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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
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Treatment of Bacterial vaginitis •••••••••••• ••••••••••• Treatment of Cervicitis •••••••••••• ••••••••••• Used in combination for prophylaxis of Secondary infection Combination Product in combination with: Fluocinolone acetonide (DB00591) •••••••••••• ••••• Treatment of Skin infections caused by tetracycline-sensitive bacteria •••••••••••• ••••• Used in combination to treat Skin inflammation Combination Product in combination with: Fluocinolone acetonide (DB00591) •••••••••••• ••••• - Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- 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 softwareAmbroxol The risk or severity of methemoglobinemia can be increased when Meclocycline is combined with Ambroxol. Articaine 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. - Food Interactions
- Not Available
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Meclocycline sulfosalicylate 46VZA7RX2B 73816-42-9 FYSVKUUNXYGFLA-CCHMMTNSSA-N - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image MECLODERM F Meclocycline sulfosalicylate (1.46 g) + Fluocinolone acetonide (0.25 mg/g) Cream Topical Medinitaly Pharma Progress S.R.L. 2014-07-08 Not applicable Italy 
MECLODERM F Meclocycline (1 %) + Fluocinolone acetonide (0.025 %) Ointment Topical Medinitaly Pharma Progress S.R.L. 2014-07-08 2022-03-05 Italy MECLODERM F Meclocycline (1 %) + Fluocinolone acetonide (0.025 %) Ointment Topical Medinitaly Pharma Progress S.R.L. 2014-07-08 2022-03-05 Italy MECLODERM F Meclocycline (1 %) + Fluocinolone acetonide (0.025 %) Ointment Topical Medinitaly Pharma Progress S.R.L. 2014-07-08 2022-03-05 Italy
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
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample data2 Completed Treatment Oral Mucositis / Stomatitis 1 somestatus stop reason just information to hide
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 splash10-056r-0000900000-d94bb0cc1b75d462cc2f Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-005c-7009800000-f360d693230839dbb89d Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-03dl-0000900000-1d445e717d8d965d05b2 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-001i-9001100000-5a611c5da6ccebf61cbb Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0k9g-5896500000-e25adf2df491efae9b6a Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-001i-9436200000-e2a14e0b9e049a461858 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 203.10196 predictedDeepCCS 1.0 (2019) [M+H]+ 204.99738 predictedDeepCCS 1.0 (2019) [M+Na]+ 210.84511 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Escherichia coli (strain K12)
- Pharmacological action
- Yes
- Actions
- Antagonist
- General 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 (PubMed:2461734). Is located at the subunit interface close to the decoding center, where it has been shown to contact mRNA (PubMed:10606263). Has been shown to contact tRNA in both the P and E sites; it probably blocks exit of the E site tRNA (PubMed:8524654).
- Specific Function
- mRNA binding
- 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
- An FAD-requiring monooxygenase active on tetracycline antibiotic derivatives, which leads to their inactivation (PubMed:15452119, PubMed:16128584). Hydroxylates carbon 11a of oxytetracycline and tigecycline (PubMed:15452119, PubMed:26097034). Acts on many tetracycline analogs (chlorotetracycline, demeclocycline, doxycycline, minocycline, oxytetracyclinee), probably by monooxygenization (PubMed:15452119, PubMed:16128584). Tigecycline, a new generation tetracycline antibiotic, is rendered less effective against E.coli by this monooxygenation, is much weaker at inhibiting translation in vitro and binds Mg(2+) considerably less well (PubMed:16128584, PubMed:26097034). Expression in E.coli BW25113 reduces its growth rate about 5%. The reaction probably proceeds by FAD reduction by NADPH and, second, hydroxylation of antibiotic in a ping-pong mechanism (PubMed:23236139). Degrades chlortetracycline, probably by monooxygenation (PubMed:15452119, PubMed:28481346). Slowly oxidizes anhydrotetracycline, the final substrate in tetracycline biosynthesis (PubMed:26097034).
- Specific Function
- FAD binding
- 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
- Forms pores that allow passive diffusion of small molecules across the outer membrane.
- Specific Function
- colicin transmembrane transporter activity
- 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
- Not Available
- Specific Function
- porin activity
- 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