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Version 2.5
Creation Date 2005-06-13 13:24:05
Update Date 2009-02-19 16:04:55
Primary Accession Number DB00231
Secondary Accession Number
  • APRD00676
Name Temazepam
Drug Type
  • Approved
  • Small Molecule
Description A benzodiazepine that acts as a gamma-aminobutyric acid modulator and anti-anxiety agent. [PubChem]
Synonyms
  1. Hydroxydiazepam
  2. Methyloxazepam
  3. N-Methyloxazepam
  4. Oxydiazepam
Brand Names
  1. Apo-Temazepam
  2. Cerepax
  3. Crisonar
  4. Euhypnos
  5. Euipnos
  6. Gelthix
  7. Levanxene
  8. Levanxol
  9. Levanzene
  10. Mabertin
  11. Normison
  12. Novo-Temazepam
  13. Perdorm
  14. Planum
  15. Remestan
  16. Restoril
  17. Signopam
  18. Temaz
Brand Mixtures Not Available
Chemical IUPAC Name 7-chloro-3-hydroxy-1-methyl-5-phenyl-3H-1,4-benzodiazepin-2-one
Chemical Formula C16H13ClN2O2
Chemical Structure Structure
CAS Registry Number 846-50-4
InChI Identifier InChI=1/C16H13ClN2O2/c1-19-13-8-7-11(17)9-12(13)14(18-15(20)16(19)21)10-5-3-2-4-6-10/h2-9,15,20H,1H3
InChI Key SEQDDYPDSLOBDC-UHFFFAOYAE
KEGG Drug D00370 Link Image
KEGG Compound Not Available
PubChem Compound 5391 Link Image
PubChem Substance 156664 Link Image
ChEBI ID Not Available
PharmGKB ID PA451608 Link Image
HET ID Not Available
GenBank ID Not Available
Drug ID Number [DIN] 02244815 Link Image
RxList Link http://www.rxlist.com/cgi/generic/temaz.htm Link Image
PDRhealth Link http://www.pdrhealth.com/drug_info/rxdrugprofiles/drugs/res1373.shtml Link Image
Wikipedia Link http://en.wikipedia.org/wiki/Temazepam Link Image
FDA Label Not Available
Material Safety Data Sheet (MSDS) Not Available
Synthesis Reference E. Reeder et al., U.S. Pat. 3,340,253 (1967)
Average Molecular Weight 300.7400
Monoisotopic Molecular Weight 300.0666
State Solid
Melting Point 119-121oC
Experimental Water Solubility 164 mg/L Source: PhysProp
Predicted Water Solubility 5.34e-02 mg/mL Calculated using ALOGPS
Experimental LogP/Hydrophobicity 3 Source: PhysProp
Predicted LogP 2.16 Calculated using ALOGPS
Experimental LogS Not Available
Predicted LogS -3.75 Calculated using ALOGPS
Experimental Caco2 Permeability Not Available
pKa/Isoelectric Point Not Available
Mass Spectrum Not Available
MOL File Show Link Image | Download Link Image
SDF File Show Link Image | Download Link Image
PDB File Show Link Image | Download Link Image
2D Structure
3D Structure
Experimental PDB ID Not Available
Isomeric SMILES CN1C(=O)[C@@H](O)N=C(C2=CC=CC=C2)C2=C1C=CC(Cl)=C2
Canonical SMILES CN1C(=O)C(O)N=C(C2=CC=CC=C2)C2=C1C=CC(Cl)=C2
Drug Category
  • Adjuvants, Anesthesia
  • Anti-anxiety Agents
  • Benzodiazepines
  • GABA Modulators
  • Hypnotics and Sedatives
ATC Codes
AHFS Codes
  • 28:24.08
Indication For the short-term treatment of insomnia (generally 7-10 days).
Pharmacology Temazepam is a benzodiazepine used as a hypnotic agent in the management of insomnia. Temazepam produces CNS depression at limbic, thalamic, and hypothalamic levels of the CNS. Temazepam increases the affinity of the neurotransmitter gamma-aminobutyric acid (GABA) for GABA receptors by binding to benzodiazepine receptors. Results are sedation, hypnosis, skeletal muscle relaxation, anticonvulsant activity, and anxiolytic action.
Mechanism of Action Benzodiazepines bind nonspecifically to benzodiazepine receptors, which affects muscle relaxation, anticonvulsant activity, motor coordination, and memory. As benzodiazepine receptors are thought to be coupled to gamma-aminobutyric acid-A (GABAA) receptors, this enhances the effects of GABA by increasing GABA affinity for the GABA receptor. Binding of the inhibitory neurotransmitter GABA to the site opens the chloride channel, resulting in a hyperpolarized cell membrane that prevents further excitation of the cell.
Absorption Well absorbed, minimal first-pass metabolism.
Toxicity Not Available
Protein Binding 96%
Biotransformation Hepatic. Temazepam is completely metabolized through conjugation prior to excretion. The major metabolite is the O-conjugate of temazepam (90%).
Half Life 10-20 hours
Dosage Forms
Form Route
Capsule Oral
Patient Information Show Link Image
Contraindications Show Link Image
Interactions Show Link Image
Drug Interactions
Drug Interaction
Aminophylline Aminophylline may decrease the efficacy of Temazepam. Monitor for changes in the therapeutic effect of Temazepam if Aminophylline is initiated, discontinued or dose changed.
Clozapine The benzodiazepine, Temazepam, may increase the adverse effects of Clozapine. Monitor for respiratory depression and hypotension if concomitant therapy is initiated.
Dyphylline Dyphylline may decrease the efficacy of Temazepam. Monitor for changes in the therapeutic effect of Temazepam if Dyphylline is initiated, discontinued or dose changed.
Ethotoin Possible increased levels of the hydantoin, decrease of benzodiazepine
Fosphenytoin Possible increased levels of the hydantoin, decrease of benzodiazepine
Kava Kava increases the effect of the benzodiazepine
Mephenytoin Possible increased levels of the hydantoin, decrease of benzodiazepine
Phenytoin Possible increased levels of the hydantoin, decrease of benzodiazepine
Theophylline Theophylline may decrease the efficacy of Temazepam. Monitor for changes in the therapeutic effect of Temazepam if Theophylline is initiated, discontinued or dose changed.
Food Interactions
  • Avoid alcohol.
  • Avoid avocado.
  • Avoid excessive quantities of coffee or tea (Caffeine).
Pathways Not Available
General References
  1. Rooke KC: The use of flurazepam (dalmane) as a substitute for barbiturates and methaqualone/diphenhydramine (mandrax) in general practice. J Int Med Res. 1976;4(5):355-9. [PubMed Link Image]
  2. Oelschlager H: [Chemical and pharmacologic aspects of benzodiazepines] Schweiz Rundsch Med Prax. 1989 Jul 4;78(27-28):766-72. [PubMed Link Image]
  3. Rickels K: The clinical use of hypnotics: indications for use and the need for a variety of hypnotics. Acta Psychiatr Scand Suppl. 1986;332:132-41. [PubMed Link Image]
  4. Vozeh S: [Pharmacokinetic of benzodiazepines in old age] Schweiz Med Wochenschr. 1981 Nov 21;111(47):1789-93. [PubMed Link Image]
  5. Shats V, Kozacov S: [Falls in the geriatric department: responsibility of the care-giver and the hospital] Harefuah. 1995 Jun 1;128(11):690-3, 743. [PubMed Link Image]
  6. Drugs.com Link Image
  7. Wikipedia Link Image
  8. RxList Link Image
  9. PDRhealth Link Image
Organisms Affected
  • Humans and other mammals
Phase 1 Metabolizing Enzymes
  1. Cytochrome P450 2C19 (CYP2C19)
Targets
  1. Translocator protein
Phase 1 Metabolizing Enzyme 1 [top]
Enzyme 1 Name Cytochrome P450 2C19 (CYP2C19)
Enzyme 1 Gene Name CYP2C19
Enzyme 1 SwissProt ID P33261 Link Image
Enzyme 1 SNPs SNPJam Report Link Image
Enzyme 1 Protein Sequence >sp|P33261|CP2CJ_HUMAN Cytochrome P450 2C19 (EC 1.14.13.80) 
MDPFVVLVLCLSCLLLLSIWRQSSGRGKLPPGPTPLPVIGNILQIDIKDVSKSLTNLSKI
YGPVFTLYFGLERMVVLHGYEVVKEALIDLGEEFSGRGHFPLAERANRGFGIVFSNGKRW
KEIRRFSLMTLRNFGMGKRSIEDRVQEEARCLVEELRKTKASPCDPTFILGCAPCNVICS
IIFQKRFDYKDQQFLNLMEKLNENIRIVSTPWIQICNNFPTIIDYFPGTHNKLLKNLAFM
ESDILEKVKEHQESMDINNPRDFIDCFLIKMEKEKQNQQSEFTIENLVITAADLLGAGTE
TTSTTLRYALLLLLKHPEVTAKVQEEIERVVGRNRSPCMQDRGHMPYTDAVVHEVQRYID
LIPTSLPHAVTCDVKFRNYLIPKGTTILTSLTSVLHDNKEFPNPEMFDPRHFLDEGGNFK
KSNYFMPFSAGKRICVGEGLARMELFLFLTFILQNFNLKSLIDPKDLDTTPVVNGFASVP
PFYQLCFIPV
Drug Target 1 [top]
Target 1 ID 811
Target 1 Name Translocator protein
Target 1 Synonyms
  1. Mitochondrial benzodiazepine receptor
  2. PBR
  3. PKBS
  4. Peripheral-type benzodiazepine receptor
Target 1 Gene Name BZRP
Target 1 Protein Sequence >Peripheral-type benzodiazepine receptor 
MAPPWVPAMGFTLAPSLGCFVGSRFVHGEGLRWYAGLQKPSWHPPHWVLGPVWGTLYSAM
GYGSYLVWKELGGFTEKAVVPLGLYTGQLALNWAWPPIFFGARQMGWALVDLLLVSGAAA
ATTVAWYQVSPLAARLLYPYLAWLAFATTLNYCVWRDNHGWHGGRRLPE
Target 1 Number of Residues 171
Target 1 Molecular Weight 18779
Target 1 Theoretical pI 9.33
Target 1 GO Classification
Function
Not Available
Process
Not Available
Component
cell
membrane
intrinsic to membrane
integral to membrane
Target 1 General Function Signal transduction mechanisms
Target 1 Specific Function Responsible for the manifestation of peripheral-type benzodiazepine recognition sites and is most likely to comprise binding domains for benzodiazepines and isoquinoline carboxamides. May play a role in the transport of porphyrins and heme
Target 1 Pathways Not Available
Target 1 Reactions Not Available
Target 1 Pfam Domain Function
Target 1 Signals
  • None
Target 1 Transmembrane Regions
  • 6-26
  • 47-67
  • 80-100
  • 106-126
  • 135-155
Target 1 Essentiality Non-Essential
Target 1 GenBank ID Protein 306883 Link Image
Target 1 UniProtKB/Swiss-Prot ID P30536 Link Image
Target 1 UniProtKB/Swiss-Prot Entry Name BZRP_HUMAN Link Image
Target 1 PDB ID Not Available
Target 1 Cellular Location
  • Mitochondrion
  • mitochondrial membrane
  • multi-pass membrane protein
Target 1 Gene Sequence >510 bp 
ATGGCCCCGCCCTGGGTGCCCGCCATGGGCTTCACGCTGGCGCCCAGCCTGGGGTGCTTC
GTGGGCTCCCGCTTTGTCCACGGCGAGGGTCTCCGCTGGTACGCCGGCCTGCAGAAGCCC
TCGTGGCACCCGCCCCACTGGGTGCTGGGCCCTGTCTGGGGCACGCTCTACTCAGCCATG
GGGTACGGCTCCTACCTGGTCTGGAAAGAGCTGGGAGGCTTCACAGAGAAGGCTGTGGTT
CCCCTGGGCCTCTACACTGGGCAGCTGGCCCTGAACTGGGCATGGCCCCCCATCTTCTTT
GGTGCCCGACAAATGGGCTGGGCCTTGGTGGATCTCCTGCTGGTCAGTGGGGCGGCGGCN
GCCACTACCGTGGCCTGGTACCAGGTGAGCCCGCTGGCCGCCCGCCTGCTCTACCCCTAC
CTGGCCTGGCTGGCCTTCGCGACCACACTCAACTACTGCGTATGGCGGGACAACCATGGC
TGGCATGGGGGACGGCGGCTGCCAGAGTGA
Target 1 GenBank Gene ID
Target 1 GeneCard ID TSPO Link Image
Target 1 GenAtlas ID TSPO Link Image
Target 1 HGNC ID HGNC:1158 Link Image
Target 1 Chromosome Location 22
Target 1 Locus 22q13.31
Target 1 SNPs SNPJam Report Link Image
Target 1 General References
  1. Dunham I, Shimizu N, Roe BA, Chissoe S, Hunt AR, Collins JE, Bruskiewich R, Beare DM, Clamp M, Smink LJ, Ainscough R, Almeida JP, Babbage A, Bagguley C, Bailey J, Barlow K, Bates KN, Beasley O, Bird CP, Blakey S, Bridgeman AM, Buck D, Burgess J, Burrill WD, O'Brien KP, et al.: The DNA sequence of human chromosome 22. Nature. 1999 Dec 2;402(6761):489-95. [PubMed Link Image]
  2. Kurumaji A, Nomoto H, Yoshikawa T, Okubo Y, Toru M: An association study between two missense variations of the benzodiazepine receptor (peripheral) gene and schizophrenia in a Japanese sample. J Neural Transm. 2000;107(4):491-500. [PubMed Link Image]
  3. Kurumaji A, Nomoto H, Yamada K, Yoshikawa T, Toru M: No association of two missense variations of the benzodiazepine receptor (peripheral) gene and mood disorders in a Japanese sample. Am J Med Genet. 2001 Mar 8;105(2):172-5. [PubMed Link Image]
  4. Riond J, Mattei MG, Kaghad M, Dumont X, Guillemot JC, Le Fur G, Caput D, Ferrara P: Molecular cloning and chromosomal localization of a human peripheral-type benzodiazepine receptor. Eur J Biochem. 1991 Jan 30;195(2):305-11. [PubMed Link Image]
  5. Yakovlev AG, Ruffo M, Jurka J, Krueger KE: Comparison of repetitive elements in the third intron of human and rodent mitochondrial benzodiazepine receptor-encoding genes. Gene. 1995 Apr 3;155(2):201-5. [PubMed Link Image]
  6. Galiegue S, Jbilo O, Combes T, Bribes E, Carayon P, Le Fur G, Casellas P: Cloning and characterization of PRAX-1. A new protein that specifically interacts with the peripheral benzodiazepine receptor. J Biol Chem. 1999 Jan 29;274(5):2938-52. [PubMed Link Image]
Target 1 Drug References
  1. Dobbin M, Martyres RF, Clode D, Champion De Crespigny FE: Association of benzodiazepine injection with the prescription of temazepam capsules. Drug Alcohol Rev. 2003 Jun;22(2):153-7. [PubMed Link Image]
  2. Miller EI, Wylie FM, Oliver JS: Detection of benzodiazepines in hair using ELISA and LC-ESI-MS-MS. J Anal Toxicol. 2006 Sep;30(7):441-8. [PubMed Link Image]
  3. Mant A, Whicker SD, McManus P, Birkett DJ, Edmonds D, Dumbrell D: Benzodiazepine utilisation in Australia: report from a new pharmacoepidemiological database. Aust J Public Health. 1993 Dec;17(4):345-9. [PubMed Link Image]

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.