You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on DrugBank.
Identification
NamePhysostigmine
Accession NumberDB00981  (APRD00406)
TypeSmall Molecule
GroupsApproved
DescriptionA cholinesterase inhibitor that is rapidly absorbed through membranes. It can be applied topically to the conjunctiva. It also can cross the blood-brain barrier and is used when central nervous system effects are desired, as in the treatment of severe anticholinergic toxicity. [PubChem]
Structure
Thumb
Synonyms
Antilirium
Eserine
Physostigmine
Physostol
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Antilirium Inj 1mg/mlLiquid1 mgIntramuscular; IntravenousForest Pharmaceuticals Inc.1975-12-311998-07-07Canada
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Physostigmine SalicylateInjection1 mg/mLIntravenousAkorn2010-08-10Not applicableUs
Physostigmine SalicylateInjection1 mg/mLIntravenousCardinal Health2010-08-10Not applicableUs
International Brands
NameCompany
AntiliriumNot Available
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Physostigmine salicylate
ThumbNot applicableDBSALT001541
Physostigmine Sulfate
Thumb
  • InChI Key: YYBNDIVPHIWTPK-KYJQVDHRSA-N
  • Monoisotopic Mass: 648.294133104
  • Average Mass: 648.771
DBSALT000243
Categories
UNII9U1VM840SP
CAS number57-47-6
WeightAverage: 275.3461
Monoisotopic: 275.163376931
Chemical FormulaC15H21N3O2
InChI KeyPIJVFDBKTWXHHD-HIFRSBDPSA-N
InChI
InChI=1S/C15H21N3O2/c1-15-7-8-17(3)13(15)18(4)12-6-5-10(9-11(12)15)20-14(19)16-2/h5-6,9,13H,7-8H2,1-4H3,(H,16,19)/t13-,15+/m1/s1
IUPAC Name
(3aS,8aR)-1,3a,8-trimethyl-1H,2H,3H,3aH,8H,8aH-pyrrolo[2,3-b]indol-5-yl N-methylcarbamate
SMILES
[H][C@]12N(C)CC[C@@]1(C)C1=C(C=CC(OC(=O)NC)=C1)N2C
Pharmacology
IndicationFor the treatment of glaucoma, and in the treatment of severe anticholinergic toxicity.
Structured Indications Not Available
PharmacodynamicsPhysostigmine is a parasympathomimetic, specifically, a reversible cholinesterase inhibitor which effectively increases the concentration of acetylcholine at the sites of cholinergic transmission. Physostigmine is used to treat glaucoma. Because it crosses the blood-brain barrier, it is also used to treat the central nervous system effects of atropine overdose and other anticholinergic drug overdoses. Physostigmine can reverse both central and peripheral anticholinergia.
Mechanism of actionPhysostigmine inhibits acetylcholinesterase, the enzyme responsible for the breakdown of used acetylcholine. By interfering with the metabolism of acetylcholine, physostigmine indirectly stimulates both nicotinic and muscarinic receptors due to the consequential increase in available acetylcholine at the synapse.
TargetKindPharmacological actionActionsOrganismUniProt ID
AcetylcholinesteraseProteinyes
inhibitor
HumanP22303 details
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism

Quickly hydrolyzed by cholinesterases

Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicitySide effects include increased sweating, loss of bladder control, muscle weakness, nausea, vomiting, diarrhea, or stomach cramps or pain, shortness of breath, tightness in chest, or wheezing, slow or irregular heartbeat, unusual tiredness or weakness, watering of mouth, blurred vision or change in near or distant vision, and eye pain.
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
Interactions
Drug Interactions
DrugInteractionDrug group
16-BromoepiandrosteroneThe risk or severity of adverse effects can be increased when 16-Bromoepiandrosterone is combined with Physostigmine.Investigational
19-norandrostenedioneThe risk or severity of adverse effects can be increased when 19-norandrostenedione is combined with Physostigmine.Experimental, Illicit
4-AndrostenedioneThe risk or severity of adverse effects can be increased when 4-Androstenedione is combined with Physostigmine.Experimental, Illicit
5-androstenedioneThe risk or severity of adverse effects can be increased when 5-androstenedione is combined with Physostigmine.Experimental, Illicit
AcebutololPhysostigmine may increase the bradycardic activities of Acebutolol.Approved
AcetylcholineThe risk or severity of adverse effects can be increased when Physostigmine is combined with Acetylcholine.Approved
AclidiniumThe therapeutic efficacy of Aclidinium can be decreased when used in combination with Physostigmine.Approved
AlclometasoneThe risk or severity of adverse effects can be increased when Alclometasone is combined with Physostigmine.Approved
AldosteroneThe risk or severity of adverse effects can be increased when Aldosterone is combined with Physostigmine.Experimental
AlprenololPhysostigmine may increase the bradycardic activities of Alprenolol.Approved, Withdrawn
AmcinonideThe risk or severity of adverse effects can be increased when Amcinonide is combined with Physostigmine.Approved
AnecortaveThe risk or severity of adverse effects can be increased when Anecortave is combined with Physostigmine.Investigational
Anisotropine MethylbromideThe therapeutic efficacy of Anisotropine Methylbromide can be decreased when used in combination with Physostigmine.Approved
Aop200704Physostigmine may increase the bradycardic activities of Aop200704.Investigational
ArecolineThe risk or severity of adverse effects can be increased when Physostigmine is combined with Arecoline.Experimental
ArotinololPhysostigmine may increase the bradycardic activities of Arotinolol.Approved
AtenololPhysostigmine may increase the bradycardic activities of Atenolol.Approved
Atracurium besylateThe therapeutic efficacy of Atracurium besylate can be decreased when used in combination with Physostigmine.Approved
AtropineThe therapeutic efficacy of Atropine can be decreased when used in combination with Physostigmine.Approved, Vet Approved
BeclomethasoneThe risk or severity of adverse effects can be increased when Beclomethasone is combined with Physostigmine.Investigational
Beclomethasone dipropionateThe risk or severity of adverse effects can be increased when Beclomethasone dipropionate is combined with Physostigmine.Approved, Investigational
BefunololPhysostigmine may increase the bradycardic activities of Befunolol.Experimental
BenactyzineThe therapeutic efficacy of Benactyzine can be decreased when used in combination with Physostigmine.Withdrawn
BenzatropineThe therapeutic efficacy of Benzatropine can be decreased when used in combination with Physostigmine.Approved
BetamethasoneThe risk or severity of adverse effects can be increased when Betamethasone is combined with Physostigmine.Approved, Vet Approved
BetaxololPhysostigmine may increase the bradycardic activities of Betaxolol.Approved
BethanecholThe risk or severity of adverse effects can be increased when Physostigmine is combined with Bethanechol.Approved
BevantololPhysostigmine may increase the bradycardic activities of Bevantolol.Approved
BiperidenThe therapeutic efficacy of Biperiden can be decreased when used in combination with Physostigmine.Approved
BisoprololPhysostigmine may increase the bradycardic activities of Bisoprolol.Approved
BopindololPhysostigmine may increase the bradycardic activities of Bopindolol.Approved
BucindololPhysostigmine may increase the bradycardic activities of Bucindolol.Investigational
BudesonideThe risk or severity of adverse effects can be increased when Budesonide is combined with Physostigmine.Approved
BufuralolPhysostigmine may increase the bradycardic activities of Bufuralol.Experimental, Investigational
BupranololPhysostigmine may increase the bradycardic activities of Bupranolol.Approved
CarbacholThe risk or severity of adverse effects can be increased when Physostigmine is combined with Carbachol.Approved
CarteololPhysostigmine may increase the bradycardic activities of Carteolol.Approved
CarvedilolPhysostigmine may increase the bradycardic activities of Carvedilol.Approved, Investigational
CeliprololPhysostigmine may increase the bradycardic activities of Celiprolol.Approved, Investigational
CevimelineThe risk or severity of adverse effects can be increased when Physostigmine is combined with Cevimeline.Approved
ChlorphenoxamineThe therapeutic efficacy of Chlorphenoxamine can be decreased when used in combination with Physostigmine.Withdrawn
CiclesonideThe risk or severity of adverse effects can be increased when Ciclesonide is combined with Physostigmine.Approved, Investigational
ClobetasolThe risk or severity of adverse effects can be increased when Clobetasol is combined with Physostigmine.Investigational
Clobetasol propionateThe risk or severity of adverse effects can be increased when Clobetasol propionate is combined with Physostigmine.Approved
ClocortoloneThe risk or severity of adverse effects can be increased when Clocortolone is combined with Physostigmine.Approved
Cortisone acetateThe risk or severity of adverse effects can be increased when Cortisone acetate is combined with Physostigmine.Approved
CyclopentolateThe therapeutic efficacy of Cyclopentolate can be decreased when used in combination with Physostigmine.Approved
DarifenacinThe therapeutic efficacy of Darifenacin can be decreased when used in combination with Physostigmine.Approved, Investigational
dehydroepiandrosterone sulfateThe risk or severity of adverse effects can be increased when dehydroepiandrosterone sulfate is combined with Physostigmine.Investigational
DesloratadineThe therapeutic efficacy of Desloratadine can be decreased when used in combination with Physostigmine.Approved, Investigational
DesoximetasoneThe risk or severity of adverse effects can be increased when Desoximetasone is combined with Physostigmine.Approved
Desoxycorticosterone acetateThe risk or severity of adverse effects can be increased when Desoxycorticosterone acetate is combined with Physostigmine.Approved
Desoxycorticosterone PivalateThe risk or severity of adverse effects can be increased when Desoxycorticosterone Pivalate is combined with Physostigmine.Experimental, Vet Approved
DexamethasoneThe risk or severity of adverse effects can be increased when Dexamethasone is combined with Physostigmine.Approved, Investigational, Vet Approved
Dexamethasone isonicotinateThe risk or severity of adverse effects can be increased when Dexamethasone isonicotinate is combined with Physostigmine.Vet Approved
DexetimideThe therapeutic efficacy of Dexetimide can be decreased when used in combination with Physostigmine.Withdrawn
DicyclomineThe therapeutic efficacy of Dicyclomine can be decreased when used in combination with Physostigmine.Approved
DiflorasoneThe risk or severity of adverse effects can be increased when Diflorasone is combined with Physostigmine.Approved
DifluocortoloneThe risk or severity of adverse effects can be increased when Difluocortolone is combined with Physostigmine.Approved
DifluprednateThe risk or severity of adverse effects can be increased when Difluprednate is combined with Physostigmine.Approved
DipyridamoleThe therapeutic efficacy of Physostigmine can be decreased when used in combination with Dipyridamole.Approved
EPIBATIDINEThe risk or severity of adverse effects can be increased when Physostigmine is combined with EPIBATIDINE.Experimental
EquileninThe risk or severity of adverse effects can be increased when Equilenin is combined with Physostigmine.Experimental
EquilinThe risk or severity of adverse effects can be increased when Equilin is combined with Physostigmine.Approved
EsmololPhysostigmine may increase the bradycardic activities of Esmolol.Approved
EstroneThe risk or severity of adverse effects can be increased when Estrone is combined with Physostigmine.Approved
Estrone sulfateThe risk or severity of adverse effects can be increased when Estrone sulfate is combined with Physostigmine.Approved
EthopropazineThe therapeutic efficacy of Ethopropazine can be decreased when used in combination with Physostigmine.Approved
FesoterodineThe therapeutic efficacy of Fesoterodine can be decreased when used in combination with Physostigmine.Approved
fluasteroneThe risk or severity of adverse effects can be increased when fluasterone is combined with Physostigmine.Investigational
FludrocortisoneThe risk or severity of adverse effects can be increased when Fludrocortisone is combined with Physostigmine.Approved
FlumethasoneThe risk or severity of adverse effects can be increased when Flumethasone is combined with Physostigmine.Approved, Vet Approved
FlunisolideThe risk or severity of adverse effects can be increased when Flunisolide is combined with Physostigmine.Approved, Investigational
Fluocinolone AcetonideThe risk or severity of adverse effects can be increased when Fluocinolone Acetonide is combined with Physostigmine.Approved, Investigational, Vet Approved
FluocinonideThe risk or severity of adverse effects can be increased when Fluocinonide is combined with Physostigmine.Approved, Investigational
FluocortoloneThe risk or severity of adverse effects can be increased when Fluocortolone is combined with Physostigmine.Approved, Withdrawn
FluorometholoneThe risk or severity of adverse effects can be increased when Fluorometholone is combined with Physostigmine.Approved
FluprednideneThe risk or severity of adverse effects can be increased when Fluprednidene is combined with Physostigmine.Approved, Withdrawn
FluprednisoloneThe risk or severity of adverse effects can be increased when Fluprednisolone is combined with Physostigmine.Approved
FlurandrenolideThe risk or severity of adverse effects can be increased when Flurandrenolide is combined with Physostigmine.Approved
Fluticasone furoateThe risk or severity of adverse effects can be increased when Fluticasone furoate is combined with Physostigmine.Approved
Fluticasone PropionateThe risk or severity of adverse effects can be increased when Fluticasone Propionate is combined with Physostigmine.Approved
FormestaneThe risk or severity of adverse effects can be increased when Formestane is combined with Physostigmine.Approved, Investigational, Withdrawn
Gallamine TriethiodideThe therapeutic efficacy of Gallamine Triethiodide can be decreased when used in combination with Physostigmine.Approved
GlycopyrroniumThe therapeutic efficacy of Glycopyrronium can be decreased when used in combination with Physostigmine.Approved, Investigational, Vet Approved
GTS-21The risk or severity of adverse effects can be increased when Physostigmine is combined with GTS-21.Investigational
HE3286The risk or severity of adverse effects can be increased when HE3286 is combined with Physostigmine.Investigational
HexamethoniumThe therapeutic efficacy of Hexamethonium can be decreased when used in combination with Physostigmine.Experimental
HomatropineThe therapeutic efficacy of Homatropine can be decreased when used in combination with Physostigmine.Approved
HydrocortisoneThe risk or severity of adverse effects can be increased when Hydrocortisone is combined with Physostigmine.Approved, Vet Approved
HyoscyamineThe therapeutic efficacy of Hyoscyamine can be decreased when used in combination with Physostigmine.Approved
IndenololPhysostigmine may increase the bradycardic activities of Indenolol.Withdrawn
Ipratropium bromideThe therapeutic efficacy of Ipratropium bromide can be decreased when used in combination with Physostigmine.Approved
IstaroximeThe risk or severity of adverse effects can be increased when Istaroxime is combined with Physostigmine.Investigational
LabetalolPhysostigmine may increase the bradycardic activities of Labetalol.Approved
LevobunololPhysostigmine may increase the bradycardic activities of Levobunolol.Approved
LobelineThe risk or severity of adverse effects can be increased when Physostigmine is combined with Lobeline.Investigational
ME-609The risk or severity of adverse effects can be increased when ME-609 is combined with Physostigmine.Investigational
MecamylamineThe therapeutic efficacy of Mecamylamine can be decreased when used in combination with Physostigmine.Approved
MedrysoneThe risk or severity of adverse effects can be increased when Medrysone is combined with Physostigmine.Approved
MelengestrolThe risk or severity of adverse effects can be increased when Melengestrol is combined with Physostigmine.Vet Approved
MethacholineThe risk or severity of adverse effects can be increased when Physostigmine is combined with Methacholine.Approved
MethanthelineThe therapeutic efficacy of Methantheline can be decreased when used in combination with Physostigmine.Approved
MethylprednisoloneThe risk or severity of adverse effects can be increased when Methylprednisolone is combined with Physostigmine.Approved, Vet Approved
MetipranololPhysostigmine may increase the bradycardic activities of Metipranolol.Approved
MetixeneThe therapeutic efficacy of Metixene can be decreased when used in combination with Physostigmine.Approved
MetoprololPhysostigmine may increase the bradycardic activities of Metoprolol.Approved, Investigational
MivacuriumPhysostigmine may decrease the neuromuscular blocking activities of Mivacurium.Approved
MometasoneThe risk or severity of adverse effects can be increased when Mometasone is combined with Physostigmine.Approved, Vet Approved
N-butylscopolammonium bromideThe therapeutic efficacy of N-butylscopolammonium bromide can be decreased when used in combination with Physostigmine.Vet Approved
NadololPhysostigmine may increase the bradycardic activities of Nadolol.Approved
NCX 1022The risk or severity of adverse effects can be increased when NCX 1022 is combined with Physostigmine.Investigational
NicotineThe risk or severity of adverse effects can be increased when Physostigmine is combined with Nicotine.Approved
Nicotine bitartrateThe risk or severity of adverse effects can be increased when Physostigmine is combined with Nicotine bitartrate.Approved
NVA237The therapeutic efficacy of NVA237 can be decreased when used in combination with Physostigmine.Investigational
Oleoyl estroneThe risk or severity of adverse effects can be increased when Oleoyl estrone is combined with Physostigmine.Investigational
OrphenadrineThe therapeutic efficacy of Orphenadrine can be decreased when used in combination with Physostigmine.Approved
OxprenololPhysostigmine may increase the bradycardic activities of Oxprenolol.Approved
OxybutyninThe therapeutic efficacy of Oxybutynin can be decreased when used in combination with Physostigmine.Approved, Investigational
OxyphenoniumThe therapeutic efficacy of Oxyphenonium can be decreased when used in combination with Physostigmine.Approved
PancuroniumThe therapeutic efficacy of Pancuronium can be decreased when used in combination with Physostigmine.Approved
ParamethasoneThe risk or severity of adverse effects can be increased when Paramethasone is combined with Physostigmine.Approved
PenbutololPhysostigmine may increase the bradycardic activities of Penbutolol.Approved, Investigational
PentoliniumThe therapeutic efficacy of Pentolinium can be decreased when used in combination with Physostigmine.Approved
PilocarpineThe risk or severity of adverse effects can be increased when Physostigmine is combined with Pilocarpine.Approved
PindololPhysostigmine may increase the bradycardic activities of Pindolol.Approved
PipecuroniumThe therapeutic efficacy of Pipecuronium can be decreased when used in combination with Physostigmine.Approved
PirenzepineThe therapeutic efficacy of Pirenzepine can be decreased when used in combination with Physostigmine.Approved
PractololPhysostigmine may increase the bradycardic activities of Practolol.Approved
PrasteroneThe risk or severity of adverse effects can be increased when Prasterone is combined with Physostigmine.Approved, Nutraceutical
PrednicarbateThe risk or severity of adverse effects can be increased when Prednicarbate is combined with Physostigmine.Approved
PrednisoloneThe risk or severity of adverse effects can be increased when Prednisolone is combined with Physostigmine.Approved, Vet Approved
PrednisoneThe risk or severity of adverse effects can be increased when Prednisone is combined with Physostigmine.Approved, Vet Approved
PregnenoloneThe risk or severity of adverse effects can be increased when Pregnenolone is combined with Physostigmine.Experimental
ProcyclidineThe therapeutic efficacy of Procyclidine can be decreased when used in combination with Physostigmine.Approved
PropanthelineThe therapeutic efficacy of Propantheline can be decreased when used in combination with Physostigmine.Approved
PropiverineThe therapeutic efficacy of Propiverine can be decreased when used in combination with Physostigmine.Investigational
PropranololPhysostigmine may increase the bradycardic activities of Propranolol.Approved, Investigational
QuinidineThe therapeutic efficacy of Quinidine can be decreased when used in combination with Physostigmine.Approved
RapacuroniumPhysostigmine may decrease the neuromuscular blocking activities of Rapacuronium.Withdrawn
RimexoloneThe risk or severity of adverse effects can be increased when Rimexolone is combined with Physostigmine.Approved
ScopolamineThe therapeutic efficacy of Scopolamine can be decreased when used in combination with Physostigmine.Approved
Scopolamine butylbromideThe therapeutic efficacy of Scopolamine butylbromide can be decreased when used in combination with Physostigmine.Approved
SolifenacinThe therapeutic efficacy of Solifenacin can be decreased when used in combination with Physostigmine.Approved
SotalolPhysostigmine may increase the bradycardic activities of Sotalol.Approved
SuccinylcholineThe serum concentration of Succinylcholine can be increased when it is combined with Physostigmine.Approved
TimololPhysostigmine may increase the bradycardic activities of Timolol.Approved
TiotropiumThe therapeutic efficacy of Tiotropium can be decreased when used in combination with Physostigmine.Approved
TixocortolThe risk or severity of adverse effects can be increased when Tixocortol is combined with Physostigmine.Approved
TolterodineThe therapeutic efficacy of Tolterodine can be decreased when used in combination with Physostigmine.Approved, Investigational
TriamcinoloneThe risk or severity of adverse effects can be increased when Triamcinolone is combined with Physostigmine.Approved, Vet Approved
TrihexyphenidylThe therapeutic efficacy of Trihexyphenidyl can be decreased when used in combination with Physostigmine.Approved
TrimethaphanThe therapeutic efficacy of Trimethaphan can be decreased when used in combination with Physostigmine.Approved
TropicamideThe therapeutic efficacy of Tropicamide can be decreased when used in combination with Physostigmine.Approved
TrospiumThe therapeutic efficacy of Trospium can be decreased when used in combination with Physostigmine.Approved
TubocurarineThe therapeutic efficacy of Tubocurarine can be decreased when used in combination with Physostigmine.Approved
UmeclidiniumThe therapeutic efficacy of Umeclidinium can be decreased when used in combination with Physostigmine.Approved
VareniclineThe risk or severity of adverse effects can be increased when Physostigmine is combined with Varenicline.Approved, Investigational
VecuroniumThe therapeutic efficacy of Vecuronium can be decreased when used in combination with Physostigmine.Approved
Food InteractionsNot Available
References
Synthesis Reference

Edward J. Glamkowski, Barbara E. Kurys, “4- and 6-carbamates related to physostigmine and intermediates for the preparation thereof.” U.S. Patent US5081117, issued September, 1978.

US5081117
General ReferencesNot Available
External Links
ATC CodesS01EB05V03AB19
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSDownload (73.3 KB)
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9975
Caco-2 permeable+0.5804
P-glycoprotein substrateSubstrate0.6631
P-glycoprotein inhibitor INon-inhibitor0.5442
P-glycoprotein inhibitor IINon-inhibitor0.8382
Renal organic cation transporterNon-inhibitor0.7046
CYP450 2C9 substrateNon-substrate0.7838
CYP450 2D6 substrateNon-substrate0.6455
CYP450 3A4 substrateSubstrate0.7321
CYP450 1A2 substrateNon-inhibitor0.9046
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorInhibitor0.8932
CYP450 2C19 inhibitorNon-inhibitor0.9026
CYP450 3A4 inhibitorNon-inhibitor0.8309
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8681
Ames testNon AMES toxic0.9133
CarcinogenicityNon-carcinogens0.9232
BiodegradationNot ready biodegradable0.8652
Rat acute toxicity4.7557 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9066
hERG inhibition (predictor II)Non-inhibitor0.8397
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
LiquidIntramuscular; Intravenous1 mg
InjectionIntravenous1 mg/mL
Prices
Unit descriptionCostUnit
Physostigmine salicyl cryst39.48USD g
Physostigmine 1 mg/ml ampul2.43USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point105.5 °CPhysProp
water solubility7760 mg/LNot Available
logP1.58HANSCH,C ET AL. (1995)
pKa6.12MERCK INDEX (1996)
Predicted Properties
PropertyValueSource
Water Solubility0.992 mg/mLALOGPS
logP1.8ALOGPS
logP2.23ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)14.77ChemAxon
pKa (Strongest Basic)6.59ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area44.81 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity78.4 m3·mol-1ChemAxon
Polarizability30.62 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Download (9.24 KB)
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as pyrroloindoles. These are compounds containing a pyrroloindole moiety, which is a tricyclic heterocycle which consists of a pyrrole ring fused to an indole. Pyrrole is 5-membered ring consisting of four carbon atoms and one nitrogen atom. Indole is a bicyclic compound consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassPyrroloindoles
Direct ParentPyrroloindoles
Alternative Parents
Substituents
  • Pyrroloindole
  • Indole
  • Dialkylarylamine
  • Benzenoid
  • N-alkylpyrrolidine
  • Pyrrolidine
  • Pyrrole
  • Tertiary aliphatic amine
  • Tertiary amine
  • Azacycle
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
inhibitor
General Function:
Serine hydrolase activity
Specific Function:
Terminates signal transduction at the neuromuscular junction by rapid hydrolysis of the acetylcholine released into the synaptic cleft. Role in neuronal apoptosis.
Gene Name:
ACHE
Uniprot ID:
P22303
Molecular Weight:
67795.525 Da
References
  1. Nguyen PV, Aniksztejn L, Catarsi S, Drapeau P: Maturation of neuromuscular transmission during early development in zebrafish. J Neurophysiol. 1999 Jun;81(6):2852-61. [PubMed:10368402 ]
  2. Tuovinen K, Kaliste-Korhonen E, Raushel FM, Hanninen O: Success of pyridostigmine, physostigmine, eptastigmine and phosphotriesterase treatments in acute sarin intoxication. Toxicology. 1999 Jun 15;134(2-3):169-78. [PubMed:10403635 ]
  3. Blasina MF, Faria AC, Gardino PF, Hokoc JN, Almeida OM, de Mello FG, Arruti C, Dajas F: Evidence for a noncholinergic function of acetylcholinesterase during development of chicken retina as shown by fasciculin. Cell Tissue Res. 2000 Feb;299(2):173-84. [PubMed:10741458 ]
  4. Monnet-Tschudi F, Zurich MG, Schilter B, Costa LG, Honegger P: Maturation-dependent effects of chlorpyrifos and parathion and their oxygen analogs on acetylcholinesterase and neuronal and glial markers in aggregating brain cell cultures. Toxicol Appl Pharmacol. 2000 Jun 15;165(3):175-83. [PubMed:10873710 ]
  5. Bolognesi ML, Andrisano V, Bartolini M, Minarini A, Rosini M, Tumiatti V, Melchiorre C: Hexahydrochromeno[4,3-b]pyrrole derivatives as acetylcholinesterase inhibitors. J Med Chem. 2001 Jan 4;44(1):105-9. [PubMed:11141093 ]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Comments
comments powered by Disqus
Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23