Details of the Drug-Related molecule(s) Interaction Atlas

General Information of Drug (ID: DM53IP1)

• Drug Name: Ethchlorvynol Drug Info
• Synonyms: Alvinol; Arvynol; Etchlorvinolo; Etclorvinol; Ethchlorovynol; Ethchlorvinol; Ethchlorvinyl; Ethchlorvynolum;Ethclorvynol; Ethochlorvynol; Ethychlorvynol; Normonson; Normosan; Normoson; Nostel; Nromoson; Placidil; Placidyl; Roeridorm; Serenesil; Serenil; Serensil; Serensiloline; A 71; Aethyl-chlorvynol; Beta-Chlorovinyl ethyl ethynyl carbinol; Beta-Chlorvinyl ethyl ethynyl carbinol; Etclorvinol [INN-Spanish]; Ethchlorvynolum [INN-Latin]; Ethyl beta-chlorovinyl ethynyl carbinol; Placidyl (TN); Ethchlorvynol [USAN:INN:BAN]; Ethchlorvynol (JAN/USP/INN); (E)-1-chloro-3-ethylpent-1-en-4-yn-3-ol; 1-Chloro-3-ethyl-1-penten-4-yn-3-ol; 1-Chloro-3-ethylpent-1-4-yn-3-ol; 1-chloro-3-ethylpent-1-en-4-yn-3-ol; 3-(beta-Chlorovinyl)-1-pentyn-3-ol; 5-Chloro-3-ethylpent-1-yn-4-en-3-ol

Indication

Disease Entry	ICD 11	Status	REF
Insomnia	7A00-7A0Z	Approved	[1]

• Therapeutic Class: Hypnotics and Sedatives
• Cross-matching ID:
  PubChem CID: 5281077
  ChEBI ID: CHEBI:4882
  CAS Number: CAS 113-18-8
  TTD Drug ID: DM53IP1
  INTEDE Drug ID: DR1753

Molecule-Related Drug Atlas

Drug(s) Targeting GABA(A) receptor alpha-1 (GABRA1)

Drug Name	Drug ID	Indication	ICD 11	Highest Status	REF
Ethanol	DMDRQZU	Chronic pain	MG30	Approved	[2]
Zolpidem	DMWOSKJ	Insomnia	7A00-7A0Z	Approved	[4]
Methoxyflurane	DML0RAE	Anaesthesia	9A78.6	Approved	[2]
Nitrazepam	DMEGIQ6	Epilepsy	8A60-8A68	Approved	[2]
Allopregnanolone	DMNLHAC	Depression	6A70-6A7Z	approved	[5]
Clobazam - Lundbeck	DMW1OQ0	Anxiety disorder	6B00-6B0Z	Approved	[2]
Hexobarbital	DMQ314B	Anaesthesia	9A78.6	Approved	[2]
THIOCOLCHICOSIDE	DMEPWYA	Muscle spasm	MB47.3	Approved	[6]
Meprobamate	DMHM93Y	Anxiety		Approved	[2]
Zaleplon	DMGFWSM	Insomnia	7A00-7A0Z	Approved	[7]

Drug(s) Targeting GABA(A) receptor beta-2 (GABRB2)

Drug Name	Drug ID	Indication	ICD 11	Highest Status	REF
Allopregnanolone	DMNLHAC	Depression	6A70-6A7Z	approved	[5]
THIOCOLCHICOSIDE	DMEPWYA	Muscle spasm	MB47.3	Approved	[6]
ZK-93423	DMFWMKZ	Epileptic seizures	8A61-8A6Z	Phase 3	[8]
GSK683699	DMTW79H	Inflammatory bowel disease	DD72	Phase 2	[6]
ELTANOLONE	DM38CIV	Premenstrual syndrome	GA34.40	Discontinued in Phase 3	[5]
U-78875	DM2WOPX	Anxiety disorder	6B00-6B0Z	Discontinued in Phase 1	[9]
CGS-9896	DM39PQI	N. A.	N. A.	Terminated	[10]
TBPS	DMFC3XP	Discovery agent	N.A.	Investigative	[11]
AMENTOFLAVONE	DMLRNV2	Discovery agent	N.A.	Investigative	[12]
Ro-15-3505	DM4NW3U	Discovery agent	N.A.	Investigative	[13]

Drug(s) Metabolized By Cytochrome P450 3A4 (CYP3A4)

Drug Name	Drug ID	Indication	ICD 11	Highest Status	REF
Doxorubicin	DMVP5YE	Acute myelogenous leukaemia	2A41	Approved	[14]
Progesterone	DMUY35B	Amenorrhea	GA20.0	Approved	[15]
Tamoxifen	DMLB0EZ	Breast cancer	2C60-2C65	Approved	[16]
Estradiol	DMUNTE3	Acne vulgaris	ED80	Approved	[17]
Acetaminophen	DMUIE76	Allergic rhinitis	CA08.0	Approved	[18]
Imatinib	DM7RJXL	Acute lymphoblastic leukaemia	2A85	Approved	[19]
Etoposide	DMNH3PG	Acute myelogenous leukaemia	2A41	Approved	[20]
Zidovudine	DM4KI7O	Human immunodeficiency virus infection	1C62	Approved	[21]
Prasterone	DM67VKL	Chronic obstructive pulmonary disease	CA22	Approved	[15]
Verapamil	DMA7PEW	Angina pectoris	BA40	Approved	[22]

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
GABA(A) receptor alpha-1 (GABRA1)	TT1MPAY	GBRA1_HUMAN	Antagonist	[2]
GABA(A) receptor beta-2 (GABRB2)	TTZA1NY	GBRB2_HUMAN	Antagonist	[2]

Drug-Metabolizing Enzyme (DME)

DME Name	DME ID	UniProt ID	MOA	REF
Cytochrome P450 3A4 (CYP3A4) Main DME	DE4LYSA	CP3A4_HUMAN	Substrate	[3]

References

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• [2] DrugBank: a knowledgebase for drugs, drug actions and drug targets. Nucleic Acids Res. 2008 Jan;36(Database issue):D901-6.
• [3] Alkylation of the prosthetic heme in cytochrome P-450 during oxidative metabolism of the sedative-hypnotic ethchlorvynol. J Med Chem. 1982 Oct;25(10):1174-9.
• [4] Zolpidem, a selective GABA(A) receptor alpha1 subunit agonist, induces comparable Fos expression in oxytocinergic neurons of the hypothalamic paraventricular and accessory but not supraoptic nuclei in the rat.Brain Res Bull.2006 Dec 11;71(1-3):200-7.
• [5] Neurosteroid analogues. 10. The effect of methyl group substitution at the C-6 and C-7 positions on the GABA modulatory and anesthetic actions of (... J Med Chem. 2005 Apr 21;48(8):3051-9.
• [6] 3-demethoxy-3-glycosylaminothiocolchicines: Synthesis of a new class of putative muscle relaxant compounds. J Med Chem. 2006 Sep 7;49(18):5571-7.
• [7] Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services.
• [8] Structural requirements for agonist actions at the benzodiazepine receptor: studies with analogues of 6-(benzyloxy)-4-(methoxymethyl)-beta-carbolin... J Med Chem. 1990 Mar;33(3):1062-9.
• [9] High-affinity alpha-aminobutyric acid A/benzodiazepine ligands: synthesis and structure-activity relationship studies of a new series of tetracycli... J Med Chem. 1996 Nov 8;39(23):4654-66.
• [10] Synthesis, pharmacology, and structure-activity relationships of novel imidazolones and pyrrolones as modulators of GABAA receptors. J Med Chem. 2006 Mar 23;49(6):1855-66.
• [11] URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Target id: 411).
• [12] Semisynthetic preparation of amentoflavone: A negative modulator at GABA(A) receptors. Bioorg Med Chem Lett. 2003 Jul 21;13(14):2281-4.
• [13] Synthesis and evaluation of imidazo[1,5-a][1,4]benzodiazepine esters with high affinities and selectivities at "diazepam-insensitive" benzodiazepin... J Med Chem. 1993 Apr 16;36(8):1001-6.
• [14] Expression levels and activation of a PXR variant are directly related to drug resistance in osteosarcoma cell lines. Cancer. 2007 Mar 1;109(5):957-65.
• [15] Contribution of human hepatic cytochrome P450 isoforms to regioselective hydroxylation of steroid hormones. Xenobiotica. 1998 Jun;28(6):539-47.
• [16] Comprehensive evaluation of tamoxifen sequential biotransformation by the human cytochrome P450 system in vitro: prominent roles for CYP3A and CYP2D6. J Pharmacol Exp Ther. 2004 Sep;310(3):1062-75.
• [17] Isoform-specific regulation of cytochromes P450 expression by estradiol and progesterone. Drug Metab Dispos. 2013 Feb;41(2):263-9.
• [18] Metabolic interactions between acetaminophen (paracetamol) and two flavonoids, luteolin and quercetin, through in-vitro inhibition studies. J Pharm Pharmacol. 2017 Dec;69(12):1762-1772.
• [19] Potent mechanism-based inhibition of CYP3A4 by imatinib explains its liability to interact with CYP3A4 substrates. Br J Pharmacol. 2012 Apr;165(8):2787-98.
• [20] Effects of morin on the pharmacokinetics of etoposide in rats. Biopharm Drug Dispos. 2007 Apr;28(3):151-6.
• [21] The metabolism of zidovudine by human liver microsomes in vitro: formation of 3'-amino-3'-deoxythymidine. Biochem Pharmacol. 1994 Jul 19;48(2):267-76.
• [22] Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675.