| Common Name |
Pivampicillin
| Description |
Pivampicillin is only found in individuals that have used or taken this drug. It is an analog of ampicillin.Ampicillin (the active metabolite of pivampicillin) has a bactericidal action resliting from inhibition of cell wall mucopeptide biosynthesis.
| Structure |
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
| Synonyms |
| Value |
Source |
Ampicillin pivaloyloxymethyl esterChEBI
Pivaloyloxymethyl ampicillinateChEBI
PivampicilinaChEBI
PivampicillineChEBI
PivampicillinumChEBI
Pivaloyloxymethyl ampicillinic acidGenerator
PivaloylampicillinHMDB
BerocillinMeSH
Serra pamies brand OF pivampicillin hydrochlorideMeSH
Pivampicillin hydrochlorideMeSH
Ampicillin pivaloyl esterMeSH
PondocillinMeSH
Ester, ampicillin pivaloylMeSH
Hydrochloride, pivampicillinMeSH
leo Brand OF pivampicillinMeSH
Monohydrochloride, pivampicillinMeSH
PivamiserMeSH
Pivampicillin monohydrochlorideMeSH
| Chemical Formlia |
C22H29N3O6S
| Average Molecliar Weight |
463.547
| Monoisotopic Molecliar Weight |
463.177706365
| IUPAC Name |
[(2S,5R,6R)-6-[(2R)-2-amino-2-phenylacetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carbonyloxy]methyl 2,2-dimethylpropanoate
| Traditional Name |
pivampicillin
| CAS Registry Number |
33817-20-8
| SMILES |
[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)[C@H](N)C1=CC=CC=C1)C(=O)OCOC(=O)C(C)(C)C
| InChI Identifier |
InChI=1S/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
| InChI Key |
ZEMIJUDPLILVNQ-ZXFNITATSA-N
| Chemical Taxonomy |
| Description |
This compound belongs to the class of chemical entities known as n-acyl-alpha amino acids and derivatives. These are compounds containing an alpha amino acid (or a derivative thereof) which bears an acyl group at its terminal nitrogen atom.
| Kingdom |
Chemical entities
| Super Class |
Organic compounds
| Class |
Organic acids and derivatives
| Sub Class |
Carboxylic acids and derivatives
| Direct Parent |
N-acyl-alpha amino acids and derivatives
| Alternative Parents |
Alpha amino acid esters
Penams
Acylals
Aralkylamines
Benzene and substituted derivatives
Dicarboxylic acids and derivatives
Tertiary carboxylic acid amides
Thiazolidines
Azetidines
Thiohemiaminal derivatives
Dialkylthioethers
Carboximidic acids
Acetals
Azacyclic compounds
Propargyl-type 1,3-dipolar organic compounds
Organic oxides
Monoalkylamines
Hydrocarbon derivatives
Carbonyl compounds
Organopnictogen compounds
| Substituents |
Alpha-amino acid ester
N-acyl-alpha amino acid or derivatives
Penam
Acylal
Aralkylamine
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Benzenoid
Beta-lactam
Tertiary carboxylic acid amide
Thiazolidine
Azetidine
Carboxamide group
Carboxylic acid ester
Lactam
Acetal
Carboximidic acid
Carboximidic acid derivative
Azacycle
Organoheterocyclic compound
Dialkylthioether
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Hemithioaminal
Thioether
Hydrocarbon derivative
Organic oxygen compound
Organopnictogen compound
Primary aliphatic amine
Organic oxide
Organonitrogen compound
Organooxygen compound
Carbonyl group
Primary amine
Organic nitrogen compound
Amine
Aromatic heteropolycyclic compound
| Molecliar Framework |
Aromatic heteropolycyclic compounds
| External Descriptors |
penicillanic acid ester (CHEBI:8255 )
| Ontology |
| Status |
Expected but not Quantified
| Origin |
Drug
| Biofunction |
Anti-Bacterial Agents
Penicillins
| Application |
Pharmaceutical
| Cellliar locations |
Cytoplasm
| Physical Properties |
| State |
Solid
| Experimental Properties |
| Property |
Value |
Reference |
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility3.54e-02 g/LNot Available
LogPNot AvailableNot Available
| Predicted Properties |
| Property |
Value |
Source |
Water Solubility0.035 mg/mLALOGPS
logP1.43ALOGPS
logP2.07ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)11.71ChemAxon
pKa (Strongest Basic)7.44ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area128.03 Å2ChemAxon
Rotatable Bond Count9ChemAxon
Refractivity116.25 m3·mol-1ChemAxon
Polarizability47.54 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rlie of FiveYesChemAxon
Ghose FilterYesChemAxon
Vebers RlieYesChemAxon
MDDR-like RlieYesChemAxon
| Spectra |
| Spectra |
| Spectrum Type |
Description |
Splash Key |
|
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available
| Biological Properties |
| Cellliar Locations |
Cytoplasm
| Biofluid Locations |
Blood
Urine
| Tissue Location |
Not Available
| Pathways |
Not Available
| Normal Concentrations |
| Biofluid |
Status |
Age |
Condition |
Reference |
Details |
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01604
21059682
details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01604
21059682
details
|
| Abnormal Concentrations |
|
Not Available
| Associated Disorders and Diseases |
| Disease References |
None
| Associated OMIM IDs |
None
| External Links |
| DrugBank ID |
DB01604
| DrugBank Metabolite ID |
Not Available
| Phenol Explorer Compound ID |
Not Available
| Phenol Explorer Metabolite ID |
Not Available
| FoodDB ID |
Not Available
| KNApSAcK ID |
Not Available
| Chemspider ID |
30899
| KEGG Compound ID |
C11750
| BioCyc ID |
Not Available
| BiGG ID |
Not Available
| Wikipedia Link |
Pivampicillin
| NuGOwiki Link |
HMDB15542
| Metagene Link |
HMDB15542
| METLIN ID |
Not Available
| PubChem Compound |
33478
| PDB ID |
Not Available
| ChEBI ID |
8255
Product: Rucaparib
References |
| Synthesis Reference |
Not Available |
| Material Safety Data Sheet (MSDS) |
Not Available |
| General References |
- Chanteux H, Van Bambeke F, Mingeot-Leclercq MP, Tulkens PM: Accumulation and oriented transport of ampicillin in Caco-2 cells from its pivaloyloxymethylester prodrug, pivampicillin. Antimicrob Agents Chemother. 2005 Apr;49(4):1279-88. [PubMed:15793098 ]
- Albertson TE, Louie S, Chan AL: The diagnosis and treatment of elderly patients with acute exacerbation of chronic obstructive pulmonary disease and chronic bronchitis. J Am Geriatr Soc. 2010 Mar;58(3):570-9. doi: 10.1111/j.1532-5415.2010.02741.x. [PubMed:20398122 ]
|
PMID: 15769863
