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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
Structure of ETANAUTINE

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 TargetPharmacologyConditionPotency
7.9 null [pKi]
2.7 µM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
ALEVE PM
Palliative
Unknown

Cmax

ValueDoseCo-administeredAnalytePopulation
93 ng/mL
50 mg single, oral
DIPHENHYDRAMINE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
667 ng × h/mL
50 mg single, oral
DIPHENHYDRAMINE plasma
Homo sapiens
887 ng × h/mL
50 mg single, intravenous
DIPHENHYDRAMINE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
9.2 h
50 mg single, oral
DIPHENHYDRAMINE plasma
Homo sapiens
8.5 h
50 mg single, intravenous
DIPHENHYDRAMINE plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
18.3%
DIPHENHYDRAMINE plasma
Homo sapiens

Doses

AEs

Drug as perpetrator​

Drug as victim

PubMed

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