terfenadine Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
2600 50679-08-8

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • terfenadine
  • ternadin
  • racemic terfenadine
  • seldane
A selective histamine H1-receptor antagonist devoid of central nervous system depressant activity. The drug was used for ALLERGY but withdrawn due to causing LONG QT SYNDROME.
  • Molecular weight: 471.69
  • Formula: C32H41NO2
  • CLOGP: 6.07
  • LIPINSKI: 1
  • HAC: 3
  • HDO: 2
  • TPSA: 43.70
  • ALOGS: -6.01
  • ROTB: 9

Drug dosage:

DoseUnitRoute
0.12 g O

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 2 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 0.01 mg/mL Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 0 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 4.24 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 1 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H

Approvals:

DateAgencyCompanyOrphan
None FDA

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Drug hypersensitivity 85.91 0 17 7 46626 2311435

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event

Pharmacologic Action:

SourceCodeDescription
ATC R06AX12 RESPIRATORY SYSTEM
ANTIHISTAMINES FOR SYSTEMIC USE
ANTIHISTAMINES FOR SYSTEMIC USE
Other antihistamines for systemic use
MeSH PA D018494 Histamine Agents
MeSH PA D006633 Histamine Antagonists
MeSH PA D006634 Histamine H1 Antagonists
MeSH PA D039563 Histamine H1 Antagonists, Non-Sedating
MeSH PA D018377 Neurotransmitter Agents

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Vasomotor rhinitis indication 8229003 DOID:4730
Allergic rhinitis indication 61582004
Nasal discharge indication 64531003
Nasal congestion indication 68235000
Sneezing indication 76067001
Common cold indication 82272006 DOID:10459
Chronic idiopathic urticaria indication 302162004
Seasonal allergic rhinitis indication 367498001
Allergic conjunctivitis indication 473460002 DOID:11204
Urticaria off-label use 126485001
Hyperthyroidism contraindication 34486009 DOID:7998
Hypertensive disorder contraindication 38341003 DOID:10763
Coronary arteriosclerosis contraindication 53741008 DOID:3393
Diabetes mellitus contraindication 73211009 DOID:9351
Benign prostatic hyperplasia contraindication 266569009
Retention of urine contraindication 267064002
Angle-closure glaucoma contraindication 392291006 DOID:13550
Hypertensive urgency contraindication 443482000

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 8.85 Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Histamine H1 receptor GPCR ANTAGONIST Ki 8.70 WOMBAT-PK IUPHAR
D(1A) dopamine receptor GPCR Ki 5.87 DRUG MATRIX
D(2) dopamine receptor GPCR Ki 5.69 DRUG MATRIX
Sodium-dependent noradrenaline transporter Transporter Ki 5.72 DRUG MATRIX
5-hydroxytryptamine receptor 2A GPCR Ki 7.14 DRUG MATRIX
5-hydroxytryptamine receptor 2B GPCR Ki 7.52 DRUG MATRIX
5-hydroxytryptamine receptor 2C GPCR Ki 6.19 DRUG MATRIX
5-hydroxytryptamine receptor 6 GPCR Ki 6.22 DRUG MATRIX
D(3) dopamine receptor GPCR Ki 6.29 DRUG MATRIX
Alpha-2C adrenergic receptor GPCR Ki 6.26 DRUG MATRIX
Sodium-dependent dopamine transporter Transporter Ki 6.69 DRUG MATRIX
Epidermal growth factor receptor Kinase IC50 5.45 DRUG MATRIX
C-C chemokine receptor type 5 GPCR Ki 6.07 DRUG MATRIX
Tyrosine-protein kinase Fyn Kinase IC50 5.21 DRUG MATRIX
Substance-K receptor GPCR Ki 6.05 DRUG MATRIX
Heat shock protein HSP 90-alpha Cytosolic other IC50 5.46 WOMBAT-PK
Multidrug resistance protein 1 Transporter IC50 5.85 WOMBAT-PK
Potassium voltage-gated channel subfamily H member 2 Ion channel IC50 7.25 WOMBAT-PK
Muscarinic acetylcholine receptor M1 GPCR IC50 5.54 CHEMBL
Cytochrome P450 2J2 Enzyme IC50 5.09 CHEMBL
Potassium voltage-gated channel subfamily H member 1 Ion channel BLOCKER IC50 7.80 IUPHAR
Adrenergic receptor alpha-1 GPCR IC50 5.63 CHEMBL
Alpha-1B adrenergic receptor GPCR Ki 5.73 DRUG MATRIX
Histamine H1 receptor GPCR Kd 7.45 CHEMBL
Transcriptional activator protein luxR Unclassified IC50 4.04 CHEMBL

External reference:

IDSource
4019295 VUID
N0000147493 NUI
C0085173 UMLSCUI
D00521 KEGG_DRUG
7BA5G9Y06Q UNII
3674 INN_ID
16037009 SNOMEDCT_US
4019295 VANDF
003412 NDDF
2365 MMSL
42330 RXNORM
387089004 SNOMEDCT_US
5550 MMSL
d00387 MMSL
CHEMBL17157 ChEMBL_ID
DB00342 DRUGBANK_ID
CHEBI:9453 CHEBI
D016593 MESH_DESCRIPTOR_UI
5405 PUBCHEM_CID
2608 IUPHAR_LIGAND_ID

Pharmaceutical products:

None