ETANAUTINE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C17H21NO.C9H10N4O4
Molecular Weight	493.5548
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

SMILES

CN1C2=C(N(CC(O)=O)C=N2)C(=O)N(C)C1=O.CN(C)CCOC(C3=CC=CC=C3)C4=CC=CC=C4

InChI

InChIKey=UFKLOBYBVCBTBP-UHFFFAOYSA-N

InChI=1S/C17H21NO.C9H10N4O4/c1-18(2)13-14-19-17(15-9-5-3-6-10-15)16-11-7-4-8-12-16;1-11-7-6(8(16)12(2)9(11)17)13(4-10-7)3-5(14)15/h3-12,17H,13-14H2,1-2H3;4H,3H2,1-2H3,(H,14,15)

HIDE SMILES / InChI

Molecular Formula	C9H10N4O4
Molecular Weight	238.2001
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	C17H21NO
Molecular Weight	255.3547
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description

Diphenhydramine is an antihistamine which is used in the combination with naproxen sodium for the relief of occasional sleeplessness when associated with minor aches and pains. Diphenhydramine has a role nighttime sleep-aid and naproxen sodium is a pain reliever. In addition, diphenhydramine used in relieving symptoms in patients with moderate-to-severe seasonal allergic rhinitis. Diphenhydramine acts as an antagonist of histamine H1 receptor. Besides, was shown potential to repurpose diphenhydramine as an anti-melanoma therapeutic agent, it induces melanoma cell apoptosis by suppressing STAT3/MCL-1 survival signaling pathway.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Histamine H1 receptor 315	Antagonist 2,778
Histamine H1 receptor 315	Antagonist 2,778	7.9 null [pKi]
Neuronal acetylcholine receptor protein alpha-7 subunit 77	Antagonist 2,778
HERG 92	Blocker 537	2.7 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Occasional sleeplessness 37	Palliative		Approved 8,429	ALEVE PM
Seasonal allergic rhinitis 64	Palliative		Approved 8,429	Unknown

C_max

Value	Dose	Co-administered	Analyte	Population
93 ng/mL	50 mg single, oral		DIPHENHYDRAMINE plasma	Homo sapiens

AUC

Value	Dose	Co-administered	Analyte	Population
667 ng × h/mL	50 mg single, oral		DIPHENHYDRAMINE plasma	Homo sapiens
887 ng × h/mL	50 mg single, intravenous		DIPHENHYDRAMINE plasma	Homo sapiens

T_1/2

Value	Dose	Co-administered	Analyte	Population
9.2 h	50 mg single, oral		DIPHENHYDRAMINE plasma	Homo sapiens
8.5 h	50 mg single, intravenous		DIPHENHYDRAMINE plasma	Homo sapiens

F_unbound

Value	Dose	Co-administered	Analyte	Population
18.3%			DIPHENHYDRAMINE plasma	Homo sapiens

Doses

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Dose	Population	Adverse events
600 mg single, oral Overdose	unknown, 13 months n = 1	Other AEs: QT interval prolonged...
400 mg 1 times / day multiple, oral	unhealthy, 28 years n = 1	Disc. AE: Liver injury, Vomiting...
50 mg single, intravenous	unhealthy n = 61	Other AEs: Hypertension...

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AEs

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AE	Significance	Dose	Population
QT interval prolonged	1 patient	600 mg single, oral Overdose	unknown, 13 months n = 1
Jaundice	1 patient Disc. AE	400 mg 1 times / day multiple, oral	unhealthy, 28 years n = 1
Liver injury	1 patient Disc. AE	400 mg 1 times / day multiple, oral	unhealthy, 28 years n = 1
Vomiting	1 patient Disc. AE	400 mg 1 times / day multiple, oral	unhealthy, 28 years n = 1
Hypertension	below serious, 5 patients	50 mg single, intravenous	unhealthy n = 61

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Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1,737	substrate 1,037	substrate 1,217 inhibitor 1,852

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
OCT1 512 OCT2 647 OCT3 150 MATE1 306 MATE2 263	CYP1A1 349 CYP1A2 1,054 CYP2A6 543 CYP2B6 664 CYP2C8 693 CYP2C18 138 CYP2C19 991 CYP2E1 667 CYP3A5 395 CYP4A11 119 UGT1A3 422 UGT1A4 347 UGT2B10 127

Drug as perpetrator

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Target	Modality	Activity	Clinical evidence
CYP2D6 1,891	inhibitor 3,277	weak [IC50 11 uM]	yes (co-administration study)
OCT2 648	inhibitor 3,277	yes [IC50 15 uM]
OCT1 543	inhibitor 3,277	yes [IC50 3.4 uM]
OCT3 150	inhibitor 3,277	yes [IC50 695 uM]
MATE2 263	inhibitor 3,277	yes [Ki 266.5 uM]

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Drug as victim

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Target	Modality	Activity
CYP2D6 1,217	substrate 3,367	major
UGT2B10 127	substrate 3,367	major
CYP1A2 1,054	substrate 3,367	minor
CYP2C19 991	substrate 3,367	minor
UGT1A3 422	substrate 3,367	minor

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Sourcing

Sourcing

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Vendor/Aggregator	ID	URL
ChEBI	CHEBI:4636	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:4636
ChemicalBook	CB6196202	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB6196202
MolPort	MolPort-001-783-508	https://www.molport.com/shop/molecule-link/MolPort-001-783-508
ZINC	ZINC000000020244	http://zinc15.docking.org/substances/ZINC000000020244
eMolecules	716786	https://www.emolecules.com/cgi-bin/more?vid=716786

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PubMed

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Title	Date	PubMed
Clinical pharmacokinetics of H1-receptor antagonists (the antihistamines).	1985 Nov-Dec	2866055
Diphenhydramine.	1986 Feb	3962845
Diphenhydramine: pharmacokinetics and pharmacodynamics in elderly adults, young adults, and children.	1990 Jul	2391399
Evaluation of diphenhydramine in talc induced type 2 diabetes mellitus in Wistar rats.	2018 Jan	29101809
A patient with anaphylaxis to diphenhydramine without cross-reactivity to loratadine.	2018 May-Jun	29196087

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Patents

Sample Use Guides

In Vivo Use Guide

occasional sleeplessness: do not take more than directed; drink a full glass of water with each dose, adults and children 12 years and over: take 2 caplets at bedtime, do not take more than 2 caplets in 24 hours, if taken with food, this product may take longer to work

Route of Administration: Oral

In Vitro Use Guide

Unknown

Substance Class	Chemical
Record UNII	97H5S09M4T
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ETANAUTINE

Common Name

English

7H-PURINE-7-ACETIC ACID, 1,2,3,6-TETRAHYDRO-1,3-DIMETHYL-2,6-DIOXO-, COMPD. WITH 2-(DIPHENYLMETHOXY)-N,N-DIMETHYLETHANAMINE (1:1)

Common Name

English

DIPHENHYDRAMINE MONOACEFYLLINATE

Common Name

English

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Classification Tree

Code System

Code

Ethers, chemically close to antihistamines

WHO-VATC

QN04AB01

Ethers chemically close to antihistamines

WHO-ATC

N04AB01

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Code System

Code

Type

Description

DRUG CENTRAL

4534

PRIMARY

DRUG BANK

DB13636

PRIMARY

PUBCHEM

10255142

PRIMARY

WIKIPEDIA

ETANAUTINE

PRIMARY

CAS

857401-00-4

PRIMARY

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Related Record

Type

Details


					8GTS82S83M

DIPHENHYDRAMINE

PARENT -> SALT/SOLVATE


					M494UE2YEP

ACEFYLLINE

PARENT -> SALT/SOLVATE

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Related Record

Type

Details


					M494UE2YEP

ACEFYLLINE

ACTIVE MOIETY


					8GTS82S83M

DIPHENHYDRAMINE

ACTIVE MOIETY

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SMILES

InChI

CNS Activity

Originator

Approval Year

Targets

Conditions

Cmax

AUC

T1/2

Funbound

Doses

AEs

Overview

OverviewOther

Drug as perpetrator​

Drug as victim

Sourcing

PubMed

Patents

Sample Use Guides

C_max

T_1/2

F_unbound

Drug as perpetrator