Cethromycin Explained

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Iupac Name:(1S,2R,5R,7R,8R,9S,11R,13R,14R)-8-[(2''S'',3''R'',4''S'',6''R'')- 4-Dimethylamino-3-hydroxy-6-methyloxan-2-yl]oxy-2-ethyl-1,5,7,9,11,13- hexamethyl-9-[(''E'')-3-quinolin-3-ylprop-2-enoxy] -3,17-dioxa-15-azabicyclo[12.3.0]heptadecane-4,6,12,16-tetrone
Legal Us Comment:Phase III Clinical Trials
Routes Of Administration:Oral
Bioavailability:Between 35.8 and 60% in animal studies.
Metabolism:Liver
Elimination Half-Life:1.6, 3.0, 4.5, 5.9 and 6 hours. Mouse, Monkey, Rat, Dog and Human respectively.
Excretion:7.0% urine 87.2% faeces
Cas Number:205110-48-1
Atc Prefix:none
Pubchem:5282045
Chebi:29506
Chembl:365528
Unii:J0086219X6
Kegg:D02391
Chemspiderid:23258189
Smiles:CC[C@@H]1[C@@]2([C@@H]([C@H](C(=O)[C@@H](C[C@]([C@@H]([C@H](C(=O)[C@H](C(=O)O1)C)C)O[C@H]3[C@@H]([C@H](C[C@H](O3)C)N(C)C)O)(C)OC/C=C/c4cc5ccccc5nc4)C)C)NC(=O)O2)C
Stdinchi:1S/C42H59N3O10/c1-11-32-42(8)36(44-40(50)55-42)25(4)33(46)23(2)21-41(7,51-18-14-15-28-20-29-16-12-13-17-30(29)43-22-28)37(26(5)34(47)27(6)38(49)53-32)54-39-35(48)31(45(9)10)19-24(3)52-39/h12-17,20,22-27,31-32,35-37,39,48H,11,18-19,21H2,1-10H3,(H,44,50)/b15-14+/t23-,24-,25+,26+,27-,31+,32-,35-,36-,37-,39+,41+,42-/m1/s1
Stdinchikey:PENDGIOBPJLVBT-HMMOOPTJSA-N
C:42
H:59
N:3
O:10
Melting Point:211
Melting High:213

Cethromycin, trade name Restanza (initially known as ABT-773[1] [2]) is a ketolide antibiotic undergoing research for the treatment of community acquired pneumonia (CAP)[1] [3] [4] [5] and for the prevention of post-exposure inhalational anthrax, and was given an "orphan drug" status for this indication.[6] Originally discovered and developed by Abbott, it was acquired by Advanced Life Sciences Inc. for further development.

On October 1, 2008, Advanced Life Sciences submitted a New Drug Application (NDA) to Food and Drug Administration (FDA) for cethromycin to treat mild-to-moderate community acquired pneumonia.[7]

On December 3, 2008, Advanced Life Sciences announced that this New Drug Application has been accepted for filing by the FDA.[8]

In June 2009, an FDA Anti-Infective Drugs Advisory Committee review found insufficient evidence for cethromycin efficacy in treatment of community acquired pneumonia, as the Phase 3 clinical trial followed standards that were updated after the clinical trial but three months prior to review. The committee did, however, find the drug safe to use.[9]

Further reading

Notes and References

  1. Lawrence LE. ABT-773 (Abbott Laboratories). Current Opinion in Investigational Drugs. 2. 6. 766–72. June 2001. 11572654.
  2. Dougherty TJ, Barrett JF. ABT-773: a new ketolide antibiotic. Expert Opinion on Investigational Drugs. 10. 2. 343–51. February 2001. 11178346. 10.1517/13543784.10.2.343 . 21855657.
  3. Zhanel GG, Hisanaga T, Nichol K, Wierzbowski A, Hoban DJ. Ketolides: an emerging treatment for macrolide-resistant respiratory infections, focusing on S. pneumoniae. Expert Opinion on Emerging Drugs. 8. 2. 297–321. November 2003. 14661991. 10.1517/14728214.8.2.297. 23004334.
  4. Reinert RR. Clinical efficacy of ketolides in the treatment of respiratory tract infections. The Journal of Antimicrobial Chemotherapy. 53. 6. 918–27. June 2004. 15117934. 10.1093/jac/dkh169. free.
  5. Hammerschlag MR, Sharma R. Use of cethromycin, a new ketolide, for treatment of community-acquired respiratory infections. Expert Opinion on Investigational Drugs. 17. 3. 387–400. March 2008. 18321237. 10.1517/13543784.17.3.387 . 70678060.
  6. http://www.advancedlifesciences.com/product.php?id=1 Cethromycin – Advanced Life Sciences
  7. https://www.drugs.com/nda/cethromycin_081001.html Cethromycin New Drug Application
  8. http://www.marketwatch.com/news/story/Advanced-Life-Sciences-Announces-Cethromycin/story.aspx?guid={03EDC600-9DFB-4B87-962C-D6700F247F3F} Cethromycin New Drug Application accepted for filing by FDA
  9. Web site: Complete Response Letter for Restanza NDA . Drugs.com . Advanced Life Sciences Holdings, Inc. . 2014-03-26.