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]
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Therapeutic Class

Analgesics

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)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

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: CHEBI:94563
CAS Number: 642-72-8
DrugBank ID: DB09084
TTD ID: D06FJO
INTEDE ID: DR0199

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]

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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]

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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]
Potassium voltage-gated channel subfamily H member 2 (KCNH2)	OTZX881H	KCNH2_HUMAN	Gene/Protein Processing	[13]

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Molecular Interaction Atlas (MIA)

MIA Detail

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.
13	Why are most phospholipidosis inducers also hERG blockers?. Arch Toxicol. 2017 Dec;91(12):3885-3895. doi: 10.1007/s00204-017-1995-9. Epub 2017 May 27.