Penamecillin

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

Identification

Generic Name
Penamecillin
DrugBank Accession Number
DB13739
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Weight
Average: 406.45
Monoisotopic: 406.11985761
Chemical Formula
C19H22N2O6S
Synonyms
  • Acetoxymethyl benzylpenicillanate
  • Benzylpenicillin acetoxymethyl ester
  • Penamecilina
  • Penamecillin
  • Pénamécilline
  • Penamecillinum
External IDs
  • WY-20,788
  • WY-20788

Pharmacology

Indication

Not Available

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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

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AcemetacinAcemetacin may decrease the excretion rate of Penamecillin which could result in a higher serum level.
AcenocoumarolPenamecillin may increase the anticoagulant activities of Acenocoumarol.
AmbroxolThe risk or severity of methemoglobinemia can be increased when Penamecillin is combined with Ambroxol.
AmikacinThe serum concentration of Amikacin can be decreased when it is combined with Penamecillin.
ArticaineThe risk or severity of methemoglobinemia can be increased when Penamecillin is combined with Articaine.
Food Interactions
Not Available

Categories

ATC Codes
J01CE06 — Penamecillin
Drug Categories
Chemical TaxonomyProvided by Classyfire
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
Acetal / Acylal / Alpha-amino acid ester / Alpha-amino acid or derivatives / Aromatic heteropolycyclic compound / Azacycle / Azetidine / Benzenoid / Carbonyl group / Carboxamide group
show 20 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
H0P1YE5581
CAS number
983-85-7
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

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. [Article]
KEGG Drug
D05406
ChemSpider
8426255
ChEBI
131733
ChEMBL
CHEMBL2106988
ZINC
ZINC000004217248
Wikipedia
Penamecillin

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

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-MSsplash10-000l-7093000000-44829c67a032f12d759e
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-000x-0960100000-114b9dd3ac73cce22c7d
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0bti-1197400000-7d2300c68c9c1b5a9c84
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-00kb-2935100000-a45b41ae3e64d9963c85
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-052e-6933000000-6ab05fa0e6b0af5a2c3b
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0k96-4920000000-b0983ea172eec021452f
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-9221000000-00a85a2c58963cda3741
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-199.697319
predicted
DarkChem Lite v0.1.0
[M-H]-187.49527
predicted
DeepCCS 1.0 (2019)
[M+H]+200.992119
predicted
DarkChem Lite v0.1.0
[M+H]+189.89082
predicted
DeepCCS 1.0 (2019)
[M+Na]+199.148519
predicted
DarkChem Lite v0.1.0
[M+Na]+195.80336
predicted
DeepCCS 1.0 (2019)

Drug created at June 23, 2017 20:47 / Updated at February 21, 2021 18:54