Camazepam

Camazepam
Systematic (IUPAC) name
	(9-Chloro-2-methyl-3-oxo-6-phenyl-2,5-diazabicyclo[5.4.0]undeca-5,8,10,12-tetraen-4-yl)-N,N-dimethylcarbamate
Clinical data
Pregnancy cat.	?
Legal status	Schedule IV(US)
Routes	Oral
Pharmacokinetic data
Bioavailability	?
Metabolism	Hepatic
Half-life	?
Excretion	Renal
Identifiers
CAS number	36104-80-0
ATC code	N05BA15
PubChem	CID 37367
DrugBank	DB01489
ChemSpider	34285
UNII	HZ3XRH03C3
KEGG	D07315
ChEMBL	CHEMBL1095282
Chemical data
Formula	C19H18ClN3O3
Mol. mass	371.8
	SMILES ClC1=CC2=C(C=C1)N(C)C(C(N=C2C3=CC=CC=C3)OC(N(C)C)=O)=O;
	InChI InChI=1S/C19H18ClN3O3/c1-22(2)19(25)26-17-18(24)23(3)15-10-9-13(20)11-14(15)16(21-17)12-7-5-4-6-8-12/h4-11,17H,1-3H3 ; Key:PXBVEXGRHZFEOF-UHFFFAOYSA-N ;
(what is this?) (verify);

Not to be confused with clonazepam, clobazam, or cinolazepam.

Camazepam¹(marketed under the brand names Albego, Limpidon, and Paxor) is a benzodiazepine psychoactive drug which is the dimethyl carbamate ester of temazepam, a metabolite of diazepam.² While it possesses anxiolytic, anticonvulsant, skeletal muscle relaxant and hypnotic properties³ it differs from other benzodiazepines in that its anxiolytic properties are particularly prominent but has comparatively limited anticonvulsant, hypnotic and skeletal muscle relaxant properties.

Compared to other benzodiazepines, it has reduced side effects such as impaired cognition, reaction times and coordination.⁴⁵⁶⁷⁸ which makes it best suited as an anxiolytic because of these reduced sides effects. With higher doses such as 40 mg of camazepam, impairments similar to those which occur with other benzodiazepines manifest as disrupted sleep patterns and impaired cognitive performance.⁹ Animal studies have shown camazepam and its active metabolites possess anticonvulsant properties.¹⁰ Skin disorders have been reported with use of camazepam however.¹¹ Camazepam is believed to increase attention.¹² Camazepam unlike other benzodiazepines does not disrupt normal sleep patterns.¹³ Camazepam has been shown in animal experiments to have a very low affinity for benzodiazepine receptors compared to other benzodiazepines.¹⁴ Camazepam is almost completely absorbed into the bloodstream after oral administration with 90 percent bioavailability achieved in humans.¹⁵ Camazepam is metabolised into an active metabolite temazepam.¹⁶ Compared to temazepam, camazepam has shown roughly equal anxiolytic properties, and less anticonvulsant, sedative and motor-impairing properties.

References

^ DE Patent 2142181
^ Tammaro, A; Picceo, MT; Gemmellaro, P; Bonaccorso, O (1977). "Camazepam versus placebo. A double-blind clinical study on geriatric patients suffering from psychic complaints. Short Communication". Arzneimittel-Forschung 27 (11): 2177–8. PMID 23793.
^ Lu, XL; Yang, SK (1994). "Enantiomer resolution of camazepam and its derivatives and enantioselective metabolism of camazepam by human liver microsomes.". Journal of Chromatography A 666 (1–2): 249–57. doi:10.1016/0021-9673(94)80387-0. PMID 7911374.
^ De Sarro, G; Chimirri, A; Zappala, M; Guisti, P; Lipartiti, M; De Sarro, A (1996). "Azirino1, 2-d1, 4benzodiazepine derivatives and related 1,4-benzodiazepines as anticonvulsant agents in DBA/2 mice". General Pharmacology 27 (7): 1155–62. doi:10.1016/S0306-3623(96)00049-3. PMID 8981061.
^ De Sarro, G; Gitto, R; Rizzo, M; Zappia, M; De Sarro, A (1996). "1,4-Benzodiazepine derivatives as anticonvulsant agents in DBA/2 mice". General Pharmacology 27 (6): 935–41. doi:10.1016/0306-3623(95)02147-7. PMID 8909973.
^ De Sarro, G; Chimirri, A; Mckernan, R; Quirk, K; Giusti, P; De Sarro, A (1997). "Anticonvulsant activity of azirino1,2-d1,4benzodiazepines and related 1,4-benzodiazepines in mice". Pharmacology, Biochemistry, and Behavior 58 (1): 281–9. doi:10.1016/S0091-3057(96)00565-5. PMID 9264104.
^ Guthy, H (1975). "The medicinal treatment of anxiety in alcoholism in the withdrawal stage (author's transl)". Munchener Medizinische Wochenschrift 117 (35): 1387–90. PMID 241014.
^ Tallone, G; Ghirardi, P; Bianchi, MC; Ravaccia, F; Bruni, G; Loreti, P (1980). "Reaction time to acoustic or visual stimuli after administration of camazepam and diazepam in man". Arzneimittel-Forschung 30 (6): 1021–4. PMID 6106497.
^ Nicholson, AN; Stone, BM (1982). "Hypnotic activity and effects on performance of lormetazepam and camazepam--analogues of temazepam". British Journal of Clinical Pharmacology 13 (3): 433–9. PMC 1402107. PMID 6120717.
^ Morino, A; Sasaki, H; Mukai, H; Sugiyama, M (1986). "Receptor-mediated model relating anticonvulsant effect to brain levels of camazepam in the presence of its active metabolites". Journal of Pharmacokinetics and Biopharmaceutics 14 (3): 309–21. doi:10.1007/BF01106709. PMID 2878071.
^ Stricker, BH (1984). "Skin disorders caused by the use of camazepam (Albego)". Nederlands tijdschrift voor geneeskunde 128 (18): 870–2. PMID 6145108.
^ Schmitt, EJ; Rochels, R; Beck, D; Mauersberg, L (1980). "Visual perception under the influence of a tranquilizer (author's transl)". Klinische Monatsblätter für Augenheilkunde 177 (6): 875–7. doi:10.1055/s-2008-1057748. PMID 6110803.
^ Ferrillo, F; Balestra, V; Carta, F; Nuvoli, G; Pintus, C; Rosadini, G (1984). "Comparison between the central effects of camazepam and temazepam. Computerized analysis of sleep recordings". Neuropsychobiology 11 (1): 72–6. doi:10.1159/000118055. PMID 6146112.
^ Shibuya, T; Field, R; Watanabe, Y; Sato, K; Salafsky, B (1984). "Structure-affinity relationships between several new benzodiazepine derivatives and 3H-diazepam receptor sites". Japanese Journal of Pharmacology 34 (4): 435–40. doi:10.1254/jjp.34.435. PMID 6144807.
^ Morino, A; Nakamura, A; Nakanishi, K; Tatewaki, N; Sugiyama, M (1985). "Species differences in the disposition and metabolism of camazepam". Xenobiotica 15 (12): 1033–43. doi:10.3109/00498258509049098. PMID 2868575.
^ Riva, R; Albani, F; Baruzzi, A (1982). "Quantitative determination of camazepam and its metabolite temazepam in man by gas-liquid chromatography with electron-capture detection". Il Farmaco; edizione pratica 37 (1): 15–9. PMID 6120096.

External links

Inchem - Camazepam

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[1] DE Patent 2142181

[2] Tammaro, A; Picceo, MT; Gemmellaro, P; Bonaccorso, O (1977). "Camazepam versus placebo. A double-blind clinical study on geriatric patients suffering from psychic complaints. Short Communication". Arzneimittel-Forschung 27 (11): 2177–8. PMID 23793.

[3] Lu, XL; Yang, SK (1994). "Enantiomer resolution of camazepam and its derivatives and enantioselective metabolism of camazepam by human liver microsomes.". Journal of Chromatography A 666 (1–2): 249–57. doi:10.1016/0021-9673(94)80387-0. PMID 7911374.

[4] De Sarro, G; Chimirri, A; Zappala, M; Guisti, P; Lipartiti, M; De Sarro, A (1996). "Azirino1, 2-d1, 4benzodiazepine derivatives and related 1,4-benzodiazepines as anticonvulsant agents in DBA/2 mice". General Pharmacology 27 (7): 1155–62. doi:10.1016/S0306-3623(96)00049-3. PMID 8981061.

[5] De Sarro, G; Gitto, R; Rizzo, M; Zappia, M; De Sarro, A (1996). "1,4-Benzodiazepine derivatives as anticonvulsant agents in DBA/2 mice". General Pharmacology 27 (6): 935–41. doi:10.1016/0306-3623(95)02147-7. PMID 8909973.

[6] De Sarro, G; Chimirri, A; Mckernan, R; Quirk, K; Giusti, P; De Sarro, A (1997). "Anticonvulsant activity of azirino1,2-d1,4benzodiazepines and related 1,4-benzodiazepines in mice". Pharmacology, Biochemistry, and Behavior 58 (1): 281–9. doi:10.1016/S0091-3057(96)00565-5. PMID 9264104.

[7] Guthy, H (1975). "The medicinal treatment of anxiety in alcoholism in the withdrawal stage (author's transl)". Munchener Medizinische Wochenschrift 117 (35): 1387–90. PMID 241014.

[8] Tallone, G; Ghirardi, P; Bianchi, MC; Ravaccia, F; Bruni, G; Loreti, P (1980). "Reaction time to acoustic or visual stimuli after administration of camazepam and diazepam in man". Arzneimittel-Forschung 30 (6): 1021–4. PMID 6106497.

[9] Nicholson, AN; Stone, BM (1982). "Hypnotic activity and effects on performance of lormetazepam and camazepam--analogues of temazepam". British Journal of Clinical Pharmacology 13 (3): 433–9. PMC 1402107. PMID 6120717.

[10] Morino, A; Sasaki, H; Mukai, H; Sugiyama, M (1986). "Receptor-mediated model relating anticonvulsant effect to brain levels of camazepam in the presence of its active metabolites". Journal of Pharmacokinetics and Biopharmaceutics 14 (3): 309–21. doi:10.1007/BF01106709. PMID 2878071.

[11] Stricker, BH (1984). "Skin disorders caused by the use of camazepam (Albego)". Nederlands tijdschrift voor geneeskunde 128 (18): 870–2. PMID 6145108.

[12] Schmitt, EJ; Rochels, R; Beck, D; Mauersberg, L (1980). "Visual perception under the influence of a tranquilizer (author's transl)". Klinische Monatsblätter für Augenheilkunde 177 (6): 875–7. doi:10.1055/s-2008-1057748. PMID 6110803.

[13] Ferrillo, F; Balestra, V; Carta, F; Nuvoli, G; Pintus, C; Rosadini, G (1984). "Comparison between the central effects of camazepam and temazepam. Computerized analysis of sleep recordings". Neuropsychobiology 11 (1): 72–6. doi:10.1159/000118055. PMID 6146112.

[14] Shibuya, T; Field, R; Watanabe, Y; Sato, K; Salafsky, B (1984). "Structure-affinity relationships between several new benzodiazepine derivatives and 3H-diazepam receptor sites". Japanese Journal of Pharmacology 34 (4): 435–40. doi:10.1254/jjp.34.435. PMID 6144807.

[15] Morino, A; Nakamura, A; Nakanishi, K; Tatewaki, N; Sugiyama, M (1985). "Species differences in the disposition and metabolism of camazepam". Xenobiotica 15 (12): 1033–43. doi:10.3109/00498258509049098. PMID 2868575.

[16] Riva, R; Albani, F; Baruzzi, A (1982). "Quantitative determination of camazepam and its metabolite temazepam in man by gas-liquid chromatography with electron-capture detection". Il Farmaco; edizione pratica 37 (1): 15–9. PMID 6120096.

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Camazepam

See also

References

External links