Antibacterial

Antimicrobial activity

Ampicillin is slightly less active than benzylpenicillin against most Gram-positive bacteria but is more active against E. faecalis. MRSA and strains of Str. pneumoniae with reduced susceptibility to benzylpenicillin are resistant. Most group D streptococci, anaerobic Gram-positive cocci and bacilli, including L. monocytogenes, Actinomyces spp. and Arachnia spp., are susceptible. Mycobacteria and nocardia are resistant.
Ampicillin has similar activity to benzylpenicillin against N. gonorrhoeae, N. meningitidis and Mor. catarrhalis. It is 2–8 times more active than benzylpenicillin against H. influenzae and many Enterobacteriaceae, but β-lactamase-producing strains are resistant. Pseudomonas spp. are resistant, but Bordetella, Brucella, Legionella and Campylobacter spp. are often susceptible. Certain Gram-negative anaerobes such as Prevotella melaninogenica and Fusobacterium spp. are susceptible, but B. fragilis is resistant, as are mycoplasmas and rickettsiae.
Activity against molecular class A β-lactamase-producing strains of staphylococci, gonococci, H. influenzae, Mor. catarrhalis, certain Enterobacteriaceae and B. fragilis is enhanced by the presence of β-lactamase inhibitors, specifically clavulanic acid.
Its bactericidal activity resembles that of benzylpenicillin. Bactericidal synergy occurs with aminoglycosides against E. faecalis and many enterobacteria, and with mecillinam against a number of ampicillin-resistant enterobacteria.

Acquired resistance

β-Lactamase-producing pathogens, including most clinical isolates of Staph. aureus, are resistant. Strains of pneumococci, enterococci, gonococci and H. influenzae with altered PBPs have reduced susceptibility to ampicillin. Isolates of N. gonorrhoeae and H. influenzae with a TEM plasmid- mediated β-lactamase (which are more common) are fully resistant. Resistance among H. influenzae is often linked with resistance to chloramphenicol, erythromycin or tetracycline, due to plasmid-encoded resistance markers that are co-transferred with the gene for the TEM enzyme. However, at least 70% of current H. influenzae isolates remain susceptible to ampicillin worldwide.
The widespread use of ampicillin and other aminopenicillins has led to resistance becoming common in formerly susceptible species of enteric pathogens as a result of the widespread dissemination of plasmid-mediated β-lactamases. Surveillance data from North America and Europe indicate less than 50% susceptibility to ampicillin in Esch. coli. At least 90% of current isolates of Mor. catarrhalis are β-lactamaseproducing strains. Ampicillin-resistant strains of salmonellae, notably S. enterica serotypes Typhi and Typhimurium (many of which are also resistant to chloramphenicol, sulfonamides and tetracyclines) present a serious problem in Africa, Asia and South America. Multiresistant strains of shigellae also predominate in many parts of the world.

General Description

Odorless white microcrystalline powder with a bitter taste. A 0.25% solution in water has a pH of 3.5 to 5.5.

Air & Water Reactions

Slightly soluble in water.

Reactivity Profile

Ampicillin absorbs insignificant amounts of moisture at 77° F and relative humidities up to approximately 80%, but under damper conditions Ampicillin absorbs significant amounts. A pH-rate profile reveals specific-acid- and specific-base- catalyzed hydrolysis. The pH of maximum stability is 5.8.

Fire Hazard

Flash point data for Ampicillin are not available; however, Ampicillin is probably combustible.

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.

Pharmacokinetics

Oral absorption: 30–40%
Cmax 500 mg oral: 3.2 mg/L after c. 2 h
500 mg intramuscular: 5–15 mg/L after 1 h
500 mg intravenous infusion: 12–29 mg/L
Plasma half-life: 1–1.5 h
Volume of distribution: 0.38 L/kg
Plasma protein binding: 20%
Absorption and distribution
Ampicillin is highly stable to acid: in 2 h at pH 2 and 37°C, only 5% of activity is lost. Absorption is impaired when it is given with meals. It is distributed in the extracellular fluid. Adequate concentrations are obtained in serous effusions. Effective CSF levels are obtained only in the presence of inflammation, variable peak concentrations around 3 mg/L being found in the first 3 days of treatment in patients receiving 150 mg/kg per day. It accumulates and persists in the amniotic fluid. Metabolism and excretion
A small proportion is converted to penicilloic acid. About 34% of an oral dose and 60–80% of parenteral doses are recoverable from the urine, where concentrations around 250–1000 mg/L appear. Excretion is partly in the glomerular filtrate and partly by tubular secretion, which can be blocked by probenecid. Impairment of renal function reduces the rate of excretion, the plasma half-life rising to 8–9 h in anuric patients.
Although excretion is mainly renal, up to 50 times the corresponding serum level may be attained in the bile. There is a degree of enterohepatic recirculation and significant quantities appear in the feces. Bioavailability may be affected in severe liver disease.

Clinical Use

Ampicillin, 6-[D-α-aminophenylacetamido]penicillanic acid,D-α-aminobenzylpenicillin (Penbritn, Polycillin, Omnipen,Amcill, Principen), meets another goal of the research onsemisynthetic penicillins—an antibacterial spectrum broaderthan that of penicillin G. This product is active against thesame Gram-positive organisms that are susceptible to otherpenicillins, and it is more active against some Gram-negativebacteria and enterococci than are other penicillins.Obviously, the α-amino group plays an important role in thebroader activity, but the mechanism for its action isunknown. It has been suggested that the amino group confersan ability to cross cell wall barriers that are impenetrableto other penicillins. D-(-)-Ampicillin, prepared from D-(-)-α-aminophenylacetic acid, is significantly more active thanL-(+)-ampicillin.
Ampicillin is water soluble and stable in acid. Theprotonated α-amino group of ampicillin has a pKa of 7.3,46and thus it is protonated extensively in acidic media, whichexplains ampicillin’s stability to acid hydrolysis and instabilityto alkaline hydrolysis. It is administered orally andis absorbed from the intestinal tract to produce peak plasmaconcentrations in about 2 hours. Oral doses must be repeatedabout every 6 hours because it is excreted rapidly andunchanged through the kidneys. It is available as a white, crystalline, anhydrous powder that is sparingly soluble inwater or as the colorless or slightly buff-colored crystallinetrihydrate that is soluble in water. Either form may be usedfor oral administration, in capsules or as a suspension.Earlier claims of higher plasma levels for the anhydrousform than for the trihydrate following oral administrationhave been disputed. The white, crystalline sodium salt isvery soluble in water, and solutions for injections should beadministered within 1 hour after being made.

Clinical Use

Isolates should be tested for susceptibility before use, especially for serious infections. For oral therapy, amoxicillin is preferable to ampicillin.
Urinary tract infections
Bacterial meningitis
Respiratory tract infections
Gastrointestinal infections, including typhoid fever and bacillary dysentery Enterococcal endocarditis and septicemia (in combination with an aminoglycoside)
Listeriosis (in combination with an aminoglycoside)

Side effects

Ampicillin is generally free from severe toxicity and, apart from gastrointestinal intolerance, the only significant side effects seen have been rashes. In common with other semisynthetic penicillins, it appears to be less likely than benzylpenicillin to elicit true allergic reactions. However, it is more likely to cause rashes, which are found in approximately 9% of treated patients and which occur more frequently in patients receiving large doses or in renal failure. Rashes occur in 95% of patients with infectious mononucleosis or other lymphoid disorders. This unusual susceptibility disappears when the disease resolves. In keeping with a toxic rather than an allergic origin, skin tests to ampicillin and to mixed-allergen moieties of benzylpenicillin are negative. Since the typical maculopapular rash of ampicillin does not have an allergic origin, its development does not indicate penicillin allergy and is not a contraindication to the use of other penicillins.
Gastrointestinal side effects are relatively common (around 10%) in patients treated with oral ampicillin, and occur in 2–3% of patients given the drug parenterally, presumably as a result of drug entering the gut through the bile. The very young and the old are most likely to suffer. Diarrhea can be sufficiently severe to require withdrawal of treatment and pseudomembranous colitis may occur. Interference with the bowel flora, which is presumably implicated in diarrhea, can also affect enterohepatic recirculation of steroids, and the derangement can be sufficient to impair the absorption of oral contraceptives and affect the interpretation of estriol levels.

Safety Profile

Mildly toxic by ingestion. An experimental teratogen. Other experimental reproductive effects. When heated to decomposition it emits toxic fumes of SO,xand NOx.

Potential Exposure

Used as an antibiotic.

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( 246)Suppliers
Supplier Tel Fax Email Country ProdList Advantage
Henan Tianfu Chemical Co.,Ltd.
0371-55170693
0371-55170693 info@tianfuchem.com CHINA 22625 55
career henan chemical co
+86-371-86658258
sales@coreychem.com CHINA 30039 58
Xiamen AmoyChem Co., Ltd
+86 592-605 1114
sales@amoychem.com CHINA 6371 58
HubeiwidelychemicaltechnologyCo.,Ltd
18627774460
faith@widelychemical.com CHINA 743 58
BOC Sciences
1-631-619-7922 1-631-619-7922
1-631-614-7828 inquiry@bocsci.com United States 20039 58
Chongqing Chemdad Co., Ltd
+86-13650506873
sales@chemdad.com CHINA 35434 58
CONIER CHEM AND PHARMA LIMITED
86-18523575427
sales@conier.com CHINA 47486 58
Zhuozhou Wenxi import and Export Co., Ltd
+8613111626072
+8613111626072 zzwenxi@126.com CHINA 7507 58
ENBRIDGE PHARMTECH CO., LTD.
13812269233
0510-83591909 sales@enbridgepharm.com CHINA 154 58
SIMAGCHEM CORP
13806087780 +86 13806087780
shaobowang@simagchem.com CHINA 17852 58

View Lastest Price from Ampicillin manufacturers

Image Release date Product Price Min. Order Purity Supply Ability Manufacturer
2020-05-09 Ampicillin Trihydrate
7177-48-2
US $1.00 / KG 1KG 99% 20T Shaanxi Dideu Medichem Co. Ltd
2019-07-09 Ampicillin
7177-48-2
US $1.00 / KG 1KG 99% 100kg career henan chemical co

Ampicillin Spectrum


7177-48-2(Ampicillin)Related Search:


Copyright 2017 © ChemicalBook. All rights reserved