Penamecillin

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

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Name
Penamecillin
Accession Number
DB13739
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
  • Acetoxymethyl benzylpenicillanate
  • Benzylpenicillin acetoxymethyl ester
  • Penamecilina
  • Penamecillin
  • Pénamécilline
  • Penamecillinum
External IDs
WY-20,788 / WY-20788
Categories
UNII
H0P1YE5581
CAS number
983-85-7
Weight
Average: 406.45
Monoisotopic: 406.11985761
Chemical Formula
C19H22N2O6S
InChI Key
NLOOMWLTUVBWAW-HLLBOEOZSA-N
InChI
InChI=1S/C19H22N2O6S/c1-11(22)26-10-27-18(25)15-19(2,3)28-17-14(16(24)21(15)17)20-13(23)9-12-7-5-4-6-8-12/h4-8,14-15,17H,9-10H2,1-3H3,(H,20,23)/t14-,15+,17-/m1/s1
IUPAC Name
[(2S,5R,6R)-3,3-dimethyl-7-oxo-6-(2-phenylacetamido)-4-thia-1-azabicyclo[3.2.0]heptane-2-carbonyloxy]methyl acetate
SMILES
[H][C@]12SC(C)(C)[C@@]([H])(N1C(=O)[C@@]2([H])NC(=O)CC1=CC=CC=C1)C(=O)OCOC(C)=O

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
Not Available
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinPenamecillin may increase the anticoagulant activities of (R)-warfarin.
(S)-WarfarinPenamecillin may increase the anticoagulant activities of (S)-Warfarin.
4-hydroxycoumarinPenamecillin may increase the anticoagulant activities of 4-hydroxycoumarin.
AcemetacinAcemetacin may decrease the excretion rate of Penamecillin which could result in a higher serum level.
AcenocoumarolPenamecillin may increase the anticoagulant activities of Acenocoumarol.
Adenovirus type 7 vaccine liveThe therapeutic efficacy of Adenovirus type 7 vaccine live can be decreased when used in combination with Penamecillin.
AlcuroniumThe therapeutic efficacy of Alcuronium can be increased when used in combination with Penamecillin.
AmikacinThe serum concentration of Amikacin can be decreased when it is combined with Penamecillin.
Anthrax immune globulin humanThe therapeutic efficacy of Anthrax immune globulin human can be decreased when used in combination with Penamecillin.
Anthrax vaccineThe therapeutic efficacy of Anthrax vaccine can be decreased when used in combination with Penamecillin.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions
Not Available

References

General References
  1. Agersborg HP, Batchelor A, Cambridge GW, Rule AW: The pharmacology of penamecillin. Br J Pharmacol Chemother. 1966 Mar;26(3):649-55. [PubMed:4959939]
External Links
KEGG Drug
D05406
ChemSpider
8426255
ChEBI
131733
ChEMBL
CHEMBL2106988
Wikipedia
Penamecillin
ATC Codes
J01CE06 — Penamecillin

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0867 mg/mLALOGPS
logP1.61ALOGPS
logP1.09ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)11.85ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area102.01 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity99.55 m3·mol-1ChemAxon
Polarizability41.56 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as penicillins. These are organic compounds containing the penicillin core structure, which is structurally characterized by a penam ring bearing two methyl groups at position 2, and an amide group at position 6 [starting from the sulfur atom at position 1].
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Lactams
Sub Class
Beta lactams
Direct Parent
Penicillins
Alternative Parents
Alpha amino acid esters / N-acyl-alpha amino acids and derivatives / Phenylacetamides / Acylals / Dicarboxylic acids and derivatives / Thiazolidines / Tertiary carboxylic acid amides / Secondary carboxylic acid amides / Azetidines / Acetals
show 8 more
Substituents
Penicillin / Alpha-amino acid ester / N-acyl-alpha amino acid or derivatives / Alpha-amino acid or derivatives / Phenylacetamide / Acylal / Monocyclic benzene moiety / Dicarboxylic acid or derivatives / Benzenoid / Tertiary carboxylic acid amide
show 20 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Drug created on June 23, 2017 14:47 / Updated on May 01, 2019 11:51