Pivampicillin

Base Information

• Chemical Name: Pivampicillin
• CAS No.: 33817-20-8
• Molecular Formula: C22H29 N3 O6 S
• Molecular Weight: 463.555
• European Community (EC) Number: 251-688-6
• UNII: 0HLM346LL7
• DSSTox Substance ID: DTXSID1045459
• Nikkaji Number: J17.773C
• Wikipedia: Pivampicillin
• Wikidata: Q3122143
• NCI Thesaurus Code: C84068
• Metabolomics Workbench ID: 43591
• ChEMBL ID: CHEMBL3182343
• Mol file: 33817-20-8.mol

Synonyms:Ampicillin Pivaloyl Ester;Berocillin;Ester, Ampicillin Pivaloyl;Hydrochloride, Pivampicillin;Monohydrochloride, Pivampicillin;Pivamiser;Pivampicillin;Pivampicillin Hydrochloride;Pivampicillin Monohydrochloride;Pondocillin

Chemical Property of Pivampicillin

Chemical Property:

• Vapor Pressure: 2.7E-18mmHg at 25°C
• Boiling Point: 679°Cat760mmHg
• PKA: pKa 7.0 (Uncertain)
• Flash Point: 364.5°C
• PSA: 153.33000
• Density: 1.33g/cm³
• LogP: 2.35260
• Solubility.: Practically insoluble in water, freely soluble in methanol, soluble in anhydrous ethanol. It dissolves in dilute acids.
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 9
• Exact Mass: 463.17770683
• Heavy Atom Count: 32
• Complexity: 774

Purity/Quality:

99% ^*data from raw suppliers

PIVAMPICILLIN 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

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)OCOC(=O)C(C)(C)C)C
• Isomeric SMILES: CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)[C@@H](C3=CC=CC=C3)N)C(=O)OCOC(=O)C(C)(C)C)C
• Description: Pivampicillin caused sensitization in 56 workers at a penicillin factory. Pivampicillin and pivmecillinam were responsible for contact dermatitis in pharmaceutical production workers. Ampicillin, mecillinam, penicillin V and penicillin G were also implicated in cross reactions.
• Uses: Antibacterial.
• Therapeutic Function: Antibacterial

Technology Process of Pivampicillin

There total 6 articles about Pivampicillin 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:

Chloromethyl pivalate (18997-19-8) → pivampicillin (33817-20-8)

Guidance literature:

Multi-step reaction with 2 steps

1: aq. NaI / acetone

2: H₂ / Pd-C

With hydrogen; sodium iodide; palladium on activated charcoal; In acetone;

DOI:10.1021/jm00298a005

Reference yield:

6β-((R)-2-azido-2-phenyl-acetylamino)-penicillanic acid; potassium salt → pivampicillin (33817-20-8)

Guidance literature:

Multi-step reaction with 2 steps

1: aq. NaI / acetone

2: H₂ / Pd-C

With hydrogen; sodium iodide; palladium on activated charcoal; In acetone;

DOI:10.1021/jm00298a005

Reference yield:

6β-((R)-2-azido-2-phenyl-acetylamino)-penicillanic acid 2,2-dimethyl-propionyloxymethyl ester → pivampicillin (33817-20-8)

Guidance literature:

With hydrogen; palladium on activated charcoal;

DOI:10.1021/jm00298a005

upstream raw materials:

Chloromethyl pivalate

Downstream raw materials:

ampicillin

Refernces

• 1、 -. "Enhancement of the efficacy of nifedipine by deuteration". . . Retrieved 2008/06/13.
• 2、 Daehne,Frederiksen,Gundersen,Lund,Morch,Petersen,Roholt,Tybring,Godtfredsen. "Acyloxymethyl esters of ampicillin.". . p. 607 - 612. Retrieved 2007/10/05.