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

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

Uses

Used in Pharmaceutical Industry:
Pivampicillin is used as an antibiotic for the treatment of bacterial infections. Its application is primarily due to its ability to inhibit bacterial cell wall synthesis, leading to the destruction of the bacterial cell. It is effective against a wide range of gram-positive and some gram-negative bacteria, making it a versatile choice for various infections.
Additionally, Pivampicillin may be used in the development of new drug delivery systems to enhance its efficacy and bioavailability, similar to the applications of Gallotannin in the field of anticancer treatments. This could involve the use of organic or metallic nanoparticles as carriers for improved delivery and therapeutic outcomes.

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.

Enhancement of the efficacy of nifedipine by deuteration

A method of enhancing the efficiency and increasing the duration of action of drugs (e.g. dihydropyridines and anti-bacterials) and particularly of nifedipine and penicillins wherein one or more hydrogen atoms are deuterated and wherein the deuterated drug has unexpectedly improved properties when used in much lower concentrations than unmodified drug. A method for determining the identity and bioequivalency of a new drug is also disclosed wherein the molecular and isotope structure of a new drug is determined by isotope ratio mass spectrometry and compared with the molecular and isotope structure of a known human drug.

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.