U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C15H10BrClN4S
Molecular Weight 393.689
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BROTIZOLAM

SMILES

CC1=NN=C2CN=C(C3=C(SC(Br)=C3)N12)C4=C(Cl)C=CC=C4

InChI

InChIKey=UMSGKTJDUHERQW-UHFFFAOYSA-N
InChI=1S/C15H10BrClN4S/c1-8-19-20-13-7-18-14(9-4-2-3-5-11(9)17)10-6-12(16)22-15(10)21(8)13/h2-6H,7H2,1H3

HIDE SMILES / InChI

Description
Curator's Comment: description was created based on several sources, including http://www.rad-ar.or.jp/siori/english/print.cgi?n=52

Brotizolam (marketed under brand name Lendormin) is a sedative-hypnotic thienotriazolodiazepine drug which is a benzodiazepine analog. It possesses anxiolytic, anticonvulsant, hypnotic, sedative and skeletal muscle relaxant properties, and is considered to be similar in effect to short-acting benzodiazepines such as triazolam. It is used in the short-term treatment of severe or debilitating insomnia and in a dose of 0.25 mg can be used as a premedication prior to surgery, this dose was found to be comparable in efficacy to 2 mg flunitrazepam as a premedicant prior to surgery. The drug was developed by a team led by T Nishiyama while working for Takeda Chemical Industries in 1976 in Japan. Brotizolam is not approved for sale in the UK, United States or Canada. It is approved for sale in the Netherlands, Germany, Spain, Belgium, Luxembourg, Austria, Portugal, Israel, Italy, Taiwan and Japan. Insomnia. Brotizolam is prescribed for the short-term treatment, 2–4 weeks only of severe or debilitating insomnia. Insomnia can be described as a difficulty falling asleep, frequent awakening, early awakenings or a combination of each. Brotizolam inhibits the hypothalamus and cerebral limbic system controlling emotion through GABA, a typical inhibitory transmitter of central nervous system. As a result, unnecessary stimulation from the autonomic nervous system and other sites is blocked, demonstrating central nervous action including hypnosis, sedation and anti-anxiety

CNS Activity

Curator's Comment: CNS depressant Known to be CNS depressant in mice, rats and rabbits. Human data not available

Originator

Curator's Comment: # by a team led by T Nishiyama while working for Takeda Chemical Industries in 1976 in Japan

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Lendormin

Approved Use

Unknown

Launch Date

2007
PubMed

PubMed

TitleDatePubMed
[Case of prolonged recovery from serotonin syndrome caused by paroxetine].
2003
[Investigations of poisonings with benzodiazepine derivatives mixtures by thin-layer chromatography].
2003
Zopiclone, but not brotizolam, impairs memory storage during sleep.
2003 Oct
CAP variables and arousals as sleep electroencephalogram markers for primary insomnia.
2003 Sep
Screening, library-assisted identification and validated quantification of 23 benzodiazepines, flumazenil, zaleplone, zolpidem and zopiclone in plasma by liquid chromatography/mass spectrometry with atmospheric pressure chemical ionization.
2004 Aug
Sustained inhibition of brotizolam induced anterograde amnesia by norharmane and retrograde amnesia by L-glutamic acid in mice.
2007 Aug 22
High plasma concentrations of paroxetine impede clinical response in patients with panic disorder.
2007 Feb
Benzodiazepine metabolism: an analytical perspective.
2008 Oct
Non-ST Elevation Myocardial Infraction after High Dose Intravenous Immunoglobulin Infusion.
2009
Influence of serotonergic/noradrenergic gene polymorphisms on nausea and sweating induced by milnacipran in the treatment of depression.
2009
Paradoxical reactions to hypnotic agents in adolescents with free-running disorder.
2009 Jun
Development of a list of potentially inappropriate drugs for the korean elderly using the delphi method.
2010 Dec
Patents

Patents

Sample Use Guides

for adults: one tablet (0.25mg of brotizolam) is orally administered once daily at bedtime
Route of Administration: Oral
In Vitro Use Guide
Using slices of the olfactory tubercle, nucleus accumbens and caudate nucleus, the effects of brotizolam on dopaminergic nerve terminals were examined in vitro. Basal release of dopamine was not affected by brotizolam in concentrations up to 10(-6) M; however, K+-stimulated release of dopamine was significantly reduced by brotizolam at 10(-7) M or above. The reduction of K+-stimulated release of dopamine was antagonized by bicuculline, added in the superfusion medium.
Name Type Language
BROTIZOLAM
EP   INN   JAN   MART.   MI   USAN   WHO-DD  
INN   USAN  
Official Name English
SINTONAL
Brand Name English
WE 941
Code English
WE-941
Code English
MEDERANTIL
Brand Name English
BROTIZOLAM [MART.]
Common Name English
BROTIZOLAM [USAN]
Common Name English
Brotizolam [WHO-DD]
Common Name English
LENDORM
Brand Name English
2-BROMO-4-(2-CHLOROPHENYL)-9-METHYL-6H-THIENO(3,2-F)-S-TRIAZOLO(4,3-A)(1,4)DIAZEPINE
Systematic Name English
BROTIZOLAM [EP MONOGRAPH]
Common Name English
8-BROMO-6-(O-CHLOROPHENYL)-1-METHYL-4H-S-TRIAZOLO(3,4-C)THIENO(2,3-E)-1,4-DIAZEPINE
Common Name English
BROTIZOLAM [MI]
Common Name English
NIMBISAN
Brand Name English
WE-941-BS
Code English
LENDORMIN
Brand Name English
BROTIZOLAM [JAN]
Common Name English
2-Bromo-4-(O-chlorophenyl)-9-methyl-6H-thieno[3,2-f]-S-triazolo[4,3-a][1,4]diazepine
Common Name English
brotizolam [INN]
Common Name English
6H-THIENO(3,2-F)(1,2,4)TRIAZOLO(4,3-A)(1,4)DIAZEPINE, 2-BROMO-4-(2-CHLOROPHENYL)-9-METHYL-
Systematic Name English
Classification Tree Code System Code
WHO-ATC N05CD09
Created by admin on Fri Dec 15 15:18:45 GMT 2023 , Edited by admin on Fri Dec 15 15:18:45 GMT 2023
NCI_THESAURUS C1012
Created by admin on Fri Dec 15 15:18:45 GMT 2023 , Edited by admin on Fri Dec 15 15:18:45 GMT 2023
WHO-VATC QN05CD09
Created by admin on Fri Dec 15 15:18:45 GMT 2023 , Edited by admin on Fri Dec 15 15:18:45 GMT 2023
Code System Code Type Description
NCI_THESAURUS
C87057
Created by admin on Fri Dec 15 15:18:45 GMT 2023 , Edited by admin on Fri Dec 15 15:18:45 GMT 2023
PRIMARY
INN
4549
Created by admin on Fri Dec 15 15:18:45 GMT 2023 , Edited by admin on Fri Dec 15 15:18:45 GMT 2023
PRIMARY
EPA CompTox
DTXSID0022692
Created by admin on Fri Dec 15 15:18:45 GMT 2023 , Edited by admin on Fri Dec 15 15:18:45 GMT 2023
PRIMARY
FDA UNII
5XZM1R3DKF
Created by admin on Fri Dec 15 15:18:45 GMT 2023 , Edited by admin on Fri Dec 15 15:18:45 GMT 2023
PRIMARY
MERCK INDEX
m2729
Created by admin on Fri Dec 15 15:18:45 GMT 2023 , Edited by admin on Fri Dec 15 15:18:45 GMT 2023
PRIMARY Merck Index
ECHA (EC/EINECS)
260-964-5
Created by admin on Fri Dec 15 15:18:45 GMT 2023 , Edited by admin on Fri Dec 15 15:18:45 GMT 2023
PRIMARY
WIKIPEDIA
BROTIZOLAM
Created by admin on Fri Dec 15 15:18:45 GMT 2023 , Edited by admin on Fri Dec 15 15:18:45 GMT 2023
PRIMARY
RXCUI
19790
Created by admin on Fri Dec 15 15:18:45 GMT 2023 , Edited by admin on Fri Dec 15 15:18:45 GMT 2023
PRIMARY RxNorm
SMS_ID
100000085858
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PRIMARY
PUBCHEM
2451
Created by admin on Fri Dec 15 15:18:45 GMT 2023 , Edited by admin on Fri Dec 15 15:18:45 GMT 2023
PRIMARY
EVMPD
SUB05933MIG
Created by admin on Fri Dec 15 15:18:45 GMT 2023 , Edited by admin on Fri Dec 15 15:18:45 GMT 2023
PRIMARY
MESH
C020960
Created by admin on Fri Dec 15 15:18:45 GMT 2023 , Edited by admin on Fri Dec 15 15:18:45 GMT 2023
PRIMARY
CAS
57801-81-7
Created by admin on Fri Dec 15 15:18:45 GMT 2023 , Edited by admin on Fri Dec 15 15:18:45 GMT 2023
PRIMARY
DRUG BANK
DB09017
Created by admin on Fri Dec 15 15:18:45 GMT 2023 , Edited by admin on Fri Dec 15 15:18:45 GMT 2023
PRIMARY
DRUG CENTRAL
409
Created by admin on Fri Dec 15 15:18:45 GMT 2023 , Edited by admin on Fri Dec 15 15:18:45 GMT 2023
PRIMARY
ChEMBL
CHEMBL32479
Created by admin on Fri Dec 15 15:18:45 GMT 2023 , Edited by admin on Fri Dec 15 15:18:45 GMT 2023
PRIMARY
USAN
T-113
Created by admin on Fri Dec 15 15:18:45 GMT 2023 , Edited by admin on Fri Dec 15 15:18:45 GMT 2023
PRIMARY