A pyrrolidinylmethyl tetracycline. It is a prodrug of tetracycline obtained by reaction of amide group with pyrrolidine and formaldehyde to provide the corresponding mannich base. Rolitetracycline is more hydrophilic than tetracycline and has sufficient water solubility to allow intravenous administration.
The spectrum of activity, the resistance pattern and therapeutic use resemble those of tetracycline. It is therefore used to treat infections sustained by Gram positive and gram negative bacteria, aerobes and anaerobes including Brucella and E.coli . The drug is used preferentially when it is necessary to reach an high plasma concentration or when the oral therapy is not advisable.
Rolitetracycline is a broad-spectrum antibiotic used in cases needing high concentrations or when oral administration is impractical. Rolitetracycline is used for the treatment of brucellosis , upper respiratory tract infections and sinusitis , pulmonary infections [4-6]. In the literature is also reported the use in the treatment of sexually transmitted disease, including gonorrhoea [7,8], intestinal infections [9,10], bone  and biliary infections .
Dosage and Administration
Adult: 350mg intramuscular injection; 275mg i.v. (2-3minutes infusion) once a day. For severe infections the dose can be administered up to three times a day.
After parenteral injections with rolitetracycline, in the treatment of infections sustained by highly sensitive bacteria, tremors and rigor have been observed as a manifestation of Herxheimer-like reaction. After the injection of rolitetracycline an unpleasant taste similar to ether has been reported.
Experimental studies on piglets have
shown that high doses of rolitetracycline (10-20 times above therapeutic doses)
can have vascular effect with a transient increase of arterial blood pressure
and ECG alterations, in particular the PQ interval . These effects are not
observed at normal therapeutic doses . Rapid endovenous injection can cause
transient vertigo, heat flushes, facial redness and occasionally perifal
Mechanism of action
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.
CAS number: 751-97-3 EINECS:
Molecular Formula: C27H33N3O8
Average mass: 527.566223 Da
Monoisotopic mass: 527.226746 Da
Systematic name: (4S,4aS,5aS,6S,12aS)-4-(Dimethylamino)-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-N-(1-pyrrolidinylmethyl)-1,4,4a,5,5a,6,11,12a-octahydro-2-tetracenecarboxamide
Std. 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
Aspect: Fine, pale yellow needles,
Melting point: dec 162-165°.
Water solubility: 1.25 g/ml at 25°C.
Rolitetracycline is unstable in aqueous solutions . At room temperature >50% of the dose is hidrolyzed in 3 hrs, and at 5°C there is a 15% hydrosysis in 21-25 hrs.
Rolitetracycline must be stored in tightly closed containers, protected from light.
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