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

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
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/mesh/68001591

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.

Originator

Curator's Comment: Fr. Patent No. 1,382,855; 21.02.1964; Assigned to Aziende Chimiche Riunite Angeloni Francesco, residant en Italie.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
PHARIXIA

Approved Use

PHARIXIA (benzydamine hydrochloride) is indicated for the relief of pain in acute sore throat and for the symptomatic relief of oro-pharyngeal mucositis caused by radiation therapy.
Primary
PHARIXIA

Approved Use

PHARIXIA (benzydamine hydrochloride) is indicated for the relief of pain in acute sore throat and for the symptomatic relief of oro-pharyngeal mucositis caused by radiation therapy.
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
68 ng/mL
5 mg single, intravenous
dose: 5 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
BENZYDAMINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
459 ng/mL
50 mg single, oral
dose: 50 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
BENZYDAMINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
35 ng/mL
100 mg single, oral transmucosal
dose: 100 mg
route of administration: Oral transmucosal
experiment type: SINGLE
co-administered:
BENZYDAMINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
546 ng/mL
50 mg single, oral
dose: 50 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
BENZYDAMINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE
food status: FASTED
14 ng/mL
100 mg single, topical
dose: 100 mg
route of administration: Topical
experiment type: SINGLE
co-administered:
BENZYDAMINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE
food status: FASTED
10 ng/mL
140 mg single, vaginal
dose: 140 mg
route of administration: Vaginal
experiment type: SINGLE
co-administered:
BENZYDAMINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE
food status: FASTED
0.8 μg/mL
100 mg single, oral
dose: 100 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
BENZYDAMINE plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
541 ng × h/mL
5 mg single, intravenous
dose: 5 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
BENZYDAMINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
4907 ng × h/mL
50 mg single, oral
dose: 50 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
BENZYDAMINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
494 ng × h/mL
100 mg single, oral transmucosal
dose: 100 mg
route of administration: Oral transmucosal
experiment type: SINGLE
co-administered:
BENZYDAMINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
4994 ng × h/mL
50 mg single, oral
dose: 50 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
BENZYDAMINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE
food status: FASTED
455 ng × h/mL
100 mg single, topical
dose: 100 mg
route of administration: Topical
experiment type: SINGLE
co-administered:
BENZYDAMINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE
food status: FASTED
162 ng × h/mL
140 mg single, vaginal
dose: 140 mg
route of administration: Vaginal
experiment type: SINGLE
co-administered:
BENZYDAMINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE
food status: FASTED
60.996 ng × h/mL
6 mg single, vaginal
dose: 6 mg
route of administration: Vaginal
experiment type: SINGLE
co-administered:
BENZYDAMINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE
food status: UNKNOWN
17.284 ng × h/mL
6 mg single, vaginal
dose: 6 mg
route of administration: Vaginal
experiment type: SINGLE
co-administered:
BENZYDAMINE N-OXIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE
food status: UNKNOWN
100.264 ng × h/mL
6 mg 1 times / day multiple, vaginal
dose: 6 mg
route of administration: Vaginal
experiment type: MULTIPLE
co-administered:
BENZYDAMINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE
food status: UNKNOWN
30.477 ng × h/mL
6 mg 1 times / day multiple, vaginal
dose: 6 mg
route of administration: Vaginal
experiment type: MULTIPLE
co-administered:
BENZYDAMINE N-OXIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
8.1 h
5 mg single, intravenous
dose: 5 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
BENZYDAMINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
7.8 h
50 mg single, oral
dose: 50 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
BENZYDAMINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
9.4 h
100 mg single, oral transmucosal
dose: 100 mg
route of administration: Oral transmucosal
experiment type: SINGLE
co-administered:
BENZYDAMINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
7.8 h
50 mg single, oral
dose: 50 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
BENZYDAMINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE
food status: FASTED
13 h
100 mg single, oral
dose: 100 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
BENZYDAMINE plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
50.4 mg 1 times / day multiple, oral
Studied dose
Dose: 50.4 mg, 1 times / day
Route: oral
Route: multiple
Dose: 50.4 mg, 1 times / day
Sources:
unhealthy, ADOLESCENT|ADULT
Health Status: unhealthy
Age Group: ADOLESCENT|ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
Disc. AE: Urticaria, Angioedema...
AEs leading to
discontinuation/dose reduction:
Urticaria (2.2%)
Angioedema (2.2%)
Sources:
1.5 mg/mL 1 times / 3 hours multiple, oromucosal
Recommended
Dose: 1.5 mg/mL, 1 times / 3 hours
Route: oromucosal
Route: multiple
Dose: 1.5 mg/mL, 1 times / 3 hours
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
Disc. AE: Pain burning, Stinging...
AEs leading to
discontinuation/dose reduction:
Pain burning
Stinging
Sources:
50 mg 3 times / day multiple, oral
Studied dose
Dose: 50 mg, 3 times / day
Route: oral
Route: multiple
Dose: 50 mg, 3 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
AEs

AEs

AESignificanceDosePopulation
Angioedema 2.2%
Disc. AE
50.4 mg 1 times / day multiple, oral
Studied dose
Dose: 50.4 mg, 1 times / day
Route: oral
Route: multiple
Dose: 50.4 mg, 1 times / day
Sources:
unhealthy, ADOLESCENT|ADULT
Health Status: unhealthy
Age Group: ADOLESCENT|ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
Urticaria 2.2%
Disc. AE
50.4 mg 1 times / day multiple, oral
Studied dose
Dose: 50.4 mg, 1 times / day
Route: oral
Route: multiple
Dose: 50.4 mg, 1 times / day
Sources:
unhealthy, ADOLESCENT|ADULT
Health Status: unhealthy
Age Group: ADOLESCENT|ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
Pain burning Disc. AE
1.5 mg/mL 1 times / 3 hours multiple, oromucosal
Recommended
Dose: 1.5 mg/mL, 1 times / 3 hours
Route: oromucosal
Route: multiple
Dose: 1.5 mg/mL, 1 times / 3 hours
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
Stinging Disc. AE
1.5 mg/mL 1 times / 3 hours multiple, oromucosal
Recommended
Dose: 1.5 mg/mL, 1 times / 3 hours
Route: oromucosal
Route: multiple
Dose: 1.5 mg/mL, 1 times / 3 hours
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
Overview

OverviewOther

Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
no [IC50 >10 uM]
no [IC50 >10 uM]
no [IC50 >10 uM]
yes [IC50 5.0119 uM]
yes [IC50 7.9433 uM]
Drug as victim
PubMed

PubMed

TitleDatePubMed
Effect on postoperative sore throat of spraying the endotracheal tube cuff with benzydamine hydrochloride, 10% lidocaine, and 2% lidocaine.
2010-10
The development and in vitro evaluation of sustained release tablet formulations of benzydamine hydrochloride and its determination.
2010-09
[Use abusive of benzydamine in Brazil: an overview in pharmacovigilance].
2010-05
Hippocampal and caudate volume reductions in antipsychotic-naive first-episode schizophrenia.
2010-03
Lymphomatoid photocontact dermatitis to benzydamine hydrochloride.
2010-02
Thermally sensitive gels based on chitosan derivatives for the treatment of oral mucositis.
2010-02
Respiratory symptoms and inflammatory responses to Difflam throat-spray intervention in half-marathon runners: a randomised controlled trial.
2010-02
Oral rinses, mouthwashes and sprays for improving recovery following tonsillectomy.
2010-01-20
Direct electrochemistry of drug metabolizing human flavin-containing monooxygenase: electrochemical turnover of benzydamine and tamoxifen.
2010-01-20
Expression and characterization of functional dog flavin-containing monooxygenase 3.
2009-10
Recreational use of benzydamine as a hallucinogen among street youth in Brazil.
2009-09
Stevens-Johnson Syndrome triggered by chemical hair relaxer: a case report.
2009-08-05
Formulation studies of benzydamine mucoadhesive formulations for vaginal administration.
2009-07
Photopatch testing with an extended series of photoallergens: a 5-year study.
2009-06
Benzydamine for prophylaxis of radiation-induced oral mucositis in head and neck cancers: a double-blind placebo-controlled randomized clinical trial.
2009-03
Ingestions of benzydamine-containing vaginal preparations.
2009-02
Benzydamine hydrochloride buccal bioadhesive gels designed for oral ulcers: preparation, rheological, textural, mucoadhesive and release properties.
2009
[Misuse of substances theoretically without abuse potential--case series].
2009
Inter-individual variation in flavin-containing monooxygenase 3 in livers from Japanese: correlation with hepatic transcription factors.
2009
Relief of radiation-induced oral mucositis in head and neck cancer.
2008-12-24
Evaluation of sutures after immersion in nonalcoholic benzydamine hydrochloride mouthrinse by scanning electron microscopy.
2008-09
Antifungal effect of mouth rinses on oral Candida counts and salivary flow in treatment-naïve HIV-infected patients.
2008-08
Altered metabolism of growth hormone receptor mutant mice: a combined NMR metabonomics and microarray study.
2008-07-23
Burning mouth syndrome.
2008-03-14
Effect of different mouth rinses on third molar surgery-related oral malodor.
2008-03
Spectrophotometric determination of benzydamine HCl, levamisole HCl and mebeverine HCl through ion-pair complex formation with methyl orange.
2008-03
New pathways for alimentary mucositis.
2008
Effect of leukocyte inhibitors benzydamine and cyclophosphamide, on lung injury caused by Tityus discrepans scorpion venom.
2007-12-15
Interventions for preventing oral mucositis for patients with cancer receiving treatment.
2007-10-17
Mucocutaneous lesions of Behcet's disease.
2007-08-31
Combined photocontact dermatitis to benzydamine hydrochloride and the emulsifiers, Span 60 and Tween 60 contained in Tantum cream.
2007-07
Reduction of mouth malodour and volatile sulphur compounds in intensive care patients using an essential oil mouthwash.
2007-07
Novel hydrogels via click chemistry: synthesis and potential biomedical applications.
2007-06
Cancer treatment-induced oral mucositis.
2007-05-01
Interventions for treating oral mucositis for patients with cancer receiving treatment.
2007-04-18
[Medicine consumption and the internet: critical evaluation of a virtual community].
2007-04-05
Cytotoxicity of mouthrinses on epithelial cells by micronucleus test.
2007-04
Digital analysis of mouthrinses' staining characteristics on provisional acrylic resins.
2007-04
Effect of genetic variants of the human flavin-containing monooxygenase 3 on N- and S-oxygenation activities.
2007-03
Dexpanthenol pastille and benzydamine hydrochloride spray for the prevention of post-operative sore throat.
2007-02
[Clinical experience with tantum rosa (benzydamine hydrochloride) in prophylaxis and treatment of vaginitis and proctitis, following radiotherapy of patients with cancer of the vagina and uterus].
2007
Recreational abuse with benzydamine hydrochloride (tantum rosa).
2007
An evaluation of the efficacy of aspirin and benzydamine hydrochloride gargle for attenuating postoperative sore throat: a prospective, randomized, single-blind study.
2006-10
A pilot study of chlorhexidine and benzydamine oral rinses for the prevention and treatment of irradiation mucositis in patients with head and neck cancer.
2006-09-29
Cancer treatment-induced mucositis pain: strategies for assessment and management.
2006-09
Oral mucositis.
2006-05
Local irritant effects of topical oral sprays on oral mucosa in mice.
2006-04-29
Interventions for preventing oral mucositis for patients with cancer receiving treatment.
2006-04-19
Several therapies may prevent or reduce the severity of oral mucositis associated with cancer treatment.
2006
Benzydamine N-oxygenation as a measure of flavin-containing monooxygenase activity.
2006
Patents

Sample Use Guides

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
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
Created
by admin
on Mon Mar 31 17:50:54 GMT 2025
Edited
by admin
on Mon Mar 31 17:50:54 GMT 2025
Record UNII
4O21U048EF
Record Status Validated (UNII)
Record Version
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Name Type Language
APO-BENZYDAMINE
Preferred Name English
BENZYDAMINE
INN   MI   WHO-DD  
INN  
Official Name English
Benzydamine [WHO-DD]
Common Name English
1-BENZYL-3-(3-(DIMETHYLAMINO)PROPOXY)-1H-INDAZOLE
Systematic Name English
1-PROPANAMINE, N,N-DIMETHYL-3-((1-(PHENYLMETHYL)-1H-INDAZOL-3-YL)OXY)-
Systematic Name English
BENZINDAMINE
Common Name English
benzydamine [INN]
Common Name English
N,N-DIMETHYL-3-((1-(PHENYLMETHYL)-1H-INDAZOL-3-YL)OXY)-1-PROPANAMINE
Systematic Name English
1-BENZYL-1H-INDAZOL-3-YL 3-(DIMETHYLAMINO)PROPYL ETHER
Systematic Name English
BENZYDAMINE [MI]
Common Name English
Classification Tree Code System Code
WHO-VATC QG02CC03
Created by admin on Mon Mar 31 17:50:54 GMT 2025 , Edited by admin on Mon Mar 31 17:50:54 GMT 2025
WHO-VATC QM02AA05
Created by admin on Mon Mar 31 17:50:54 GMT 2025 , Edited by admin on Mon Mar 31 17:50:54 GMT 2025
WHO-ATC M02AA05
Created by admin on Mon Mar 31 17:50:54 GMT 2025 , Edited by admin on Mon Mar 31 17:50:54 GMT 2025
WHO-ATC R02AX03
Created by admin on Mon Mar 31 17:50:54 GMT 2025 , Edited by admin on Mon Mar 31 17:50:54 GMT 2025
WHO-VATC QM01AX07
Created by admin on Mon Mar 31 17:50:54 GMT 2025 , Edited by admin on Mon Mar 31 17:50:54 GMT 2025
WHO-ATC G02CC03
Created by admin on Mon Mar 31 17:50:54 GMT 2025 , Edited by admin on Mon Mar 31 17:50:54 GMT 2025
WHO-ATC A01AD02
Created by admin on Mon Mar 31 17:50:54 GMT 2025 , Edited by admin on Mon Mar 31 17:50:54 GMT 2025
WHO-VATC QA01AD02
Created by admin on Mon Mar 31 17:50:54 GMT 2025 , Edited by admin on Mon Mar 31 17:50:54 GMT 2025
NCI_THESAURUS C257
Created by admin on Mon Mar 31 17:50:54 GMT 2025 , Edited by admin on Mon Mar 31 17:50:54 GMT 2025
WHO-ATC M01AX07
Created by admin on Mon Mar 31 17:50:54 GMT 2025 , Edited by admin on Mon Mar 31 17:50:54 GMT 2025
Code System Code Type Description
INN
1927
Created by admin on Mon Mar 31 17:50:54 GMT 2025 , Edited by admin on Mon Mar 31 17:50:54 GMT 2025
PRIMARY
SMS_ID
100000086414
Created by admin on Mon Mar 31 17:50:54 GMT 2025 , Edited by admin on Mon Mar 31 17:50:54 GMT 2025
PRIMARY
EPA CompTox
DTXSID7047859
Created by admin on Mon Mar 31 17:50:54 GMT 2025 , Edited by admin on Mon Mar 31 17:50:54 GMT 2025
PRIMARY
DRUG CENTRAL
3881
Created by admin on Mon Mar 31 17:50:54 GMT 2025 , Edited by admin on Mon Mar 31 17:50:54 GMT 2025
PRIMARY
MERCK INDEX
m2395
Created by admin on Mon Mar 31 17:50:54 GMT 2025 , Edited by admin on Mon Mar 31 17:50:54 GMT 2025
PRIMARY Merck Index
RXCUI
1425
Created by admin on Mon Mar 31 17:50:54 GMT 2025 , Edited by admin on Mon Mar 31 17:50:54 GMT 2025
PRIMARY RxNorm
MESH
D001591
Created by admin on Mon Mar 31 17:50:54 GMT 2025 , Edited by admin on Mon Mar 31 17:50:54 GMT 2025
PRIMARY
FDA UNII
4O21U048EF
Created by admin on Mon Mar 31 17:50:54 GMT 2025 , Edited by admin on Mon Mar 31 17:50:54 GMT 2025
PRIMARY
DRUG BANK
DB09084
Created by admin on Mon Mar 31 17:50:54 GMT 2025 , Edited by admin on Mon Mar 31 17:50:54 GMT 2025
PRIMARY
WIKIPEDIA
Benzydamine
Created by admin on Mon Mar 31 17:50:54 GMT 2025 , Edited by admin on Mon Mar 31 17:50:54 GMT 2025
PRIMARY
ECHA (EC/EINECS)
211-388-8
Created by admin on Mon Mar 31 17:50:54 GMT 2025 , Edited by admin on Mon Mar 31 17:50:54 GMT 2025
PRIMARY
ChEMBL
CHEMBL12610
Created by admin on Mon Mar 31 17:50:54 GMT 2025 , Edited by admin on Mon Mar 31 17:50:54 GMT 2025
PRIMARY
PUBCHEM
12555
Created by admin on Mon Mar 31 17:50:54 GMT 2025 , Edited by admin on Mon Mar 31 17:50:54 GMT 2025
PRIMARY
EVMPD
SUB05770MIG
Created by admin on Mon Mar 31 17:50:54 GMT 2025 , Edited by admin on Mon Mar 31 17:50:54 GMT 2025
PRIMARY
CAS
642-72-8
Created by admin on Mon Mar 31 17:50:54 GMT 2025 , Edited by admin on Mon Mar 31 17:50:54 GMT 2025
PRIMARY
CHEBI
134500
Created by admin on Mon Mar 31 17:50:54 GMT 2025 , Edited by admin on Mon Mar 31 17:50:54 GMT 2025
PRIMARY
CHEBI
94563
Created by admin on Mon Mar 31 17:50:54 GMT 2025 , Edited by admin on Mon Mar 31 17:50:54 GMT 2025
PRIMARY
NCI_THESAURUS
C83548
Created by admin on Mon Mar 31 17:50:54 GMT 2025 , Edited by admin on Mon Mar 31 17:50:54 GMT 2025
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
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ACTIVE MOIETY