Adinazolam: Difference between revisions

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Adinazolam
Clinical data
Pregnancy; category	?;
Routes of; administration	Oral
ATC code	N05BA07 (WHO) ;
Legal status
Legal status	Schedule IV(US);
Pharmacokinetic data
Bioavailability	?
Metabolism	Hepatic
Elimination half-life	< 3 hours
Excretion	Renal
Identifiers
	IUPAC name 1-(8-chloro-6-phenyl-4H-[1,2,4]triazolo[4,5-a]; [1,4]benzodiazepin-1-yl)-N,N-dimethylmethanamine;
CAS Number	37115-32-5 ;
PubChem CID	37632;
DrugBank	DB00546 ;
ChemSpider	34519 ;
UNII	KN08449444;
KEGG	D02770 ;
ChEBI	CHEBI:251412 ;
ChEMBL	ChEMBL328250 ;
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	C19H18ClN5
Molar mass	351.8
3D model (JSmol)	Interactive image;
	SMILES Clc3cc2\C(=N/Cc1nnc(n1c2cc3)CN(C)C)c4ccccc4;
	InChI InChI=1S/C19H18ClN5/c1-24(2)12-18-23-22-17-11-21-19(13-6-4-3-5-7-13)15-10-14(20)8-9-16(15)25(17)18/h3-10H,11-12H2,1-2H3 ; Key:GJSLOMWRLALDCT-UHFFFAOYSA-N ;
(verify)

VisualWikitext

Latest revision as of 13:06, 10 April 2015

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

Overview

Adinazolam^[1] (marketed under the brand name Deracyn) is a benzodiazepine derivative, and more specifically, a triazolobenzodiazepine (TBZD). It possesses anxiolytic, anticonvulsant, sedative, and antidepressant^[2] properties. Adinazolam was developed by Dr. Jackson B. Hester, who was seeking to enhance the antidepressant properties of alprazolam, which he also developed.^[3] Adinazolam was never FDA approved and never made available to the public market.

Indications

Adinazolam is indicated as a treatment for depression and anxiety.

Pharmacodynamics and pharmacokinetics

Adinazolam binds to peripheral-type benzodiazepine receptors that interact allosterically with GABA receptors as an agonist to produce inhibitory effects.

Metabolism

Adinazolam was reported to have active metabolites in the August 1984 issue of The Journal of Pharmacy and Pharmacology.^[4] The main metabolite is N-desmethyladinazolam.^[5] NDMAD has an approximately 25-fold high affinity for benzodiazepine receptors as compared to its precursor, accounting for the benzodiazepine-like effects after oral administration. (REF1) Multiple N-dealkylations lead to the removal dimethyl-aminoethyl side chain, leading to the difference in its potency. (REF5) The other two metabolites are alpha-hydroxyalprazolam and estazolam.^[6] In the August 1986 issue of that same journal, Sethy, Francis and Day reported that proadifen inhibited the formation of N-desmethyladinazolam.^[7]

References

↑ FR Patent 2248050
↑ Lahti, Robert A.; Vimala H. Sethy; Craig Barsuhn; Jackson B. Hester (November 1983). "Pharmacological profile of the antidepressant adinazolam, a triazolobenzodiazepine". Neuropharmacology. 22 (11): 1277–82. doi:10.1016/0028-3908(83)90200-9. PMID 6320036.
↑ "Discovers Award 2004" (PDF). Special Publications. Pharmaceutical Research and Manufacturers of America. April 2004. p. 39. Archived from the original (PDF) on August 24, 2006. Retrieved August 18, 2006.
↑ Sethy, Vimala H.; R. J. Collins; E. G. Daniels (August 1984). "Determination of biological activity of adinazolam and its metabolites". Journal of Pharmacy and Pharmacology. 36 (8): 546–8. doi:10.1111/j.2042-7158.1984.tb04449.x. PMID 6148400.
↑ Peng, G. W. (August 1984). "Assay of adinazolam in plasma by liquid chromatography". Journal of Pharmaceutical Sciences. 73 (8): 1173–5. doi:10.1002/jps.2600730840. PMID 6491930.
↑ Fraser, A. D.; A. F. Isner; W. Bryan (November–December 1993). "Urinary screening for adinazolam and its major metabolites by the Emit d.a.u. and FPIA benzodiazepine assays with confirmation by HPLC". Journal of Analytical Toxicology. 17 (7): 427–31. doi:10.1093/jat/17.7.427. PMID 8309217.
↑ Sethy, Vimala H.; Jonathan W. Francis; J. S. Day (August 1986). "The effect of proadifen on the metabolism of adinazolam". Journal of Pharmacy and Pharmacology. 38 (8): 631–2. doi:10.1111/j.2042-7158.1986.tb03099.x. PMID 2876087.

Template:Anxiolytics Template:Benzodiazepines

[1] FR Patent 2248050

[antidepressant-2] Lahti, Robert A.; Vimala H. Sethy; Craig Barsuhn; Jackson B. Hester (November 1983). "Pharmacological profile of the antidepressant adinazolam, a triazolobenzodiazepine". Neuropharmacology. 22 (11): 1277–82. doi:10.1016/0028-3908(83)90200-9. PMID 6320036.

[Jackson_B_Hester-3] "Discovers Award 2004" (PDF). Special Publications. Pharmaceutical Research and Manufacturers of America. April 2004. p. 39. Archived from the original (PDF) on August 24, 2006. Retrieved August 18, 2006.

[active_metabolites-4] Sethy, Vimala H.; R. J. Collins; E. G. Daniels (August 1984). "Determination of biological activity of adinazolam and its metabolites". Journal of Pharmacy and Pharmacology. 36 (8): 546–8. doi:10.1111/j.2042-7158.1984.tb04449.x. PMID 6148400.

[Peng_1984-5] Peng, G. W. (August 1984). "Assay of adinazolam in plasma by liquid chromatography". Journal of Pharmaceutical Sciences. 73 (8): 1173–5. doi:10.1002/jps.2600730840. PMID 6491930.

[other_metabolites-6] Fraser, A. D.; A. F. Isner; W. Bryan (November–December 1993). "Urinary screening for adinazolam and its major metabolites by the Emit d.a.u. and FPIA benzodiazepine assays with confirmation by HPLC". Journal of Analytical Toxicology. 17 (7): 427–31. doi:10.1093/jat/17.7.427. PMID 8309217.

[Sethy_Francis_Day_1986-7] Sethy, Vimala H.; Jonathan W. Francis; J. S. Day (August 1986). "The effect of proadifen on the metabolism of adinazolam". Journal of Pharmacy and Pharmacology. 38 (8): 631–2. doi:10.1111/j.2042-7158.1986.tb03099.x. PMID 2876087.

[1]

[2]

[3]

[4]

[5]

[6]

[7]

@@ Line 1: / Line 1: @@
-{{Drugbox|
+{{Drugbox
-|IUPAC_name = 1-(8-chloro-6-phenyl-4H-[1,2,4]triazolo[4,5-a][1,4]benzodiazepin-1-yl)-N,N-dimethylmethanamine
+| verifiedrevid = 477242623
-| image=Adinazolam.svg
+| IUPAC_name = 1-(8-chloro-6-phenyl-4H-[1,2,4]triazolo[4,5-a]<br>[1,4]benzodiazepin-1-yl)-N,N-dimethylmethanamine
-| width=200
+| image = Adinazolam.png
-| image2=Adinazolam3d.png
+| width = 200
-| CAS_number=37115-32-5
+| image2 = Adinazolam00.png
-| ATC_prefix=N05
-| ATC_suffix=BA07
+<!--Clinical data-->
-| ATC_supplemental=
+| tradename =
-| PubChem=37632
-| DrugBank=APRD00724
-| C = 19 | H = 18 | Cl = 1 | N = 5
-| molecular_weight = 351.8
-| bioavailability= ?
-| metabolism = [[Liver|Hepatic]]
-| elimination_half-life= < 3 hours
-| excretion =  [[Kidney|Renal]]
 | pregnancy_category = ?
 | legal_status = Schedule IV<sub>([[United States|US]])</sub>
-| routes_of_administration= Oral
+| routes_of_administration = Oral
+<!--Pharmacokinetic data-->
+| bioavailability = ?
+| metabolism = [[Liver|Hepatic]]
+| elimination_half-life = < 3 hours
+| excretion = [[Kidney|Renal]]
+<!--Identifiers-->
+| CASNo_Ref = {{cascite|correct|CAS}}
+| CAS_number_Ref = {{cascite|correct|??}}
+| CAS_number = 37115-32-5
+| ATC_prefix = N05
+| ATC_suffix = BA07
+| PubChem = 37632
+| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
+ | DrugBank = DB00546
+| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
+| ChemSpiderID = 34519
+| UNII_Ref = {{fdacite|correct|FDA}}
+| UNII = KN08449444
+| KEGG_Ref = {{keggcite|correct|kegg}}
+| KEGG = D02770
+| ChEBI_Ref = {{ebicite|correct|EBI}}
+| ChEBI = 251412
+| ChEMBL_Ref = {{ebicite|correct|EBI}}
+| ChEMBL = 328250
+<!--Chemical data-->
+| C=19 | H=18 | Cl=1 | N=5
+| molecular_weight = 351.8
+| smiles = Clc3cc2\C(=N/Cc1nnc(n1c2cc3)CN(C)C)c4ccccc4
+| InChI = 1/C19H18ClN5/c1-24(2)12-18-23-22-17-11-21-19(13-6-4-3-5-7-13)15-10-14(20)8-9-16(15)25(17)18/h3-10H,11-12H2,1-2H3
+| InChIKey = GJSLOMWRLALDCT-UHFFFAOYAY
+| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
+| StdInChI = 1S/C19H18ClN5/c1-24(2)12-18-23-22-17-11-21-19(13-6-4-3-5-7-13)15-10-14(20)8-9-16(15)25(17)18/h3-10H,11-12H2,1-2H3
+| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
+| StdInChIKey = GJSLOMWRLALDCT-UHFFFAOYSA-N
 }}
-'''Adinazolam''' (Deracyn®) is a [[benzodiazepine]] derivative. It possesses [[anxiolytic]], [[anticonvulsant]], [[sedative]], and [[antidepressant]]<ref name=antidepressant>{{cite journal | first = Robert A. | last = Lahti | coauthors = Vimala H. Sethy, Craig Barsuhn, Jackson B. Hester | month = November | year = 1983 | title = Pharmacological profile of the antidepressant adinazolam, a triazolobenzodiazepine. | journal = Neuropharmacology | volume = 22 | issue = 11 | pages = 1277-82 | id = {{PMID|6320036}} }}</ref> properties. Adinazolam was developed by Dr. Jackson B. Hester, who was seeking to enhance the antidepressant properties of [[alprazolam]], which he also developed.<ref name=Jackson_B_Hester>{{cite web | url = http://international.phrma.org/publications/publications//admin/2004-10-12.1086.pdf | title = Discovers Award 2004 | accessmonthday = August 18 | accessyear = 2006 | year = 2004 | month = April | format = PDF | work = Special Publications | publisher = Pharmaceutical Research and Manufactureres of America | pages = 39}}</ref>
+__NOTOC__
+{{SI}}
+{{CMG}}
+==Overview==
+'''Adinazolam'''<ref>FR Patent 2248050</ref> (marketed under the brand name '''Deracyn''') is a [[benzodiazepine]] derivative, and more specifically, a triazolobenzodiazepine (TBZD). It possesses [[anxiolytic]], [[anticonvulsant]], [[sedative]], and [[antidepressant]]<ref name=antidepressant>{{cite journal | first = Robert A. | last = Lahti |author2=Vimala H. Sethy|author3=Craig Barsuhn|author4=Jackson B. Hester |date=November 1983 | title = Pharmacological profile of the antidepressant adinazolam, a triazolobenzodiazepine. | journal = Neuropharmacology | volume = 22 | issue = 11 | pages = 1277–82 | pmid = 6320036 | doi = 10.1016/0028-3908(83)90200-9 }}</ref> properties. Adinazolam was developed by Dr. Jackson B. Hester, who was seeking to enhance the antidepressant properties of [[alprazolam]], which he also developed.<ref name=Jackson_B_Hester>{{cite web | url = http://international.phrma.org/publications/publications//admin/2004-10-12.1086.pdf | title = Discovers Award 2004 | accessdate = August 18, 2006 |date=April 2004| format = PDF | work = Special Publications | publisher = Pharmaceutical Research and Manufacturers of America | pages = 39 |archiveurl = http://web.archive.org/web/20060824202348/http://international.phrma.org/publications/publications/admin/2004-10-12.1086.pdf <!-- Bot retrieved archive --> |archivedate = August 24, 2006}}</ref> Adinazolam was never FDA approved and never made available to the public market.
+==Indications==
+Adinazolam is indicated as a treatment for depression and anxiety.
-==Pharmacology==
+==Pharmacodynamics and pharmacokinetics==
-Adinazolam produces inhibitory effects by binding to GABA receptors. This increases the effects of GABA.
+Adinazolam binds to peripheral-type benzodiazepine receptors that interact allosterically with GABA receptors as an [[agonist]] to produce inhibitory effects.
 ==Metabolism==
-Adinazolam was reported to have active metabolites in the August 1984 issue of ''The Journal of Pharmacy and Pharmacology''.<ref name=active_metabolites>{{cite journal | first = Vimala H. | last = Sethy | coauthors = R. J. Collins and E. G. Daniels | month = August | year = 1984 | title =
+Adinazolam was reported to have active metabolites in the August 1984 issue of ''The Journal of Pharmacy and Pharmacology''.<ref name=active_metabolites>{{cite journal | first = Vimala H. | last = Sethy |author2=R. J. Collins|author3=E. G. Daniels |date=August 1984 | title = Determination of biological activity of adinazolam and its metabolites. | journal = Journal of Pharmacy and Pharmacology | volume = 36 | issue = 8 | pages = 546–8 | pmid = 6148400 | doi = 10.1111/j.2042-7158.1984.tb04449.x }}</ref> The main metabolite is N-desmethyladinazolam.<ref name=Peng_1984>{{cite journal | first = G. W. | last = Peng |date=August 1984 | title = Assay of adinazolam in plasma by liquid chromatography | journal = Journal of Pharmaceutical Sciences | volume = 73 | issue = 8 | pages = 1173–5 | pmid = 6491930 | doi = 10.1002/jps.2600730840 }}</ref> NDMAD has an approximately 25-fold high affinity for benzodiazepine receptors as compared to its precursor, accounting for the benzodiazepine-like effects after oral administration. (REF1) Multiple N-dealkylations lead to the removal dimethyl-aminoethyl side chain, leading to the difference in its potency. (REF5) The other two metabolites are [[alpha-hydroxyalprazolam]] and [[estazolam]].<ref name=other_metabolites>{{cite journal | first = A. D. | last = Fraser |author2=A. F. Isner|author3=W. Bryan |date=November–December 1993 | title = Urinary screening for adinazolam and its major metabolites by the Emit d.a.u. and FPIA benzodiazepine assays with confirmation by HPLC | journal = Journal of Analytical Toxicology | volume = 17 | issue = 7 | pages = 427–31 | pmid = 8309217 | doi=10.1093/jat/17.7.427}}</ref> In the August 1986 issue of that same journal, Sethy, Francis and Day reported that [[proadifen]] inhibited the formation of [[N-desmethyladinazolam]].<ref name=Sethy_Francis_Day_1986>{{cite journal | first = Vimala H. | last = Sethy |author2=Jonathan W. Francis|author3=J. S. Day |date=August 1986 | title = The effect of proadifen on the metabolism of adinazolam | journal = Journal of Pharmacy and Pharmacology | volume = 38 | issue = 8 | pages = 631–2 | pmid = 2876087 | doi = 10.1111/j.2042-7158.1986.tb03099.x }}</ref>
-Determination of biological activity of adinazolam and its metabolites. | journal = Journal of Pharmacy and Pharmacology | volume = 36 | issue = 8 | pages = 546-8 | id = {{PMID|6148400}} }}</ref> The main metabolite is N-desmethyladinazolam.<ref name=Peng_1984>{{cite journal | first = G. W. | last = Peng | month = August | year = 1984 | title = Assay of adinazolam in plasma by liquid chromatography. | journal = Journal of Pharmaceutical Sciences | volume = 73 | issue = 8 | pages = 1173-5 | id = {{PMID|6491930}} }}</ref> The other two metabolites are alpha-hydroxyalprazolam and [[estazolam]].<ref name=other_metabolites>{{cite journal | first = A. D. | last = Fraser | coauthors = A. F. Isner and W. Bryan | month = November-December | year = 1993 | title = Urinary screening for adinazolam and its major metabolites by the Emit d.a.u. and FPIA benzodiazepine assays with confirmation by HPLC. | journal = Journal of Analytical Toxicology | volume = 17 | issue = 7 | pages = 427-31 | id = {{PMID|8309217}} }}</ref> In the August 1986 issue of that same journal, Sethy, Francis and Day reported that [[proadifen]] inhibited the formation of N-desmethyladinazolam.<ref name=Sethy_Francis_Day_1986>{{cite journal | first = Vimala H. | last = Sethy | coauthors = Jonathan W. Francis and J. S. Day | month = August | year = 1986 | title = The effect of proadifen on the metabolism of adinazolam. | journal = Journal of Pharmacy and Pharmacology | volume = 38 | issue = 8 | pages = 631-2 | id = {{PMID|2876087}} }}</ref>
-==Indications==
+==See also==
-Adinazolam is indicated as a treatment for [[anxiety]] and [[status epilepticus]].
+* [[Benzodiazepine]]
+* [[Alprazolam]]
 ==References==
-<div class="references-small"><references/></div>
+{{Reflist|2}}
+{{Anxiolytics}}
 {{Benzodiazepines}}
-{{psychoactive-stub}}
 [[Category:Benzodiazepines]]
 [[Category:Hypnotics]]
-{{WikiDoc Help Menu}}
+[[Category:Organochlorides]]
+[[Category:Drug]]

Clinical data


Pregnancy category	?
Routes of administration	Oral
ATC code	N05BA07 (WHO)
Legal status
Legal status	Schedule IV_(US)
Pharmacokinetic data
Bioavailability	?
Metabolism	Hepatic
Elimination half-life	< 3 hours
Excretion	Renal
Identifiers
IUPAC name 1-(8-chloro-6-phenyl-4H-[1,2,4]triazolo[4,5-a] [1,4]benzodiazepin-1-yl)-N,N-dimethylmethanamine
CAS Number	37115-32-5^Y
PubChem CID	37632
DrugBank	DB00546^Y
ChemSpider	34519^Y
UNII	KN08449444
KEGG	D02770^Y
ChEBI	CHEBI:251412^Y
ChEMBL	ChEMBL328250^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	C₁₉H₁₈ClN₅
Molar mass	351.8
3D model (JSmol)	Interactive image
SMILES Clc3cc2\C(=N/Cc1nnc(n1c2cc3)CN(C)C)c4ccccc4
InChI InChI=1S/C19H18ClN5/c1-24(2)12-18-23-22-17-11-21-19(13-6-4-3-5-7-13)15-10-14(20)8-9-16(15)25(17)18/h3-10H,11-12H2,1-2H3^Y Key:GJSLOMWRLALDCT-UHFFFAOYSA-N^Y
(verify)