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Details

Stereochemistry ACHIRAL
Molecular Formula C19H23N3O
Molecular Weight 309.4054
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BENZYDAMINE

SMILES

CN(C)CCCOC1=NN(CC2=CC=CC=C2)C3=C1C=CC=C3

InChI

InChIKey=CNBGNNVCVSKAQZ-UHFFFAOYSA-N
InChI=1S/C19H23N3O/c1-21(2)13-8-14-23-19-17-11-6-7-12-18(17)22(20-19)15-16-9-4-3-5-10-16/h3-7,9-12H,8,13-15H2,1-2H3

HIDE SMILES / InChI

Molecular Formula C19H23N3O
Molecular Weight 309.4054
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

Benzydamine (benzydamine hydrochloride, PHARIXIA®) is a benzyl-indazole having analgesic, antipyretic, and anti-inflammatory effects. It is indicated for the relief of pain in acute sore throat and for the symptomatic relief of oro-pharyngeal mucositis caused by radiation therapy.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
PHARIXIA
Primary
PHARIXIA

Cmax

ValueDoseCo-administeredAnalytePopulation
68 ng/mL
5 mg single, intravenous
BENZYDAMINE plasma
Homo sapiens
459 ng/mL
50 mg single, oral
BENZYDAMINE plasma
Homo sapiens
35 ng/mL
100 mg single, oral transmucosal
BENZYDAMINE plasma
Homo sapiens
546 ng/mL
50 mg single, oral
BENZYDAMINE plasma
Homo sapiens
14 ng/mL
100 mg single, topical
BENZYDAMINE plasma
Homo sapiens
10 ng/mL
140 mg single, vaginal
BENZYDAMINE plasma
Homo sapiens
0.8 μg/mL
100 mg single, oral
BENZYDAMINE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
541 ng × h/mL
5 mg single, intravenous
BENZYDAMINE plasma
Homo sapiens
4907 ng × h/mL
50 mg single, oral
BENZYDAMINE plasma
Homo sapiens
494 ng × h/mL
100 mg single, oral transmucosal
BENZYDAMINE plasma
Homo sapiens
4994 ng × h/mL
50 mg single, oral
BENZYDAMINE plasma
Homo sapiens
455 ng × h/mL
100 mg single, topical
BENZYDAMINE plasma
Homo sapiens
162 ng × h/mL
140 mg single, vaginal
BENZYDAMINE plasma
Homo sapiens
60.996 ng × h/mL
6 mg single, vaginal
BENZYDAMINE plasma
Homo sapiens
17.284 ng × h/mL
6 mg single, vaginal
BENZYDAMINE N-OXIDE plasma
Homo sapiens
100.264 ng × h/mL
6 mg 1 times / day multiple, vaginal
BENZYDAMINE plasma
Homo sapiens
30.477 ng × h/mL
6 mg 1 times / day multiple, vaginal
BENZYDAMINE N-OXIDE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
8.1 h
5 mg single, intravenous
BENZYDAMINE plasma
Homo sapiens
7.8 h
50 mg single, oral
BENZYDAMINE plasma
Homo sapiens
9.4 h
100 mg single, oral transmucosal
BENZYDAMINE plasma
Homo sapiens
7.8 h
50 mg single, oral
BENZYDAMINE plasma
Homo sapiens
13 h
100 mg single, oral
BENZYDAMINE plasma
Homo sapiens

Doses

AEs

Drug as perpetrator​

Drug as victim

PubMed

Sample Use Guides

In Vivo Use Guide
Not less than 15 mL of the liquid should be used for each gargle or rinse and repeated three or four times a day, depending on the severity of the treated condition. The liquid should be kept in contact with the inflamed mucosa for at least 30 seconds and then expelled from the mouth. Administration should begin the day prior to commencement of radiation therapy and continue daily during the treatment period as well as after cessation of radiation applications until desired improvement is obtained. In acute sore throat, gargle with 15 mL every 1.5 to 3 hours. The solution should be expelled from the mouth after use.
Route of Administration: Other
In Vitro Use Guide
Benzydamine significantly reduced the basal production of both prostaglandin E2 (PGE2) and 6-keto-PGF1 alpha, the stable breakdown product of prostaglandin I2 (PGI2), in unstimulated human gingival fibroblasts. When the cells were treated simultaneously with benzydamine and the cytokines IL-1beta or TNF-alpha, the agent benzydamine reduced (P < 0.05) the stimulatory effect of IL-1beta and TNF-alpha respectively, on PGE2 and PGI2 production in human gingival fibroblasts. Furthermore, benzydamine reduced (P < 0.05) both the basal level and the cytokine-induced 3H-arachidonic acid release in gingival fibroblasts. The addition of exogenous arachidonic acid to the cells resulted in enhanced PGE2 production, which was reduced (P < 0.05) in the presence of benzydamine.
Substance Class Chemical
Record UNII
4O21U048EF
Record Status Validated (UNII)
Record Version