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Updating {{drugbox}} (no changed fields - added verified revid - updated 'ChemSpiderID_Ref', 'DrugBank_Ref', 'ChEMBL_Ref', 'ChEBI_Ref', 'StdInChI_Ref', 'StdInChIKey_Ref', 'ChEBI_Ref') per [[Wikipedia:WikiProject Chemicals/Chembox validation|Chem/Drug
m →‎top: clean up, typo(s) fixed: October 1, 2008 → October 1, 2008, (2)
 
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{{Short description|Chemical compound}}
{{drugbox
{{Infobox drug
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 445236160
| IUPAC_name = (1''S'',2''R'',5''R'',7''R'',8''R'',9''S'',11''R'',13''R'',14''R'')-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
| image = Cethromycin1.svg

<!--Clinical data-->
| tradename =
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| pregnancy_US = <!-- A / B / C / D / X -->
| pregnancy_category =
| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled-->
| legal_CA = <!-- Schedule I, II, III, IV, V, VI, VII, VIII -->
| legal_UK = <!-- GSL, P, POM, CD, or Class A, B, C -->
| legal_US_comment = [[Clinical trial|Phase III Clinical Trials]]
| routes_of_administration = Oral

<!--Pharmacokinetic data-->
| 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

<!--Identifiers-->
| 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_Ref = {{fdacite|correct|FDA}}
| UNII = J0086219X6
| UNII = J0086219X6
| KEGG_Ref = {{keggcite|changed|kegg}}
| verifiedrevid = 437180771
| KEGG = D02391| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| IUPAC_name = (1''S'',2''R'',5''R'',7''R'',8''R'',9''S'',11''R'',13''R'',14''R'')-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
| ChemSpiderID = 23258189
| image = Cethromycin.png
| 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
| CAS_number = 205110-48-1
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| CAS_supplemental =
| 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
| ATC_prefix = none
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| ATC_suffix =
| StdInChIKey = PENDGIOBPJLVBT-HMMOOPTJSA-N
| ATC_supplemental =

| PubChem = 5282045
<!--Chemical data-->
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| chemical_formula =
| DrugBank =
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D02391
| chemical_formula =
| C=42 | H=59 | N=3 | O=10
| C=42 | H=59 | N=3 | O=10
| melting_point = 211
| molecular_weight = 765.931 g/mol
| melting_high = 213
| melting_point = 211
| melting_high = 213
| 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
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| pregnancy_US = <!-- A / B / C / D / X -->
| pregnancy_category=
| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled-->
| legal_CA = <!-- Schedule I, II, III, IV, V, VI, VII, VIII -->
| legal_UK = <!-- GSL, P, POM, CD, or Class A, B, C -->
| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V -->
| legal_status = [[Clinical trial|Phase III Clinical Trials in US]]
| routes_of_administration = Oral
}}
}}


'''Cethromycin''' (initially known as '''ABT-773'''<ref name="pmid11572654">{{cite journal
'''Cethromycin''', trade name Restanza (initially known as '''ABT-773'''<ref name="pmid11572654">{{cite journal
|author=Lawrence LE
|author=Lawrence LE
|title=ABT-773 (Abbott Laboratories)
|title=ABT-773 (Abbott Laboratories)
Line 43: Line 62:
|issue=6
|issue=6
|pages=766–72
|pages=766–72
|year=2001
|date=June 2001
|month=June
|pmid=11572654
|pmid=11572654
|doi=
|doi=
|url=
|url=
|issn=
|accessdate=2009-06-21
}}</ref><ref name="pmid11178346">{{cite journal
}}</ref><ref name="pmid11178346">{{cite journal
|author=Dougherty TJ, Barrett JF
|vauthors=Dougherty TJ, Barrett JF
|title=ABT-773: a new ketolide antibiotic
|title=ABT-773: a new ketolide antibiotic
|journal=Expert Opinion on Investigational Drugs
|journal=Expert Opinion on Investigational Drugs
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|issue=2
|issue=2
|pages=343–51
|pages=343–51
|year=2001
|date=February 2001
|month=February
|pmid=11178346
|pmid=11178346
|doi=10.1517/13543784.10.2.343
|doi=10.1517/13543784.10.2.343
|s2cid=21855657
|url=
|url=
}}</ref>) is a [[ketolide]] [[antibiotic]] undergoing research for the treatment of [[community acquired pneumonia]] (CAP)<ref name="pmid11572654"/><ref name="pmid14661991">{{cite journal
|issn=
|vauthors=Zhanel GG, Hisanaga T, Nichol K, Wierzbowski A, Hoban DJ
|accessdate=2009-06-21
}}</ref>) is a [[ketolide]] [[antibiotic]] undergoing research for the treatment of [[community acquired pneumonia]] (CAP)<ref name="pmid11572654">{{cite journal
|author=Lawrence LE
|title=ABT-773 (Abbott Laboratories)
|journal=Current Opinion in Investigational Drugs (London, England : 2000)
|volume=2
|issue=6
|pages=766–72
|year=2001
|month=June
|pmid=11572654
|doi=
|url=
|issn=
|accessdate=2009-06-21
}}</ref><ref name="pmid14661991">{{cite journal
|author=Zhanel GG, Hisanaga T, Nichol K, Wierzbowski A, Hoban DJ
|title=Ketolides: an emerging treatment for macrolide-resistant respiratory infections, focusing on S. pneumoniae
|title=Ketolides: an emerging treatment for macrolide-resistant respiratory infections, focusing on S. pneumoniae
|journal=Expert Opinion on Emerging Drugs
|journal=Expert Opinion on Emerging Drugs
Line 85: Line 85:
|issue=2
|issue=2
|pages=297–321
|pages=297–321
|year=2003
|date=November 2003
|month=November
|pmid=14661991
|pmid=14661991
|doi=10.1517/14728214.8.2.297
|doi=10.1517/14728214.8.2.297
|s2cid=23004334
|url=
|url=
|issn=
|accessdate=2009-06-21
}}</ref><ref name="pmid15117934">{{cite journal
}}</ref><ref name="pmid15117934">{{cite journal
|author=Reinert RR
|author=Reinert RR
|title=Clinical efficacy of ketolides in the treatment of respiratory tract infections
|title=Clinical efficacy of ketolides in the treatment of respiratory tract infections
|journal=The Journal of Antimicrobial Chemotherapy
|journal=[[The Journal of Antimicrobial Chemotherapy]]
|volume=53
|volume=53
|issue=6
|issue=6
|pages=918–27
|pages=918–27
|year=2004
|date=June 2004
|month=June
|pmid=15117934
|pmid=15117934
|doi=10.1093/jac/dkh169
|doi=10.1093/jac/dkh169
|url=
|url=
|doi-access=free
|issn=
|accessdate=2009-06-21
}}</ref><ref name="pmid18321237">{{cite journal
}}</ref><ref name="pmid18321237">{{cite journal
|author=Hammerschlag MR, Sharma R
|vauthors=Hammerschlag MR, Sharma R
|title=Use of cethromycin, a new ketolide, for treatment of community-acquired respiratory infections
|title=Use of cethromycin, a new ketolide, for treatment of community-acquired respiratory infections
|journal=Expert Opinion on Investigational Drugs
|journal=Expert Opinion on Investigational Drugs
Line 113: Line 109:
|issue=3
|issue=3
|pages=387–400
|pages=387–400
|year=2008
|date=March 2008
|month=March
|pmid=18321237
|pmid=18321237
|doi=10.1517/13543784.17.3.387
|doi=10.1517/13543784.17.3.387
|s2cid=70678060
|url=
|url=
}}</ref> and for the prevention of post-exposure inhalational [[anthrax]], and was given an "[[orphan drug]]" status for this indication.<ref>[http://www.advancedlifesciences.com/product.php?id=1 Cethromycin – Advanced Life Sciences<!-- Bot generated title -->] {{webarchive |url=https://web.archive.org/web/20080420171224/http://www.advancedlifesciences.com/product.php?id=1 |date=April 20, 2008 }}</ref> Originally discovered and developed by [[Abbott Laboratories|Abbott]], it was acquired by Advanced Life Sciences Inc. for further development.
|issn=
|accessdate=2009-06-21
}}</ref> and for the prevention of post-exposure inhalational [[anthrax]], and was given an "[[orphan drug]]" status for this indication.<ref>[http://www.advancedlifesciences.com/product.php?id=1 Cethromycin - Advanced Life Sciences<!-- Bot generated title -->]</ref> Originally discovered and developed by [[Abbott Laboratories|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.<ref>[http://www.drugs.com/nda/cethromycin_081001.html Cethromycin New Drug Application]</ref>
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.<ref>[https://www.drugs.com/nda/cethromycin_081001.html Cethromycin New Drug Application]</ref>


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

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.<ref>{{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}}</ref>


==References==
==References==
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{{Macrolides, lincosamides and streptogramins}}
{{Macrolides, lincosamides and streptogramins}}



[[Category:Quinolines]]
[[Category:Quinolines]]
[[Category:Ketolide antibiotics]]
[[Category:Ketolide antibiotics]]


{{antibiotic-stub}}

[[de:Cethromycin]]
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