Cethromycin

{{Short description|Chemical compound}}

{{Infobox drug

| 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

| 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 = {{cascite|correct|??}}

| CAS_number = 205110-48-1

| ATC_prefix = none

| ATC_suffix =

| ATC_supplemental =

| PubChem = 5282045

| ChEBI = 29506

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| DrugBank =

| ChEMBL_Ref = {{ebicite|changed|EBI}}

| ChEMBL = 365528

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = J0086219X6

| KEGG_Ref = {{keggcite|changed|kegg}}

| KEGG = D02391| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| 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_Ref = {{stdinchicite|changed|chemspider}}

| 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 = {{stdinchicite|changed|chemspider}}

| 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=

}}{{cite journal

|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=

}}) is a ketolide antibiotic undergoing research for the treatment of community acquired pneumonia (CAP){{cite journal

|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=

}}{{cite journal

|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

}}{{cite journal

|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=

}} and for the prevention of post-exposure inhalational anthrax, and was given an "orphan drug" status for this indication.[http://www.advancedlifesciences.com/product.php?id=1 Cethromycin – Advanced Life Sciences] {{webarchive |url=https://web.archive.org/web/20080420171224/http://www.advancedlifesciences.com/product.php?id=1 |date=April 20, 2008 }} 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.[https://www.drugs.com/nda/cethromycin_081001.html Cethromycin New Drug Application]

On December 3, 2008, Advanced Life Sciences announced that this New Drug Application has been accepted for filing by the FDA.[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]{{Dead link|date=June 2019 |bot=InternetArchiveBot |fix-attempted=yes }}

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.{{cite web |url=https://www.drugs.com/nda/restanza_090806.html |title=Complete Response Letter for Restanza NDA |publisher=Drugs.com |author=Advanced Life Sciences Holdings, Inc. |accessdate=2014-03-26}}