Benzodiazepine Derivatives

Applications 3-Methyl Clobazam is a metabolite of Clobazam (C582500), a benzodiazepine psychotherapeutic agent that has proven efficacy against multiple seizure types. An anxiolytic; anticonvulsant.
References Gastaut, H., et al.: Epilepsia, 20, 437 (1979); Guberman, A., et al.: Can J. Neurol. Sci., 17, 311 (1990); Munn, R., et al.: Pediatr. Neurol. 9, 465 (1993)

Stability Air Sensitive
Applications 3-Amino-6-bromo-4-(2-pyridinyl)-2(1H)-quinolinone is an impurity of Bromazepam (B678500); a controlled substance (depressant) and anxiolytic.
References Schwartz, M.A., et al.: J. Pharm. Sci., 62, 1776 (1973); Chalmers, P., et al.: Anesthesia, 39, 370 (1984); Hassan, M.M., et al.: Anal. Profiles Drug Subs., 16, 1 (1987)

Applications A metabolite of Alprazolam (A575650).
References Schwartz, M.A., et al.: J. Pharmacol. Exp. Ther., 149, 423 (1965), Childress, S.J., et al.: J. Pharm. Sci., 53, 577 (1964), Gall, M., et al.: J. Med. Chem., 21, 1290 (1978)

Impurity Flumazenil EP Impurity E
Applications Ethyl 5-Methyl-6-oxo-5,6-dihydro-4H-benzo[f]imidazo[1,5-a][1,4]diazepine-3-carboxylate (Flumazenil EP Impurity E) is used in the biological studies and preparation of imidazobenzodiazepines as probes for diazepaminsensitive receptor pharmacophore.
References Zhang, P., et al.: J. Med. Chem., 38, 1679 (1995)

Applications A hypnotic and a sedative, also used in veterinary medicine as an appetite stimulant
References Sato, T., et al.: J. Med. Chem., 51, 7705 (2008), Nishino, T., et al.: J. Pharmacol. Sci., 107, 349 (2008), Yamashiro, T., et al.: J. Clin. Pharm, Ther., 33, 273 (2008), Ma, C., et al.: J. Pharm. Biomed. Anal., 47, 677 (2008),

Impurity Flumazenil EP Impurity F
Applications 8-Chloro-5,6-dihydro-5-methyl-6-oxo-4H-Imidazo[1,5-a][1,4]benzodiazepine-3-carboxylic Acid Ethyl Ester is an impurity of Flumazenil (F500450), an imidazodiazepine which selectively blocks the central effects of classic benzodiazepines.
References Hunkeler, W., et al.: Nature, 290, 514 (1981), Pole, P., et al.: Arch. Pharmacol., 316, 317 (1981), Timm, U., et al.: Arzneim.-Forsch., 33, 358 (1983),

Applications Shows sedative and anxiolytic properties. Impairment of psychomotor performance reported. Activity blocked by flumazenil.
References Doumont, A., et al.: Psychopharmacology, 87, 130 (1985), Psychopharmacology, 94(4), 501 (1988)

Applications 7-Chloro-1,3-dihydro-5-phenyl-2H-1,4-benzodiazepine-2-thione (cas# 4547-02-8) is a positive allosteric modulator for the muscarinic M1 receptor, which could be a potential treament for the Alzheimer's disease or Schizophrenia.
References Flohr, A., et al.: Bioorg. Med. Chem. Lett., 27, 5415 (2017)

Applications 5-Chloro-2-(3-chloromethyl-4H-1,2,4-triazol-4-yl)-benzophenone is an impurity in the synthesis of Estazolam (E668380), a benzodiazepine derivative possessing anxiolytic, anticonvulsant, and muscle relaxant properties. It is commonly prescribed to treat short-term insomnia.
References Barroso, M., et al.: Anal. Bioanal. Chem., 396, 3059 (2010), Rodgers, A., et al.: Chem. Res., Toxicol., 23, 724 (2010), Dresen, S., et al.: Anal. Bioanal. Chem., 396, 2425 (2010),

Applications An impurity from the synthesis of clonazepam (C587080)

Applications The major labelled metabolite of Clobazam (C582500). Controlled substance (depressant).
References Bardy, A., et al.: Brain Develop., 13, 174 (1991), Patsalos, P., et al.: Epilepsia, 43, 365 (2002), Venisse, N., et al.: J. Anal. Toxicol., 27, 7 (2003),

Applications Controlled substance (depressant). Anxiolytic. Labelled Bromazepam.
References Schwartz, M.A., et al.: J. Pharm. Sci., 62, 1776 (1973), Chalmers, P., et al.: Anesthesia, 39, 370 (1984), Hassan, M.M., et al.: Anal. Profiles Drug Subs., 16, 1 (1987),

Applications 2-(2-Acetylhydrazino)-7-chloro-5-phenyl-3H-1,4-benzodiazepine is an impurity of Alprazolam (A575650.
References Hester, J.B., et al.: J. Org. Chem., 44, 2688, (1979); Anjaneyulu, Y., et al.: Asian. J. Chem., 19, 3375 (2007);

Impurity Clonazepam EP Impurity A
Applications 2-Amino-5-nitro-2'-chlorobenzophenone (Clonazepam EP Impurity A) is an impurity of Clonazepam (C587080).

Applications Flunitrazepam is used as an hypnotic. This is a controlled substance (depressant).
References Sternbach, L.H., et al.: J. Med. Chem., 6, 261 (1963), Eidelberg, E., et al.: Neurology, 5, 223 (1965), Caplan, Y., et al.: J. Anal. Toxicol., 25, 396 (2001), Wood, M., et al.: Forensic Sci. Int., 150, 227 (2005),

Impurity Clonazepam EP Impurity B
Applications 3-Amino-4-(2-chlorophenyl)-6-nitro-2(1H)-quinolinone (Clonazepam EP Impurity B) is an impurity of Clonazepam (C587080), antiepileptic agent with anxiolytic and antimanic properties.
References Mayer, W., et al.: Pharmazie, 29, 700 (1974), Blum, et al.: Arzneim.-Forsch., 23, 377 (1973), Winslow, W.C., et al.: Anal. Profiles Drug Subs., 6, 61 (1977)

Applications The major metabolite of Clonazepam (C587080).
References Clark, D., et al.: Drugs, 29, 342 (1985), Colmenero, J., et al.: Antimicrob. Agents Chemother., 38, 2798 (1994), Grant, D., et al.: Pharmacology, 61, 204 (2000), Negrusz, A., et al.: Anal. Bioanal. Chem., 376, 1198 (2003),

Applications A metabolite of Diazepam; but has a much weaker anticonvulsant effect.
References Hara, T., et al.: J. Med. Chem., 21, 263 (1978),

Applications Controlled substance (depressant). Anxiolytic.
References Sethy, V.H., et al.: Arch. Pharmacol., 301, 157 (1978), Fawcett, J.A., et al.: Pharmacotherapy, 2, 242 (1982),

Applications Controlled substance (depressant). Anxiolytic.
References Schwartz, M.A., et al.: J. Pharm. Sci., 62, 1776 (1973), Chalmers, P., et al.: Anesthesia, 39, 370 (1984), Hassan, M.M., et al.: Anal. Profiles Drug Subs., 16, 1 (1987),

Applications Intermediate in the preparation of Alprazolam impurities.
References Hanawa, T., et al.: Drug Dev. Ind. Pharm., 26, 1199 (2000), Cheng, P., et al.: Bioorg. Med. Chem. Lett., 18, 3787 (2008),

Applications N-Desmethyl Clobazam is an impurity of Clobazam (C582500), which is a benzodiazepine, psychotherapeutic agent. Clobazam (CLB) has proven efficacy against multiple seizure types and is an anxiolytic, anticonvulsant and controlled substance (depressant).
References Gastaut, H., et al.: Epilepsia, 20, 437 (1979), Guberman, A., et al.: Can J. Neurol. Sci., 17, 311 (1990), Munn, R., et al.: Pediatr. Neurol. 9, 465 (1993)

Applications Flumazenil carboxylic acid is a derivative of Flumazenil (F500450), a benzodiazepine antagonist that can prevent or abolish (at the receptor level) the effects of a benzodiazepine.
References Brogden, R. & Goa, K.: Drugs, 35, 448 (1988); Klotz, U. & Kanto, J.: Clin. Pharmacokinet., 14, 1 (1988)

Applications Benzodiazepine psychotherapeutic agent. Clobazam (CLB) has proven efficacy against multiple seizure types. An anxiolytic; anticonvulsant. Controlled substance (depressant).
References Gastaut, H., et al.: Epilepsia, 20, 437 (1979), Guberman, A., et al.: Can J. Neurol. Sci., 17, 311 (1990), Munn, R., et al.: Pediatr. Neurol. 9, 465 (1993)

Applications An impurity of Alprazolam (A575650).
References Nudelman, N., et al.: J. Pharm. Sci., 91, 1274 (2002), Marin, A., et al.: Anal. Chem., 77, 471 (2005),

Applications Controlled substance (depressant). Anxiolytic.
References Sethy, V.H., et al.: Arch. Pharmacol., 301, 157 (1978), Fawcett, J.A., et al.: Pharmacotherapy, 2, 242 (1982),

Applications Flumazenil-D5 is a labelled analogue of Flumazenil (F500450), a benzodiazepine antagonist that can prevent or abolish (at the receptor level) the effects of a benzodiazepine.
References Brogden, R. & Goa, K.: Drugs, 35, 448 (1988); Klotz, U. & Kanto, J.: Clin. Pharmacokinet., 14, 1 (1988)

Applications An impurity of Alprazolam (A575650).
References Cho, M., et al.: J. Med. Chem., 29, 1346 (1986), Hall, M., et al.: J. Anal. Toxicol., 19, 511 (1995), Nudelman, N., et al.: J. Pharm. Sci., 84, 998 (1995), Yuan, R., et al.: J. Clin. Pharmacol., 39, 1109 (1999),

Applications Clonazepam-13C2 ,15N, is the labeled analogue of Clonazepam (C587080), an antiepileptic agent with anxiolytic and antimanic properties.
References Blum, et al.: Arzneim.-Forsch., 23, 377 (1973), Winslow, W.C., et al.: Anal. Profiles Drug Subs., 6, 61 (1977)

Applications A metabolite of Flunitrazepam (F500700).
References Asai, H., et al.: J. Pharmacol. Exp. Ther., 277, 1004 (1996), Kilicarslan, T., et al.: Drug Metab. Dispos., 29, 460 (2001), Tanaka, E., et al.: J. Toxicol. Clin. Toxicol., 40, 69 (2002),

Applications N-Desmethyl Clobazam-13C6 is an isotope labelled metabolite of Clobazam (C582500), a benzodiazepine psychotherapeutic agent that has proven efficacy against multiple seizure types.
References Gastaut, H., et al.: Epilepsia, 20, 437 (1979); Guberman, A., et al.: Can J. Neurol. Sci., 17, 311 (1990); Munn, R., et al.: Pediatr. Neurol. 9, 465 (1993)

Applications Major metabolite of labelled Bromazepam (B678502)
References Musshoff, F., et al.: Clin. Chem. Lab. Med., 36, 803 (1998), El-Haj, B., et al.: J. Anal. Toxicol., 25, 316 (2001), Darzy, K., et al.: Clin. Endocrinol., 70, 287 (2009),

Applications Labelled Clonazepam (C587080). Antiepileptic agent with anxiolytic and antimanic properties. Anticonvulsant.This is a controlled substance (depressant).
References Blum, et al.: Arzneim.-Forsch., 23, 377 (1973), Winslow, W.C., et al.: Anal. Profiles Drug Subs., 6, 61 (1977)

Applications Flumazenil is an imidazodiazepine which selectively blocks the central effects of classic benzodiazepines. It is used as benzodiazepine antagonist.
References Hunkeler, W., et al.: Nature, 290, 514 (1981), Pole, P., et al.: Arch. Pharmacol., 316, 317 (1981), Timm, U., et al.: Arzneim.-Forsch., 33, 358 (1983),

Impurity Bromazepam EP impurity A
Applications Intermediate in the preparation of Bromazepam.
References Panderi, I., et al.: J. Pharm. Biomed. Anal., 17, 327 (1998), El-Haj, B., et al.: J. Anal. Toxicol., 25, 316 (2001), Hansen, S., et al.: J. Pharm. Biomed. Anal., 39, 322 (2005),

Applications Labelled Clobazam (C582500). Benzodiazepine psychotherapeutic agent. Clobazam (CLB) has proven efficacy against multiple seizure types. An anxiolytic; anticonvulsant. Controlled substance (depressant).
References Gastaut, H., et al.: Epilepsia, 20, 437 (1979), Guberman, A., et al.: Can J. Neurol. Sci., 17, 311 (1990), Munn, R., et al.: Pediatr. Neurol. 9, 465 (1993),

Applications Cloxazolam is a benzodiazepine derivative with anxiolytic, hypnotic and antihypertensive properties used as an anti-anxiety drug. It is metabolized into the active metabolite Delorezepam (D230675). Controlled Substance.
References Oliveira-Silva, D. et al.: Biomed. Chrom., 23, 1266 (2009); Kamioka, T. et al.: Psychopharmacol., 52, 17 (1977); Fischer-Cornelssen, K.A. et al.: Arzneim.-Forsch., 31, 1757 (1981);

Applications Antiepileptic agent with anxiolytic and antimanic properties. Anticonvulsant.This is a controlled substance (depressant).
References Blum, et al.: Arzneim.-Forsch., 23, 377 (1973), Winslow, W.C., et al.: Anal. Profiles Drug Subs., 6, 61 (1977)

Applications Deschloro Clobazam is a metabolite of Clobazam (C582500), a benzodiazepine psychotherapeutic agent that has proven efficacy against multiple seizure types. An anxiolytic; anticonvulsant.
References Guberman, A., et al.: Can J. Neurol. Sci., 17, 311 (1990); Munn, R., et al.: Pediatr. Neurol. 9, 465 (1993)

Applications 6-Chloro-2,3-dimethyl-1-phenyl-1H-benzo[d]imidazol-3-ium Chloride is a degradation product of Clobazam (C582500), a benzodiazepine psychotherapeutic agent that has proven efficacy against multiple seizure types. An anxiolytic; anticonvulsant.
References Guberman, A., et al.: Can J. Neurol. Sci., 17, 311 (1990); Munn, R., et al.: Pediatr. Neurol. 9, 465 (1993)

Applications Clobazam-13C6 is the isotope labelled analog of Clobazam (C582500); a benzodiazepine psychotherapeutic agent. Clobazam (CLB) has proven efficacy against multiple seizure types. An anxiolytic and anticonvulsant. Controlled substance (depressant).
References Gastaut, H., et al.: Epilepsia, 20, 437 (1979); Guberman, A., et al.: Can J. Neurol. Sci., 17, 311 (1990); Munn, R., et al.: Pediatr. Neurol. 9, 465 (1993)

Applications Clonazepam (C587080) metabolite.
References Huang, W., et al.: J. Anal. Toxicol., 19, 333 (1995), Rittner, M., et al.: J. Anal. Toxicol., 25, 115 (2001),

Stability Unstable in Solution, Moisture Sensitive
Applications Used in the synthesis of Cloxazolam and its metabolites.
References Ji, M. et al.: Zhongguo Yaoke Daxue Xuebao 24, 180 (1993); Ji, M. et al.: Zhongguo Yaoke Daxue Xuebao 25, 69 (1994).

Applications Nitrazepam derivative.
References Hagishita, S., et al.: Bioorg. Med. Chem., 5, 1433 (1997), Amblard, M., et al.: J. Med. Chem., 42, 4185 (1999), Schafferhans, A., et al.: J. Mol. Biol., 307, 407 (2001).

Applications Major metabolite of Bromazepam (B678500)
References Musshoff, F., et al.: Clin. Chem. Lab. Med., 36, 803 (1998), El-Haj, B., et al.: J. Anal. Toxicol., 25, 316 (2001), Darzy, K., et al.: Clin. Endocrinol., 70, 287 (2009),

Applications An impurity of Alprazolam (A575650). The major degradation product in Alprazolam tablets during their stability assay.
References Nudelman, N., et al.: J. Pharm. Sci., 91, 1274 (2002), Marin, A., et al.: Anal. Chem., 77, 471 (2005),