Meclocycline

Identification

Generic Name
Meclocycline
DrugBank Accession Number
DB13092
Background

Meclocycline is under investigation in clinical trial NCT00385515 (Efficacy of SNX-1012 in the Treatment of Oral Mucositis) 3.

Type
Small Molecule
Groups
Investigational
Structure
Thumb
Weight
Average: 476.87
Monoisotopic: 476.0986433
Chemical Formula
C22H21ClN2O8
Synonyms
  • Meclociclina
  • Meclocycline
  • Meclocyclinum
External IDs
  • GS 2989
  • GS-2989
  • NSC-78502

Pharmacology

Indication

Currently under investigation for the topical treatment of ulcerative oral mucositis 3

Pharmacology
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Associated Conditions
Contraindications & Blackbox Warnings
Contraindications
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Pharmacodynamics

Tetracyclines such as meclocycline are broad spectrum bacteriostatic agents 1. Meclocyclin likely inhibits the growth of bacterial species present in the damaged oral mucosa, allowing the immune system to more easily eliminate infections.

Mechanism of action

As a tetracycline, meclocycline likely works by reversably associating with the 30s subint of the bacterial ribosome 1. A likely binding site for tetracyclines has been identified on protein S7 of this subunit. This association blocks the association of aminoacyl-tRNA with the ribosome, inhibiting protein synthesis. Ultimately this inhibits bacterial growth due to a lack of proteins necessary for reproduction.

TargetActionsOrganism
A30S ribosomal protein S7
antagonist
Escherichia coli (strain K12)
Absorption

Estimated oral bioavailability of ~66% and tmax of 4h based on that of demeclocycline due to structural similarity 2.

Volume of distribution

Estimated Vd of 121L based on that of demeclocycline due to structural similarity 2.

Protein binding

Estimated plasma protein binding of ~75-91% based on that of demeclocycline due to structural similarity 2.

Metabolism

Most tetracyclines are not metabolized. It is unlikely that meclocycline would be metabolized 2.

Route of elimination

Estimated urinary excretion of ~40% and fecal excretion of ~43% based on that of demeclocycline due to structural similarity 2.

Half-life

Half life estimated to be ~5.6h based on that of chlortetracycline due to structural similarity 2.

Clearance

Not Available

Adverse Effects
Medicalerrors
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Toxicity

Oral LD50 of 6443mg/kg in rats MSDS.

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
Collagenase clostridium histolyticumThe therapeutic efficacy of Collagenase clostridium histolyticum can be decreased when used in combination with Meclocycline.
DidanosineDidanosine can cause a decrease in the absorption of Meclocycline resulting in a reduced serum concentration and potentially a decrease in efficacy.
EstetrolThe therapeutic efficacy of Estetrol can be decreased when used in combination with Meclocycline.
MagnesiumMagnesium can cause a decrease in the absorption of Meclocycline resulting in a reduced serum concentration and potentially a decrease in efficacy.
MethoxyfluraneThe risk or severity of renal failure can be increased when Methoxyflurane is combined with Meclocycline.
Vibrio cholerae CVD 103-HgR strain live antigenThe therapeutic efficacy of Vibrio cholerae CVD 103-HgR strain live antigen can be decreased when used in combination with Meclocycline.
Interactions
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Food Interactions
Not Available

Products

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Product Ingredients
IngredientUNIICASInChI Key
Meclocycline sulfosalicylate46VZA7RX2B73816-42-9FYSVKUUNXYGFLA-CCHMMTNSSA-N

Categories

ATC Codes
D10AF04 — Meclocycline
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as tetracyclines. These are polyketides having an octahydrotetracene-2-carboxamide skeleton, substituted with many hydroxy and other groups.
Kingdom
Organic compounds
Super Class
Phenylpropanoids and polyketides
Class
Tetracyclines
Sub Class
Not Available
Direct Parent
Tetracyclines
Alternative Parents
Naphthacenes / Anthracenecarboxylic acids and derivatives / Tetralins / Aryl ketones / 1-hydroxy-2-unsubstituted benzenoids / Cyclohexenones / Aryl chlorides / Vinylogous acids / Tertiary alcohols / Trialkylamines
show 9 more
Substituents
1-hydroxy-2-unsubstituted benzenoid / Alcohol / Amine / Amino acid or derivatives / Anthracene carboxylic acid or derivatives / Aromatic homopolycyclic compound / Aryl chloride / Aryl halide / Aryl ketone / Benzenoid
show 26 more
Molecular Framework
Aromatic homopolycyclic compounds
External Descriptors
Not Available
Affected organisms
  • Gram negative and gram positive bacteria

Chemical Identifiers

UNII
23Q8M2HE6S
CAS number
2013-58-3
InChI Key
GGQJXCQBBONZFX-IWVLMIASSA-N
InChI
InChI=1S/C22H21ClN2O8/c1-6-9-7(23)4-5-8(26)11(9)16(27)12-10(6)17(28)14-15(25(2)3)18(29)13(21(24)32)20(31)22(14,33)19(12)30/h4-5,10,14-15,17,26,28-30,33H,1H2,2-3H3,(H2,24,32)/t10-,14-,15+,17+,22+/m1/s1
IUPAC Name
(4S,4aR,5S,5aR,12aS)-7-chloro-4-(dimethylamino)-3,5,10,12,12a-pentahydroxy-6-methylidene-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide
SMILES
[H][C@@]12[C@@H](O)[C@]3([H])C(=C)C4=C(C(O)=CC=C4Cl)C(=O)C3=C(O)[C@]1(O)C(=O)C(C(N)=O)=C(O)[C@H]2N(C)C

References

General References
  1. Chopra I, Roberts M: Tetracycline antibiotics: mode of action, applications, molecular biology, and epidemiology of bacterial resistance. Microbiol Mol Biol Rev. 2001 Jun;65(2):232-60 ; second page, table of contents. [PubMed:11381101]
  2. Agwuh KN, MacGowan A: Pharmacokinetics and pharmacodynamics of the tetracyclines including glycylcyclines. J Antimicrob Chemother. 2006 Aug;58(2):256-65. Epub 2006 Jul 1. [PubMed:16816396]
  3. Meclocycline Phase II Trial: Oral Mucositis [Link]
  4. Torrino Medica: Mecloderm (meclocycline) vaginal ovules [Link]
  5. Torrino Medica: Mecloderm (meclocycline) topical cream [Link]
PubChem Compound
54676539
PubChem Substance
347829216
ChemSpider
16735890
RxNav
29418
ChEBI
135772
ChEMBL
CHEMBL1237124
ZINC
ZINC000084402690
Wikipedia
Meclocycline
MSDS
Download (316 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2CompletedTreatmentOral Mucositis / Stomatitis1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
Aerosol, foamTopical
CreamTopical
PowderTopical
SolutionTopical
SuppositoryVaginal
CreamTopical
OintmentTopical
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
water solubilitySolubleMSDS
Predicted Properties
PropertyValueSource
Water Solubility0.542 mg/mLALOGPS
logP0.11ALOGPS
logP-3ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)2.95ChemAxon
pKa (Strongest Basic)8.82ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area181.62 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity118.47 m3·mol-1ChemAxon
Polarizability44.05 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
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

Targets

Drugtargets
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Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Yes
Actions
Antagonist
General Function
Trna binding
Specific Function
One of the primary rRNA binding proteins, it binds directly to 16S rRNA where it nucleates assembly of the head domain of the 30S subunit. Is located at the subunit interface close to the decoding ...
Gene Name
rpsG
Uniprot ID
P02359
Uniprot Name
30S ribosomal protein S7
Molecular Weight
20018.91 Da
References
  1. Chopra I, Roberts M: Tetracycline antibiotics: mode of action, applications, molecular biology, and epidemiology of bacterial resistance. Microbiol Mol Biol Rev. 2001 Jun;65(2):232-60 ; second page, table of contents. [PubMed:11381101]

Enzymes

Kind
Protein
Organism
Bacteroides thetaiotaomicron
Pharmacological action
No
Actions
Substrate
General Function
Oxidoreductase activity
Specific Function
Not Available
Gene Name
tetX2
Uniprot ID
Q93L51
Uniprot Name
TetX family tetracycline inactivation enzyme
Molecular Weight
43707.345 Da
References
  1. Chopra I, Roberts M: Tetracycline antibiotics: mode of action, applications, molecular biology, and epidemiology of bacterial resistance. Microbiol Mol Biol Rev. 2001 Jun;65(2):232-60 ; second page, table of contents. [PubMed:11381101]

Transporters

Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
No
Actions
Substrate
General Function
Porin activity
Specific Function
Forms pores that allow passive diffusion of small molecules across the outer membrane. It is also a receptor for the bacteriophage T2.
Gene Name
ompF
Uniprot ID
P02931
Uniprot Name
Outer membrane protein F
Molecular Weight
39333.105 Da
References
  1. Chopra I, Roberts M: Tetracycline antibiotics: mode of action, applications, molecular biology, and epidemiology of bacterial resistance. Microbiol Mol Biol Rev. 2001 Jun;65(2):232-60 ; second page, table of contents. [PubMed:11381101]
Kind
Protein
Organism
Escherichia coli
Pharmacological action
Unknown
Actions
Substrate
General Function
Porin activity
Specific Function
Not Available
Gene Name
ompC
Uniprot ID
Q9K597
Uniprot Name
Membrane protein
Molecular Weight
40311.865 Da
References
  1. Chopra I, Roberts M: Tetracycline antibiotics: mode of action, applications, molecular biology, and epidemiology of bacterial resistance. Microbiol Mol Biol Rev. 2001 Jun;65(2):232-60 ; second page, table of contents. [PubMed:11381101]

Drug created on October 21, 2016 02:57 / Updated on February 21, 2021 18:54