Identification
- Summary
Meclocycline is a tetracycline antibiotic indicated in the treatment of susceptible skin infections, bacterial vaginitis, vulvovaginitis, and cervicitis.
- 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
Structure for Meclocycline (DB13092)
- 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
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- Contraindications & Blackbox Warnings
Avoid life-threatening adverse drug eventsImprove clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events & improve clinical decision support.- 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.
Target Actions Organism A30S ribosomal protein S7 antagonistEscherichia 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
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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.
Drug Interaction Integrate drug-drug
interactions in your softwareArticaine The risk or severity of methemoglobinemia can be increased when Meclocycline is combined with Articaine. Benzocaine The risk or severity of methemoglobinemia can be increased when Meclocycline is combined with Benzocaine. Benzyl alcohol The risk or severity of methemoglobinemia can be increased when Meclocycline is combined with Benzyl alcohol. Bupivacaine The risk or severity of methemoglobinemia can be increased when Meclocycline is combined with Bupivacaine. Butacaine The risk or severity of methemoglobinemia can be increased when Meclocycline is combined with Butacaine. Butamben The risk or severity of methemoglobinemia can be increased when Meclocycline is combined with Butamben. Capsaicin The risk or severity of methemoglobinemia can be increased when Meclocycline is combined with Capsaicin. Chloroprocaine The risk or severity of methemoglobinemia can be increased when Meclocycline is combined with Chloroprocaine. Cinchocaine The risk or severity of methemoglobinemia can be increased when Meclocycline is combined with Cinchocaine. Cisatracurium Meclocycline may increase the neuromuscular blocking activities of Cisatracurium. 
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- Not Available
Products
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Ingredient UNII CAS InChI Key Meclocycline sulfosalicylate 46VZA7RX2B 73816-42-9 FYSVKUUNXYGFLA-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
- 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. [Article]
- 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. [Article]
- Meclocycline Phase II Trial: Oral Mucositis [Link]
- Torrino Medica: Mecloderm (meclocycline) vaginal ovules [Link]
- Torrino Medica: Mecloderm (meclocycline) topical cream [Link]
- External Links
- PubChem Compound
- 54676539
- PubChem Substance
- 347829216
- ChemSpider
- 16735890
- 29418
- ChEBI
- 135772
- ChEMBL
- CHEMBL1237124
- ZINC
- ZINC000084402690
- Wikipedia
- Meclocycline
- MSDS
- Download (316 KB)
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 2 Completed Treatment Oral Mucositis / Stomatitis 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Cream Topical Aerosol, foam Topical 2 % Cream Topical 1 % Cream Topical 15 G Cream Topical 20 G Powder Topical 1 G Solution Topical 2 % Suppository Vaginal 35 mg Cream Topical Ointment Topical - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source water solubility Soluble MSDS - Predicted Properties
Property Value Source Water Solubility 0.542 mg/mL ALOGPS logP 0.11 ALOGPS logP -3 Chemaxon logS -2.9 ALOGPS pKa (Strongest Acidic) 2.95 Chemaxon pKa (Strongest Basic) 8.82 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 9 Chemaxon Hydrogen Donor Count 6 Chemaxon Polar Surface Area 181.62 Å2 Chemaxon Rotatable Bond Count 2 Chemaxon Refractivity 118.47 m3·mol-1 Chemaxon Polarizability 44.05 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 1 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
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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
- 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. [Article]
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
- 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. [Article]
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
- 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. [Article]
- 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
- 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. [Article]
Drug created at October 21, 2016 02:57 / Updated at June 12, 2021 10:55