Etahalon

Etahalon
IUPAC ime
	3-(2-etilfenil)-2-metil-hinazolin-4-on
Klinički podaci
Drugs.com	Monografija
Identifikatori
CAS broj	7432-25-9
ATC kod	none
PubChem	CID 23914
ChemSpider	22357
UNII	HFS3HB32J7
Hemijski podaci
Formula	C17H16N2O
Molarna masa	264,322
	SMILES CCc1ccccc1N2C(=Nc3ccccc3C2=O)C; ;
	InChI InChI=1S/C17H16N2O/c1-3-13-8-4-7-11-16(13)19-12(2)18-15-10-6-5-9-14(15)17(19)20/h4-11H,3H2,1-2H3 ; Key:UVTJKLLUVOTSOB-UHFFFAOYSA-N ;

Etahalon (Aolan, Atinazon, Etinazon^[1]) je GABAergik klase hinazolinona i analog je metahalonu koji je razvijen tokom 1960-ih^[2]^[3] i plasiran uglavnom u Francuskoj i nekim drugim evropskim zemljama. Ima sedativna, hipnotička, mišićna relaksantna i depresivna svojstva centralnog nervnog sistema koja su rezultat njegove agonističke aktivnosti na β-podtipu GABA_A receptora, i korišćen je za lečenje nesanice.

Osobine

Etahalon je organsko jedinjenje, koje sadrži 17 atoma ugljenika i ima molekulsku masu od 264,322 Da.

Osobina	Vrednost
Broj akceptora vodonika	2
Broj donora vodonika	0
Broj rotacionih veza	2
Particioni koeficijent^[4] (ALogP)	3,6
Rastvorljivost^[5] (logS, log(mol/L))	-4,4
Polarna površina^[6] (PSA, Å²)	32,7

Reference

^ Pflegel P, Wagner G (новембар 1967). „[On the polarography of 2-methyl-3-(2-methylphenyl)-3,4-dihydroquinazolinone-(4) methaqualone, Dormutil) and 2-methyl-3-(2-ethylphenyl-3,4-dihydroquinazolinone-(4) (ethinazone, Aolan). 5. Polarography of heterocyclic compounds]” [On the Polarography of 2-Methyl-3-(2-methylphenyl)-3,4-dihydroquinazolinone-(4) (methaqualone, Dormutil) and 2-methyl-3-(2-ethylphenyl-3,4-dihydroquinazolinone-(4) (ethinazone, Aolan). 5. Polarography of Heterocyclic Compounds]. Die Pharmazie (на језику: German). 22 (11): 643—50. PMID 5619478.
^ GB patent 936902, "Quinazolinone Derivatives", issued 1963-09-18, assigned to Beiersdorf
^ Parmar SS, Kishor K, Seth PK, Arora RC (јануар 1969). „Role of alkyl substitution in 2,3-disubstituted and 3-substituted 4-quinazolones on the inhibition of pyruvic acid oxidation”. Journal of Medicinal Chemistry. 12 (1): 138—41. PMID 4303122. doi:10.1021/jm00301a035.
^ Ghose, A.K.; Viswanadhan V.N. & Wendoloski, J.J. (1998). „Prediction of Hydrophobic (Lipophilic) Properties of Small Organic Molecules Using Fragment Methods: An Analysis of AlogP and CLogP Methods”. J. Phys. Chem. A. 102: 3762—3772. doi:10.1021/jp980230o.
^ Tetko IV, Tanchuk VY, Kasheva TN, Villa AE (2001). „Estimation of Aqueous Solubility of Chemical Compounds Using E-State Indices”. Chem Inf. Comput. Sci. 41: 1488—1493. PMID 11749573. doi:10.1021/ci000392t.
^ Ertl P.; Rohde B.; Selzer P. (2000). „Fast calculation of molecular polar surface area as a sum of fragment based contributions and its application to the prediction of drug transport properties”. J. Med. Chem. 43: 3714—3717. PMID 11020286. doi:10.1021/jm000942e.

Literatura

Hardman JG, Limbird LE, Gilman AG (2001). Goodman & Gilman's The Pharmacological Basis of Therapeutics (10. изд.). New York: McGraw-Hill. ISBN 0071354697. doi:10.1036/0071422803.
Thomas L. Lemke; David A. Williams, ур. (2007). Foye's Principles of Medicinal Chemistry (6. изд.). Baltimore: Lippincott Willams & Wilkins. ISBN 0781768799.

Spoljašnje veze

Etaqualone

[1] Pflegel P, Wagner G (новембар 1967). „[On the polarography of 2-methyl-3-(2-methylphenyl)-3,4-dihydroquinazolinone-(4) methaqualone, Dormutil) and 2-methyl-3-(2-ethylphenyl-3,4-dihydroquinazolinone-(4) (ethinazone, Aolan). 5. Polarography of heterocyclic compounds]” [On the Polarography of 2-Methyl-3-(2-methylphenyl)-3,4-dihydroquinazolinone-(4) (methaqualone, Dormutil) and 2-methyl-3-(2-ethylphenyl-3,4-dihydroquinazolinone-(4) (ethinazone, Aolan). 5. Polarography of Heterocyclic Compounds]. Die Pharmazie (на језику: German). 22 (11): 643—50. PMID 5619478.

[2] GB patent 936902, "Quinazolinone Derivatives", issued 1963-09-18, assigned to Beiersdorf

[3] Parmar SS, Kishor K, Seth PK, Arora RC (јануар 1969). „Role of alkyl substitution in 2,3-disubstituted and 3-substituted 4-quinazolones on the inhibition of pyruvic acid oxidation”. Journal of Medicinal Chemistry. 12 (1): 138—41. PMID 4303122. doi:10.1021/jm00301a035.

[4] Ghose, A.K.; Viswanadhan V.N. & Wendoloski, J.J. (1998). „Prediction of Hydrophobic (Lipophilic) Properties of Small Organic Molecules Using Fragment Methods: An Analysis of AlogP and CLogP Methods”. J. Phys. Chem. A. 102: 3762—3772. doi:10.1021/jp980230o.

[5] Tetko IV, Tanchuk VY, Kasheva TN, Villa AE (2001). „Estimation of Aqueous Solubility of Chemical Compounds Using E-State Indices”. Chem Inf. Comput. Sci. 41: 1488—1493. PMID 11749573. doi:10.1021/ci000392t.

[6] Ertl P.; Rohde B.; Selzer P. (2000). „Fast calculation of molecular polar surface area as a sum of fragment based contributions and its application to the prediction of drug transport properties”. J. Med. Chem. 43: 3714—3717. PMID 11020286. doi:10.1021/jm000942e.

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