Details of the Drug

General Information of Drug (ID: DMEQL9U)

Drug Name
Benzydamine
Synonyms
Bencidamina; Benzidamina; Benzidamine; Benzindamine; Benzydaminum; Benzidamina [DCIT]; Benzydamine Monohydrochoride; C 1523; Apo-Benzydamine; Bencidamina [INN-Spanish]; Benzydamine (INN); Benzydamine [INN:BAN]; Benzydaminum [INN-Latin]; Apo-Benzydamine (TN); {3-[(1-benzyl-1H-indazol-3-yl)oxy]propyl}dimethylamine; 1-Benzyl-3-(3-(dimethylamino)propoxy)-1H-indazole; 3-(1-benzylindazol-3-yl)oxy-N,N-dimethylpropan-1-amine; 3-[(1-benzyl-1H-indazol-3-yl)oxy]-N,N-dimethylpropan-1-amine
Indication
Disease Entry ICD 11 Status REF
Chemotherapy or radiotherapy-induced mucositis DA42-DA60 Discontinued in Phase 2 [1]
Therapeutic Class
Analgesics
Affected Organisms
Humans and other mammals
ATC Code
A01AD02: Benzydamine
A01AD: Other agents for local oral treatment
A01A: STOMATOLOGICAL PREPARATIONS
A01: STOMATOLOGICAL PREPARATIONS
A: ALIMENTARY TRACT AND METABOLISM
G02CC03: Benzydamine
G02CC: Antiinflammatory products for vaginal administration
G02C: OTHER GYNECOLOGICALS
G02: OTHER GYNECOLOGICALS
G: GENITO URINARY SYSTEM AND SEX HORMONES
M01AX07: Benzydamine
M01AX: Other antiinflammatory and antirheumatic agents, non-steroids
M01A: ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS, NON-STEROIDS
M01: ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS
M: MUSCULO-SKELETAL SYSTEM
M01AX07: Benzydamine
M01AX: Other antiinflammatory and antirheumatic agents, non-steroids
M01A: ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS, NON-STEROIDS
M01: ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS
M: MUSCULO-SKELETAL SYSTEM
M02AA05: Benzydamine
M02AA: Antiinflammatory preparations, non-steroids for topical use
M02A: TOPICAL PRODUCTS FOR JOINT AND MUSCULAR PAIN
M02: TOPICAL PRODUCTS FOR JOINT AND MUSCULAR PAIN
M: MUSCULO-SKELETAL SYSTEM
R02AX03: Benzydamine
R02AX: Other throat preparations
R02A: THROAT PREPARATIONS
R02: THROAT PREPARATIONS
R: RESPIRATORY SYSTEM
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 309.4
Logarithm of the Partition Coefficient (xlogp) 3.9
Rotatable Bond Count (rotbonds) 7
Hydrogen Bond Donor Count (hbonddonor) 0
Hydrogen Bond Acceptor Count (hbondacc) 3
ADMET Property
Bioavailability
87% of drug becomes completely available to its intended biological destination(s) [2]
Clearance
The sytemic clearance of drug is 170 mL/min [3]
Elimination
The relatively high lipid solubility of the weak base benzydamine is thought to be associated with considerable passive resorption within the renal tubule, which suggests that only approximately 5% of benzydamine is excreted unchanged in the urine [4]
Half-life
The concentration or amount of drug in body reduced by one-half in 13 hours [5]
Metabolism
The drug is metabolized via oxidation, dealkylation, and conjugation into hydroxy, dealkylated, and N-oxide metabolites [5]
Unbound Fraction
The unbound fraction of drug in plasma is 0.8% [6]
Vd
The volume of distribution (Vd) of drug is 10 L [4]
Chemical Identifiers
Formula
C19H23N3O
IUPAC Name
3-(1-benzylindazol-3-yl)oxy-N,N-dimethylpropan-1-amine
Canonical SMILES
CN(C)CCCOC1=NN(C2=CC=CC=C21)CC3=CC=CC=C3
InChI
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
InChIKey
CNBGNNVCVSKAQZ-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
12555
ChEBI ID
CHEMBL12610
CAS Number
642-72-8
UNII
4O21U048EF
DrugBank ID
DB09084
TTD ID
D06FJO
INTEDE ID
DR0199
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Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Prostaglandin G/H synthase (COX) TTK0943 PGH1_HUMAN ; PGH2_HUMAN Inhibitor [1]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 3A4 (CYP3A4) DE4LYSA CP3A4_HUMAN Substrate [7]
Cytochrome P450 2E1 (CYP2E1) DEVDYN7 CP2E1_HUMAN Substrate [8]
Cytochrome P450 2D6 (CYP2D6) DECB0K3 CP2D6_HUMAN Substrate [7]
Cytochrome P450 1A1 (CYP1A1) DE6OQ3W CP1A1_HUMAN Substrate [7]
Mephenytoin 4-hydroxylase (CYP2C19) DEGTFWK CP2CJ_HUMAN Substrate [8]
Cytochrome P450 1A2 (CYP1A2) DEJGDUW CP1A2_HUMAN Substrate [9]
Dimethylaniline oxidase 4 (FMO4) DEGAZ8O FMO4_HUMAN Substrate [7]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Flavin-containing monooxygenase 1 (FMO1) OTTHSQKP FMO1_HUMAN Biotransformations [10]
Flavin-containing monooxygenase 2 (FMO2) OTUJUL9S FMO2_HUMAN Biotransformations [11]
Flavin-containing monooxygenase 3 (FMO3) OT1G2EV3 FMO3_HUMAN Regulation of Drug Effects [12]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

1 Emerging drugs for chemotherapy-induced mucositis. Expert Opin Emerg Drugs. 2008 Sep;13(3):511-22.
2 Critical Evaluation of Human Oral Bioavailability for Pharmaceutical Drugs by Using Various Cheminformatics Approaches
3 Quane PA, Graham GG, Ziegler JB: Pharmacology of benzydamine. Inflammopharmacology. 1998;6(2):95-107. doi: 10.1007/s10787-998-0026-0.
4 Baldock GA, Brodie RR, Chasseaud LF, Taylor T, Walmsley LM, Catanese B: Pharmacokinetics of benzydamine after intravenous, oral, and topical doses to human subjects. Biopharm Drug Dispos. 1991 Oct;12(7):481-92.
5 Electronic Medicines Compedium Benzydamine Hydrochloride 0.15% w/v Mouthwash Monograph
6 Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
7 In vitro evaluation of potential in vivo probes for human flavin-containing monooxygenase (FMO): metabolism of benzydamine and caffeine by FMO and P450 isoforms. Br J Clin Pharmacol. 2000 Oct;50(4):311-4.
8 Characterization of moclobemide N-oxidation in human liver microsomes. Xenobiotica. 2001 Jul;31(7):387-97.
9 Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448.
10 Characterization of enzyme activities of Cytochrome P450 enzymes, Flavin-dependent monooxygenases, N-acetyltransferases and UDP-glucuronyltransferases in human reconstructed epidermis and full-thickness skin models. Toxicol In Vitro. 2011 Sep;25(6):1209-14. doi: 10.1016/j.tiv.2011.03.012. Epub 2011 Mar 22.
11 Human FMO2-based microbial whole-cell catalysts for drug metabolite synthesis. Microb Cell Fact. 2015 Jun 12;14:82.
12 Effect of genetic variants of the human flavin-containing monooxygenase 3 on N- and S-oxygenation activities. Drug Metab Dispos. 2007 Mar;35(3):328-30. doi: 10.1124/dmd.106.013094. Epub 2006 Dec 1.