Details
Stereochemistry | ACHIRAL |
Molecular Formula | C17H21NO |
Molecular Weight | 255.3547 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CN(C)CCOC(C1=CC=CC=C1)C2=CC=CC=C2
InChI
InChIKey=ZZVUWRFHKOJYTH-UHFFFAOYSA-N
InChI=1S/C17H21NO/c1-18(2)13-14-19-17(15-9-5-3-6-10-15)16-11-7-4-8-12-16/h3-12,17H,13-14H2,1-2H3
Molecular Formula | C17H21NO |
Molecular Weight | 255.3547 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
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
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: P35367 Gene ID: 3269.0 Gene Symbol: HRH1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/16702624 |
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Target ID: CHEMBL231 |
7.9 null [pKi] | ||
Target ID: CHEMBL2492 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25445036 |
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Target ID: CHEMBL240 |
2.7 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Palliative | ALEVE PM Approved Usefor relief of occasional sleeplessness when associated with minor aches and pains; helps you fall asleep and stay asleep Launch Date2014 |
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Palliative | Unknown Approved UseUnknown |
Cmax
Value | Dose | Co-administered | Analyte | Population |
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93 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/28967696 |
50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered: |
DIPHENHYDRAMINE plasma | Homo sapiens population: UNKNOWN age: ADOLESCENT sex: FEMALE / MALE food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
667 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/3760245 |
50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered: |
DIPHENHYDRAMINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
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887 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/3760245 |
50 mg single, intravenous dose: 50 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
DIPHENHYDRAMINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
9.2 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/3760245 |
50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered: |
DIPHENHYDRAMINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
8.5 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/3760245 |
50 mg single, intravenous dose: 50 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
DIPHENHYDRAMINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
18.3% EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/2369804 |
DIPHENHYDRAMINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
600 mg single, oral Overdose |
unknown, 13 months n = 1 Health Status: unknown Age Group: 13 months Sex: F Population Size: 1 Sources: |
Other AEs: QT interval prolonged... |
400 mg 1 times / day multiple, oral Dose: 400 mg, 1 times / day Route: oral Route: multiple Dose: 400 mg, 1 times / day Sources: |
unhealthy, 28 years n = 1 Health Status: unhealthy Condition: insomnia Age Group: 28 years Sex: M Population Size: 1 Sources: |
Disc. AE: Liver injury, Vomiting... AEs leading to discontinuation/dose reduction: Liver injury (1 patient) Sources: Vomiting (1 patient) Jaundice (1 patient) |
50 mg single, intravenous Dose: 50 mg Route: intravenous Route: single Dose: 50 mg Sources: |
unhealthy n = 61 Health Status: unhealthy Condition: Opioid dependence Population Size: 61 Sources: |
Other AEs: Hypertension... Other AEs: Hypertension (below serious, 5 patients) Sources: |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
QT interval prolonged | 1 patient | 600 mg single, oral Overdose |
unknown, 13 months n = 1 Health Status: unknown Age Group: 13 months Sex: F Population Size: 1 Sources: |
Jaundice | 1 patient Disc. AE |
400 mg 1 times / day multiple, oral Dose: 400 mg, 1 times / day Route: oral Route: multiple Dose: 400 mg, 1 times / day Sources: |
unhealthy, 28 years n = 1 Health Status: unhealthy Condition: insomnia Age Group: 28 years Sex: M Population Size: 1 Sources: |
Liver injury | 1 patient Disc. AE |
400 mg 1 times / day multiple, oral Dose: 400 mg, 1 times / day Route: oral Route: multiple Dose: 400 mg, 1 times / day Sources: |
unhealthy, 28 years n = 1 Health Status: unhealthy Condition: insomnia Age Group: 28 years Sex: M Population Size: 1 Sources: |
Vomiting | 1 patient Disc. AE |
400 mg 1 times / day multiple, oral Dose: 400 mg, 1 times / day Route: oral Route: multiple Dose: 400 mg, 1 times / day Sources: |
unhealthy, 28 years n = 1 Health Status: unhealthy Condition: insomnia Age Group: 28 years Sex: M Population Size: 1 Sources: |
Hypertension | below serious, 5 patients | 50 mg single, intravenous Dose: 50 mg Route: intravenous Route: single Dose: 50 mg Sources: |
unhealthy n = 61 Health Status: unhealthy Condition: Opioid dependence Population Size: 61 Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
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Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
weak [IC50 11 uM] | yes (co-administration study) Comment: diphenhydramine coadministration significantly altered the pharmacokinetics, heart rate, systolic blood pressure, and peak acceleration response of metoprolol in extensive metabolizers but not in poor metabolizers Sources: https://pubmed.ncbi.nlm.nih.gov/9616188/ |
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yes [IC50 15 uM] | ||||
yes [IC50 3.4 uM] | ||||
yes [IC50 695 uM] | ||||
yes [Ki 266.5 uM] | ||||
yes [Ki 87 uM] |
Drug as victim
Sample Use Guides
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/3559970
Curator's Comment: In vitro, [14C] diphenhydramine was accumulated by a saturable, energy-requiring system in choroid plexus. The results show that diphenhydramine, unlike diazepam, is transported between blood, brain and cerebrospinal fluid, in part, by saturable, carrier-mediated transport processes at both the blood-brain and blood-cerebrospinal fluid barriers.
Unknown
Substance Class |
Chemical
Created
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on
Edited
Fri Dec 15 17:42:07 GMT 2023
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on
Fri Dec 15 17:42:07 GMT 2023
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Record UNII |
8GTS82S83M
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Record Status |
Validated (UNII)
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WHO-VATC |
QD04AA32
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WHO-VATC |
QR06AA52
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QR06AA02
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NDF-RT |
N0000175587
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WHO-ATC |
R06AA02
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R06AA52
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LIVERTOX |
NBK548470
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NDF-RT |
N0000000190
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NCI_THESAURUS |
C267
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C29578
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WHO-ATC |
D04AA32
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m4609
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1774
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CHEMBL657
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Diphenhydramine
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DTXSID4022949
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DB01075
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DIPHENHYDRAMINE
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D004155
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C61728
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8GTS82S83M
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3066
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Related Record | Type | Details | ||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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METABOLIC ENZYME -> SUBSTRATE |
N-demethylation of diphenhydramine is mainly catalyzed by CYP2D6 as a high-affinity P450 isozyme at a clinically relevant concentration.
MAJOR
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TRANSPORTER -> INHIBITOR | |||
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TARGET -> INHIBITOR | |||
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SALT/SOLVATE -> PARENT | |||
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METABOLIC ENZYME -> SUBSTRATE |
CYP1A2, CYP2C9, and CYP2C19 are involved in the metabolism of diphenhydramine as low-affinity P450 isozymes.
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TRANSPORTER -> INHIBITOR | |||
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METABOLIC ENZYME -> INHIBITOR |
POTENT
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TRANSPORTER -> INHIBITOR | |||
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TRANSPORTER -> INHIBITOR | |||
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METABOLIC ENZYME -> SUBSTRATE |
CYP1A2, CYP2C9, and CYP2C19 are involved in the metabolism of diphenhydramine as low-affinity P450 isozymes.
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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METABOLIC ENZYME -> SUBSTRATE |
CYP1A2, CYP2C9, and CYP2C19 are involved in the metabolism of diphenhydramine as low-affinity P450 isozymes.
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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TRANSPORTER -> INHIBITOR | |||
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SUBSTANCE->BASIS OF STRENGTH |
Related Record | Type | Details | ||
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METABOLITE -> PARENT | |||
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METABOLITE -> PARENT |
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METABOLITE -> PARENT |
Related Record | Type | Details | ||
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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ACTIVE MOIETY |