NAV

Rolitetracycline

Identification

Summary

Rolitetracycline is a broad-spectrum tetracycline antibiotic used in cases needing high concentrations or when oral administration is impractical.

Generic Name
Rolitetracycline
DrugBank Accession Number
DB01301
Background

A pyrrolidinylmethyl tetracycline.

Type
Small Molecule
Groups
Approved
Structure
Similar Structures
Weight
Average: 527.5662
Monoisotopic: 527.226765047
Chemical Formula
C27H33N3O8
Synonyms
  • N-(1-Pyrrolidinylmethyl)-tetracycline
  • N-(Pyrrolidinomethyl)tetracycline
  • Pyrrolidino-methyl-tetracycline
  • Rolitetraciclina
  • Rolitetracycline
  • Rolitetracyclinum
External IDs
  • SQ 15,659
  • SQ-15659

Pharmacology

Indication

Rolitetracycline is a broad-spectrum antibiotic used in cases needing high concentrations or when oral administration is impractical.

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action

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.

TargetActionsOrganism
A30S ribosomal protein S9
inhibitor
Escherichia coli (strain K12)
A16S ribosomal RNA
inhibitor
Enteric bacteria and other eubacteria
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Symptoms of overdose include anorexia, nausea, diarrhoea, glossitis, dysphagia, enterocolitis and inflammatory lesions (with monilial overgrowth) in the anogenital region, skin reactions such as maculopapular and erythematous rashes, exfoliative dermatitis, photosensitivity, hypersensitivity reactions such as urticaria, angioneurotic oedema, anaphylaxis, anaphyl-actoid purpura, pericarditis, and exacerbation of systemic lupus erythematosus, benign intracranial hypertension in adults disappearing on discontinuation of the medicine, haematologic abnormalities such as haemolytic anaemia, thrombocytopenia, neutropenia, and eosinophilia. LD50=262 mg/kg (I.P. in rat).

Pathways
PathwayCategory
Rolitetracycline Action PathwayDrug 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.
DrugInteraction
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interactions in your software
AcenocoumarolRolitetracycline may increase the anticoagulant activities of Acenocoumarol.
AcitretinThe risk or severity of pseudotumor cerebri can be increased when Acitretin is combined with Rolitetracycline.
AlitretinoinThe risk or severity of pseudotumor cerebri can be increased when Alitretinoin is combined with Rolitetracycline.
AmbroxolThe risk or severity of methemoglobinemia can be increased when Rolitetracycline is combined with Ambroxol.
AmoxicillinThe therapeutic efficacy of Amoxicillin can be decreased when used in combination with Rolitetracycline.
AmpicillinThe therapeutic efficacy of Ampicillin can be decreased when used in combination with Rolitetracycline.
ArticaineThe risk or severity of methemoglobinemia can be increased when Rolitetracycline is combined with Articaine.
AtracuriumThe therapeutic efficacy of Atracurium can be increased when used in combination with Rolitetracycline.
Atracurium besylateThe therapeutic efficacy of Atracurium besylate can be increased when used in combination with Rolitetracycline.
AzlocillinThe therapeutic efficacy of Azlocillin can be decreased when used in combination with Rolitetracycline.
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Food Interactions
  • Avoid milk and dairy products. Dairy products contain cations such as calcium which may interfere with the absorption of rolitetracycline.

Products

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International/Other Brands
Reverin / Synterin
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Reverin 275mgPowder, for solution275 mg / vialIntra-articular; Intraperitoneal; Intrapleural; Intrathecal; IntravenousHoechst Canada Inc.1959-12-311996-12-12Canada flag

Categories

ATC Codes
J01AA20 — Combinations of tetracyclinesJ01AA09 — Rolitetracycline
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 / Aralkylamines / Cyclohexenones / N-alkylpyrrolidines / Vinylogous acids
show 10 more
Substituents
1-hydroxy-2-unsubstituted benzenoid / 1-hydroxy-4-unsubstituted benzenoid / Alcohol / Amine / Amino acid or derivatives / Anthracene carboxylic acid or derivatives / Aralkylamine / Aromatic heteropolycyclic compound / Aryl ketone / Azacycle
show 27 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
tetracyclines (CHEBI:63334)
Affected organisms
Not Available

Chemical Identifiers

UNII
GH9IW85221
CAS number
751-97-3
InChI Key
HMEYVGGHISAPJR-IAHYZSEUSA-N
InChI
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
IUPAC Name
(4S,4aS,5aS,6S,12aS)-4-(dimethylamino)-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-N-[(pyrrolidin-1-yl)methyl]-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide
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

References

Synthesis Reference

Horacio Alfredo Priestap, Carlos Rappaport, "Process for producing rolitetracycline." U.S. Patent US3985768, issued September, 1963.

US3985768
General References
Not Available
Human Metabolome Database
HMDB0015414
KEGG Drug
D02282
PubChem Compound
54682938
PubChem Substance
46507805
ChemSpider
21111754
BindingDB
50477463
RxNav
9462
ChEBI
63334
ChEMBL
CHEMBL1237046
ZINC
ZINC000014880004
Therapeutic Targets Database
DAP000884
PharmGKB
PA164779049
Wikipedia
Rolitetracycline

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
OintmentOphthalmic
Solution / dropsOphthalmic
Powder, for solutionIntra-articular; Intraperitoneal; Intrapleural; Intrathecal; Intravenous275 mg / vial
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
water solubility5.55E+005 mg/LMERCK INDEX (1996)
Predicted Properties
PropertyValueSource
Water Solubility1.81 mg/mLALOGPS
logP-0.08ALOGPS
logP-3Chemaxon
logS-2.5ALOGPS
pKa (Strongest Acidic)3.25Chemaxon
pKa (Strongest Basic)9.26Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count10Chemaxon
Hydrogen Donor Count6Chemaxon
Polar Surface Area170.87 Å2Chemaxon
Rotatable Bond Count4Chemaxon
Refractivity139.45 m3·mol-1Chemaxon
Polarizability54.37 Å3Chemaxon
Number of Rings5Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.7999
Blood Brain Barrier-0.9659
Caco-2 permeable-0.6259
P-glycoprotein substrateSubstrate0.9289
P-glycoprotein inhibitor INon-inhibitor0.875
P-glycoprotein inhibitor IIInhibitor0.7922
Renal organic cation transporterNon-inhibitor0.7671
CYP450 2C9 substrateNon-substrate0.7614
CYP450 2D6 substrateNon-substrate0.7656
CYP450 3A4 substrateSubstrate0.7527
CYP450 1A2 substrateNon-inhibitor0.9068
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorNon-inhibitor0.923
CYP450 2C19 inhibitorNon-inhibitor0.8968
CYP450 3A4 inhibitorNon-inhibitor0.926
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8647
Ames testNon AMES toxic0.6931
CarcinogenicityNon-carcinogens0.9246
BiodegradationNot ready biodegradable0.6204
Rat acute toxicity2.7094 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8692
hERG inhibition (predictor II)Inhibitor0.7194
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
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

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Details1. 30S ribosomal protein S9
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Yes
Actions
Inhibitor
General Function
Trna binding
Specific Function
The C-terminal tail plays a role in the affinity of the 30S P site for different tRNAs. Mutations that decrease this affinity are suppressed in the 70S ribosome.
Gene Name
rpsI
Uniprot ID
P0A7X3
Uniprot Name
30S ribosomal protein S9
Molecular Weight
14856.105 Da
References
  1. Carrasco-Pancorbo A, Casado-Terrones S, Segura-Carretero A, Fernandez-Gutierrez A: Reversed-phase high-performance liquid chromatography coupled to ultraviolet and electrospray time-of-flight mass spectrometry on-line detection for the separation of eight tetracyclines in honey samples. J Chromatogr A. 2008 Jun 27;1195(1-2):107-16. doi: 10.1016/j.chroma.2008.05.003. Epub 2008 May 10. [Article]
  2. Griffin MO, Fricovsky E, Ceballos G, Villarreal F: Tetracyclines: a pleitropic family of compounds with promising therapeutic properties. Review of the literature. Am J Physiol Cell Physiol. 2010 Sep;299(3):C539-48. doi: 10.1152/ajpcell.00047.2010. Epub 2010 Jun 30. [Article]
Details2. 16S ribosomal RNA
Kind
Nucleotide
Organism
Enteric bacteria and other eubacteria
Pharmacological action
Yes
Actions
Inhibitor
In prokaryotes, the 16S rRNA is essential for recognizing the 5' end of mRNA and hence positioning it correctly on the ribosome. The 16S rRNA has a characteristic secondary structure in which half of the nucleotides are base-paired. The 16S rRNA sequence has been highly conserved and is often used for evolutionary and species comparative analysis.
References
  1. 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]
  2. Kumar S, Kutlin A, Roblin P, Kohlhoff S, Bodetti T, Timms P, Hammerschlag MR: Isolation and antimicrobial susceptibilities of Chlamydial isolates from Western barred bandicoots. J Clin Microbiol. 2007 Feb;45(2):392-4. Epub 2006 Nov 22. [Article]
  3. Ross JI, Eady EA, Cove JH, Cunliffe WJ: 16S rRNA mutation associated with tetracycline resistance in a gram-positive bacterium. Antimicrob Agents Chemother. 1998 Jul;42(7):1702-5. [Article]

Drug created at June 30, 2007 14:26 / Updated at June 16, 2021 12:31