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 65.23 28.97 27 1840 26379 53320820
Dystonia 60.01 28.97 21 1846 13000 53334199
Neuromuscular block prolonged 58.82 28.97 11 1856 542 53346657
Anaphylactic reaction 50.20 28.97 29 1838 58297 53288902
Atrioventricular dissociation 47.41 28.97 8 1859 217 53346982
Procedural hypertension 45.90 28.97 8 1859 264 53346935
Subileus 44.18 28.97 12 1855 3204 53343995
Vascular encephalopathy 41.79 28.97 8 1859 447 53346752
Apnoea 41.36 28.97 14 1853 7839 53339360
Pulmonary oedema 34.10 28.97 22 1845 53701 53293498
Drug interaction 32.34 28.97 39 1828 219290 53127909
Myopia 32.08 28.97 8 1859 1531 53345668
Delayed recovery from anaesthesia 31.12 28.97 7 1860 862 53346337
Ileus 29.33 28.97 13 1854 14942 53332257
Generalised tonic-clonic seizure 29.33 28.97 16 1851 28742 53318457

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 124.95 33.37 40 1099 19077 32493310
Bradycardia 85.34 33.37 44 1095 71518 32440869
Metabolic acidosis 57.11 33.37 28 1111 40671 32471716
Cardiac arrest 55.32 33.37 37 1102 96739 32415648
Pseudomonal sepsis 54.54 33.37 14 1125 3015 32509372
Drug interaction 50.45 33.37 49 1090 218136 32294251
Appendicitis perforated 40.55 33.37 10 1129 1830 32510557
Atrioventricular block second degree 38.86 33.37 11 1128 3419 32508968

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
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 acetylcholine esterase inhibitor
CHEBI has role CHEBI:74530 curare antidote
CHEBI has role CHEBI:37733 BChE inhibitor
FDA EPC N0000175723 Cholinesterase 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 IC50 7.46 CHEMBL
Acetylcholinesterase Enzyme Ki 6 CHEMBL
Cholinesterase Enzyme IC50 7.15 CHEMBL

External reference:

IDSource
4019856 VUID
N0000147942 NUI
D00995 KEGG_DRUG
51-60-5 SECONDARY_CAS_RN
4017784 VANDF
4017785 VANDF
4019856 VANDF
C0027679 UMLSCUI
CHEBI:7514 CHEBI
CHEMBL54126 ChEMBL_ID
CHEMBL278020 ChEMBL_ID
DB01400 DRUGBANK_ID
CHEMBL211471 ChEMBL_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 0404-9925 INJECTION 1 mg INTRAVENOUS ANDA 15 sections
Neostigmine Methylsulfate HUMAN PRESCRIPTION DRUG LABEL 1 0517-1133 INJECTION 0.50 mg INTRAVENOUS ANDA 24 sections
Neostigmine Methylsulfate HUMAN PRESCRIPTION DRUG LABEL 1 0517-1134 INJECTION 1 mg INTRAVENOUS ANDA 24 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 14445-413 INJECTION 0.50 mg INTRAVENOUS ANDA 24 sections
NEOSTIGMINE METHYLSULFATE Human Prescription Drug Label 1 14445-414 INJECTION 1 mg INTRAVENOUS ANDA 24 sections
Neostigmine Methylsulfate HUMAN PRESCRIPTION DRUG LABEL 1 25021-610 INJECTION, SOLUTION 0.50 mg INTRAVENOUS ANDA 28 sections
Neostigmine Methylsulfate HUMAN PRESCRIPTION DRUG LABEL 1 25021-611 INJECTION, SOLUTION 1 mg INTRAVENOUS ANDA 28 sections
neostigmine methylsulfate Human Prescription Drug Label 1 31722-994 INJECTION 0.50 mg INTRAVENOUS ANDA 24 sections
neostigmine methylsulfate Human Prescription Drug Label 1 31722-995 INJECTION 1 mg INTRAVENOUS ANDA 24 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