Metampicillin

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

Identification

Generic Name
Metampicillin
DrugBank Accession Number
DB13836
Background

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.

Type
Small Molecule
Groups
Experimental
Structure
Thumb
Weight
Average: 361.42
Monoisotopic: 361.109627278
Chemical Formula
C17H19N3O4S
Synonyms
  • Metampicilina
  • Metampicillin
  • Metampicilline
  • Metampicillinum

Pharmacology

Indication

Not Available

Pharmacology
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Contraindications & Blackbox Warnings
Contraindications
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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
Medicalerrors
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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 Metampicillin which could result in a higher serum level.
AcenocoumarolMetampicillin may increase the anticoagulant activities of Acenocoumarol.
AmikacinThe serum concentration of Amikacin can be decreased when it is combined with Metampicillin.
AtracuriumThe therapeutic efficacy of Atracurium can be increased when used in combination with Metampicillin.
Atracurium besylateThe therapeutic efficacy of Atracurium besylate can be increased when used in combination with Metampicillin.
BCG vaccineThe therapeutic efficacy of BCG vaccine can be decreased when used in combination with Metampicillin.
CapreomycinThe serum concentration of Capreomycin can be decreased when it is combined with Metampicillin.
CinoxacinThe serum concentration of Cinoxacin can be increased when it is combined with Metampicillin.
CiprofloxacinThe serum concentration of Ciprofloxacin can be increased when it is combined with Metampicillin.
CisatracuriumThe therapeutic efficacy of Cisatracurium can be increased when used in combination with Metampicillin.
Interactions
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Food Interactions
Not Available

Products

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International/Other Brands
Micinovo / Pravacilin / Ruticina / Viderpen

Categories

ATC Codes
J01CA14 — Metampicillin
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
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
show 8 more
Substituents
Alpha-amino acid amide / Alpha-amino acid or derivatives / Aromatic heteropolycyclic compound / Azacycle / Azetidine / Benzenoid / Carbonyl group / Carboxamide group / Carboxylic acid / Carboxylic acid derivative
show 21 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
penicillin (CHEBI:52060)
Affected organisms
Not Available

Chemical Identifiers

UNII
G0H6U7VSTK
CAS number
6489-97-0
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

References

General References
Not Available
KEGG Drug
D07234
ChemSpider
5145919
BindingDB
50370588
RxNav
29629
ChEBI
52060
ChEMBL
CHEMBL1908324
ZINC
ZINC000003874216
Wikipedia
Metampicillin

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 Solubility0.109 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

Drug created on June 23, 2017 20:49 / Updated on February 21, 2021 18:54