Rolitetracycline

Title: Rolitetracycline
CAS Registry Number: 751-97-3
CAS Name: [4S-(4a,4aa,5aa,6b,12aa)]-4-(Dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-N-(1-pyrrolidinylmethyl)-2-naphthacenecarboxamide
Additional Names: N-(pyrrolidinomethyl)tetracycline; N-(1-pyrrolidinylmethyl)tetracycline
Trademarks: Reverin (HMR); Syntetrin (BMS); Tetraverin (Polfa); Transcycline (HMR)
Molecular Formula: C27H33N3O8
Molecular Weight: 527.57
Percent Composition: C 61.47%, H 6.30%, N 7.96%, O 24.26%
Literature References: Semi-synthetic antibiotic prepd from tetracycline: Siedel et al., Muench. Med. Wochenschr. 100, 661 (1958); Lindner et al., ZA 5703169. Alternate procedure and structure: Gottstein et al., J. Am. Chem. Soc. 81, 1198 (1959); Cheney et al., US 3104240 (1963 to Bristol-Myers). Toxicity: E. I. Goldenthal, Toxicol. Appl. Pharmacol. 18, 185 (1971).
Properties: Fine, pale yellow needles, dec 162-165°. Amphoteric. More sol than tetracycline and tetracycline hydrochloride. Soly in water at 25°: 1.25 g/ml. Freely sol in alc. Sol in dil acids and alkalies.
Derivative Type: Nitrate sesquihydrate
CAS Registry Number: 26657-13-6
Trademarks: Bristacin (BMS); Pyrrocycline-N (Banyu)
Molecular Formula: C27H33N3O8.HNO3.1½H2O
Molecular Weight: 599.59
Percent Composition: C 54.09%, H 5.88%, N 9.34%, O 30.69%
Properties: LD50 i.v. in rats: 91 mg/kg (Goldenthal).
Toxicity data: LD50 i.v. in rats: 91 mg/kg (Goldenthal)
Derivative Type: Compd with chloramphenicol succinate
CAS Registry Number: 4154-10-3
Additional Names: Cafrolicycline; gradocycline; levocycline; senociclin
Trademarks: Clorociclin (Panthox & Burck); Crovicina (Viti); Metilcaf (Ital Suisse); Proterciclina (Proter); Reicaf (San Carlo); Tecaf (Farmochim. Ital.); Tetrafenicol (Medici Domus)
Molecular Formula: C27H33N3O8.C15H16Cl2N2O8
Molecular Weight: 950.77
Percent Composition: C 53.06%, H 5.19%, N 7.37%, O 26.92%, Cl 7.46%
Literature References: Prepn: BE 636234; Scevola, US 3218335 (1963, 1965 both to Lab. Pro-Ter).
Properties: Bright yellow powder, dec 140-144°. Bitter taste. Very sol in water. Practically insol in ether, ligroin, hexane.
Therap-Cat: Antibacterial.
Keywords: Antibacterial (Antibiotics); Tetracyclines.
Romurtide Ronidazole Ronifibrate Ronnel Roquinimex

Rolitetracycline
Rolitetracycline.png
Systematic (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
Clinical data
Legal status  ?
Identifiers
CAS number 751-97-3 YesY
ATC code J01AA09
PubChem CID 5282179
DrugBank DB01301
ChemSpider 10469507 YesY
UNII GH9IW85221 YesY
KEGG D02282 YesY
ChEMBL CHEMBL1214184 N
Synonyms (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
Chemical data
Formula C27H33N3O8 
Mol. mass 527.566 g/mol
 N (what is this?)  (verify)

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.