Rolitetracycline

Rolitetracycline is a tetracycline antibiotic.[1] 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.[2][3]

Rolitetracycline
Clinical data
Other names(2Z,4S,4aS,5aS,6S,12aS)-4-Dimethylamino-6,10,11,12a-tetrahydroxy-2-[hydroxy-(pyrrolidin-1-ylmethylamino)methylidene]-6-methyl-4,4a,5,5a-tetrahydrotetracene-1,3,12-trione
ATC code
Identifiers
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
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.010.938
Chemical and physical data
FormulaC27H33N3O8
Molar mass527.574 g·mol−1
3D model (JSmol)
SMILES
  • O=C(NCN1CCCC1)\C2=C(/O)[C@@H](N(C)C)[C@@H]3CC5C(=C(\O)[C@]3(O)C2=O)\C(=O)c4c(O)cccc4[C@@]5(C)O
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 Y
  • Key:HMEYVGGHISAPJR-VQCPGFMQSA-N Y
 NY (what is this?)  (verify)

References
  1. "Rolitetracycline". PubChem. National Library of Medicine. Retrieved 8 June 2020.
  2. PubChem. "Rolitetracycline". pubchem.ncbi.nlm.nih.gov. Retrieved 2022-07-29.
  3. Smith L (January 1964). "Rolitetracycline, an antibiotic for parenteral use. (syntetrin, velacycline)". JAMA. 187 (2): 141. doi:10.1001/jama.1964.03060150065017. PMID 14066734.


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