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

Stem definitionDrug idCAS RN
acetylcholinesterase inhibitors 1897 59-99-4

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • neostigmine
  • eustigmin
  • eustigmine
  • prostigmin
  • prostigmine
  • vagostigmine
  • neostigmine methylsulfate
  • neostigmine bromide
A cholinesterase inhibitor used in the treatment of myasthenia gravis and to reverse the effects of muscle relaxants such as gallamine and tubocurarine. Neostigmine, unlike PHYSOSTIGMINE, does not cross the blood-brain barrier.
  • Molecular weight: 223.30
  • Formula: C12H19N2O2
  • CLOGP: -2.81
  • LIPINSKI: 0
  • HAC: 4
  • HDO: 0
  • TPSA: 29.54
  • ALOGS: -3.58
  • ROTB: 3

  • Status: OFP

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

Drug dosage:

DoseUnitRoute
60 mg O
2 mg P
0.40 ml None
40 mg ointment

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 3 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 100 mg/mL Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 67 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 0.12 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 2 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution) 0.74 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 9.20 mL/min/kg Lombardo F, Berellini G, Obach RS
t_half (Half-life) 1.30 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
May 31, 2013 FDA ECLAT PHARMS LLC

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
Serotonin syndrome 65.61 26.90 27 1729 24193 46660113
Neuromuscular block prolonged 58.17 26.90 11 1745 535 46683771
Anaphylactic reaction 50.79 26.90 29 1727 53083 46631223
Atrioventricular dissociation 46.84 26.90 8 1748 217 46684089
Dystonia 46.28 26.90 17 1739 11240 46673066
Procedural hypertension 43.71 26.90 8 1748 325 46683981
Vascular encephalopathy 41.74 26.90 8 1748 418 46683888
Apnoea 41.30 26.90 14 1742 7325 46676981
Subileus 34.98 26.90 10 1746 2993 46681313
Pulmonary oedema 33.66 26.90 22 1734 51083 46633223
Delayed recovery from anaesthesia 30.68 26.90 7 1749 854 46683452
Ileus 29.20 26.90 13 1743 14051 46670255
Generalised tonic-clonic seizure 29.13 26.90 16 1740 27106 46657200

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
Serotonin syndrome 128.80 35.56 40 979 17851 29933608
Bradycardia 64.14 35.56 35 984 65491 29885968
Metabolic acidosis 60.14 35.56 28 991 37433 29914026
Pseudomonal sepsis 55.10 35.56 14 1005 2986 29948473
Appendicitis perforated 41.30 35.56 10 1009 1748 29949711

Pharmacologic Action:

SourceCodeDescription
ATC N07AA01 NERVOUS SYSTEM
OTHER NERVOUS SYSTEM DRUGS
PARASYMPATHOMIMETICS
Anticholinesterases
ATC N07AA51 NERVOUS SYSTEM
OTHER NERVOUS SYSTEM DRUGS
PARASYMPATHOMIMETICS
Anticholinesterases
ATC S01EB06 SENSORY ORGANS
OPHTHALMOLOGICALS
ANTIGLAUCOMA PREPARATIONS AND MIOTICS
Parasympathomimetics
FDA MoA N0000000177 Cholinesterase Inhibitors
FDA EPC N0000175723 Cholinesterase Inhibitor
MeSH PA D018678 Cholinergic Agents
MeSH PA D002800 Cholinesterase Inhibitors
MeSH PA D004791 Enzyme Inhibitors
MeSH PA D018377 Neurotransmitter Agents
MeSH PA D010277 Parasympathomimetics
MeSH PA D018373 Peripheral Nervous System Agents
CHEBI has role CHEBI:38462 acetylcholinesterase inhibitors
CHEBI has role CHEBI:74530 curare antidote
CHEBI has role CHEBI:37733 bche inhibitor

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Myasthenia gravis indication 91637004 DOID:437
Reversal of neuromuscular blockade indication 241703000
Retention of urine indication 267064002
Urinary tract obstruction contraindication 7163005 DOID:5200
Peptic ulcer contraindication 13200003 DOID:750
Increased gastric tonus contraindication 18644006
Hyperthyroidism contraindication 34486009 DOID:7998
Conduction disorder of the heart contraindication 44808001
Peritonitis contraindication 48661000
Sinus bradycardia contraindication 49710005
Coronary occlusion contraindication 63739005
Gastrointestinal obstruction contraindication 126765001
Seizure disorder contraindication 128613002
Asthma contraindication 195967001 DOID:2841
Macrocolon contraindication 367495003
Gastrointestinal hypomotility contraindication 421807004
Increased Bronchial Secretions contraindication
Colonic Necrosis contraindication

Acid dissociation constants calculated using MoKa v3.0.0

None

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
Acetylcholinesterase Enzyme INHIBITOR IC50 7.59 WOMBAT-PK CHEMBL
Cholinesterase Enzyme IC50 7.22 CHEMBL
Acetylcholinesterase Enzyme IC50 8.34 CHEMBL
Acetylcholinesterase Enzyme Ki 6 CHEMBL
Acetylcholinesterase Enzyme IC50 7.46 CHEMBL
Cholinesterase Enzyme IC50 7.15 CHEMBL

External reference:

IDSource
4019856 VUID
N0000147942 NUI
D00995 KEGG_DRUG
114-80-7 SECONDARY_CAS_RN
4017784 VANDF
4017785 VANDF
4019856 VANDF
C0027679 UMLSCUI
CHEBI:7514 CHEBI
CHEMBL278020 ChEMBL_ID
CHEMBL54126 ChEMBL_ID
CHEMBL211471 ChEMBL_ID
DB01400 DRUGBANK_ID
D009388 MESH_DESCRIPTOR_UI
4456 PUBCHEM_CID
8993 IUPHAR_LIGAND_ID
401 INN_ID
3982TWQ96G UNII
262500 RXNORM
3968 MMSL
5165 MMSL
5166 MMSL
72417 MMSL
9863 MMSL
d00313 MMSL
001703 NDDF
001704 NDDF
001705 NDDF
373346001 SNOMEDCT_US
387294009 SNOMEDCT_US
80024007 SNOMEDCT_US
87151005 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Neostigmine Methylsulfate HUMAN PRESCRIPTION DRUG LABEL 1 0517-1133 INJECTION 0.50 mg INTRAVENOUS ANDA 25 sections
Neostigmine Methylsulfate HUMAN PRESCRIPTION DRUG LABEL 1 0517-1134 INJECTION 1 mg INTRAVENOUS ANDA 25 sections
NEOSTIGMINE METHYLSULFATE HUMAN PRESCRIPTION DRUG LABEL 1 0548-9601 INJECTION 0.50 mg INTRAVENOUS ANDA 16 sections
NEOSTIGMINE METHYLSULFATE HUMAN PRESCRIPTION DRUG LABEL 1 0548-9602 INJECTION 1 mg INTRAVENOUS ANDA 16 sections
Neostigmine Methylsulfate HUMAN PRESCRIPTION DRUG LABEL 1 0641-6149 INJECTION 1 mg INTRAVENOUS ANDA 24 sections
Neostigmine Methylsulfate HUMAN PRESCRIPTION DRUG LABEL 1 0641-6150 INJECTION 0.50 mg INTRAVENOUS ANDA 24 sections
neostigmine methylsulfate Human Prescription Drug Label 1 31722-994 INJECTION 0.50 mg INTRAVENOUS ANDA 25 sections
neostigmine methylsulfate Human Prescription Drug Label 1 31722-995 INJECTION 1 mg INTRAVENOUS ANDA 25 sections
NEOSTIGMINE METHYLSULFATE HUMAN PRESCRIPTION DRUG LABEL 1 42023-188 INJECTION 0.50 mg INTRAVENOUS ANDA 23 sections
NEOSTIGMINE METHYLSULFATE HUMAN PRESCRIPTION DRUG LABEL 1 42023-189 INJECTION 1 mg INTRAVENOUS ANDA 23 sections
Neostigmine HUMAN PRESCRIPTION DRUG LABEL 1 43598-528 INJECTION 0.50 mg INTRAVENOUS ANDA 24 sections
Neostigmine HUMAN PRESCRIPTION DRUG LABEL 1 43598-529 INJECTION 1 mg INTRAVENOUS ANDA 24 sections
NEOSTIGMINE METHYLSULFATE HUMAN PRESCRIPTION DRUG LABEL 1 50090-4532 INJECTION 1 mg INTRAVENOUS ANDA 17 sections
Neostigmine methylsulfate HUMAN PRESCRIPTION DRUG LABEL 1 50090-5197 INJECTION 0.50 mg INTRAVENOUS ANDA 25 sections
NEOSTIGMINE METHYLSULFATE HUMAN PRESCRIPTION DRUG LABEL 1 51662-1557 INJECTION 1 mg INTRAVENOUS ANDA 16 sections
Bloxiverz HUMAN PRESCRIPTION DRUG LABEL 1 51754-1210 INJECTION 0.50 mg INTRAVENOUS NDA 25 sections
Bloxiverz HUMAN PRESCRIPTION DRUG LABEL 1 51754-1220 INJECTION 1 mg INTRAVENOUS NDA 25 sections
Bloxiverz HUMAN PRESCRIPTION DRUG LABEL 1 51754-1240 INJECTION 1 mg INTRAVENOUS NDA 26 sections
Bloxiverz HUMAN PRESCRIPTION DRUG LABEL 1 51754-1240 INJECTION 1 mg INTRAVENOUS NDA 26 sections
NEOSTIGMINE METHYLSULFATE HUMAN PRESCRIPTION DRUG LABEL 1 52584-057 INJECTION 1 mg INTRAVENOUS ANDA 15 sections
Neostigmine Methylsulfate HUMAN PRESCRIPTION DRUG LABEL 1 63323-413 INJECTION, SOLUTION 0.50 mg INTRAVENOUS NDA 24 sections
Neostigmine Methylsulfate HUMAN PRESCRIPTION DRUG LABEL 1 63323-413 INJECTION, SOLUTION 0.50 mg INTRAVENOUS NDA 24 sections
Neostigmine Methylsulfate HUMAN PRESCRIPTION DRUG LABEL 1 63323-415 INJECTION, SOLUTION 1 mg INTRAVENOUS NDA 24 sections
Neostigmine Methylsulfate HUMAN PRESCRIPTION DRUG LABEL 1 63323-415 INJECTION, SOLUTION 1 mg INTRAVENOUS NDA 24 sections
Neostigmine Methylsulfate Human Prescription Drug Label 1 65145-111 INJECTION 0.50 mg INTRAVENOUS ANDA 20 sections
Neostigmine Methylsulfate Human Prescription Drug Label 1 65145-112 INJECTION 1 mg INTRAVENOUS ANDA 20 sections
Neostigmine methylsulfate Human Prescription Drug Label 1 68083-383 INJECTION 0.50 mg INTRAVENOUS ANDA 24 sections
Neostigmine methylsulfate Human Prescription Drug Label 1 68083-384 INJECTION 1 mg INTRAVENOUS ANDA 24 sections
Neostigmine methylsulfate HUMAN PRESCRIPTION DRUG LABEL 1 70121-1478 INJECTION 0.50 mg INTRAVENOUS ANDA 24 sections
Neostigmine methylsulfate HUMAN PRESCRIPTION DRUG LABEL 1 70121-1479 INJECTION 1 mg INTRAVENOUS ANDA 24 sections