DIPHENHYDRAMINE TANNATE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C76H52O46.C17H21NO
Molecular Weight	1956.5532
Optical Activity	UNSPECIFIED
Defined Stereocenters	5 / 5
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

SMILES

CN(C)CCOC(C1=CC=CC=C1)C2=CC=CC=C2.OC3=CC(=CC(O)=C3O)C(=O)OC4=C(O)C(O)=CC(=C4)C(=O)OC[C@H]5O[C@@H](OC(=O)C6=CC(OC(=O)C7=CC(O)=C(O)C(O)=C7)=C(O)C(O)=C6)[C@H](OC(=O)C8=CC(OC(=O)C9=CC(O)=C(O)C(O)=C9)=C(O)C(O)=C8)[C@@H](OC(=O)C%10=CC(OC(=O)C%11=CC(O)=C(O)C(O)=C%11)=C(O)C(O)=C%10)[C@@H]5OC(=O)C%12=CC(OC(=O)C%13=CC(O)=C(O)C(O)=C%13)=C(O)C(O)=C%12

InChI

InChIKey=JUPRSNHHBNEGEK-HBNMXAOGSA-N

InChI=1S/C76H52O46.C17H21NO/c77-32-1-22(2-33(78)53(32)92)67(103)113-47-16-27(11-42(87)58(47)97)66(102)112-21-52-63(119-72(108)28-12-43(88)59(98)48(17-28)114-68(104)23-3-34(79)54(93)35(80)4-23)64(120-73(109)29-13-44(89)60(99)49(18-29)115-69(105)24-5-36(81)55(94)37(82)6-24)65(121-74(110)30-14-45(90)61(100)50(19-30)116-70(106)25-7-38(83)56(95)39(84)8-25)76(118-52)122-75(111)31-15-46(91)62(101)51(20-31)117-71(107)26-9-40(85)57(96)41(86)10-26;1-18(2)13-14-19-17(15-9-5-3-6-10-15)16-11-7-4-8-12-16/h1-20,52,63-65,76-101H,21H2;3-12,17H,13-14H2,1-2H3/t52-,63-,64+,65-,76+;/m1./s1

HIDE SMILES / InChI

Molecular Formula	C76H52O46
Molecular Weight	1701.1985
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	5 / 5
E/Z Centers	3
Optical Activity	UNSPECIFIED

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 316	Antagonist 2,849
Histamine H1 receptor 316	Antagonist 2,849	7.9 null [pKi]
Neuronal acetylcholine receptor protein alpha-7 subunit 78	Antagonist 2,849
HERG 99	Blocker 555	2.7 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Occasional sleeplessness 37	Palliative		Approved 8,583	ALEVE PM
Seasonal allergic rhinitis 64	Palliative		Approved 8,583	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
887 ng × h/mL	50 mg single, intravenous		DIPHENHYDRAMINE plasma	Homo sapiens
667 ng × h/mL	50 mg single, oral		DIPHENHYDRAMINE plasma	Homo sapiens

T_1/2

Value	Dose	Co-administered	Analyte	Population
8.5 h	50 mg single, intravenous		DIPHENHYDRAMINE plasma	Homo sapiens
9.2 h	50 mg single, oral		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	Other AEs: QT interval prolonged...
400 mg 1 times / day multiple, oral	unhealthy, 28 years	Disc. AE: Liver injury, Vomiting...
50 mg single, intravenous	unhealthy	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
Jaundice	1 patient Disc. AE	400 mg 1 times / day multiple, oral	unhealthy, 28 years
Liver injury	1 patient Disc. AE	400 mg 1 times / day multiple, oral	unhealthy, 28 years
Vomiting	1 patient Disc. AE	400 mg 1 times / day multiple, oral	unhealthy, 28 years
Hypertension	below serious, 5 patients	50 mg single, intravenous	unhealthy

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Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1,946	substrate 1,193	substrate 1,388 inhibitor 2,507

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
OCT1 620 OCT2 779 OCT3 159 MATE1 415 MATE2 267	CYP1A1 389 CYP1A2 1,197 CYP2A6 626 CYP2B6 776 CYP2C8 810 CYP2C18 149 CYP2C19 1,119 CYP2E1 729 CYP3A5 446 CYP4A11 137 UGT1A3 470 UGT1A4 399 UGT2B10 131

Drug as perpetrator

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Target	Modality	Activity	Clinical evidence
CYP2D6 2,546	inhibitor 4,027	weak [IC50 11 uM]	yes (co-administration study)
OCT2 782	inhibitor 4,027	yes [IC50 15 uM]
OCT1 656	inhibitor 4,027	yes [IC50 3.4 uM]
OCT3 161	inhibitor 4,027	yes [IC50 695 uM]
MATE2 267	inhibitor 4,027	yes [Ki 266.5 uM]

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Drug as victim

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Target	Modality	Activity
CYP2D6 1,388	substrate 4,014	major
UGT2B10 131	substrate 4,014	major
CYP1A2 1,197	substrate 4,014	minor
CYP2C19 1,119	substrate 4,014	minor
UGT1A3 470	substrate 4,014	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
eMolecules	716786	https://www.emolecules.com/cgi-bin/more?vid=716786
MolPort	MolPort-001-783-508	https://www.molport.com/shop/molecule-link/MolPort-001-783-508
ZINC	ZINC000000020244	http://zinc15.docking.org/substances/ZINC000000020244

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PubMed

Title	Date	PubMed
No data available in table

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	OPI52249ZG
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

DIPHENHYDRAMINE TANNATE

Common Name

English

2-(DIPHENYLMETHOXY)-N,N-DIMETHYLETHYLAMINE TANNATE

Preferred Name

English

DIPHENHYDRAMINE TANNATE [WHO-DD]

Common Name

English

DIPHENHYDRAMINE TANNATE [JAN]

Common Name

English

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Code System

Code

Type

Description

ChEMBL

CHEMBL657

PRIMARY

FDA UNII

OPI52249ZG

PRIMARY

PUBCHEM

165411844

PRIMARY

RXCUI

360283

PRIMARY

RxNorm

SMS_ID

100000087518

PRIMARY

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Related Record

Type

Details


					8GTS82S83M

DIPHENHYDRAMINE

PARENT -> SALT/SOLVATE

Amount:

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Related Record

Type

Details


					8GTS82S83M

DIPHENHYDRAMINE

ACTIVE MOIETY

Amount:

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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