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

Details

Stereochemistry ABSOLUTE
Molecular Formula C76H52O46.C16H19BrN2
Molecular Weight 2020.438
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 6
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DEXBROMPHENIRAMINE TANNATE

SMILES

CN(C)CC[C@@H](C1=CC=C(Br)C=C1)C2=CC=CC=N2.OC3=CC(=CC(O)=C3O)C(=O)OC4=CC(=CC(O)=C4O)C(=O)OC[C@H]5O[C@@H](OC(=O)C6=CC(O)=C(O)C(OC(=O)C7=CC(O)=C(O)C(O)=C7)=C6)[C@H](OC(=O)C8=CC(O)=C(O)C(OC(=O)C9=CC(O)=C(O)C(O)=C9)=C8)[C@@H](OC(=O)C%10=CC(O)=C(O)C(OC(=O)C%11=CC(O)=C(O)C(O)=C%11)=C%10)[C@@H]5OC(=O)C%12=CC(O)=C(O)C(OC(=O)C%13=CC(O)=C(O)C(O)=C%13)=C%12

InChI

InChIKey=YZAQFXRNFPSDQX-RKGSNTPUSA-N
InChI=1S/C76H52O46.C16H19BrN2/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;1-19(2)12-10-15(16-5-3-4-11-18-16)13-6-8-14(17)9-7-13/h1-20,52,63-65,76-101H,21H2;3-9,11,15H,10,12H2,1-2H3/t52-,63-,64+,65-,76+;15-/m10/s1

HIDE SMILES / InChI
Molecular Formula C16H19BrN2
Molecular Weight 319.239
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED
Molecular Formula C76H52O46
Molecular Weight 1701.1985
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 5 / 5
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

DEXBROMPHENIRAMINE is an alkylamine derivative with anticholinergic and sedative properties. It is a histamine H1-receptor antagonist that competes with histamine for the H1-receptor sites on effector cells in the gastrointestinal tract, blood vessels, and respiratory tract. The antagonistic action of this agent blocks the activities of endogenous histamine, which subsequently leads to temporary relief from the negative histamine-mediated symptoms of an allergic reaction such as bronchoconstriction, vasodilation, increased capillary permeability and spasmodic contractions of the gastrointestinal smooth muscle. DEXBROMPHENIRAMINE as a part of combination medicine is used to treat symptoms of the common cold or seasonal allergies, including sneezing, runny or stuffy nose, and itchy, watery eyes.

Approval Year

1959
138
Targets

Targets

Primary TargetPharmacologyConditionPotency
Antagonist
2778
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
Approved
8429
PANATUSS PEDIATRIC DROPS DXP

Approved Use

Uses: - Temporarily relieves cough due to minor throat and bronchial irritations as may occur with the common cold; - Temporarily relieves nasal congestions due to common cold; - For temporary relief of runny nose, sneezing, itching of the nose or throat, and itchy, watery eyes due to hay fever or allergic rhinitis.

Launch Date

2005
Palliative
Approved
8429
PANATUSS PEDIATRIC DROPS DXP

Approved Use

Uses: - Temporarily relieves cough due to minor throat and bronchial irritations as may occur with the common cold; - Temporarily relieves nasal congestions due to common cold; - For temporary relief of runny nose, sneezing, itching of the nose or throat, and itchy, watery eyes due to hay fever or allergic rhinitis.

Launch Date

2005
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
27.98 ng/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/3981411/
6 mg 2 times / day steady-state, oral
dose: 6 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
DEXBROMPHENIRAMINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
234.2 ng × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/3981411/
6 mg 2 times / day steady-state, oral
dose: 6 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
DEXBROMPHENIRAMINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
22 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/3981411/
6 mg 2 times / day steady-state, oral
dose: 6 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
DEXBROMPHENIRAMINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
Doses

Doses

DosePopulationAdverse events​
0.3 % 1 times / day steady, ophthalmic
Recommended
Dose: 0.3 %, 1 times / day
Route: ophthalmic
Route: steady
Dose: 0.3 %, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/1687324/
unhealthy, adult
n = 1
Health Status: unhealthy
Condition: Allergic conjunctivitis
Age Group: adult
Sex: unknown
Population Size: 1
Sources:
https://pubmed.ncbi.nlm.nih.gov/1687324/
Sources:
https://pubmed.ncbi.nlm.nih.gov/1687324/
6 mg 4 times / day steady, oral
Recommended
Dose: 6 mg, 4 times / day
Route: oral
Route: steady
Dose: 6 mg, 4 times / day
Co-administed with::
pseudoephedrine sulfate(120 mg)
Sources:
https://pubmed.ncbi.nlm.nih.gov/3981411/
healthy, adult
n = 12
Health Status: healthy
Age Group: adult
Sex: M
Population Size: 12
Sources:
https://pubmed.ncbi.nlm.nih.gov/3981411/
Sources:
https://pubmed.ncbi.nlm.nih.gov/3981411/
Sourcing

Sourcing

Vendor/AggregatorIDURL
ChEBI
CHEBI:59269
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:59269
ChemicalBook
CB6164683
https://www.chemicalbook.com/ChemicalProductProperty_EN_CB6164683
ZINC
ZINC000000000096
http://zinc15.docking.org/substances/ZINC000000000096
PubMed

PubMed

TitleDatePubMed
Non-antibiotic treatments for upper-respiratory tract infections (common cold).
2005 Dec
Transient receptor potential vanilloid-1-mediated calcium responses are inhibited by the alkylamine antihistamines dexbrompheniramine and chlorpheniramine.
2008 Dec
Acute cough: a diagnostic and therapeutic challenge.
2009 Dec 16
Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2.
2011 Jul 14
Patents

Patents

20010022964
11

Sample Use Guides

In Vivo Use Guide
Children 6 years of age to under 12 years; 2 mL every 4 - 6 hours.
Route of Administration: Oral
Substance Class Chemical
Created
by admin
on Fri Dec 15 21:31:27 GMT 2023
Edited
by admin
on Fri Dec 15 21:31:27 GMT 2023
Record UNII
XI2Z928Y41
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DEXBROMPHENIRAMINE TANNATE
Common Name English
Code System Code Type Description
RXCUI
686390
Created by admin on Fri Dec 15 21:31:27 GMT 2023 , Edited by admin on Fri Dec 15 21:31:27 GMT 2023
PRIMARY RxNorm
FDA UNII
XI2Z928Y41
Created by admin on Fri Dec 15 21:31:27 GMT 2023 , Edited by admin on Fri Dec 15 21:31:27 GMT 2023
PRIMARY
PUBCHEM
139031032
Created by admin on Fri Dec 15 21:31:27 GMT 2023 , Edited by admin on Fri Dec 15 21:31:27 GMT 2023
PRIMARY
Related Record Type Details
Structure of DEXBROMPHENIRAMINE
PARENT -> SALT/SOLVATE
Related Record Type Details
Structure of DEXBROMPHENIRAMINE
ACTIVE MOIETY
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
For language access assistance, contact the NCATS Public Information Officer
National Center for Advancing Translational Sciences (NCATS),
6701 Democracy Boulevard, Bethesda MD 20892-4874 • 301-594-8966