2751-09-9 Usage
Description
Troleandomycin, also known as Tao, is a semi-synthetic macrolide antibiotic derived from Oleandomycin. It is characterized by its ability to inhibit cytochrome P450, specifically acting as a CYP3A4 inhibitor. This property can lead to potential drug interactions. Troleandomycin is primarily found in individuals who have taken the drug and is sold under the brand name Tao by Pfizer, predominantly in Italy and Turkey.
Uses
Used in Pharmaceutical Industry:
Troleandomycin is used as an antibiotic for treating bacterial infections. As a macrolide antibiotic, it works by inhibiting protein synthesis in bacteria, thereby stopping their growth and spread.
Used in Drug Interaction Studies:
Due to its role as a CYP3A4 inhibitor, Troleandomycin is used in the study of drug interactions. Its ability to block CYP450-dependent drug oxidation can impact the metabolism of other medications, which is crucial for understanding potential side effects and adjusting dosages accordingly.
Clinical Use
Oleandomycin contains three hydroxyl groups that aresubject to acylation, one in each of the sugars and one in theoleandolide. The triacetyl derivative retains the in vivo antibacterialactivity of the parent antibiotic but possesses superiorpharmacokinetic properties. It is hydrolyzed in vivo tooleandomycin. Troleandomycin achieves more rapid andhigher plasma concentrations following oral administrationthan oleandomycin phosphate, and it has the additionaladvantage of being practically tasteless. Troleandomycinoccurs as a white, crystalline solid that is nearly insoluble inwater. It is relatively stable in the solid state but undergoeschemical degradation in either aqueous acidic or alkalineconditions.Because the antibacterial spectrum of activity of oleandomycinis considered inferior to that of erythromycin, thepharmacokinetics of troleandomycin have not been studiedextensively. Oral absorption is apparently good, and detectableblood levels of oleandomycin persist up to 12 hoursafter a 500-mg dose of troleandomycin. Approximately 20%is recovered in the urine, with most excreted in the feces, primarilyas a result of biliary excretion. There is some epigastricdistress following oral administration, with an incidencesimilar to that caused by erythromycin. Troleandomycin isthe most potent inhibitor of cytochrome P450 enzymes of thecommercially available macrolides. It may potentiate the hepatictoxicity of certain anti-inflammatory steroids and oralcontraceptive drugs as well as the toxic effects of theophylline,carbamazepine, and triazolam. Several allergic reactions,including cholestatic hepatitis, have also been reportedwith the use of troleandomycin.Approved medical indications for troleandomycin arecurrently limited to the treatment of upper respiratory infectionscaused by such organisms as S. pyogenes and S. pneumoniae.It may be considered an alternative to oral forms oferythromycin. It is available in capsules and as a suspension.
References
References/Citations
1) Patki et al. (2004), Mechanism-based inhibition of CYP3A4 and CYP3A5 by seven inhibitors; Clin. Pharmacol. Therap., 75 P83
2) Kozlov et al. (2003), Various intracellular compartments cooperate in the release of nitric oxide from glycerol trinitrate in liver; Br. J. Pharmacol., 139 989
3) Ludden et al. (1985), Pharmacokinetic interactions of the macrolide antibiotics; Clin. Pharmacokinet., 10 63
Check Digit Verification of cas no
The CAS Registry Mumber 2751-09-9 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 2,7,5 and 1 respectively; the second part has 2 digits, 0 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 2751-09:
(6*2)+(5*7)+(4*5)+(3*1)+(2*0)+(1*9)=79
79 % 10 = 9
So 2751-09-9 is a valid CAS Registry Number.
InChI:InChI=1/C41H67NO15/c1-19-17-41(18-49-41)38(46)23(5)34(53-27(9)43)21(3)25(7)52-39(47)24(6)35(56-32-16-31(48-14)36(26(8)51-32)54-28(10)44)22(4)33(19)57-40-37(55-29(11)45)30(42(12)13)15-20(2)50-40/h19-26,30-37,40H,15-18H2,1-14H3
