U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C17H21NO.C12H26O4S
Molecular Weight 521.752
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DIPHENHYDRAMINE LAURYLSULFATE

SMILES

CCCCCCCCCCCCOS(O)(=O)=O.CN(C)CCOC(C1=CC=CC=C1)C2=CC=CC=C2

InChI

InChIKey=AJZFEQIFKBZILH-UHFFFAOYSA-N
InChI=1S/C17H21NO.C12H26O4S/c1-18(2)13-14-19-17(15-9-5-3-6-10-15)16-11-7-4-8-12-16;1-2-3-4-5-6-7-8-9-10-11-12-16-17(13,14)15/h3-12,17H,13-14H2,1-2H3;2-12H2,1H3,(H,13,14,15)

HIDE SMILES / InChI

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