5-[(2R)-pentan-2-yl]-5-(prop-2-en-1-yl)-1,3-diazinane-2,4,6-trione

• ChemBase ID: 301
• Molecular Formular: C12H18N2O3
• Molecular Mass: 238.28292
• Monoisotopic Mass: 238.13174245
• SMILES: O=C1NC(=O)NC(=O)C1([C@@H](CCC)C)CC=C
• Canonical SMILES: CCC[C@H](C1(CC=C)C(=O)NC(=O)NC1=O)C
• InChI: InChI=1S/C12H18N2O3/c1-4-6-8(3)12(7-5-2)9(15)13-11(17)14-10(12)16/h5,8H,2,4,6-7H2,1,3H3,(H2,13,14,15,16,17)/t8-/m1/s1
• InChIKey: KQPKPCNLIDLUMF-MRVPVSSYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-[(2R)-pentan-2-yl]-5-(prop-2-en-1-yl)-1,3-diazinane-2,4,6-trione
• IUPAC Traditional name: pramil
• Brand Name: Barbosec; Bipanal; Bipinal sodium; Evronal; Evronal Sodium; Evrronal; Hypotrol; Hyptran; Imesonal; Immenoctal; Immenox; Meballymal; Meballymal sodium; Meballymalum; Novosecobarb; Pramil; Quinalbarbital; Quinalbarbitone; Quinalbarbitone sodium; Quinalspan; Sebar; Seco 8; Secobarbitone; Seconal; Sedutain; Seotal; Somosal; Synate; Trisomnin
• Synonyms: (+/-)-Secobarbital; Secobarbital Sodium; Secobarbitale [DCIT]; Secobarbitalum [INN-Latin]; Sodium quinalbarbitone; Sodium Secobarbital; Secobarbital

Database IDs

• CAS Number: 76-73-3
• PubChem SID: 160963764
• PubChem CID: 31143

CALCULATED PROPERTIES

JChem

• Acid pKa: 8.478766
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 2.0333812
• LogD (pH = 7.4): 1.9994502
• Log P: 2.0338318
• Molar Refractivity: 62.648 cm^3
• Polarizability: 24.39162 Å^3
• Polar Surface Area: 75.27 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.2
• LOG S: -2.29
• Solubility (Water): 1.21e+00 g/l

PROPERTIES

Physical Property

• Solubility: 550 mg/L
• Hydrophobicity(logP): 2.3

DETAILS

DrugBank - DB00418

• Drug Groups: approved
• Description: Secobarbital (marketed by Eli Lilly and Company under the brand names Seconal? and Tuinal) is a barbiturate derivative drug. It possesses anaesthetic, anticonvulsant, sedative and hypnotic properties. In the United Kingdom, it was known as Quinalbarbitone.
• Indication: For the Short-term treatment of intractable insomnia for patients habituated to barbiturates
• Pharmacology: Secobarbital, a barbiturate, is used for the induction of anesthesia prior to the use of other general anesthetic agents and for induction of anesthesia for short surgical, diagnostic, or therapeutic procedures associated with minimal painful stimuli. Little analgesia is conferred by barbiturates; their use in the presence of pain may result in excitation.
• Toxicity: Symptoms of an overdose typically include sluggishness, incoordination, difficulty in thinking, slowness of speech, faulty judgment, drowsiness or coma, shallow breathing, staggering, and in severe cases coma and death.
• Affected Organisms: Humans and other mammals
• Elimination: Barbiturates are metabolized primarily by the hepatic microsomal enzyme system, and the metabolic products are excreted in the urine and, less commonly, in the feces.
• External Links: Wikipedia; Drugs.com