7-chloro-5-(2-chlorophenyl)-2,3-dihydro-1H-1,4-benzodiazepin-2-one

• ChemBase ID: 1301
• Molecular Formular: C15H10Cl2N2O
• Molecular Mass: 305.1587
• Monoisotopic Mass: 304.01701831
• SMILES: Clc1cc2C(=NCC(=O)Nc2cc1)c1c(Cl)cccc1
• Canonical SMILES: O=C1CN=C(c2c(N1)ccc(c2)Cl)c1ccccc1Cl
• InChI: InChI=1S/C15H10Cl2N2O/c16-9-5-6-13-11(7-9)15(18-8-14(20)19-13)10-3-1-2-4-12(10)17/h1-7H,8H2,(H,19,20)
• InChIKey: CHIFCDOIPRCHCF-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 7-chloro-5-(2-chlorophenyl)-2,3-dihydro-1H-1,4-benzodiazepin-2-one
• IUPAC Traditional name: @delorazepam; delorazepam; 7-chloro-5-(2-chlorophenyl)-2,3-dihydro-1H-1,4-benzodiazepin-2-one
• Synonyms: Delorazepam; 7-Chloro-5-(o-chlorophenyl)-1,3-dihydro-2H-1,4-benzodiazepin-2-one; Delorazepam; 7-Chloro-5-(2-chlorophenyl)-1,3-dihydro-2H-1,4-benzodiazepin-2-one; 2'-Chloronordiazepam; 7-Chloro-5-(2-chlorophenyl)-3H-1,4-benzodiazepin-2(1H)-one; Chlordemethyldiazepam; NSC 169895; RV 12165; Ro 5-3027; 2-Chlorophenyl- N -desmethyldiazepam; Chloronordiazepam; Briantum; Aurazepam; 7-氯-5-(2-氯苯基)-1,3-二氢-2H-1,4-苯并二氮杂卓-2-酮; 地洛西泮

Database IDs

• CAS Number: 2894-67-9
• EC Number: 220-771-9
• MDL Number: MFCD00079156
• PubChem SID: 24894151; 46504957; 160964761
• PubChem CID: 17925
• CHEMBL: 268254
• Chemspider ID: 16929
• DrugBank ID: DB01511
• KEGG ID: D07784
• Unique Ingredient Identifier: O91W32476G
• Wikipedia Title: Delorazepam

CALCULATED PROPERTIES

ALOGPS 2.1

• Solubility (Water): 6.42e-03 g/l
• Log P: 3.46
• LOG S: -4.68

JChem

• Acid pKa: 12.293636
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 3.8159113
• LogD (pH = 7.4): 3.816058
• Log P: 3.816065
• Molar Refractivity: 81.5008 cm^3
• Polarizability: 30.377464 Å^3
• Polar Surface Area: 41.46 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Ethyl Acetate
• Apperance: Off-White to Pale Yellow Solid
• Melting Point: 187-189°C

Safety Information

• Storage Condition: Controlled Substance, -20°C Freezer
• RTECS: DF2367500
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• Safety Statements: 36/37/39
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Drug Control: USDEA Schedule IV; Home Office Schedule 4.1; psychotrope; kontrollierte Droge in Deutschland; regulated under CDSA - not available from Sigma-Aldrich Canada

Pharmacology Properties

• Admin Routes: Oral
• Bioavailability: 87%
• Excretion: Renal
• Half Life: [60-140]
• Metabolism: Hepatic
• Mechanism of Action: Benzodiazepine agonist; Dopamine-2-antagonis;; Dopamine-turnover stimulant; Heat-regulating centre inhibitor; Membranestabilizer; Prolactin-release stimulant; Sympatholytic-alpha

Product Information

• Application(s): Ganglionplegic; Parasympatholytic; Psychosedatives; Tranquilizers
• Empirical Formula (Hill Notation): C15H10Cl2N2O

DETAILS

DrugBank - DB01511

Drug information: illicit; experimental

Toronto Research Chemicals - D230675

Controlled Substance.

REFERENCES

• Ger. Pat., 1974, 2 519 318; CA, 84, 31152, (pivalate)
• Bandoli, G. et al., J.C.S. Perkin 2, 1976, 413, (cryst struct)
• Bogatskii, A.V. et al., Khim.-Farm. Zh., 1977, 11, 85, (synth)
• De Angelis, L., Drugs of Today (Barcelona), 1979, 15, 173, (rev)
• Chananont, P. et al., Acta Cryst. B, 1981, 37, 1371, (cryst struct)
• Quaglio, M.P. et al., Farmaco, Ed. Prat., 1981, 36, 487, (glc)
• Homan, R.W. et al., Antiepileptic Drugs, (Eds. Levy, R. et al), Raven Press, New York, 1989, 841
• Kondo, T. et al., Ther. Drug Monit., 1993, 15, 35, (hplc)
• Negwer, M., Organic-Chemical Drugs and their Synonyms, 7th edn., Akademie-Verlag, 1994, 4330; 4331, (synonyms)
• Jurand, A. et al., Pharmacol. Toxicol., 1994, 74, 228, (tox)
• Martindale, The Extra Pharmacopoeia, 32nd edn., Pharmaceutical Press, 1999, 675