Metacycline
Explore a selection of our essential drug information below, or:
Identification
- Generic Name
- Metacycline
- DrugBank Accession Number
- DB00931
- Background
A broad-spectrum semisynthetic antibiotic related to tetracycline but excreted more slowly and maintaining effective blood levels for a more extended period.
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Structure
- Weight
- Average: 442.424
Monoisotopic: 442.137615676 - Chemical Formula
- C22H22N2O8
- Synonyms
- 6-Demethyl-6-deoxy-5-hydroxy-6-methylenetetracycline
- 6-Deoxy-6-demethyl-6-methylene-5-oxytetracycline
- 6-Methylene-5-hydroxytetracycline
- 6-Methylene-5-oxytetracycline
- 6-Methyleneoxytetracycline
- Metaciclina
- Metacycline
- Methacycline
- Methacyclinum
- Methylenecycline
- Tri-methacycline
- External IDs
- GS-2876
Pharmacology
- Indication
For the treatment of acute bacterial exacerbations of chronic bronchitis
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.- 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
Methacycline is a tetracycline antibiotic. Similar to other tetracyclines, it has a wide spectrum of antimicrobial action. It is active against most Gram-positive bacteria (pneumococci, streptococci, staphylococci) and Gram-negative bacteria (E. coli, salmonella, shigella, etc.), and towards agents causing onithosis, psittacosis, trachoma, and some Protozoa. Like other tetracyclines, the general usefulness of methacycline has been reduced with the onset of bacterial resistance.
- Mechanism of action
Methacycline, a tetracycline antibiotic, is a protein synthesis inhibitors, inhibiting the binding of aminoacyl-tRNA to the mRNA-ribosome complex. Methacycline inhibits cell growth by inhibiting translation. It binds to the 16S part of the 30S ribosomal subunit and prevents the amino-acyl tRNA from binding to the A site of the ribosome. The binding is reversible in nature. Tetracyclines also have been found to inhibit matrix metalloproteinases. This mechanism does not add to their antibiotic effects, but has led to extensive research on chemically modified tetracyclines or CMTs (like incyclinide) for the treatmet of rosacea, acne, and various types of neoplasms.
Target Actions Organism A16S ribosomal RNA inhibitorEnteric bacteria and other eubacteria - Absorption
58% absorbed
- Volume of distribution
Not Available
- Protein binding
75-78% protein bound
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
14 hours
- Clearance
Not Available
- Adverse Effects
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- Toxicity
Not Available
- Pathways
Pathway Category Methacycline Action Pathway Drug action - 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 softwareAcenocoumarol Metacycline may increase the anticoagulant activities of Acenocoumarol. Acitretin The risk or severity of pseudotumor cerebri can be increased when Acitretin is combined with Metacycline. Alitretinoin The risk or severity of pseudotumor cerebri can be increased when Alitretinoin is combined with Metacycline. Almasilate Almasilate can cause a decrease in the absorption of Metacycline resulting in a reduced serum concentration and potentially a decrease in efficacy. Aluminium Aluminium can cause a decrease in the absorption of Metacycline resulting in a reduced serum concentration and potentially a decrease in efficacy. - 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 Metacycline hydrochloride 9GJ0N7ZAP0 3963-95-9 VZQARNDJLLWXGL-CCHMMTNSSA-N - International/Other Brands
- Rondomycin
Categories
- ATC Codes
- J01AA05 — Metacycline
- J01AA — Tetracyclines
- J01A — TETRACYCLINES
- J01 — ANTIBACTERIALS FOR SYSTEMIC USE
- J — ANTIINFECTIVES FOR SYSTEMIC USE
- 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 / 1-hydroxy-4-unsubstituted benzenoids / Cyclohexenones / Vinylogous acids / Tertiary alcohols / Trialkylamines show 8 more
- Substituents
- 1-hydroxy-2-unsubstituted benzenoid / 1-hydroxy-4-unsubstituted benzenoid / Alcohol / Amine / Amino acid or derivatives / Anthracene carboxylic acid or derivatives / Aromatic homopolycyclic compound / Aryl ketone / Benzenoid / Carbonyl group show 23 more
- Molecular Framework
- Aromatic homopolycyclic compounds
- External Descriptors
- tetracyclines (CHEBI:6805)
- Affected organisms
- Enteric bacteria and other eubacteria
Chemical Identifiers
- UNII
- IR235I7C5P
- CAS number
- 914-00-1
- InChI Key
- MHIGBKBJSQVXNH-IWVLMIASSA-N
- InChI
- InChI=1S/C22H22N2O8/c1-7-8-5-4-6-9(25)11(8)16(26)12-10(7)17(27)14-15(24(2)3)18(28)13(21(23)31)20(30)22(14,32)19(12)29/h4-6,10,14-15,17,25,27-29,32H,1H2,2-3H3,(H2,23,31)/t10-,14-,15+,17+,22+/m1/s1
- IUPAC Name
- (4S,4aR,5S,5aR,12aS)-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=C4)C(=O)C3=C(O)[C@]1(O)C(=O)C(C(N)=O)=C(O)[C@H]2N(C)C
References
- General References
- 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]
- Li J, Chen L, Wang X, Jin H, Ding L, Zhang K, Zhang H: Determination of tetracyclines residues in honey by on-line solid-phase extraction high-performance liquid chromatography. Talanta. 2008 Jun 15;75(5):1245-52. doi: 10.1016/j.talanta.2008.01.027. Epub 2008 Jan 20. [Article]
- External Links
- KEGG Drug
- D04972
- KEGG Compound
- C07654
- PubChem Compound
- 54675785
- PubChem Substance
- 46506631
- ChemSpider
- 10468596
- BindingDB
- 50046500
- 6812
- ChEBI
- 6805
- ChEMBL
- CHEMBL249837
- ZINC
- ZINC000085650610
- Therapeutic Targets Database
- DAP000883
- PharmGKB
- PA164750512
- Wikipedia
- Metacycline
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 data0 Terminated Treatment Osteomyelitis 1 somestatus stop reason just information to hide
Pharmacoeconomics
- Manufacturers
- Medpointe pharmaceuticals medpointe healthcare inc
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Capsule Oral 300 MG Capsule Oral - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source water solubility 7550 mg/L (at 21 °C) YALKOWSKY,SH & DANNENFELSER,RM (1992) logP -0.3 Not Available - Predicted Properties
Property Value Source Water Solubility 1.14 mg/mL ALOGPS logP -0.46 ALOGPS logP -3.5 Chemaxon logS -2.6 ALOGPS pKa (Strongest Acidic) 2.88 Chemaxon pKa (Strongest Basic) 7.44 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 9 Chemaxon Hydrogen Donor Count 6 Chemaxon Polar Surface Area 181.62 Å2 Chemaxon Rotatable Bond Count 2 Chemaxon Refractivity 113.67 m3·mol-1 Chemaxon Polarizability 41.95 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
Property Value Probability Human Intestinal Absorption + 0.7183 Blood Brain Barrier - 0.9833 Caco-2 permeable - 0.8232 P-glycoprotein substrate Substrate 0.7092 P-glycoprotein inhibitor I Non-inhibitor 0.802 P-glycoprotein inhibitor II Non-inhibitor 0.9317 Renal organic cation transporter Non-inhibitor 0.9464 CYP450 2C9 substrate Non-substrate 0.8384 CYP450 2D6 substrate Non-substrate 0.8989 CYP450 3A4 substrate Substrate 0.6228 CYP450 1A2 substrate Non-inhibitor 0.9046 CYP450 2C9 inhibitor Non-inhibitor 0.9071 CYP450 2D6 inhibitor Non-inhibitor 0.923 CYP450 2C19 inhibitor Non-inhibitor 0.9026 CYP450 3A4 inhibitor Non-inhibitor 0.8309 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8019 Ames test Non AMES toxic 0.8374 Carcinogenicity Non-carcinogens 0.8692 Biodegradation Not ready biodegradable 0.9955 Rat acute toxicity 2.4401 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.995 hERG inhibition (predictor II) Non-inhibitor 0.7584
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-002f-0000900000-b5c42489815a1e34518f Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0596-0024900000-49a70190e70696b650a8 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-056r-0000900000-c8565e139b6944d41ac0 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-00di-1059700000-230bce665309ed89a909 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0f6x-5984300000-6bd39ab1d3d2ddc8c9c1 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0100-0689300000-144219742fff1acd7d2d 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]- 209.9154417 predictedDarkChem Lite v0.1.0 [M-H]- 198.1391 predictedDeepCCS 1.0 (2019) [M+H]+ 211.9093417 predictedDarkChem Lite v0.1.0 [M+H]+ 200.48651 predictedDeepCCS 1.0 (2019) [M+Na]+ 210.6716417 predictedDarkChem Lite v0.1.0 [M+Na]+ 206.394 predictedDeepCCS 1.0 (2019)
Targets
References
- Nawaz M, Sung K, Khan SA, Khan AA, Steele R: Biochemical and molecular characterization of tetracycline-resistant Aeromonas veronii isolates from catfish. Appl Environ Microbiol. 2006 Oct;72(10):6461-6. [Article]
- Domingue GJ Sr: Cryptic bacterial infection in chronic prostatitis: diagnostic and therapeutic implications. Curr Opin Urol. 1998 Jan;8(1):45-9. [Article]
- Pringle M, Fellstrom C, Johansson KE: Decreased susceptibility to doxycycline associated with a 16S rRNA gene mutation in Brachyspira hyodysenteriae. Vet Microbiol. 2007 Jul 20;123(1-3):245-8. Epub 2007 Feb 25. [Article]
- Aminov RI, Chee-Sanford JC, Garrigues N, Mehboob A, Mackie RI: Detection of tetracycline resistance genes by PCR methods. Methods Mol Biol. 2004;268:3-13. [Article]
Carriers
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- General Function
- Binds water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs (Probable). Its main function is the regulation of the colloidal osmotic pressure of blood (Probable). Major zinc transporter in plasma, typically binds about 80% of all plasma zinc (PubMed:19021548). Major calcium and magnesium transporter in plasma, binds approximately 45% of circulating calcium and magnesium in plasma (By similarity). Potentially has more than two calcium-binding sites and might additionally bind calcium in a non-specific manner (By similarity). The shared binding site between zinc and calcium at residue Asp-273 suggests a crosstalk between zinc and calcium transport in the blood (By similarity). The rank order of affinity is zinc > calcium > magnesium (By similarity). Binds to the bacterial siderophore enterobactin and inhibits enterobactin-mediated iron uptake of E.coli from ferric transferrin, and may thereby limit the utilization of iron and growth of enteric bacteria such as E.coli (PubMed:6234017). Does not prevent iron uptake by the bacterial siderophore aerobactin (PubMed:6234017)
- Specific Function
- antioxidant activity
- Gene Name
- ALB
- Uniprot ID
- P02768
- Uniprot Name
- Albumin
- Molecular Weight
- 69365.94 Da
References
- Bratlid D, Bergan T: Displacement of albumin-bound antimicrobial agents by bilirubin. Pharmacology. 1976;14(5):464-72. doi: 10.1159/000136629. [Article]
Drug created at June 13, 2005 13:24 / Updated at June 02, 2024 21:46