Cethromycin
Chemical compound
title: "Cethromycin" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["quinolines", "ketolide-antibiotics", "fourteen-membered-rings"] description: "Chemical compound" topic_path: "general/quinolines" source: "https://en.wikipedia.org/wiki/Cethromycin" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0
::summary Chemical compound ::
::data[format=table title="Infobox drug"]
| Field | Value |
|---|---|
| Verifiedfields | changed |
| Watchedfields | changed |
| verifiedrevid | 445236160 |
| IUPAC_name | (1S,2R,5R,7R,8R,9S,11R,13R,14R)-8-[(2S,3R,4S,6R)- 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 |
| image | Cethromycin1.svg |
| image_class | skin-invert-image |
| pregnancy_AU | |
| pregnancy_US | |
| legal_AU | |
| legal_CA | |
| legal_UK | |
| 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_Ref | |
| CAS_number | 205110-48-1 |
| ATC_prefix | none |
| PubChem | 5282045 |
| ChEBI | 29506 |
| DrugBank_Ref | |
| ChEMBL_Ref | |
| ChEMBL | 365528 |
| UNII_Ref | |
| UNII | J0086219X6 |
| KEGG_Ref | |
| KEGG | D02391 |
| ChemSpiderID | 23258189 |
| smiles | CC[C@@H]1[C@@]2(C@@HNC(=O)O2)C |
| StdInChI_Ref | |
| 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_Ref | |
| StdInChIKey | PENDGIOBPJLVBT-HMMOOPTJSA-N |
| C | 42 |
| melting_point | 211 |
| melting_high | 213 |
| :: |
| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 445236160 | IUPAC_name = (1S,2R,5R,7R,8R,9S,11R,13R,14R)-8-[(2S,3R,4S,6R)- 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 | image = Cethromycin1.svg | image_class = skin-invert-image
| tradename = | pregnancy_AU = | pregnancy_US = | pregnancy_category = | legal_AU = | legal_CA = | legal_UK = | legal_US_comment = Phase III Clinical Trials | routes_of_administration = Oral
| bioavailability = Between 35.8 and 60% in animal studies. | protein_bound = | 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_Ref = | CAS_number = 205110-48-1 | ATC_prefix = none | ATC_suffix = | ATC_supplemental = | PubChem = 5282045 | ChEBI = 29506 | DrugBank_Ref = | DrugBank = | ChEMBL_Ref = | ChEMBL = 365528 | UNII_Ref = | UNII = J0086219X6 | KEGG_Ref = | KEGG = D02391| ChemSpiderID_Ref = | ChemSpiderID = 23258189 | smiles = CC[C@@H]1[C@@]2(C@@HNC(=O)O2)C | StdInChI_Ref = | 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_Ref = | StdInChIKey = PENDGIOBPJLVBT-HMMOOPTJSA-N
| chemical_formula = | C=42 | H=59 | N=3 | O=10 | melting_point = 211 | melting_high = 213
Cethromycin, trade name Restanza (initially known as ABT-773{{cite journal |author=Lawrence LE |title=ABT-773 (Abbott Laboratories) |journal=Current Opinion in Investigational Drugs |volume=2 |issue=6 |pages=766–72 |date=June 2001 |pmid=11572654 |doi= |url= |vauthors=Dougherty TJ, Barrett JF |title=ABT-773: a new ketolide antibiotic |journal=Expert Opinion on Investigational Drugs |volume=10 |issue=2 |pages=343–51 |date=February 2001 |pmid=11178346 |doi=10.1517/13543784.10.2.343 |s2cid=21855657 |url= |vauthors=Zhanel GG, Hisanaga T, Nichol K, Wierzbowski A, Hoban DJ |title=Ketolides: an emerging treatment for macrolide-resistant respiratory infections, focusing on S. pneumoniae |journal=Expert Opinion on Emerging Drugs |volume=8 |issue=2 |pages=297–321 |date=November 2003 |pmid=14661991 |doi=10.1517/14728214.8.2.297 |s2cid=23004334 |url= |author=Reinert RR |title=Clinical efficacy of ketolides in the treatment of respiratory tract infections |journal=The Journal of Antimicrobial Chemotherapy |volume=53 |issue=6 |pages=918–27 |date=June 2004 |pmid=15117934 |doi=10.1093/jac/dkh169 |url= |doi-access=free |vauthors=Hammerschlag MR, Sharma R |title=Use of cethromycin, a new ketolide, for treatment of community-acquired respiratory infections |journal=Expert Opinion on Investigational Drugs |volume=17 |issue=3 |pages=387–400 |date=March 2008 |pmid=18321237 |doi=10.1517/13543784.17.3.387 |s2cid=70678060 |url=
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.
On December 3, 2008, Advanced Life Sciences announced that this New Drug Application has been accepted for filing by the FDA.
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.
References
References
- link. (April 20, 2008)
- [https://www.drugs.com/nda/cethromycin_081001.html Cethromycin New Drug Application]
- (June 2019)
- Advanced Life Sciences Holdings, Inc.. "Complete Response Letter for Restanza NDA". Drugs.com.
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