Fludiazepam: Difference between revisions

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Fludiazepam
Clinical data
AHFS/Drugs.com	International Drug Names
Pregnancy; category	?;
Routes of; administration	Oral
ATC code	N05BA17 (WHO) ;
Legal status
Legal status	US: Schedule IV ;
Pharmacokinetic data
Bioavailability	?
Metabolism	Hepatic
Elimination half-life	?
Excretion	Renal
Identifiers
	IUPAC name 7-chloro-5-(2-fluorophenyl)-1-methyl-1H-benzo[e][1,4]diazepin-2(3H)-one;
CAS Number	3900-31-0 ;
PubChem CID	3369;
DrugBank	DB01567 ;
ChemSpider	3252 ;
UNII	7F64A2K16Z;
KEGG	D01354 ;
ChEBI	CHEBI:31618 ;
ChEMBL	ChEMBL13291 ;
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
Formula	C16H12ClFN2O
Molar mass	302.7
3D model (JSmol)	Interactive image;
	SMILES O=C1CN=C(C2=CC=CC=C2F)C3=CC(Cl)=CC=C3N1C;
	InChI InChI=1S/C16H12ClFN2O/c1-20-14-7-6-10(17)8-12(14)16(19-9-15(20)21)11-4-2-3-5-13(11)18/h2-8H,9H2,1H3 ; Key:ROYOYTLGDLIGBX-UHFFFAOYSA-N ;
(verify)

VisualWikitext

Latest revision as of 19:29, 9 April 2015

Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]

Overview

Fludiazepam, marketed under the brand name Erispan^[1]^[2] is a potent benzodiazepine and 2'-fluoro derivative of diazepam,^[3] originally developed by Hoffman-La Roche in the 1960s.^[4] It is marketed in Japan and Taiwan in the form of 0.25 mg tablets, making it around 40x more potent than diazepam. It exerts its pharmacological properties via enhancement of GABAergic inhibition.^[5] Fludiazepam has 4 times more binding affinity for benzodiazepine receptors than diazepam.^[6] It possesses anxiolytic,^[7]^[8]^[9] anticonvulsant, sedative, hypnotic and skeletal muscle relaxant properties.^[10]

As with all benzodiazepines, fludiazepam is used recreationally.^[11]

References

↑ Su, TP.; Chen, TJ.; Hwang, SJ.; Chou, LF.; Fan, AP.; Chen, YC. (Aug 2002). "Utilization of psychotropic drugs in Taiwan: an overview of outpatient sector in 2000". Zhonghua Yi Xue Za Zhi (Taipei). 65 (8): 378–91. PMID 12455808.
↑ "Benzodiazepine Names". non-benzodiazepines.org.uk. Retrieved 2008-12-29.
↑ Neville, GA.; Beckstead, HD.; Shurvell, HF. (Feb 1994). "A Fourier transform-Raman and infrared vibrational study of delorazepam, fludiazepam, flurazepam, and tetrazepam". J Pharm Sci. 83 (2): 143–51. doi:10.1002/jps.2600830207. PMID 7909552.
↑ US Patent 3299053 -ARYL-JH-L,X-BENZODIAZEPIN-Z(LH)-ONES
↑ Tsuchiya, T.; Fukushima, H. (Apr 1978). "Effects of benzodiazepines and pentobarbitone on the gaba-ergic recurrent inhibition of hippocampal neurons". Eur J Pharmacol. 48 (4): 421–4. doi:10.1016/0014-2999(78)90169-3. PMID 648585.
↑ Nakatsuka, I.; Shimizu, H.; Asami, Y.; Katoh, T.; Hirose, A.; Yoshitake, A. (Jan 1985). "Benzodiazepines and their metabolites: relationship between binding affinity to the benzodiazepine receptor and pharmacological activity". Life Sci. 36 (2): 113–9. doi:10.1016/0024-3205(85)90089-X. PMID 2857046.
↑ Okada, S.; Ichiki, K.; Tanokuchi, S.; Ishii, K.; Hamada, H.; Ota, Z. (1994). "Effect of an anxiolytic on lipid profile in non-insulin-dependent diabetes mellitus". J Int Med Res. 22 (6): 338–42. PMID 7895897.
↑ Okada, S.; Ichiki, K.; Tanokuchi, S.; Ishii, K.; Hamada, H.; Ota, Z. (1995). "Improvement of stress reduces glycosylated haemoglobin levels in patients with type 2 diabetes". J Int Med Res. 23 (2): 119–22. PMID 7601294.
↑ Okada, S.; Ichiki, K.; Tanokuchi, S.; Ishii, K.; Hamada, H.; Ota, Z. (1995). "How blood pressure in patients with non-insulin-dependent diabetes mellitus is influenced by stress". J Int Med Res. 23 (5): 377–80. PMID 8529781.
↑ Inoue, H.; Maeno, Y.; Iwasa, M.; Matoba, R.; Nagao, M. (Sep 2000). "Screening and determination of benzodiazepines in whole blood using solid-phase extraction and gas chromatography/mass spectrometry". Forensic Sci Int. 113 (1–3): 367–73. doi:10.1016/S0379-0738(00)00226-7. PMID 10978650.
↑ Shimamine, M.; Masunari, T.; Nakahara, Y. (1993). "[Studies on identification of drugs of abuse by diode array detection. I. Screening-test and identification of benzodiazepines by HPLC-DAD with ICOS software system]". Eisei Shikenjo Hokoku (111): 47–56. PMID 7920567.

Template:Benzodiazepines Template:Anxiolytics

[1] Su, TP.; Chen, TJ.; Hwang, SJ.; Chou, LF.; Fan, AP.; Chen, YC. (Aug 2002). "Utilization of psychotropic drugs in Taiwan: an overview of outpatient sector in 2000". Zhonghua Yi Xue Za Zhi (Taipei). 65 (8): 378–91. PMID 12455808.

[2] "Benzodiazepine Names". non-benzodiazepines.org.uk. Retrieved 2008-12-29.

[3] Neville, GA.; Beckstead, HD.; Shurvell, HF. (Feb 1994). "A Fourier transform-Raman and infrared vibrational study of delorazepam, fludiazepam, flurazepam, and tetrazepam". J Pharm Sci. 83 (2): 143–51. doi:10.1002/jps.2600830207. PMID 7909552.

[4] US Patent 3299053 -ARYL-JH-L,X-BENZODIAZEPIN-Z(LH)-ONES

[5] Tsuchiya, T.; Fukushima, H. (Apr 1978). "Effects of benzodiazepines and pentobarbitone on the gaba-ergic recurrent inhibition of hippocampal neurons". Eur J Pharmacol. 48 (4): 421–4. doi:10.1016/0014-2999(78)90169-3. PMID 648585.

[6] Nakatsuka, I.; Shimizu, H.; Asami, Y.; Katoh, T.; Hirose, A.; Yoshitake, A. (Jan 1985). "Benzodiazepines and their metabolites: relationship between binding affinity to the benzodiazepine receptor and pharmacological activity". Life Sci. 36 (2): 113–9. doi:10.1016/0024-3205(85)90089-X. PMID 2857046.

[7] Okada, S.; Ichiki, K.; Tanokuchi, S.; Ishii, K.; Hamada, H.; Ota, Z. (1994). "Effect of an anxiolytic on lipid profile in non-insulin-dependent diabetes mellitus". J Int Med Res. 22 (6): 338–42. PMID 7895897.

[8] Okada, S.; Ichiki, K.; Tanokuchi, S.; Ishii, K.; Hamada, H.; Ota, Z. (1995). "Improvement of stress reduces glycosylated haemoglobin levels in patients with type 2 diabetes". J Int Med Res. 23 (2): 119–22. PMID 7601294.

[9] Okada, S.; Ichiki, K.; Tanokuchi, S.; Ishii, K.; Hamada, H.; Ota, Z. (1995). "How blood pressure in patients with non-insulin-dependent diabetes mellitus is influenced by stress". J Int Med Res. 23 (5): 377–80. PMID 8529781.

[10] Inoue, H.; Maeno, Y.; Iwasa, M.; Matoba, R.; Nagao, M. (Sep 2000). "Screening and determination of benzodiazepines in whole blood using solid-phase extraction and gas chromatography/mass spectrometry". Forensic Sci Int. 113 (1–3): 367–73. doi:10.1016/S0379-0738(00)00226-7. PMID 10978650.

[11] Shimamine, M.; Masunari, T.; Nakahara, Y. (1993). "[Studies on identification of drugs of abuse by diode array detection. I. Screening-test and identification of benzodiazepines by HPLC-DAD with ICOS software system]". Eisei Shikenjo Hokoku (111): 47–56. PMID 7920567.

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[2]

[3]

[4]

[5]

[6]

[7]

[8]

[9]

[10]

[11]

@@ Line 1: / Line 1: @@
-{{drugbox |
+{{Drugbox
-|IUPAC_name = ''9-chloro-6-(2-fluorophenyl)- 2-methyl-2,5-diazabicyclo [5.4.0]undeca- 5,8,10,12-tetraen-3-one''
+| Watchedfields = changed
-| image = Fludiazepam.svg
+| verifiedrevid = 443821344
-| width=180
+| IUPAC_name = ''7-chloro-5-(2-fluorophenyl)-1-methyl-1H-benzo[e][1,4]diazepin-2(3H)-one''
-| image2 = Fludiazepam3d.png
+| image = Fludiazepam00.png
-| CAS_number=3900-31-0
+| width = 170
-| ATC_prefix=N05
+| image2 = Fludiazepam000.png
-| ATC_suffix=BA17
-| PubChem=3369
+<!--Clinical data-->
-| DrugBank=?
+| tradename =
-| C=16 | H=12 | Cl=1 | F=1 | N=2 | O=1
+| Drugs.com = {{drugs.com|international|fludiazepam}}
-|molecular_weight = 302.7
+| pregnancy_category = ?
-|bioavailability = ?
+| legal_US = Schedule IV
-|metabolism = [[Liver|Hepatic]]
+| routes_of_administration = Oral
-|elimination_half-life = ?
-|excretion = [[Kidney|Renal]]
+<!--Pharmacokinetic data-->
-|pregnancy_category = ?
+| bioavailability = ?
-|legal_status = [[Schedule IV controlled substance|Schedule IV]](US)
+| metabolism = [[Liver|Hepatic]]
-|routes_of_administration = Oral
+| elimination_half-life = ?
+| excretion = [[Kidney|Renal]]
+<!--Identifiers-->
+| CASNo_Ref = {{cascite|correct|CAS}}
+| CAS_number_Ref = {{cascite|correct|??}}
+| CAS_number = 3900-31-0
+| ATC_prefix = N05
+| ATC_suffix = BA17
+| PubChem = 3369
+| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
+| DrugBank = DB01567
+| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
+| ChemSpiderID = 3252
+| UNII_Ref = {{fdacite|correct|FDA}}
+| UNII = 7F64A2K16Z
+| KEGG_Ref = {{keggcite|correct|kegg}}
+| KEGG = D01354
+| ChEBI_Ref = {{ebicite|correct|EBI}}
+| ChEBI = 31618
+| ChEMBL_Ref = {{ebicite|correct|EBI}}
+| ChEMBL = 13291
+<!--Chemical data-->
+| C=16 | H=12 | Cl=1 | F=1 | N=2 | O=1
+| molecular_weight = 302.7
+| smiles = O=C1CN=C(C2=CC=CC=C2F)C3=CC(Cl)=CC=C3N1C
+| InChI = 1/C16H12ClFN2O/c1-20-14-7-6-10(17)8-12(14)16(19-9-15(20)21)11-4-2-3-5-13(11)18/h2-8H,9H2,1H3
+| InChIKey = ROYOYTLGDLIGBX-UHFFFAOYAM
+| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
+| StdInChI = 1S/C16H12ClFN2O/c1-20-14-7-6-10(17)8-12(14)16(19-9-15(20)21)11-4-2-3-5-13(11)18/h2-8H,9H2,1H3
+| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
+| StdInChIKey = ROYOYTLGDLIGBX-UHFFFAOYSA-N
 }}
-'''Fludiazepam''' (marketed under the brand name Erispan) is a drug which is a [[benzodiazepine]] derivative. It possesses [[anxiolytic]], [[anticonvulsant]], [[sedative]] and [[skeletal muscle relaxant]] properties.
+__NOTOC__
+{{SI}}
+{{CMG}}
+==Overview==
+'''Fludiazepam''', marketed under the brand name '''Erispan'''<ref>{{Cite journal | last1 = Su | first1 = TP. | last2 = Chen | first2 = TJ. | last3 = Hwang | first3 = SJ. | last4 = Chou | first4 = LF. | last5 = Fan | first5 = AP. | last6 = Chen | first6 = YC. | title = Utilization of psychotropic drugs in Taiwan: an overview of outpatient sector in 2000. | journal = Zhonghua Yi Xue Za Zhi (Taipei) | volume = 65 | issue = 8 | pages = 378–91 |date=Aug 2002 | PMID = 12455808 }}</ref><ref>{{cite web| url= http://www.non-benzodiazepines.org.uk/benzodiazepine-names.html| title=Benzodiazepine Names| accessdate=2008-12-29| publisher=non-benzodiazepines.org.uk}}</ref> is a potent [[benzodiazepine]] and 2'-fluoro derivative of [[diazepam]],<ref>{{Cite journal | last1 = Neville | first1 = GA. | last2 = Beckstead | first2 = HD. | last3 = Shurvell | first3 = HF. | title = A Fourier transform-Raman and infrared vibrational study of delorazepam, fludiazepam, flurazepam, and tetrazepam. | journal = J Pharm Sci | volume = 83 | issue = 2 | pages = 143–51 |date=Feb 1994 | PMID = 7909552 | doi=10.1002/jps.2600830207}}</ref> originally developed by [[Hoffman-La Roche]] in the 1960s.<ref>US Patent 3299053 -ARYL-JH-L,X-BENZODIAZEPIN-Z(LH)-ONES</ref> It is marketed in [[Japan]] and [[Taiwan]] in the form of 0.25&nbsp;mg tablets, making it around 40x more potent than diazepam. It exerts its pharmacological properties via enhancement of GABAergic inhibition.<ref>{{Cite journal | last1 = Tsuchiya | first1 = T. | last2 = Fukushima | first2 = H. | title = Effects of benzodiazepines and pentobarbitone on the gaba-ergic recurrent inhibition of hippocampal neurons. | journal = Eur J Pharmacol | volume = 48 | issue = 4 | pages = 421–4 |date=Apr 1978 | PMID = 648585 | doi=10.1016/0014-2999(78)90169-3}}</ref> Fludiazepam has 4 times more binding affinity for benzodiazepine receptors than [[diazepam]].<ref>{{Cite journal | last1 = Nakatsuka | first1 = I. | last2 = Shimizu | first2 = H. | last3 = Asami | first3 = Y. | last4 = Katoh | first4 = T. | last5 = Hirose | first5 = A. | last6 = Yoshitake | first6 = A. | title = Benzodiazepines and their metabolites: relationship between binding affinity to the benzodiazepine receptor and pharmacological activity. | journal = Life Sci | volume = 36 | issue = 2 | pages = 113–9 |date=Jan 1985 | pmid = 2857046 | doi=10.1016/0024-3205(85)90089-X}}</ref> It possesses [[anxiolytic]],<ref>{{Cite journal | last1 = Okada | first1 = S. | last2 = Ichiki | first2 = K. | last3 = Tanokuchi | first3 = S. | last4 = Ishii | first4 = K. | last5 = Hamada | first5 = H. | last6 = Ota | first6 = Z. | title = Effect of an anxiolytic on lipid profile in non-insulin-dependent diabetes mellitus. | journal = J Int Med Res | volume = 22 | issue = 6 | pages = 338–42 | PMID = 7895897 | year=1994}}</ref><ref>{{Cite journal | last1 = Okada | first1 = S. | last2 = Ichiki | first2 = K. | last3 = Tanokuchi | first3 = S. | last4 = Ishii | first4 = K. | last5 = Hamada | first5 = H. | last6 = Ota | first6 = Z. | title = Improvement of stress reduces glycosylated haemoglobin levels in patients with type 2 diabetes. | journal = J Int Med Res | volume = 23 | issue = 2 | pages = 119–22 | PMID = 7601294 | year=1995}}</ref><ref>{{Cite journal | last1 = Okada | first1 = S. | last2 = Ichiki | first2 = K. | last3 = Tanokuchi | first3 = S. | last4 = Ishii | first4 = K. | last5 = Hamada | first5 = H. | last6 = Ota | first6 = Z. | title = How blood pressure in patients with non-insulin-dependent diabetes mellitus is influenced by stress. | journal = J Int Med Res | volume = 23 | issue = 5 | pages = 377–80 | PMID = 8529781 | year=1995}}</ref> [[anticonvulsant]], [[sedative]], [[hypnotic]] and [[skeletal muscle relaxant]] properties.<ref>{{Cite journal | last1 = Inoue | first1 = H. | last2 = Maeno | first2 = Y. | last3 = Iwasa | first3 = M. | last4 = Matoba | first4 = R. | last5 = Nagao | first5 = M. | title = Screening and determination of benzodiazepines in whole blood using solid-phase extraction and gas chromatography/mass spectrometry. | journal = Forensic Sci Int | volume = 113 | issue = 1-3 | pages = 367–73 |date=Sep 2000 | pmid = 10978650 | doi=10.1016/S0379-0738(00)00226-7}}</ref>
+As with all benzodiazepines, fludiazepam is used recreationally.<ref>{{Cite journal | last1 = Shimamine | first1 = M. | last2 = Masunari | first2 = T. | last3 = Nakahara | first3 = Y. | title = [Studies on identification of drugs of abuse by diode array detection. I. Screening-test and identification of benzodiazepines by HPLC-DAD with ICOS software system] | journal = Eisei Shikenjo Hokoku | issue = 111 | pages = 47–56 | year = 1993 | PMID = 7920567 }}</ref>
 ==References==
-* {{ja icon}} [http://med.ds-pharma.co.jp/medicine/ryouiki/seishin/doc/erispan_tabfgr_tenpu.pdf Erispan® フルジアゼパム錠，細粒] (PDF) Dainippon Sumitomo Pharma. November 2005.
+{{Reflist|2}}
-==External links==
-* {{ja icon}} [http://www.ds-pharma.co.jp Official Dainippon Sumitomo Pharma Website]
 {{Benzodiazepines}}
 {{Anxiolytics}}
 [[Category:Benzodiazepines]]
 [[Category:Sedatives]]
 [[Category:Hypnotics]]
 [[Category:Anticonvulsants]]
-[[Category:Muscle relaxants]]
 [[Category:Anxiolytics]]
+[[Category:Lactams]]
+[[Category:Organochlorides]]
-{{pharma-stub}}
+[[Category:Organofluorides]]
+[[Category:Drug]]
-[[ja:フルジアゼパム]]
-[[sv:Fludiazepam]]
-{{WikiDoc Sources}}

Clinical data


AHFS/Drugs.com	International Drug Names
Pregnancy category	?
Routes of administration	Oral
ATC code	N05BA17 (WHO)
Legal status
Legal status	US: Schedule IV
Pharmacokinetic data
Bioavailability	?
Metabolism	Hepatic
Elimination half-life	?
Excretion	Renal
Identifiers
IUPAC name 7-chloro-5-(2-fluorophenyl)-1-methyl-1H-benzo[e][1,4]diazepin-2(3H)-one
CAS Number	3900-31-0^Y
PubChem CID	3369
DrugBank	DB01567^Y
ChemSpider	3252^Y
UNII	7F64A2K16Z
KEGG	D01354^Y
ChEBI	CHEBI:31618^Y
ChEMBL	ChEMBL13291^Y
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
Formula	C₁₆H₁₂ClFN₂O
Molar mass	302.7
3D model (JSmol)	Interactive image
SMILES O=C1CN=C(C2=CC=CC=C2F)C3=CC(Cl)=CC=C3N1C
InChI InChI=1S/C16H12ClFN2O/c1-20-14-7-6-10(17)8-12(14)16(19-9-15(20)21)11-4-2-3-5-13(11)18/h2-8H,9H2,1H3^Y Key:ROYOYTLGDLIGBX-UHFFFAOYSA-N^Y
(verify)

Fludiazepam: Difference between revisions

Latest revision as of 19:29, 9 April 2015

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