Jump to content

Alatrofloxacin: Difference between revisions

From Wikipedia, the free encyclopedia
Browse history interactively
← Previous edit
Content deleted Content added
VisualWikitext
CheMoBot (talk | contribs)
Bots
141,565 edits
Updating {{drugbox}} (changes to verified fields - added verified revid - updated 'ChEBI_Ref', 'KEGG_Ref', 'CAS_number_Ref') per Chem/Drugbox validation (report errors or [[user talk:Che...
m Cleaned up using AutoEd
 
(32 intermediate revisions by 23 users not shown)
Line 1: Line 1:
{{Short description|Chemical compound}}
{{ref improve|date=August 2014}}
{{Drugbox
{{Drugbox
| Verifiedfields = changed
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 456676786
| verifiedrevid = 477316351
| IUPAC_name = 7-[(1''R'',5''S'')-6-{[(2''S'')-1-{[(2''S'')-<br>2-aminopropanoyl]amino}-1-oxopropan-2-yl]amino}-<br>3-azabicyclo[3.1.0]hexan-3-yl]-1-(2,4-difluorophenyl)-<br>6-fluoro-4-oxo-1,8-naphthyridine-3-carboxylic&nbsp;acid
| IUPAC_name = 7-[(1''R'',5''S'')-6-<nowiki/>{[(2''S'')-1-<nowiki/>{[(2''S'')-2-Aminopropanoyl]amino}-1-oxopropan-2-yl]amino}-3-azabicyclo[3.1.0]hexan-3-yl]-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,8-naphthyridine-3-carboxylic acid
| image = Alatrofloxacin.svg
| image = Alatrofloxacin.svg
| width = 250
| width = 250


<!--Clinical data-->
<!--Clinical data-->
| tradename =
| tradename =
| Drugs.com = {{drugs.com|CONS|alatrofloxacin}}
| Drugs.com = {{drugs.com|CONS|alatrofloxacin}}
| MedlinePlus = a605016
| MedlinePlus = a605016
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| pregnancy_US = C
| pregnancy_US = C
| pregnancy_category =
| pregnancy_category =
| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
| legal_CA = <!-- / Schedule I, II, III, IV, V, VI, VII, VIII -->
| legal_CA = <!-- / Schedule I, II, III, IV, V, VI, VII, VIII -->
Line 29: Line 32:
<!--Identifiers-->
<!--Identifiers-->
| CAS_number_Ref = {{cascite|changed|??}}
| CAS_number_Ref = {{cascite|changed|??}}
| CAS_number = 157182-32-6
| CAS_number = 146961-76-4
| CAS_supplemental = {{CAS|157605-25-9}}
| ATC_prefix = none
| ATC_prefix = none
| ATC_suffix =
| ATC_suffix =
| PubChem = 5489474
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank =
| DrugBank =
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 21106252
| ChemSpiderID = 21243647
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 7QVV6I50DT
| UNII = 7QVV6I50DT
Line 44: Line 45:


<!--Chemical data-->
<!--Chemical data-->
| C=26 | H=25 | F=3 | N=6 | O=5
| C=26 | H=25 | F=3 | N=6 | O=5

| molecular_weight = 558.509 g/mol
| smiles = Fc1ccc(c(F)c1)N/3c2nc(c(F)cc2C(=O)C(\C(=O)O)=C\3)N5C[C@@H]4C(NC(=O)[C@@H](NC(=O)[C@@H](N)C)C)[C@@H]4C5
| smiles = C[C@@H](C(=O)N[C@@H](C)C(=O)N[C@H]1[C@H]2[C@@H]1CN(C2)C3=C(C=C4C(=O)C(=CN(C4=N3)C5=C(C=C(C=C5)F)F)C(=O)O)F)N
⚫
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| InChI = 1/C26H25F3N6O5/c1-10(30)24(37)31-11(2)25(38)32-20-14-7-34(8-15(14)20)23-18(29)6-13-21(36)16(26(39)40)9-35(22(13)33-23)19-4-3-12(27)5-17(19)28/h3-6,9-11,14-15,20H,7-8,30H2,1-2H3,(H,31,37)(H,32,38)(H,39,40)/t10-,11-,14-,15+,20?/m0/s1
| StdInChI = 1S/C26H25F3N6O5/c1-10(30)24(37)31-11(2)25(38)32-20-14-7-34(8-15(14)20)23-18(29)6-13-21(36)16(26(39)40)9-35(22(13)33-23)19-4-3-12(27)5-17(19)28/h3-6,9-11,14-15,20H,7-8,30H2,1-2H3,(H,31,37)(H,32,38)(H,39,40)/t10-,11-,14-,15+,20+/m0/s1
⚫
| InChIKey = UUZPPAMZDFLUHD-LZGARRQBBY
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
⚫
| StdInChIKey = UUZPPAMZDFLUHD-VUJLHGSVSA-N
| StdInChI = 1S/C26H25F3N6O5/c1-10(30)24(37)33-25(38)11(2)31-20-14-7-34(8-15(14)20)23-18(29)6-13-21(36)16(26(39)40)9-35(22(13)32-23)19-4-3-12(27)5-17(19)28/h3-6,9-11,14-15,20,31H,7-8,30H2,1-2H3,(H,39,40)(H,33,37,38)/t10?,11?,14-,15+,20?
⚫
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = GAJLLIJXQAMBHW-HVOYUNNHSA-N
}}
}}
'''Alatrofloxacin''' ('''Trovan IV''') is a [[fluoroquinolone]] [[antibiotic]] developed by [[Pfizer]], delivered as a [[mesylate]] salt.<ref>{{cite web|url=http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=5489474|title=PubChem CID 5489474}}</ref> It is the parental [[prodrug]] of [[trovafloxacin]] (Trovan) meant for [[intravenous therapy|intravenous]] administration. Trovafloxacin is a broad-spectrum antibiotic introduced in 1998 that encountered criticism for its Nigerian trials and adverse clinical reactions.<ref>{{cite journal |author=Hall IH, Schwab UE, Ward ES, Ives TJ |title=Effects of alatrofloxacin, the parental prodrug of trovafloxacin, on phagocytic, anti-inflammatory and immunomodulation events of human THP-1 monocytes |journal=Biomed. Pharmacother. |volume=57 |issue=8 |pages=359–65 |year=2003 |pmid=14568230 |doi=10.1016/S0753-3322(03)00054-4}}</ref><ref>{{cite journal |author=Lenzer J |title=Secret report surfaces showing that Pfizer was at fault in Nigerian drug tests |journal=[[British Medical Journal|BMJ]] |volume=332 |issue=7552 |pages=1233 |year=2006 |pmid=16735322 |doi=10.1136/bmj.332.7552.1233-a |pmc=1471980}}</ref>


'''Alatrofloxacin''' ('''Trovan IV''') is a [[fluoroquinolone antibiotic]] developed by [[Pfizer]], delivered as a [[mesylate]] [[salt (chemistry)|salt]].<ref>{{cite web|title=Center for Drug Evaluation and Research {{ndash}} Application Number: 020759/020760 {{ndash}} Chemistry Review(s)|publisher=[[Food and Drug Administration]]|url=http://www.accessdata.fda.gov/drugsatfda_docs/nda/97/020760a_chemr.pdf|access-date=29 August 2014}}</ref>
Trovafloxacin and alatrofloxacin were both withdrawn from the U.S. market in 2001.


[[Trovafloxacin]] and alatrofloxacin were both withdrawn from the U.S. market in June 2006 due to [[hepatotoxicity]] leading to liver transplant or death.<ref>{{cite journal | vauthors = Qureshi ZP, Seoane-Vazquez E, Rodriguez-Monguio R, Stevenson KB, Szeinbach SL | title = Market withdrawal of new molecular entities approved in the United States from 1980 to 2009 | journal = Pharmacoepidemiology and Drug Safety | volume = 20 | issue = 7 | pages = 772–777 | date = July 2011 | pmid = 21574210 | doi = 10.1002/pds.2155 | s2cid = 23821961 }}</ref>
==See also==
*[[Fluoroquinolone toxicity]]
*[[Fluoroquinolone]]


==References==
== See also ==
* [[Fluoroquinolones]]
<references />

== References ==
{{Reflist}}


{{QuinoloneAntiBiotics}}
{{QuinoloneAntiBiotics}}
Line 69: Line 68:
[[Category:Fluoroquinolone antibiotics]]
[[Category:Fluoroquinolone antibiotics]]
[[Category:Prodrugs]]
[[Category:Prodrugs]]
[[Category:Hepatotoxins]]
[[Category:Withdrawn drugs]]
[[Category:Withdrawn drugs]]
[[Category:1,8 Naphthyridines]]
[[Category:Naphthyridines]]
[[Category:Carboxylic acids]]
⚫
{{antibiotic-stub}}


⚫
{{antibiotic-stub}}
[[it:Alatrofloxacina]]

Latest revision as of 01:55, 31 December 2022

Alatrofloxacin
Clinical data
AHFS/Drugs.comMicromedex Detailed Consumer Information
MedlinePlusa605016
Routes of
administration		Intravenous
ATC code
  • none
Legal status
Legal status
  • Withdrawn
Pharmacokinetic data
BioavailabilityN/A
Protein binding76% (trovafloxacin)
MetabolismQuickly hydrolyzed to trovafloxacin
Elimination half-life9 to 12 hours (trovafloxacin)
ExcretionFecal and renal (trovafloxacin)
Identifiers
  • 7-[(1R,5S)-6-{[(2S)-1-{[(2S)-2-Aminopropanoyl]amino}-1-oxopropan-2-yl]amino}-3-azabicyclo[3.1.0]hexan-3-yl]-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,8-naphthyridine-3-carboxylic acid
CAS Number
ChemSpider
UNII
ChEMBL
Chemical and physical data
FormulaC26H25F3N6O5
Molar mass558.518 g·mol−1
3D model (JSmol)
  • C[C@@H](C(=O)N[C@@H](C)C(=O)N[C@H]1[C@H]2[C@@H]1CN(C2)C3=C(C=C4C(=O)C(=CN(C4=N3)C5=C(C=C(C=C5)F)F)C(=O)O)F)N
  • InChI=1S/C26H25F3N6O5/c1-10(30)24(37)31-11(2)25(38)32-20-14-7-34(8-15(14)20)23-18(29)6-13-21(36)16(26(39)40)9-35(22(13)33-23)19-4-3-12(27)5-17(19)28/h3-6,9-11,14-15,20H,7-8,30H2,1-2H3,(H,31,37)(H,32,38)(H,39,40)/t10-,11-,14-,15+,20+/m0/s1 ☒N
  • Key:UUZPPAMZDFLUHD-VUJLHGSVSA-N ☒N
 ☒NcheckY (what is this?)  (verify)

Alatrofloxacin (Trovan IV) is a fluoroquinolone antibiotic developed by Pfizer, delivered as a mesylate salt.[1]

Trovafloxacin and alatrofloxacin were both withdrawn from the U.S. market in June 2006 due to hepatotoxicity leading to liver transplant or death.[2]

See also[edit]

References[edit]

  1. ^ "Center for Drug Evaluation and Research – Application Number: 020759/020760 – Chemistry Review(s)" (PDF). Food and Drug Administration. Retrieved 29 August 2014.
  2. ^ Qureshi ZP, Seoane-Vazquez E, Rodriguez-Monguio R, Stevenson KB, Szeinbach SL (July 2011). "Market withdrawal of new molecular entities approved in the United States from 1980 to 2009". Pharmacoepidemiology and Drug Safety. 20 (7): 772–777. doi:10.1002/pds.2155. PMID 21574210. S2CID 23821961.
Stub icon

This systemic antibiotic-related article is a stub. You can help Wikipedia by expanding it.

Retrieved from "https://en.wikipedia.org/w/index.php?title=Alatrofloxacin&oldid=1130610533"