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{{Drugbox|
{{Drugbox
|IUPAC_name = ''9-chloro-6-(2-fluorophenyl)-4-hydroxy''<br />''-2-(2-hydroxyethyl)-2,5-diazabicyclo''<br />''[5.4.0]undeca-5,8,10,12-tetraen-3-one''
| Verifiedfields = changed
| Watchedfields = changed
| IUPAC_name = ''9-chloro-6-(2-fluorophenyl)-4-hydroxy''<br />''-2-(2-hydroxyethyl)-2,5-diazabicyclo''<br />''[5.4.0]undeca-5,8,10,12-tetraen-3-one''
| image = Doxefazepam.svg
| image = Doxefazepam.svg
| width=180
| width = 170
| image2= Doxefazepam3d.png
| image2 = Doxefazepam3d.png
| CAS_number=40762-15-0
| width2 = 140
| ATC_prefix=N05
 
| ATC_suffix=CD12
<!--Clinical data-->
| ATC_supplemental=
| tradename =   
| PubChem=38668
| DrugBank=?
| C=17 | H=14 | Cl=1 | F=1 | N=2 | O=3
| molecular_weight = 348.8
| bioavailability= ?
| metabolism = [[Liver|Hepatic]]
| elimination_half-life= ?
| excretion =  [[Kidney|Renal]]
| pregnancy_category = ?
| pregnancy_category = ?
| legal_status = [[Schedule IV controlled substance|Schedule IV]](US)
| legal_status = [[Schedule IV controlled substance|Schedule IV]](US)
| routes_of_administration= Oral
| routes_of_administration = Oral
 
<!--Pharmacokinetic data-->
| bioavailability = ?
| metabolism = [[Liver|Hepatic]]
| elimination_half-life = 3-4 hours<ref>http://www.intox.org/databank/documents/pharm/doxefzpm/iarc796.htm</ref>
| excretion = [[Kidney|Renal]]
 
<!--Identifiers-->
| CAS_number_Ref = {{cascite|changed|??}}
| CAS_number = 40762-15-0
| ATC_prefix = N05
| ATC_suffix = CD12
| PubChem = 38668
| DrugBank_Ref = {{drugbankcite|changed|drugbank}}
| DrugBank = ?
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 35431
| UNII_Ref = {{fdacite|changed|FDA}}
| UNII = 231RV72C8L verifiedrevid = 457288969
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D07327
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 64677
 
<!--Chemical data-->
| C=17 | H=14 | Cl=1 | F=1 | N=2 | O=3
| molecular_weight = 348.8
| smiles = FC1=CC=CC=C1C2=NC(C(N(CCO)C3=C2C=C(C=C3)Cl)=O)O
| InChI = 1/C17H14ClFN2O3/c18-10-5-6-14-12(9-10)15(11-3-1-2-4-13(11)19)20-16(23)17(24)21(14)7-8-22/h1-6,9,16,22-23H,7-8H2
| InChIKey = VOJLELRQLPENHL-UHFFFAOYAT
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C17H14ClFN2O3/c18-10-5-6-14-12(9-10)15(11-3-1-2-4-13(11)19)20-16(23)17(24)21(14)7-8-22/h1-6,9,16,22-23H,7-8H2
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = VOJLELRQLPENHL-UHFFFAOYSA-N
}}
}}
'''Doxefazepam''' (marketed under brand name Doxans) is a drug which is a [[benzodiazepine]] derivative. It possesses [[anxiolytic]], [[anticonvulsant]], [[sedative]] and [[skeletal muscle relaxant]] properties. According to Babbini and colleagues in 1975, this derivative of [[flurazepam]] was between 2 and 4 times more potent than the latter while at the same time being half as toxic in laboratory animals.<ref name=SAS_643_1975>{{cite journal | first = M. | last = Babbini | coauthors = Torrielli MV, Strumia E, Gaiardi M, Bartoletti M, De Marchi F. | month = August | year = 1975 | title = Sedative-hypnotic properties of a new benzodiazepine in comparison with flurazepam. Pharmacological and clinical findings | journal = Arzneimittel-Forschung | volume = 25 | issue = 8 | pages = 1294-1300 | id = {{PMID|241364}}}}</ref>
'''Doxefazepam''' (marketed under brand name '''Doxans''') is a [[benzodiazepine]] derivative drug developed by Schiapparelli in the 1970s.<ref>DE Patent 2338058 - BENZODIAZEPINVERBINDUNGEN FUER DIE THERAPIE</ref> It possesses [[anxiolytic]], [[anticonvulsant]], [[sedative]] and [[skeletal muscle relaxant]] properties. It is used therapeutically as a [[hypnotic]].<ref>{{cite journal |pmid=6483162 |year=1984 |last1=Rodriguez |first1=G |last2=Rosadini |last3=Sannita |last4=Strumia |title=Effects of doxefazepam on normal sleep. An EEG and neuropsychological study |volume=11 |issue=2 |pages=133–9 |journal=Neuropsychobiology |first2=G |first3=WG |first4=E |doi=10.1159/000118066}}</ref> According to Babbini and colleagues in 1975, this derivative of [[flurazepam]] was between 2 and 4 times more potent than the latter while at the same time being half as toxic in laboratory animals.<ref name=SAS_643_1975>{{cite journal | first = M. | last = Babbini | coauthors = Torrielli MV, Strumia E, Gaiardi M, Bartoletti M, De Marchi F. |date=August 1975 | title = Sedative-hypnotic properties of a new benzodiazepine in comparison with flurazepam. Pharmacological and clinical findings | journal = Arzneimittel-Forschung | volume = 25 | issue = 8 | pages = 1294–1300 | pmid = 241364 }}</ref> Section 5.5 of the article ''Doxefazepam'' in volume 66 of the [[World Health Organization|World Health Organization's]] (WHO) and [[International Agency for Research on Cancer|International Agency for Research on Cancer's]] (IARC) ''IARC Monographs On The Evaluation Of Carcinogenic Risks To Humans'', an article describing the carcinogenic/toxic effects of doxefazepam on humans and experimental animals, states that there is "inadequate evidence in humans for the [[carcinogen]]icity of doxefazepam" and limited evidence in experimental for the carcinogenicity of doxefazepam," and concluded that the overall evaluation of the substance's carcinogenicity to humans is "not classifiable."<ref>{{cite journal |date=13–20 Feb 1996 |title=Doxefazepam |url=http://monographs.iarc.fr/ENG/Monographs/vol66/mono66-7.pdf |journal=IARC Monographs On The Evaluation Of Carcinogenic Risks To Humans |publisher=International Agency For Research On Cancer (IARC) |volume=66 |pages=97–104 |accessdate=10 July 2014}}</ref>
 
==See also==
*[[Benzodiazepine]]


Doxefazepam is not approved for sale in the United States or Canada.
==References==
==References==
<div class="references-small"><references/></div>
{{reflist}}
 
==External links==
==External links==
* [http://www.inchem.org/documents/pims/pharm/pim924.htm Inchem.org - Doxefazepam]
* [http://www.inchem.org/documents/pims/pharm/pim924.htm Inchem.org - Doxefazepam]
* [http://monographs.iarc.fr/ENG/Monographs/vol66/mono66-7.pdf IARC Monographs - Doxefazepam]


{{Benzodiazepines}}
{{Benzodiazepines}}
{{Hypnotics and sedatives}}
{{Hypnotics and sedatives}}
{{GABAAR PAMs}}
[[Category:Benzodiazepines]]
[[Category:Benzodiazepines]]
[[Category:Hypnotics]]
[[Category:Hypnotics]]
[[Category:Organochlorides]]
[[Category:Organofluorides]]
[[Category:Lactams]]
[[Category:Alcohols]]
[[Category:GABAA receptor positive allosteric modulators]]


{{pharma-stub}}


[[la:Doxefazepamum]]
{{sedative-stub}}

Revision as of 13:51, 10 April 2015

Doxefazepam
File:Doxefazepam.svg
Clinical data
Pregnancy
category
  • ?
Routes of
administration		Oral
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability?
MetabolismHepatic
Elimination half-life3-4 hours[1]
ExcretionRenal
Identifiers
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
E number{{#property:P628}}
ECHA InfoCard{{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
FormulaC17H14ClFN2O3
Molar mass348.8
3D model (JSmol)
 ☒N☑Y (what is this?)

Doxefazepam (marketed under brand name Doxans) is a benzodiazepine derivative drug developed by Schiapparelli in the 1970s.[2] It possesses anxiolytic, anticonvulsant, sedative and skeletal muscle relaxant properties. It is used therapeutically as a hypnotic.[3] According to Babbini and colleagues in 1975, this derivative of flurazepam was between 2 and 4 times more potent than the latter while at the same time being half as toxic in laboratory animals.[4] Section 5.5 of the article Doxefazepam in volume 66 of the World Health Organization's (WHO) and International Agency for Research on Cancer's (IARC) IARC Monographs On The Evaluation Of Carcinogenic Risks To Humans, an article describing the carcinogenic/toxic effects of doxefazepam on humans and experimental animals, states that there is "inadequate evidence in humans for the carcinogenicity of doxefazepam" and limited evidence in experimental for the carcinogenicity of doxefazepam," and concluded that the overall evaluation of the substance's carcinogenicity to humans is "not classifiable."[5]

See also

References

  1. ↑ http://www.intox.org/databank/documents/pharm/doxefzpm/iarc796.htm
  2. ↑ DE Patent 2338058 - BENZODIAZEPINVERBINDUNGEN FUER DIE THERAPIE
  3. ↑ Rodriguez, G; Rosadini, G; Sannita, WG; Strumia, E (1984). "Effects of doxefazepam on normal sleep. An EEG and neuropsychological study". Neuropsychobiology. 11 (2): 133–9. doi:10.1159/000118066. PMID 6483162.
  4. ↑ Babbini, M. (August 1975). "Sedative-hypnotic properties of a new benzodiazepine in comparison with flurazepam. Pharmacological and clinical findings". Arzneimittel-Forschung. 25 (8): 1294–1300. PMID 241364. Unknown parameter |coauthors= ignored (help)
  5. ↑ "Doxefazepam" (PDF). IARC Monographs On The Evaluation Of Carcinogenic Risks To Humans. International Agency For Research On Cancer (IARC). 66: 97–104. 13–20 Feb 1996. Retrieved 10 July 2014.

External links

Template:Benzodiazepines

Template:GABAAR PAMs


Template:Sedative-stub

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