Ampicillin trihydrate

Base Information

• Chemical Name: Ampicillin trihydrate
• CAS No.: 7177-48-2
• Molecular Formula: C₁₆H₁₉N₃O₄S*3H₂O
• Molecular Weight: 403.456
• Hs Code.: 2941101100
• UNII: HXQ6A1N7R6
• DSSTox Substance ID: DTXSID9020083
• Wikidata: Q27114210
• NCI Thesaurus Code: C47960
• RXCUI: 203115
• ChEMBL ID: CHEMBL453388
• Mol file: 7177-48-2.mol

Synonyms:Amcill;Aminobenzyl Penicillin;Aminobenzylpenicillin;Ampicillin;Ampicillin Sodium;Ampicillin Trihydrate;Antibiotic KS R1;Antibiotic KS-R1;KS-R1, Antibiotic;Omnipen;Penicillin, Aminobenzyl;Pentrexyl;Polycillin;Sodium, Ampicillin;Trihydrate, Ampicillin;Ukapen

Chemical Property of Ampicillin trihydrate

Chemical Property:

• Appearance/Colour: Odorless white microcrystalline powder with a bitter taste
• Vapor Pressure: 1.21E-19mmHg at 25°C
• Melting Point: 208 °C (dec.)(lit.)
• Refractive Index: 265 ° (C=0.1, H2O)
• Boiling Point: 683.9 °C at 760 mmHg
• PKA: 2.5 (COOH)(at 25℃)
• Flash Point: 367.4 °C
• PSA: 165.72000
• LogP: 1.15430
• Storage Temp.: 2-8°C
• Solubility.: NH4OH 1 M: 50 mg/mL, clear, colorless
• Water Solubility.: 0.1-1 g/100 mL at 21 ºC
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 4
• Exact Mass: 403.14132132
• Heavy Atom Count: 27
• Complexity: 562

Purity/Quality:

99% ^*data from raw suppliers

Ampicillin trihydrate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, Xi
• Hazard Codes: Xn,Xi
• Statements: 36/37/38-42/43
• Safety Statements: 22-26-36/37-36-45-23

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(C(N2C(S1)C(C2=O)NC(=O)C(C3=CC=CC=C3)N)C(=O)O)C.O.O.O
• Isomeric SMILES: CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)[C@@H](C3=CC=CC=C3)N)C(=O)O)C.O.O.O
• Recent EU Clinical Trials: EFFICACY, PHARMACOKINETICS AND SAFETY OF MEROPENEM IN INFANTS BELOW 90 DAYS OF AGE (INCLUSIVE) WITH CLINICAL OR CONFIRMED LATE-ONSET SEPSIS: A EUROPEAN MULTICENTER RANDOMISED PHASE III TRIAL
• 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.
• Uses: Commonly used to select for ampicillin resistance in mutated and transformed cells
• 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.
• Therapeutic Function: Antibacterial
• 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. 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)
• Drug interactions: Potentially hazardous interactions with other drugs Ciclosporin: may increase ciclosporin levels. Reduces excretion of methotrexate (increased risk of toxicity).

Technology Process of Ampicillin trihydrate

There total 9 articles about Ampicillin trihydrate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 89.0%

→ ampicillin trihydrate (5187-94-0,7177-48-2,32388-53-7,57095-77-9,145454-26-8)

Guidance literature:

Reference yield: 87.6%

N,N-Bis(trimethylsilyl)urea (57397-48-5) + 6-Aminopenicillanic Acid (551-16-6) → ampicillin trihydrate (5187-94-0,7177-48-2,32388-53-7,57095-77-9,145454-26-8)

Guidance literature:

With chloro-trimethyl-silane; triethylamine; In dichloromethane;

Reference yield: 56.0%

6-aminopenicillanic acid (551-16-6,1079-37-4,3115-55-7,21794-93-4,145920-51-0) + ammonium hydroxide + phenylglycidylchloride hydrochloride (5321-31-3) → ampicillin trihydrate (5187-94-0,7177-48-2,32388-53-7,57095-77-9,145454-26-8)

Guidance literature:

With chloro-trimethyl-silane; triethylamine; In dichloromethane; water; acetone;

upstream raw materials:

6-aminopenicillanic acid

phenylglycidylchloride hydrochloride

6-Aminopenicillanic Acid

N,N'-bis(trimethylsilyl)urea

Downstream raw materials:

penicillin G

Refernces

• 1、 -. "Beta lactam production". . . Retrieved 2008/06/13.
• 2、 Sakamoto,Ikeda,Tsukamoto. "Studies on prodrugs. I. Preparation and characterization of acyloxyallylester of ampicillin". . p. 2698 - 2707. Retrieved 2007/10/02.