bis(1,3-dimethyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione); ethane-1,2-diamine

• ChemBase ID: 1093
• Molecular Formular: C16H24N10O4
• Molecular Mass: 420.42636
• Monoisotopic Mass: 420.1981993
• SMILES: O=c1n(c(=O)n(c2nc[nH]c12)C)C.O=c1n(c(=O)n(c2nc[nH]c12)C)C.NCCN
• Canonical SMILES: Cn1c(=O)n(C)c2c(c1=O)[nH]cn2.Cn1c(=O)n(C)c2c(c1=O)[nH]cn2.NCCN
• InChI: InChI=1S/2C7H8N4O2.C2H8N2/c2*1-10-5-4(8-3-9-5)6(12)11(2)7(10)13;3-1-2-4/h2*3H,1-2H3,(H,8,9);1-4H2
• InChIKey: FQPFAHBPWDRTLU-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: bis(1,3-dimethyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione); ethane-1,2-diamine; bis(1,3-dimethyl-2,3,6,9-tetrahydro-1H-purine-2,6-dione); ethane-1,2-diamine
• IUPAC Traditional name: bis(1,3-dimethyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione); ethane-1,2-diamine; ethylenediamine; bis(theophylline); bis(constant-T); ethylenediamine
• Brand Name: Aminocardol; Aminodur; Ammophyllin; Cardiofilina; Cardiomin; Cardophylin; Cardophyllin; Carena; Cariomin; Diaphylline; Diophllin; Diuxanthine; Dobo; Dura-Tab S.M. Aminophylline; Ethophylline; Etilen-Xantisan Tabl.; Eurphyllin; Euufillin; Genophyllin; Grifomin; Inophylline; Lasodex; Linampheta; Lixaminol; Metaphyllin; Metaphylline; Methophylline; Minaphil; Miofilin; Neophyiline; Norofilina; Peterphyllin; Phylcardin; Phyllindon; Phyllocontin; Phyllocontin-350; Rectalad Aminophylline; Rectalad-Aminophylline; Somophyllin; Somophyllin O; Somophyllin-O; Stenovasan; Syntophyllin; Theodrox; Theolamine; Theolone; Theophyldine; Theophyline Ethylenediamine; Theophyllamine; Theophyllaminum; Theophyllin Aethylendiamin; Theophyllin Ethylenediamine; Theophylline Ethylenediamine; Thephyldine; Truphylline; Variaphylline; Vasofilina
• Synonyms: Truphylline; Aminophyllin; Aminophylline Anhydrous; Aminophylline Dihydrate; Aminophylline Dye Free; Aminophylline; (Theophylline)2 aO Ethylenediamine; 3,7Dihydro1,3dimethyl1Hpurine2,6dione, Cmpd. with 1,2ethanediamine (2:1); Theophyllin hemiethylenediamine complex; Theophylline, compound with ethylenediamine (2:1) dihydrate; Aminophyllin hydrate; (Theophylline)2 · Ethylenediamine; 3,7-Dihydro-1,3-dimethyl-1H-purine-2,6-dione, cmpd. with 1,2-ethanediamine (2:1); Theophylline hemi(ethylenediamine) complex; Theophylline hemiethylenediamine complex; Aminophylline; Somopphyllin; Aminocadol; Phyllocontin; (茶碱)2 aO 乙二胺; 1,3-二甲基-3,7-二氢-1H-嘌呤-2,6-二酮-1,2-乙二胺盐配混物 (2:1); 茶碱与乙二胺配混物 (2:1) 二水合物; 茶碱半乙二胺络合物; 氨茶碱 水合物; Aminophylline dihydrochloride hyderate

Database IDs

• CAS Number: 317-34-0
• EC Number: 206-264-5
• MDL Number: MFCD00013221
• PubChem SID: 24277691; 46508784; 160964556
• PubChem CID: 9433
• ATC CODE: R03DA05
• CHEMBL: 1210
• Chemspider ID: 9062
• DrugBank ID: DB01223
• KEGG ID: D00227
• Unique Ingredient Identifier: 27Y3KJK423
• Wikipedia Title: Aminophylline
• Medline Plus: a601015

CALCULATED PROPERTIES

• Acid pKa: 7.8151274
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): -0.7712048
• LogD (pH = 7.4): -0.89392424
• Log P: -0.7693217
• Molar Refractivity: 44.9345 cm^3
• Polarizability: 16.128607 Å^3
• Polar Surface Area: 69.3 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: 2E+005 mg/L; alcohol: insoluble; H2O: soluble50 mg/mL (solutions should be freshly prepared.)
• Apperance: white to off-white powder
• Hydrophobicity(logP): -3.03

Safety Information

• Storage Condition: -20°C
• RTECS: XH5600000
• European Hazard Symbols: Harmful (Xn)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 22; R:22
• Safety Statements: S:36/37/39
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301
• GHS Precautionary statements: P301 + P310
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• RID/ADR: UN 2811 6.1/PG 3
• Storage Temperature: -20°C

Pharmacology Properties

• Admin Routes: oral, i.v.
• Half Life: 7-9 hours
• Protein Bound: 60%
• Legal Status: P (UK)
• Mechanism of Action: Calcium antagonist; CNS stimulant; Phosphodiesterase inhibitor; Vasodilator

Product Information

• Purity: ≥98%; 99%
• Salt Data: ethane-1,2-diamine; Ethylenediamine
• Application(s): Cardiac stimulant; Diuretic; Smooth muscle relaxant
• Empirical Formula (Hill Notation): C14H16N8O4 · C2H8N2 · xH2O

DETAILS

DrugBank - DB01223

• Drug Groups: approved
• Description: Aminophylline is a drug combination that contains theophylline and ethylenediamine in 2:1 ratio. [Wikipedia]
• Indication: For the treatment of bronchospasm due to asthma, emphysema and chronic bronchitis.
• Pharmacology: Aminophylline is the ethylenediamine salt of theophylline. Theophylline stimulates the CNS, skeletal muscles, and cardiac muscle. It relaxes certain smooth muscles in the bronchi through PDE3 inhibition, produces diuresis, and causes an increase in gastric secretion.
• Affected Organisms: Humans and other mammals
• Half Life: 7-9 hours
• Protein Binding: 60%
• Distribution: * 0.3 to 0.7 L/kg
• Clearance: * 0.29 mL/kg/min [postnatal age 3-15 days]; * 0.64 mL/kg/min [postnatal age 25-57 days]; * 1.7 mL/kg/min [?1-4 years]; * 1.6 mL/kg/min [4-12 years]; * 0.9 mL/kg/min [13-15 years]; * 1.4 mL/kg/min [16-17 years]; * 0.65 mL/kg/min [Adults (16-60 years), non-smoking asthmatics]; * 0.41 mL/kg/min [Elderly (>60 years). liver, and renal function]; * 0.33 mL/kg/min [Acute pulmonary edema]; * 0.54 mL/kg/min [COPD->60 years, stable non-smoker >1 year]; * 0.48 mL/kg/min [COPD with cor pulmonale]; * 1.25 mL/kg/min [Cystic fibrosis (14-28 years)]; * 0.31 mL/kg/min [Liver disease -cholestasis]; * 0.35 mL/kg/min [cirrhosis]; * 0.65 mL/kg/min [acute hepatitis]; * 0.47 mL/kg/min [Sepsis with multi-organ failure]; * 0.38 mL/kg/min [hypothyroid]; * 0.8 mL/kg/min [hyperthyroid]
• External Links: Wikipedia; Drugs.com

Selleck Chemicals - S1673

Research Area: Respiratory Diseases
Biological Activity:
Aminophylline(Phyllocontin, Truphylline) is a competitive nonselective phosphodiesterase inhibitor with an IC50 of 0.12 mM and also a nonselective adenosine receptor antagonist. It is a bronchodilator. It is a compound of the bronchodilator theophylline with ethylenediamine in 2:1 ratio. [1][2] [3]

Sigma Aldrich - A1755

Biochem/physiol Actions
Non-selective phosphodiesterase (PDE) inhibitor. Antiepileptic drug
包装
25, 100 g in poly bottle

REFERENCES

• http://en.wikipedia.org/wiki/Aminophylline
• Spiteller, G. et al., Monatsh. Chem., 1962, 93, 632, (ms)
• Twanmoh, L.-M. et al., J. Het. Chem., 1973, 10, 187, (pmr)
• Takayama, S. et al., Chem. Pharm. Bull., 1974, 22, 1200, (synth, uv)
• Nicolau, C. et al., Z. Naturforsch., C, 1974, 29, 475, (cmr)
• Cohen, J.L., Anal. Profiles Drug Subst., 1975, 4, 466, (rev, ir, pmr, uv, ms, anal)
• Goeber, B. et al., Pharmazie, 1978, 33, 717, (ms)
• Naqvi, A.A. et al., J. Appl. Crystallogr., 1981, 14, 464, (cryst struct)
• Thakker, K.D. et al., Anal. Profiles Drug Subst., 1982, 11, 1, (rev, Aminophylline)
• Nishijo, J. et al., Chem. Pharm. Bull., 1982, 30, 391, (salts)
• Bukowsky, M. et al., Ann. Intern. Med., 1984, 101, 63, (rev, pharmacol)
• Weinberger, M., J. Allergy Clin. Immunol., 1984, 73, 525, (rev, pharmacol, tox)
• Grant, J.A. et al., J. Allergy Clin. Immunol., 1986, 78, 669, (rev, pharmacol)
• Rowe, D.J.F. et al., Ann. Clin. Biochem., 1988, 25, 4, (rev, pharmacol, tox, metab)
• Agostini, O. et al., Arzneim.-Forsch., 1990, 40, 1089, (Isbufylline, props, pmr, ms, ir, uv, cmr, cryst struct)
• Atta-ur-Rahman et al., The Alkaloids, 1990, 38, 232, (spectra)
• IARC Monog., 1991, 51, 391, (rev, tox)
• Kondo, K. et al., Tetrahedron, 1992, 48, 7145-7148, (Aplysidine)
• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 1314; 1315; 1319
• Negwer, M., Organic-Chemical Drugs and their Synonyms, 7th edn., Akademie-Verlag, 1994, 793, (synonyms)
• Ebisuzaki, Y. et al., Acta Cryst. C, 1997, 53, 777-779, (cryst struct)
• Markham, A. et al., Drugs, 1998, 56, 1081-1091, (rev)
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, TEP000; TEP500
• Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 3, 214B, (nmr)
• U.S. Pat., 1946, 2 404 319; CA, 40, 6214, (Ambuphylline)
• Blout, E.R. et al., J.A.C.S., 1950, 72, 479, (ir)