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59467-96-8 molecular structure
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12-chloro-9-(2-fluorophenyl)-3-methyl-2,4,8-triazatricyclo[8.4.0.0^{2,6}]tetradeca-1(10),3,5,8,11,13-hexaene

ChemBase ID: 565
Molecular Formular: C18H13ClFN3
Molecular Mass: 325.7673232
Monoisotopic Mass: 325.07820333
SMILES and InChIs

SMILES:
Clc1cc2c(n3c(CN=C2c2c(F)cccc2)cnc3C)cc1
Canonical SMILES:
Clc1ccc2c(c1)C(=NCc1n2c(C)nc1)c1ccccc1F
InChI:
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
InChIKey:
DDLIGBOFAVUZHB-UHFFFAOYSA-N

Cite this record

CBID:565 http://www.chembase.cn/molecule-565.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
12-chloro-9-(2-fluorophenyl)-3-methyl-2,4,8-triazatricyclo[8.4.0.0^{2,6}]tetradeca-1(10),3,5,8,11,13-hexaene
12-chloro-9-(2-fluorophenyl)-3-methyl-2,4,8-triazatricyclo[8.4.0.02,6]tetradeca-1(14),3,5,8,10,12-hexaene
12-chloro-9-(2-fluorophenyl)-3-methyl-2,4,8-triazatricyclo[8.4.0.02,6]tetradeca-1(10),3,5,8,11,13-hexaene
IUPAC Traditional name
midazolam
Brand Name
Dormicum
Versed
Synonyms
Dea No. 2884
Midazolam Base
Midazolam Hcl
Midazolamum [INN-Latin]
Midazolam
8-Chloro-6-(2-fluorophenyl)-1-methyl-4H-imidazo[1,5a][1,4]benzodiazepine hydrochloride
Midazolam hydrochloride
Midanium
Midazolam
Midosed
Rohipnol
Sumianxin
8-Chloro-6-(2-fluorophenyl)-1-methyl-4H-imidazo[1,5-a][1,4]benzodiazepine
Dazolam
Dormicum
CAS Number
59467-96-8
59467-70-8
EC Number
261-776-6
MDL Number
MFCD00864445
PubChem SID
160964028
46507611
24724654
PubChem CID
4192

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
H Acceptors H Donor
LogD (pH = 5.5) 2.4297755  LogD (pH = 7.4) 3.2779806 
Log P 3.3348  Molar Refractivity 99.4297 cm3
Polarizability 33.933826 Å3 Polar Surface Area 30.18 Å2
Rotatable Bonds Lipinski's Rule of Five true 
Log P 3.89  LOG S -4.52 
Solubility (Water) 9.87e-03 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
0.024 mg/mL [Thorsteinn Loftsson and Dagny Hreinsdóttir, 2006] expand Show data source
Chloroform expand Show data source
DiMSO expand Show data source
Methanol expand Show data source
Apperance
white to off-white solid expand Show data source
White to Off-White Solid expand Show data source
Melting Point
161-164°C expand Show data source
Storage Condition
Controlled Substance, -20°C Freezer expand Show data source
RTECS
NI2922250 expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Personal Protective Equipment
Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter expand Show data source
Drug Control
USDEA Schedule IV; Home Office Schedule 3; psychotrope; kontrollierte Droge in Deutschland; regulated under CDSA - not available from Sigma-Aldrich Canada expand Show data source
Storage Temperature
2-8°C expand Show data source
Gene Information
human ... ABCB1(5243), CYP3A4(1576)mouse ... Abcb1a(18671), Abcb1b(18669)rat ... Gabbr1(81657), Gabra1(29705) expand Show data source
Certificate of Analysis
Download expand Show data source
Empirical Formula (Hill Notation)
C18H13ClFN3 · HCl expand Show data source

DETAILS

DETAILS

DrugBank DrugBank Sigma Aldrich Sigma Aldrich TRC TRC
DrugBank - DB00683 external link
Item Information
Drug Groups illicit; approved
Description A short-acting hypnotic-sedative drug with anxiolytic and amnestic properties. It is used in dentistry, cardiac surgery, endoscopic procedures, as preanesthetic medication, and as an adjunct to local anesthesia. The short duration and cardiorespiratory stability makes it useful in poor-risk, elderly, and cardiac patients. It is water-soluble at pH less than 4 and lipid-soluble at physiological pH. [PubChem] Midazolam is a schedule IV drug in the United States.
Indication For use as a sedative perioperatively.
Pharmacology Midazolam is a short-acting benzodiazepine central nervous system (CNS) depressant. Pharmacodynamic properties of midazolam and its metabolites, which are similar to those of other benzodiazepines, include sedative, anxiolytic, amnesic and hypnotic activities. Benzodiazepine pharmacologic effects appear to result from reversible interactions with the (gamma)-amino butyric acid (GABA) benzodiazepine receptor in the CNS, the major inhibitory neurotransmitter in the central nervous system. The action of midazolam is readily reversed by the benzodiazepine receptor antagonist, flumazenil.
Toxicity LD50=825 mg/kg (Orally in rats). Signs of overdose include sedation, somnolence, confusion, impaired coordination, diminished reflexes, coma, and deleterious effects on vital signs.
Affected Organisms
Humans and other mammals
Biotransformation Midazolam is primarily metabolized in the liver and gut by human cytochrome P450 IIIA4 (CYP3A4) to its pharmacologic active metabolite, (alpha)-hydroxymidazolam, and 4-hydroxymidazolam.
Absorption Rapidly absorbed after oral administration (absolute bioavailability of the midazolam syrup in pediatric patients is about 36%, and intramuscular is greater than 90%).
Half Life 2.2-6.8 hours
Protein Binding 97%
Elimination Midazolam is primarily metabolized in the liver and gut by human cytochrome P450 IIIA4 (CYP3A4) to its pharmacologic active metabolite, α-hydroxymidazolam, followed by glucuronidation of the α–hydroxyl metabolite which is present in unconjugated and conjugated forms in human plasma. The α- hydroxymidazolam glucuronide is then excreted in urine. No significant amount of parent drug or metabolites is extractable from urine before beta-glucuronidase and sulfatase deconjugation, indicating that the urinary metabolites are excreted mainly as conjugates.
Distribution * 1.24 to 2.02 L/kg [pediatric patients (6 months to <16 years) receiving 0.15 mg/kg IV midazolam,]
Clearance * 9.3 to 11 mL/min/kg [pediatric patients (6 months to <16 years old)]
References
Skerritt JH, Johnston GA: Enhancement of GABA binding by benzodiazepines and related anxiolytics. Eur J Pharmacol. 1983 May 6;89(3-4):193-8. [Pubmed]
Isojarvi JI, Tokola RA: Benzodiazepines in the treatment of epilepsy in people with intellectual disability. J Intellect Disabil Res. 1998 Dec;42 Suppl 1:80-92. [Pubmed]
Garratt JC, Gent JP, Feely M, Haigh JR: Can benzodiazepines be classified by characterising their anticonvulsant tolerance-inducing potential? Eur J Pharmacol. 1988 Jan 5;145(1):75-80. [Pubmed]
Tokunaga S, Takeda Y, Shinomiya K, Hirase M, Kamei C: Effects of some H1-antagonists on the sleep-wake cycle in sleep-disturbed rats. J Pharmacol Sci. 2007 Feb;103(2):201-6. Epub 2007 Feb 8. [Pubmed]
Vermeeren A: Residual effects of hypnotics: epidemiology and clinical implications. CNS Drugs. 2004;18(5):297-328. [Pubmed]
External Links
Wikipedia
RxList
Drugs.com
Sigma Aldrich - UC429 external link
Biochem/physiol Actions
Sedative/hypnotic; ligand for the GABAA receptor benzodiazepine modulatory site; CYP3A4 substrate.
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. UC429.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.
Toronto Research Chemicals - M343000 external link
Anesthetic; anticonvulsant; sedative; hypnotic.

REFERENCES

REFERENCES

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  • • Skerritt JH, Johnston GA: Enhancement of GABA binding by benzodiazepines and related anxiolytics. Eur J Pharmacol. 1983 May 6;89(3-4):193-8. Pubmed
  • • Isojarvi JI, Tokola RA: Benzodiazepines in the treatment of epilepsy in people with intellectual disability. J Intellect Disabil Res. 1998 Dec;42 Suppl 1:80-92. Pubmed
  • • Garratt JC, Gent JP, Feely M, Haigh JR: Can benzodiazepines be classified by characterising their anticonvulsant tolerance-inducing potential? Eur J Pharmacol. 1988 Jan 5;145(1):75-80. Pubmed
  • • Tokunaga S, Takeda Y, Shinomiya K, Hirase M, Kamei C: Effects of some H1-antagonists on the sleep-wake cycle in sleep-disturbed rats. J Pharmacol Sci. 2007 Feb;103(2):201-6. Epub 2007 Feb 8. Pubmed
  • • Vermeeren A: Residual effects of hypnotics: epidemiology and clinical implications. CNS Drugs. 2004;18(5):297-328. Pubmed
  • • Dundee, J. W., et al.: Drugs, 28, 519 (1984)
  • • Lahat, E., et al.: Br. Med. J., 321, 83 (1984)
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PATENTS

PATENTS

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