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

Stem definitionDrug idCAS RN
serotonin receptor antagonists (5-HT3) 1329 109889-09-0

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • granisetron monohydrochloride
  • BRL-43694
  • granisetron
  • sancuso
  • kevatril
  • granisetron hydrochloride
  • granisetron HCl
A serotonin receptor (5HT-3 selective) antagonist that has been used as an antiemetic for cancer chemotherapy patients.
  • Molecular weight: 312.42
  • Formula: C18H24N4O
  • CLOGP: 1.72
  • LIPINSKI: 0
  • HAC: 5
  • HDO: 1
  • TPSA: 50.16
  • ALOGS: -2.86
  • ROTB: 2

  • Status: OFP

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
2 mg O
3 mg P
3.10 mg TD

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 1 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 100 mg/mL Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 11 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 0.03 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 60 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution) 3.70 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 9.10 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.35 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 5.20 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
Dec. 29, 1993 FDA ROCHE

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
Tooth erosion 98.08 48.29 13 292 132 2357648
Dyspnoea 94.48 48.29 39 266 78694 2279086
Pulpitis dental 87.50 48.29 12 293 160 2357620
Vomiting 84.10 48.29 35 270 71567 2286213
Respiratory depth decreased 82.36 48.29 9 296 11 2357769
Nausea 81.19 48.29 39 266 112150 2245630
Periodontitis 78.11 48.29 13 292 661 2357119
Venous thrombosis limb 60.58 48.29 10 295 481 2357299
Serotonin syndrome 56.60 48.29 13 292 3527 2354253
Mucosal inflammation 56.59 48.29 14 291 5210 2352570
General physical health deterioration 55.31 48.29 17 288 14122 2343658
Sensory disturbance 54.81 48.29 12 293 2620 2355160
Chest discomfort 54.77 48.29 17 288 14578 2343202

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
Diarrhoea 49.35 37.62 21 136 53831 1692793
Colitis ischaemic 43.31 37.62 8 149 880 1745744
Vomiting 38.40 37.62 16 141 38299 1708325

Pharmacologic Action:

SourceCodeDescription
ATC A04AA02 ALIMENTARY TRACT AND METABOLISM
ANTIEMETICS AND ANTINAUSEANTS
ANTIEMETICS AND ANTINAUSEANTS
Serotonin (5HT3) antagonists
FDA MoA N0000175817 Serotonin 3 Receptor Antagonists
FDA EPC N0000175818 Serotonin-3 Receptor Antagonist
CHEBI has role CHEBI:48279 serotonergic antagonist
CHEBI has role CHEBI:50919 antiemetic
MeSH PA D000932 Antiemetics
MeSH PA D002491 Central Nervous System Agents
MeSH PA D005765 Gastrointestinal Agents
MeSH PA D018377 Neurotransmitter Agents
MeSH PA D018373 Peripheral Nervous System Agents
MeSH PA D018490 Serotonin Agents
MeSH PA D012702 Serotonin Antagonists

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Chemotherapy-induced nausea and vomiting indication 236084000
Prevention of Radiation-Induced Nausea and Vomiting indication
Prevention of Post-Operative Nausea and Vomiting indication
Post-Operative Nausea and Vomiting indication
Prolonged-Severe Nausea and Vomiting off-label use
Hypokalemia contraindication 43339004
Conduction disorder of the heart contraindication 44808001
Prolonged QT interval contraindication 111975006
Hypomagnesemia contraindication 190855004
Congenital long QT syndrome contraindication 442917000
Doxorubicin Induced Cardiomyopathy contraindication

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 13.79 acidic
pKa2 9.5 Basic

Orange Book patent data (new drug applications)

Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRoutePatent numberPatent expiration datePatent use
10MG/0.4ML (10MG/0.4ML) SUSTOL HERON THERAPS INC N022445 Aug. 9, 2016 RX INJECTION, EXTENDED RELEASE SUBCUTANEOUS 10357570 Sept. 28, 2024 PROPHYLACTIC TREATMENT OF NAUSEA AND VOMITING, INCLUDING PREVENTION OF ACUTE AND DELAYED NAUSEA AND VOMITING ASSOCIATED CHEMOTHERAPY
10MG/0.4ML (10MG/0.4ML) SUSTOL HERON THERAPS INC N022445 Aug. 9, 2016 RX INJECTION, EXTENDED RELEASE SUBCUTANEOUS 8252305 Sept. 28, 2024 TREATMENT OR PREVENTION OF NAUSEA AND VOMITING
10MG/0.4ML (10MG/0.4ML) SUSTOL HERON THERAPS INC N022445 Aug. 9, 2016 RX INJECTION, EXTENDED RELEASE SUBCUTANEOUS 9913910 Sept. 28, 2024 PROPHYLACTIC TREATMENT OF NAUSEA AND VOMITING, INCLUDING PREVENTION OF ACUTE AND DELAYED NAUSEA AND VOMITING ASSOCIATED CHEMOTHERAPY
3.1MG/24HR SANCUSO KYOWA KIRIN N022198 Sept. 12, 2008 RX FILM, EXTENDED RELEASE TRANSDERMAL 7608282 Jan. 22, 2025 USE OF GRANISETRON TRANSDERMAL SYSTEM TO TREAT/PREVENT CHEMOTHERAPY INDUCED NAUSEA AND VOMITING

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
5-hydroxytryptamine receptor 3A Ion channel ANTAGONIST Ki 8.70 WOMBAT-PK CHEMBL
Neuronal acetylcholine receptor; alpha4/beta2 Ion channel Ki 4.42 CHEMBL
Solute carrier family 22 member 2 Transporter IC50 5.37 CHEMBL
Neuronal acetylcholine receptor subunit alpha-3 Ion channel Ki 4.17 CHEMBL
5-hydroxytryptamine receptor 3B Ion channel Ki 8.80 CHEMBL
Multidrug and toxin extrusion protein 1 Transporter IC50 5.30 CHEMBL
Potassium voltage-gated channel subfamily H member 2 Ion channel IC50 5.43 WOMBAT-PK
Serotonin 3 (5-HT3) receptor Ion channel Ki 9.46 CHEMBL

External reference:

IDSource
4020855 VUID
N0000179527 NUI
C0543476 UMLSCUI
D00677 KEGG_DRUG
318F6L70J8 UNII
107007-99-8 SECONDARY_CAS_RN
108424001 SNOMEDCT_US
4023910 VANDF
25895 MMSL
003975 NDDF
26237 RXNORM
372489005 SNOMEDCT_US
d03171 MMSL
CHEMBL289469 ChEMBL_ID
DB00889 DRUGBANK_ID
CWB PDB_CHEM_ID
CHEBI:5537 CHEBI
6230 INN_ID
5284566 PUBCHEM_CID
CHEMBL1237080 ChEMBL_ID
D017829 MESH_DESCRIPTOR_UI
2300 IUPHAR_LIGAND_ID

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Granisetron Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0054-0143 TABLET 1 mg ORAL ANDA 13 sections
Granisetron Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0143-9744 INJECTION 1 mg INTRAVENOUS ANDA 17 sections
Granisetron Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0143-9745 INJECTION 1 mg INTRAVENOUS ANDA 17 sections
Granisetron Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 16714-221 TABLET, FILM COATED 1 mg ORAL ANDA 13 sections
Granisetron Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 17478-546 INJECTION 1 mg INTRAVENOUS ANDA 17 sections
Granisetron Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 17478-547 INJECTION 0.10 mg INTRAVENOUS ANDA 17 sections
Granisetron Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 42043-390 TABLET, FILM COATED 1 mg ORAL ANDA 13 sections
Sancuso HUMAN PRESCRIPTION DRUG LABEL 1 42747-726 PATCH 3.10 mg TRANSDERMAL NDA 18 sections
SUSTOL HUMAN PRESCRIPTION DRUG LABEL 1 47426-101 INJECTION 10 mg SUBCUTANEOUS NDA 18 sections
Granisetron Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 51991-735 TABLET 1 mg ORAL ANDA 12 sections
Sancuso HUMAN PRESCRIPTION DRUG LABEL 1 54868-5985 PATCH 3.10 mg TRANSDERMAL NDA 17 sections
Granisetron Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 55150-175 INJECTION, SOLUTION 1 mg INTRAVENOUS ANDA 16 sections
Granisetron Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 55150-176 INJECTION, SOLUTION 4 mg INTRAVENOUS ANDA 16 sections
GRANISETRON HYDROCHLORIDE HUMAN PRESCRIPTION DRUG LABEL 1 55648-661 INJECTION 1 mg INTRAVENOUS ANDA 15 sections
GRANISETRON HYDROCHLORIDE HUMAN PRESCRIPTION DRUG LABEL 1 55648-662 INJECTION 0.10 mg INTRAVENOUS ANDA 15 sections
Granisetron HUMAN PRESCRIPTION DRUG LABEL 1 63323-317 INJECTION, SOLUTION 0.10 mg INTRAVENOUS ANDA 16 sections
Granisetron HUMAN PRESCRIPTION DRUG LABEL 1 63323-318 INJECTION, SOLUTION 1 mg INTRAVENOUS ANDA 16 sections
Granisetron HUMAN PRESCRIPTION DRUG LABEL 1 63323-319 INJECTION, SOLUTION 1 mg INTRAVENOUS ANDA 16 sections
Granisetron hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 63850-0005 TABLET, FILM COATED 1 mg ORAL ANDA 13 sections
GRANISETRON HYDROCHLORIDE HUMAN PRESCRIPTION DRUG LABEL 1 64679-661 INJECTION 1 mg INTRAVENOUS ANDA 17 sections
GRANISETRON HYDROCHLORIDE HUMAN PRESCRIPTION DRUG LABEL 1 64679-662 INJECTION 0.10 mg INTRAVENOUS ANDA 17 sections
GRANISETRON HYDROCHLORIDE HUMAN PRESCRIPTION DRUG LABEL 1 64679-841 INJECTION 1 mg INTRAVENOUS ANDA 17 sections
Granisetron HUMAN PRESCRIPTION DRUG LABEL 1 66758-035 INJECTION 1 mg INTRAVENOUS ANDA 17 sections
Granisetron HUMAN PRESCRIPTION DRUG LABEL 1 66758-036 INJECTION 1 mg INTRAVENOUS ANDA 17 sections
Granisetron Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 67457-861 INJECTION, SOLUTION 0.10 mg INTRAVENOUS ANDA 16 sections
Granisetron Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 67457-863 INJECTION, SOLUTION 1 mg INTRAVENOUS ANDA 16 sections
Granisetron Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 67457-864 INJECTION, SOLUTION 1 mg INTRAVENOUS ANDA 16 sections
Granisetron Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 67877-184 TABLET 1 mg ORAL ANDA 11 sections
GRANISETRON HYDROCHLORIDE HUMAN PRESCRIPTION DRUG LABEL 1 69097-195 INJECTION 0.10 mg INTRAVENOUS ANDA 17 sections
GRANISETRON HYDROCHLORIDE HUMAN PRESCRIPTION DRUG LABEL 1 69097-197 INJECTION 4 mg INTRAVENOUS ANDA 17 sections