33817-20-8

Basic information

• Product Name: PIVAMPICILLIN
• Synonyms: 4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylicacid,6-(2-amino-2-phenylacetami;ampicillinpivaloyloxymethylester;hydroxymethylester,pivalate(ester),d-(-)-do)-3-dimethyl-7-oxo-;mk191;pivaloylampicillin;pivaloyloxymethylampicillinate;PIVAMPICILLIN;PIVAPICILLIN
• CAS NO: 33817-20-8
• Molecular Formula: C₂₂H₂₉N₃O₆S
• Molecular Weight: 463.55
• EINECS: 251-688-6
• Mol File: 33817-20-8.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 679°Cat760mmHg
• Flash Point: 364.5°C
• Appearance: /
• Density: 1.33g/cm³
• Vapor Pressure: 2.7E-18mmHg at 25°C
• Refractive Index: 1.604
• Solubility: Practically insoluble in water, freely soluble in methanol, soluble in anhydrous ethanol. It dissolves in dilute acids.
• PKA: pKa 7.0 (Uncertain)
• CAS DataBase Reference: PIVAMPICILLIN(CAS DataBase Reference)
• NIST Chemistry Reference: PIVAMPICILLIN(33817-20-8)
• EPA Substance Registry System: PIVAMPICILLIN(33817-20-8)

Safety Data

• Hazardous Substances Data: 33817-20-8(Hazardous Substances Data)

Usage

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.

Chemical Properties

White or almost white, crystalline powder.

Uses

Antibacterial.

Therapeutic Function

Antibacterial

InChI:InChI=1/C22H29N3O6S/c1-21(2,3)20(29)31-11-30-19(28)15-22(4,5)32-18-14(17(27)25(15)18)24-16(26)13(23)12-9-7-6-8-10-12/h6-10,13-15,18H,11,23H2,1-5H3,(H,24,26)/t13-,14-,15+,18-/m1/s1

Synthetic route

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

Conditions	Yield
With hydrogen; palladium on activated charcoal

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

Conditions	Yield
Multi-step reaction with 2 steps 1: aq. NaI / acetone 2: H2 / Pd-C View Scheme

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

Conditions	Yield
Multi-step reaction with 2 steps 1: aq. NaI / acetone 2: H2 / Pd-C View Scheme

pivampicillin (33817-20-8) → (2R,4S)-2-[(R)-((R)-2-Amino-2-phenyl-acetylamino)-carboxy-methyl]-5,5-dimethyl-thiazolidine-4-carboxylic acid 2,2-dimethyl-propionyloxymethyl ester

Conditions	Yield
With phosphate buffer; penicillinamide β-lactamhydrolase at 25℃; Product distribution; Mechanism; enzymatic hydrolysis under various conditions;

pivampicillin (33817-20-8) → ampicillin (69-53-4)

Conditions	Yield
With phosphate buffer; sodium chloride In water at 37℃; half-life value, pH 7.4, other ampicillin esters;

Upstream product

• 18997-19-8 Chloromethyl pivalate 

Downstream Products

• 69-53-4 ampicillin 

Relevant articles and documents

Method of using deuterated calcium channel blockers

Therapeutic methods and compositions using deuterated enriched 2-[(2-aminoethoxy)methyl]-4-(2-chlorophenyl)-1,4-dihydro-6-methyl-3,5-pyridinedicarboxylic acid 3-ethyl 5-methyl ester and other deuterated dihydropyridine compounds are described. The deuterated compounds exhibit enhanced efficacy in blocking calcium channels over non-deuterated dihydropyridines.

Crystalline pivaloyloxymethyl d(-)-α-aminobenzylpenicillinate

The present invention relates to pivaloyloxymethyl D(-)-α-aminobenzylpenicillinate of the formula I in a novel and improved form, i.e. the crystalline form SPC1 To methods of producing said crystalline pivaloyloxymethyl D(-)-α-aminobenzylpenicillinate and to pharmaceutical preparations containing said crystalline pivaloyloxymethyl D(-)-α-aminobenzylpenicillinate. Crystalline pivaloyloxymethyl D(-)-α-aminobenzylpenicillinate has no bitter taste, is only slightly soluble in water, and is stable and readily absorbable.