08J

8-chloro-6-(2-fluorophenyl)-1-methyl-4H-imidazo[1,5-a][1,4]benzodiazepine

Created: 2011-10-13
Last modified:  2020-06-05

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Chemical Details

Formal Charge0
Atom Count36
Chiral Atom Count0
Bond Count39
Aromatic Bond Count17
2D diagram of 08J

Chemical Component Summary

Name8-chloro-6-(2-fluorophenyl)-1-methyl-4H-imidazo[1,5-a][1,4]benzodiazepine
SynonymsMidazolam
Systematic Name (OpenEye OEToolkits)8-chloranyl-6-(2-fluorophenyl)-1-methyl-4H-imidazo[1,5-a][1,4]benzodiazepine
FormulaC18 H13 Cl F N3
Molecular Weight325.767
TypeNON-POLYMER

Chemical Descriptors

TypeProgram Version Descriptor
SMILESACDLabs12.01Fc4ccccc4C2=NCc1cnc(n1c3c2cc(Cl)cc3)C
SMILESCACTVS3.370Cc1ncc2CN=C(c3ccccc3F)c4cc(Cl)ccc4n12
SMILESOpenEye OEToolkits1.7.2Cc1ncc2n1-c3ccc(cc3C(=NC2)c4ccccc4F)Cl
Canonical SMILESCACTVS3.370 Cc1ncc2CN=C(c3ccccc3F)c4cc(Cl)ccc4n12
Canonical SMILESOpenEye OEToolkits1.7.2 Cc1ncc2n1-c3ccc(cc3C(=NC2)c4ccccc4F)Cl
InChIInChI1.03 InChI=1S/C18H13ClFN3/c1-11-21-9-13-10-22-18(14-4-2-3-5-16(14)20)15-8-12(19)6-7-17(15)23(11)13/h2-9H,10H2,1H3
InChIKeyInChI1.03 DDLIGBOFAVUZHB-UHFFFAOYSA-N

Drug Info: DrugBank

DrugBank IDDB00683 
NameMidazolam
Groups
  • illicit
  • approved
DescriptionMidazolam is a short-acting hypnotic-sedative drug with anxiolytic, muscle relaxant, anticonvulsant, sedative, hypnotic, and amnesic properties.[A173842] It belongs to a class of drugs called _benzodiazepines_. This drug is unique from others in this class due to its rapid onset of effects and short duration of action.[A173842] Midazolam is available by oral, rectal, intranasal, intramuscular (IM), and intravenous (IV) routes and has been used in various biomedical applications, including dentistry, cardiac surgery, and endoscopic procedures as pre-anesthetic medication, and as an adjunct to local anesthesia.[F2977] This drug was initially approved by the US FDA in 1985, and has been approved for various indications since.[L45098] In late 2018, the intramuscular preparation was approved by the FDA for the treatment of status epilepticus in adults.[L45098] In May 2019, the nasal spray of midazolam was approved for the acute treatment of distinctive intermittent, stereotypic seizure episodes in patients 12 years of age and older.[A257153] Midazolam is considered a schedule IV drug in the United States due to the low potential for abuse and low risk of dependence.[L5074]
Synonyms
  • Midazolam hydrochloride
  • Midazolam
  • Midazolam maleate
  • Midazolamum
Brand Names
  • Buccolam
  • Seizalam
  • MKH Dose Pack
  • MKO Melt Dose Pack
  • Apo-midazolam Injectable 5 mg/ml
IndicationMidazolam has different indications depending on its formulation by the FDA. **Nasal** For the nasal spray formulation, midazolam is indicated for the acute treatment of intermittent, stereotypic episodes of frequent seizure activity (i.e., seizure clusters, acute repetitive seizures) that are distinct from a patient’s usual seizure pattern in patients with epilepsy 12 years of age and older.[L44773] **Intravenous** For the intravenous injection formulation, midazolam is indicated as an agent for sedation/anxiolysis/amnesia and prior to or during diagnostic, therapeutic or endoscopic procedures, such as bronchoscopy, gastroscopy, cystoscopy, coronary angiography, cardiac catheterization, oncology procedures, radiologic procedures, suture of lacerations and other procedures either alone or in combination with other CNS depressants.[L12981] The sedative, anxiolytic and amnestic use of midazolam can also be employed pre-operatively.[L12981] It can also be indicated for induction of general anesthesia, before administration of other anesthetic agents or as a component of intravenous supplementation of nitrous oxide and oxygen for a balanced anesthesia.[L12981] A relatively narrower dose range of midazolam and a shorter period of induction can be achieved if midazolam is combined with narcotic premedication.[L12981] Finally, midazolam can be indicated as a continous intravenous infusion for sedation of intubated and mechanically ventilated patients as a component of anesthesia or during treatment in a critical care setting.[L12981] **Intramuscular** For the intramusuclar injection formulation, midazolam is indicated for preoperative sedation/anxiolysis/amnesia or for treatment of status epilepticus in adults.[L12981,L45048] **Oral** Midazolam syrup is indicated for use in pediatric patients for sedation, anxiolysis and amnesia prior to diagnostic, therapeutic or endoscopic procedures or before induction of anesthesia. It is only approved in monitored settings only and not for chronic or home use.[L5092] In Europe, a buccal formulation of midazolam is also approved for the treatment of prolonged, acute, convulsive seizures in infants, toddlers, children and adolescents (from 3 months to < 18 years). For infants between 3-6 months of age treatment should be in a hospital setting where monitoring is possible and resuscitation equipment is available.[L45053]
Categories
  • Adjuvants, Anesthesia
  • Anesthetics
  • Anti-Anxiety Agents
  • Benzodiazepine hypnotics and sedatives
  • Benzodiazepines and benzodiazepine derivatives
ATC-CodeN05CD08
CAS number59467-70-8

Drug Targets

NameTarget SequencePharmacological ActionActions
GABA(A) ReceptorMRKSPGLSDCLWAWILLLSTLTGRSYGQPSLQDELKDNTTVFTRILDRLL...unknownpositive allosteric modulator
GABA(A) Receptor Benzodiazepine Binding SiteMRKSPGLSDCLWAWILLLSTLTGRSYGQPSLQDELKDNTTVFTRILDRLL...unknownligand
Adenosine receptor A2aMPIMGSSVYITVELAIAVLAILGNVLVCWAVWLNSNLQNVTNYFVVSLAA...unknownpotentiator
Cytochrome P450 3A4MALIPDLAMETWLLLAVSLVLLYLYGTHSHGLFKKLGIPGPTPLPFLGNI...unknownsubstrate,inhibitor
UDP-glucuronosyltransferase 1-4MARGLQVPLPRLATGLLLLLSVQPWAESGKVLVVPTDGSPWLSMREALRE...unknownsubstrate
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Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
Pharos CHEMBL655
PubChem 4192
ChEMBL CHEMBL655
ChEBI CHEBI:6931
CCDC/CSD CUYCAB
COD 4502706