Cloxazolam

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Cloxazolam
Clinical data
AHFS/Drugs.com	International Drug Names
Pregnancy; category	?;
Routes of; administration	Oral
ATC code	N05BA22 (WHO) ;
Legal status
Legal status	Schedule IV(US);
Pharmacokinetic data
Bioavailability	?
Metabolism	Hepatic
Elimination half-life	65 Hours
Excretion	Renal
Identifiers
	IUPAC name 13-chloro-2-(2-chlorophenyl)-3-oxa-6,9-diazatricyclo[8.4.0.02,6]tetradeca-1(10),11,13-trien-8-one;
CAS Number	24166-13-0 ;
PubChem CID	2816;
DrugBank	DB01553 ;
ChemSpider	2714 ;
UNII	GYL649Z0HY;
KEGG	D01268 ;
ChEMBL	ChEMBL2107254 ;
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	C17H14Cl2N2O2
Molar mass	349.2
3D model (JSmol)	Interactive image;
	SMILES Clc1ccccc1C42OCCN2CC(=O)Nc3c4cc(Cl)cc3;
	InChI InChI=1S/C17H14Cl2N2O2/c18-11-5-6-15-13(9-11)17(12-3-1-2-4-14(12)19)21(7-8-23-17)10-16(22)20-15/h1-6,9H,7-8,10H2,(H,20,22) ; Key:ZIXNZOBDFKSQTC-UHFFFAOYSA-N ;
(what is this?) (verify)

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

Overview

Cloxazolam^[1] (marketed under brand name Sepazon, Olcadil (Brazil, Portugal and Spain), Akton (Belgium), Lubalix (Switzerland) is a drug which is a benzodiazepine derivative.^[2] Cloxazolam is metabolised into the active metabolite chlordesmethyldiazepam (delorazepam).^[3] It possesses anxiolytic,^[4] anticonvulsant,^[5] hypnotic,^[6] sedative^[7] and skeletal muscle relaxant properties.^[8]

Indications

Cloxazolam's main use is as an anti-anxiety drug.^[9]

Side effects

An increased heart rate may occur as an adverse effect of cloxazolam.^[10]

Pharmacology

The pharmacological effects of cloxazolam are a result of mainly its active metabolites, thus cloxazolam is a prodrug. The main site of action of cloxazolam and its active metabolites are the benzodiazepine receptor.^[11]

The pharmacological actions of benzodiazepines at the GABAa receptor are similar to those of neurosteroids. Neuroactive steroids are positive allosteric modulators of the GABAa receptor, enhancing GABA function and in turn have effects on mood and other functions. Many benzodiazepines (diazepam, medazepam, estazolam, temazepam, flunitrazepam and nitrazepam) potently inhibit the enzymes involved in the metabolism of neurosteroids. The tetrahydroxazole ring that cloxazolam and oxazolam have decreases the inhibitory potency of benzodiazepines on neurosteroids. Thus there could be subtle differences between cloxazolam and other benzodiazepines.^[12] However, because the parent prodrugs of cloxazolam and oxazolam were tested rather than the active metabolites, this is purely speculative.

References

↑ DE Patent 1817923
↑ "Benzodiazepine Names". non-benzodiazepines.org.uk. Retrieved 2008-12-29.
↑ Oliveira-Silva, D.; Oliveira, CH.; Mendes, GD.; Galvinas, PA.; Barrientos-Astigarraga, RE.; De Nucci, G. (Dec 2009). "Quantification of chlordesmethyldiazepam by liquid chromatography-tandem mass spectrometry: application to a cloxazolam bioequivalence study". Biomed Chromatogr. 23 (12): 1266–75. doi:10.1002/bmc.1249. PMID 19488979.
↑ Kamioka, T.; Nakayama, I.; Akiyama, S.; Takagi, H. (Mar 1977). "Effects of oxazolam, cloxazolam, and CS-386, new anti-anxiety drugs, on socially induced suppression and aggression in pairs of monkeys". Psychopharmacology (Berl). 52 (1): 17–23. doi:10.1007/BF00426594. PMID 15296.
↑ Ito, M.; Miyajima, T.; Fujii, T.; Okuno, T. (Feb 2004). "Cloxazolam treatment for patients with intractable epilepsy". Pediatr Neurol. 30 (2): 111–4. doi:10.1016/j.pediatrneurol.2003.07.004. PMID 14984903.
↑ 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.
↑ Brisse, B.; Tetsch, P.; Toye, A. (1980). "[Clinical study on stress protective action of cloxazolam in jaw surgery in double blind comparison to placebo (author's transl)]". Arzneimittelforschung. 30 (4): 679–82. PMID 6104969.
↑ Ansseau, M.; von Frenckell, R. (1990). "Controlled comparison of two anxiolytic benzodiazepines, cloxazolam and bromazepam". Neuropsychobiology. 24 (1): 25–9. doi:10.1159/000119038. PMID 1983433.
↑ Fischer-Cornelssen, KA. (1981). "Multicenter trials and complementary studies of cloxazolam, a new anxiolytic drug". Arzneimittelforschung. 31 (10): 1757–65. PMID 6119092.
↑ Boucsein, W.; Wendt-Suhl, G. (Mar 1982). "[Psychological and physiological effects of cloxazolam and diazepam under anxiety-evoking and control conditions on healthy subjects (author's transl)]". Pharmacopsychiatria. 15 (2): 48–56. doi:10.1055/s-2007-1019508. PMID 6123123.
↑ 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.
↑ Usami N; Yamamoto T; Shintani S; Ishikura S; Higaki Y; Katagiri Y; Hara A. (Apr 2002). "Substrate specificity of human 3(20)alpha-hydroxysteroid dehydrogenase for neurosteroids and its inhibition by benzodiazepines" (pdf). Biol Pharm Bull. 25 (4): 441–5. doi:10.1248/bpb.25.441. PMID 11995921.

External links

Inchem.org - Cloxazolam

Template:Anxiolytics Template:Benzodiazepines Template:GABAAR PAMs

[1] DE Patent 1817923

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

[3] Oliveira-Silva, D.; Oliveira, CH.; Mendes, GD.; Galvinas, PA.; Barrientos-Astigarraga, RE.; De Nucci, G. (Dec 2009). "Quantification of chlordesmethyldiazepam by liquid chromatography-tandem mass spectrometry: application to a cloxazolam bioequivalence study". Biomed Chromatogr. 23 (12): 1266–75. doi:10.1002/bmc.1249. PMID 19488979.

[4] Kamioka, T.; Nakayama, I.; Akiyama, S.; Takagi, H. (Mar 1977). "Effects of oxazolam, cloxazolam, and CS-386, new anti-anxiety drugs, on socially induced suppression and aggression in pairs of monkeys". Psychopharmacology (Berl). 52 (1): 17–23. doi:10.1007/BF00426594. PMID 15296.

[5] Ito, M.; Miyajima, T.; Fujii, T.; Okuno, T. (Feb 2004). "Cloxazolam treatment for patients with intractable epilepsy". Pediatr Neurol. 30 (2): 111–4. doi:10.1016/j.pediatrneurol.2003.07.004. PMID 14984903.

[6] 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.

[7] Brisse, B.; Tetsch, P.; Toye, A. (1980). "[Clinical study on stress protective action of cloxazolam in jaw surgery in double blind comparison to placebo (author's transl)]". Arzneimittelforschung. 30 (4): 679–82. PMID 6104969.

[8] Ansseau, M.; von Frenckell, R. (1990). "Controlled comparison of two anxiolytic benzodiazepines, cloxazolam and bromazepam". Neuropsychobiology. 24 (1): 25–9. doi:10.1159/000119038. PMID 1983433.

[9] Fischer-Cornelssen, KA. (1981). "Multicenter trials and complementary studies of cloxazolam, a new anxiolytic drug". Arzneimittelforschung. 31 (10): 1757–65. PMID 6119092.

[10] Boucsein, W.; Wendt-Suhl, G. (Mar 1982). "[Psychological and physiological effects of cloxazolam and diazepam under anxiety-evoking and control conditions on healthy subjects (author's transl)]". Pharmacopsychiatria. 15 (2): 48–56. doi:10.1055/s-2007-1019508. PMID 6123123.

[11] 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.

[12] Usami N; Yamamoto T; Shintani S; Ishikura S; Higaki Y; Katagiri Y; Hara A. (Apr 2002). "Substrate specificity of human 3(20)alpha-hydroxysteroid dehydrogenase for neurosteroids and its inhibition by benzodiazepines" (pdf). Biol Pharm Bull. 25 (4): 441–5. doi:10.1248/bpb.25.441. PMID 11995921.

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