Structure via PubChem · Public domain (PubChem)
rolitetracycline
Sign in to saveAlso known as Syntetrin, SO-15659, Rolitetraciclina, N-(1-Pyrrolidinylmethyl)-tetracycline, Synterin, N-(Pyrrolidinomethyl)tetracycline, Reverin, Pyrrolidino-methyl-tetracycline
Rolitetracycline is a tetracycline antibiotic. Tetracycline is N-Mannich base prodrug that is prepared from tetracycline by condensation with pyrrolidine and formaldehyde to produce rolitetracycline. Rolitetracycline is used as an antibacterial drug, a protein synthesis inhibitor, an antiprotozoal drug and a prodrug.
Chemical data
- Formula
- C27H33N3O8
- Molecular weight
- 527.6 g/mol
- IUPAC name
- (4S,4aS,5aS,6S,12aR)-4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-N-(pyrrolidin-1-ylmethyl)-4,4a,5,5a-tetrahydrotetracene-2-carboxamide
- SMILES
- C[C@@]1([C@H]2C[C@H]3[C@@H](C(=O)C(=C([C@]3(C(=O)C2=C(C4=C1C=CC=C4O)O)O)O)C(=O)NCN5CCCC5)N(C)C)O
- InChIKey
- IKQRPFTXKQQLJF-IAHYZSEUSA-N
- XLogP
- -0.9
- Polar surface area
- 171 Ų
- H-bond donors
- 6
- H-bond acceptors
- 10
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Phase 2
- Molecule type
- Small molecule
- Indications
- bacterial disease
via ChEMBL · EBI
Research
404 papers- Tetracyclines.2012
- Pharmacokinetics and pharmacodynamics of the tetracyclines including glycylcyclines.The Journal of antimicrobial chemotherapy · 2006
- The site of the neuromuscular block produced by polymyxin B and rolitetracycline.Canadian journal of physiology and pharmacology · 1976
- Binding and displacement study of gentamicin, 5-fluorouracil, oxytetracycline and rolitetracycline with (BSA: Drug2) complex using spectroscopic and calorimetric techniques: Biophysical approach.International journal of biological macromolecules · 2024
- Combination of bacteriostatic and bactericidal drugs: lack of significant in vitro antagonism between penicillin, cephalothin, and rolitetracycline.Antimicrobial agents and chemotherapy · 1976
via PubMed
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 527.226765016
- Has use
- medication
Show 7 more facts
- Commons category
- Rolitetracycline
- chemical formula
- C₂₇H₃₃N₃O₈
- isomeric SMILES
- CN(C)[C@H]1[C@@H]2C[C@H]3C(=C(O)[C@]2(O)C(=O)C(=C1O)C(=O)NCN4CCCC4)C(=O)c5c(O)cccc5[C@@]3(C)O
- defined daily dose
- 0.35
- NCI Thesaurus ID
- C80801
- subject has role
- bactericide
- canonical SMILES
- CN(C)C1C(O)=C(C(=O)NCN2CCCC2)C(=O)C2(O)C(O)=C3C(=O)c4c(O)cccc4C(C)(O)C3CC12
Sources (3)
via Wikidata · CC0
~2 min read
Encyclopedic overview
1 sectionsContents
- References
{{Drugbox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 464383386 | IUPAC_name = (2Z,4S,4aS,5aS,6S,12aS)-4-(Dimethylamino)-6,10,11,12a-tetrahydroxy-2-{hydroxy[(pyrrolidin-1-ylmethyl)amino]methylene}-6-methyl-4a,5a,6,12a-tetrahydrotetracene-1,3,12(2H,4H,5H)-trione | image = Rolitetracycline.svg | image_class = skin-invert-image | alt = Skeletal formula of rolitetracycline | width = 240 | image2 = Rolitetracycline 3D spacefill.png | image_class2 = bg-transparent | alt2 = Space-filling model of the rolitetracycline molecule | width2 = 260
| tradename = | pregnancy_AU = | pregnancy_US = | pregnancy_category = | legal_AU = | legal_CA = | legal_UK = | legal_US = | legal_status = | routes_of_administration =
Excerpted from Wikipedia’s “rolitetracycline” article, available under the CC BY-SA 4.0 licence.
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