Cethromycin

Cethromycin
Clinical data
Routes of; administration	Oral
ATC code	none;
Legal status
Legal status	US: Phase III Clinical Trials;
Pharmacokinetic data
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
Identifiers
	IUPAC name (1S,2R,5R,7R,8R,9S,11R,13R,14R)-8-oxy-2-ethyl-1,5,7,9,11,13- hexamethyl-9- -3,17-dioxa-15-azabicycloheptadecane-4,6,12,16-tetrone;
CAS Number	205110-48-1 ;
PubChem CID	5282045;
ChemSpider	23258189 ;
UNII	J0086219X6;
KEGG	D02391 ;
ChEBI	CHEBI:29506;
ChEMBL	ChEMBL365528 ;
Chemical and physical data
Formula	C42H59N3O10
Molar mass	765.945 g·mol−1
3D model (JSmol)	Interactive image;
Melting point	211 to 213 °C (412 to 415 °F)
	SMILES CC12(((C(=O)(C(((C(=O)(C(=O)O1)C)C)O3((C(O3)C)N(C)C)O)(C)OC/C=C/c4cc5ccccc5nc4)C)C)NC(=O)O2)C;
	InChI InChI=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 ; Key:PENDGIOBPJLVBT-HMMOOPTJSA-N ;
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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]

References

^ ^a ^b Lawrence LE (June 2001). "ABT-773 (Abbott Laboratories)". Current Opinion in Investigational Drugs. 2 (6): 766–72. PMID 11572654.
^ Dougherty TJ, Barrett JF (February 2001). "ABT-773: a new ketolide antibiotic". Expert Opinion on Investigational Drugs. 10 (2): 343–51. doi:10.1517/13543784.10.2.343. PMID 11178346. S2CID 21855657.
^ Zhanel GG, Hisanaga T, Nichol K, Wierzbowski A, Hoban DJ (November 2003). "Ketolides: an emerging treatment for macrolide-resistant respiratory infections, focusing on S. pneumoniae". Expert Opinion on Emerging Drugs. 8 (2): 297–321. doi:10.1517/14728214.8.2.297. PMID 14661991. S2CID 23004334.
^ Reinert RR (June 2004). "Clinical efficacy of ketolides in the treatment of respiratory tract infections". The Journal of Antimicrobial Chemotherapy. 53 (6): 918–27. doi:10.1093/jac/dkh169. PMID 15117934.
^ Hammerschlag MR, Sharma R (March 2008). "Use of cethromycin, a new ketolide, for treatment of community-acquired respiratory infections". Expert Opinion on Investigational Drugs. 17 (3): 387–400. doi:10.1517/13543784.17.3.387. PMID 18321237. S2CID 70678060.
^ Cethromycin – Advanced Life Sciences Archived April 20, 2008, at the Wayback Machine
^ Cethromycin New Drug Application
^ Cethromycin New Drug Application accepted for filing by FDA^{[permanent dead link]}
^ Advanced Life Sciences Holdings, Inc. "Complete Response Letter for Restanza NDA". Drugs.com. Retrieved 2014-03-26.

Clinical data

Routes of administration	Oral
ATC code	none
Legal status
Legal status	US: Phase III Clinical Trials
Pharmacokinetic data
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
Identifiers
IUPAC name (1S,2R,5R,7R,8R,9S,11R,13R,14R)-8-oxy-2-ethyl-1,5,7,9,11,13- hexamethyl-9- -3,17-dioxa-15-azabicycloheptadecane-4,6,12,16-tetrone
CAS Number	205110-48-1^Y
PubChem CID	5282045
ChemSpider	23258189^N
UNII	J0086219X6
KEGG	D02391^N
ChEBI	CHEBI:29506
ChEMBL	ChEMBL365528^N
Chemical and physical data
Formula	C₄₂H₅₉N₃O₁₀
Molar mass	765.945 g·mol⁻¹
3D model (JSmol)	Interactive image
Melting point	211 to 213 °C (412 to 415 °F)
SMILES CC12(((C(=O)(C(((C(=O)(C(=O)O1)C)C)O3((C(O3)C)N(C)C)O)(C)OC/C=C/c4cc5ccccc5nc4)C)C)NC(=O)O2)C
InChI InChI=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^N Key:PENDGIOBPJLVBT-HMMOOPTJSA-N^N
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References

Further reading