Metampicillin

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
Metampicillin
Accession Number
DB13836
Type
Small Molecule
Groups
Experimental
Description

Metampicillin is a penicillin antibiotic prepared by the reaction of ampicillin with formaldehyde. It is hydrolysed in aqueous solution to form ampicillin. Hydrolysis is rapid under acid conditions like the stomach.

Structure
Thumb
Synonyms
  • Metampicilina
  • Metampicillin
  • Metampicilline
  • Metampicillinum
International/Other Brands
Micinovo / Pravacilin / Ruticina / Viderpen
Categories
UNII
G0H6U7VSTK
CAS number
6489-97-0
Weight
Average: 361.42
Monoisotopic: 361.109627278
Chemical Formula
C17H19N3O4S
InChI Key
FZECHKJQHUVANE-MCYUEQNJSA-N
InChI
InChI=1S/C17H19N3O4S/c1-17(2)12(16(23)24)20-14(22)11(15(20)25-17)19-13(21)10(18-3)9-7-5-4-6-8-9/h4-8,10-12,15H,3H2,1-2H3,(H,19,21)(H,23,24)/t10-,11-,12+,15-/m1/s1
IUPAC Name
(2S,5R,6R)-3,3-dimethyl-6-[(2R)-2-(methylideneamino)-2-phenylacetamido]-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
SMILES
[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)[C@H](N=C)C1=CC=CC=C1)C(O)=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)-warfarinMetampicillin may increase the anticoagulant activities of (R)-warfarin.
(S)-WarfarinMetampicillin may increase the anticoagulant activities of (S)-Warfarin.
4-hydroxycoumarinMetampicillin may increase the anticoagulant activities of 4-hydroxycoumarin.
AcemetacinAcemetacin may decrease the excretion rate of Metampicillin which could result in a higher serum level.
AcenocoumarolMetampicillin 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 Metampicillin.
AlcuroniumThe therapeutic efficacy of Alcuronium can be increased when used in combination with Metampicillin.
AmikacinThe serum concentration of Amikacin can be decreased when it is combined with Metampicillin.
Anthrax immune globulin humanThe therapeutic efficacy of Anthrax immune globulin human can be decreased when used in combination with Metampicillin.
Anthrax vaccineThe therapeutic efficacy of Anthrax vaccine can be decreased when used in combination with Metampicillin.
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
Not Available
External Links
KEGG Drug
D07234
ChemSpider
5145919
BindingDB
50370588
ChEBI
52060
ChEMBL
CHEMBL1908324
Wikipedia
Metampicillin
ATC Codes
J01CA14 — Metampicillin

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 Solubility0.109 mg/mLALOGPS
logP1.74ALOGPS
logP-0.38ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)3.24ChemAxon
pKa (Strongest Basic)4.14ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area99.07 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity90.87 m3·mol-1ChemAxon
Polarizability36.36 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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
N-acyl-alpha amino acids and derivatives / Alpha amino acid amides / Phenylacetamides / Thiazolidines / Tertiary carboxylic acid amides / Secondary carboxylic acid amides / Azetidines / Thiohemiaminal derivatives / Azacyclic compounds / Propargyl-type 1,3-dipolar organic compounds
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Substituents
Penicillin / N-acyl-alpha amino acid or derivatives / Alpha-amino acid amide / Alpha-amino acid or derivatives / Phenylacetamide / Monocyclic benzene moiety / Benzenoid / Tertiary carboxylic acid amide / Thiazolidine / Azetidine
show 21 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
penicillin (CHEBI:52060)

Drug created on June 23, 2017 14:49 / Updated on May 09, 2019 00:19