Posted inUncategorized

Rolitetracycline

Common Name

Rolitetracycline Description

Rolitetracycline is only found in individuals that have used or taken this drug. It is a pyrrolidinylmethyl tetracycline.Rolitetracycline is a semisynthetic broad-spectrum tetracycline antibiotic used especially for parenteral administration in cases requiring high concentrations or when oral administration is impractical. Rolitetracycline passively diffuses through porin channels in the bacterial membrane and reversibly binds to the 30S ribosomal subunit, preventing binding of tRNA to the mRNA-ribosome complex, and thus interfering with protein synthesis. Structure

MOLSDFPDBSMILESInChI

Synonyms

Value Source N-(1-Pyrrolidinylmethyl)-tetracyclineChEBI N-(Pyrrolidinomethyl)tetracyclineChEBI pyrrolidino-Methyl-tetracyclineChEBI ReverinChEBI RolitetraciclinaChEBI RolitetracyclinumChEBI SynterinChEBI

Chemical Formlia

C27H33N3O8 Average Molecliar Weight

527.5662 Monoisotopic Molecliar Weight

527.226765047 IUPAC Name

(4S,4aS,5aS,6S,12aS)-4-(dimethylamino)-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-N-(pyrrolidin-1-ylmethyl)-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide Traditional Name

rolitetracycline CAS Registry Number

751-97-3 SMILES

[H][C@@]12C[C@@]3([H])C(C(=O)C4=C(O)C=CC=C4[C@@]3(C)O)=C(O)[C@]1(O)C(=O)C(C(=O)NCN1CCCC1)=C(O)[C@H]2N(C)C

InChI Identifier

InChI=1S/C27H33N3O8/c1-26(37)13-7-6-8-16(31)17(13)21(32)18-14(26)11-15-20(29(2)3)22(33)19(24(35)27(15,38)23(18)34)25(36)28-12-30-9-4-5-10-30/h6-8,14-15,20,31,33-34,37-38H,4-5,9-12H2,1-3H3,(H,28,36)/t14-,15-,20-,26+,27-/m0/s1

InChI Key

HMEYVGGHISAPJR-IAHYZSEUSA-N Chemical Taxonomy Description

This compound belongs to the class of chemical entities known as tetracyclines. These are polyketides having an octahydrotetracene-2-carboxamide skeleton, substituted with many hydroxy and other groups. Kingdom

Chemical entities Super Class

Organic compounds Class

Phenylpropanoids and polyketides Sub Class

Tetracyclines Direct Parent

Tetracyclines Alternative Parents

  • Naphthacenes
  • Anthracenecarboxylic acids and derivatives
  • Tetralins
  • Aryl ketones
  • 1-hydroxy-2-unsubstituted benzenoids
  • 1-hydroxy-4-unsubstituted benzenoids
  • Aralkylamines
  • Cyclohexenones
  • N-alkylpyrrolidines
  • Vinylogous acids
  • Tertiary alcohols
  • Secondary carboxylic acid amides
  • Amino acids and derivatives
  • Trialkylamines
  • Enols
  • Azacyclic compounds
  • Polyols
  • Hydrocarbon derivatives
  • Organopnictogen compounds
  • Organic oxides

    • Substituents

  • Tetracycline
  • Naphthacene
  • Tetracene
  • Anthracene carboxylic acid or derivatives
  • Tetralin
  • Aryl ketone
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Cyclohexenone
  • Aralkylamine
  • Benzenoid
  • N-alkylpyrrolidine
  • Pyrrolidine
  • Tertiary alcohol
  • Vinylogous acid
  • Amino acid or derivatives
  • Carboxamide group
  • Ketone
  • Secondary carboxylic acid amide
  • Tertiary amine
  • Tertiary aliphatic amine
  • Polyol
  • Enol
  • Carboxylic acid derivative
  • Azacycle
  • Organoheterocyclic compound
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Alcohol
  • Amine
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Aromatic heteropolycyclic compound

    • Molecliar Framework

    Aromatic heteropolycyclic compounds External Descriptors

  • tetracyclines (CHEBI:63334 )

    • Ontology Status

    Expected but not Quantified Origin

  • Drug

    • Biofunction

  • Anti-Bacterial Agents
  • Tetracyclines

    • Application

  • Pharmaceutical

    • Cellliar locations

  • Cytoplasm
  • Membrane

    • Physical Properties State

    Solid Experimental Properties

    Property Value Reference Melting PointNot AvailableNot Available Boiling PointNot AvailableNot Available Water Solubility1.81e+00 g/LNot Available LogPNot AvailableNot Available

    Predicted Properties

    Property Value Source Water Solubility1.81 mg/mLALOGPS logP-0.08ALOGPS logP-3.8ChemAxon logS-2.5ALOGPS pKa (Strongest Acidic)0.31ChemAxon pKa (Strongest Basic)8.24ChemAxon Physiological Charge-1ChemAxon Hydrogen Acceptor Count10ChemAxon Hydrogen Donor Count6ChemAxon Polar Surface Area170.87 Å2ChemAxon Rotatable Bond Count4ChemAxon Refractivity139.45 m3·mol-1ChemAxon Polarizability54.05 Å3ChemAxon Number of Rings5ChemAxon Bioavailability0ChemAxon Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

    Spectra Spectra

    Not Available Biological Properties Cellliar Locations

  • Cytoplasm
  • Membrane

    • Biofluid Locations

  • Blood
  • Urine

    • Tissue Location

    Not Available Pathways

    Name SMPDB Link KEGG Link Rolitetracycline Action PathwaySMP00726Not Available

    Normal Concentrations

    Biofluid Status Value Age Sex Condition Reference Details BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01301

  • 21059682

    • details UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01301

  • 21059682

    • details

    Abnormal Concentrations

    Not Available Associated Disorders and Diseases Disease References

    None Associated OMIM IDs

    None External Links DrugBank ID

    DB01301 DrugBank Metabolite ID

    Not Available Phenol Explorer Compound ID

    Not Available Phenol Explorer Metabolite ID

    Not Available FoodDB ID

    Not Available KNApSAcK ID

    Not Available Chemspider ID

    21111754 KEGG Compound ID

    Not Available BioCyc ID

    Not Available BiGG ID

    Not Available Wikipedia Link

    Rolitetracycline NuGOwiki Link

    HMDB15414 Metagene Link

    HMDB15414 METLIN ID

    Not Available PubChem Compound

    Not Available PDB ID

    Not Available ChEBI ID

    63334

    Product: Eicosapentaenoic Acid

    References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Not Available General References Not Available

    Enzymes

    General function:
    Involved in monooxygenase activity
    Specific function:
    Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
    Gene Name:
    CYP3A4
    Uniprot ID:
    P08684
    Molecular weight:
    57255.585
    References
    1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

    PMID: 26594146