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Inhibitor Report for: Physostigmine~Eserine

Carbamate alkaloid purified from the calabar bean: Physostigma venenosum. Physostigmine is a 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.


General
Type Derivative of physostigmine-eserine, Natural, Carbamate, Drug
Chemical_Nomenclature 1'methylpyrrolidino (2':3':2:3) 1,3-dimethylindolin-%-yl N-methylcarbamate
Canonical SMILES CC12CCN(C1N(C3=C2C=C(C=C3)OC(=O)NC)C)C CC12CC[NH+](C1[NH+](C3=C2C=C(C=C3)OC(=O)NC)C)C.C1=CC=C(C(=C1)C(=O)[O-])[O-] CC12CC[NH+](C1N(C3=C2C=C(C=C3)OC(=O)NC)C)C.CC12CC[NH+](C1N(C3=C2C=C(C=C3)OC(=O)NC)C)C.[O-]S(=O)(=O)[O-] CC12CCN(C1N(C3=C2C=C(C=C3)OC(=O)NC)C)C.Br CC12CN(CC1N(C3=C2C=C(C=C3)OC(=O)NC)C)C
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) 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 InChI=1S/C15H21N3O2.C7H6O3/c1-15-7-8-17(3)13(15)18(4)12-6-5-10(9-11(12)15)20-14(19)16-2;8-6-4-2-1-3-5(6)7(9)10/h5-6,9,13H,7-8H2,1-4H3,(H,16,19);1-4,8H,(H,9,10)/t13-,15+;/m1./s1 InChI=1S/2C15H21N3O2.H2O4S/c2*1-15-7-8-17(3)13(15)18(4)12-6-5-10(9-11(12)15)20-14(19)16-2;1-5(2,3)4/h2*5-6,9,13H,7-8H2,1-4H3,(H,16,19);(H2,1,2,3,4)/t2*13-,15+;/m11./s1 InChI=1S/C15H21N3O2.BrH/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);1H/t13-,15+;/m1./s1 InChI=1S/C15H21N3O2/c1-15-9-17(3)8-13(15)18(4)12-6-5-10(7-11(12)15)20-14(19)16-2/h5-7,13H,8-9H2,1-4H3,(H,16,19)/t13-,15-/m0/s1
InChIKey PIJVFDBKTWXHHD-UHFFFAOYSA-N PIJVFDBKTWXHHD-HIFRSBDPSA-N HZOTZTANVBDFOF-PBCQUBLHSA-N YYBNDIVPHIWTPK-KYJQVDHRSA-N HFIWKRLOGGSAQX-PBCQUBLHSA-N WCXQPZYRWMPGRA-ZFWWWQNUSA-N
Other name(s) Physostigmine ; Antilirium ; Esromiotin ; Physostol ; Ezerin ; Calabarine ; Erserine ; Cogmine Erserine ; Eserine sulfate ; Eserine sulphate ; Physostigmine SO4 ; Physostigmine sulphate ; Physostigmine hemisulfate ; Physostigmine hydrobromide ; Physostigmine monohydrobromide ; Isopto Eserine ; Eserine salicylate ; Isopto P-ES ; Physostol salicylate ; Physostigmine salicylate ; Physostigmine monosalicylate ; CCRIS 3405 ; Physostigmine, salicylate (1:1) ; EINECS 228-032-2 ; 6091-13-0 ; Physotol ; Anticholium ; Eserine ; E-serine
________________________________________________________________________________________________
MW|275.34
Formula|C15H21N3O2
CAS_number|57-47-6
PubChem|5983, 6150, 656508, 4811, 5992, 111151
UniChem|PIJVFDBKTWXHHD-UHFFFAOYSA-N, PIJVFDBKTWXHHD-HIFRSBDPSA-N, HZOTZTANVBDFOF-PBCQUBLHSA-N, YYBNDIVPHIWTPK-KYJQVDHRSA-N, HFIWKRLOGGSAQX-PBCQUBLHSA-N, WCXQPZYRWMPGRA-ZFWWWQNUSA-N
IUPHAR|6598
Wikipedia|Physostigmine

Target
Families | Physostigmine~Eserine ligand of proteins in family: ACHE, BCHE, Arylacetamide_deacetylase

References:
Search PubMed for references concerning: Physostigmine~Eserine

86 more
    Title: Genetic variants of human serum cholinesterase influence metabolism of the muscle relaxant succinylcholine.
    Lockridge O
    Ref: Pharmacol Ther, 47:35, 1990 : PubMed

            

    Title: Treatment of myasthenia gravis with physostigmine
    Walker MB
    Ref: Lancet, 1:1200, 1934 : PubMed

            

    Title: Physostigmine (eserine). Part III
    Stedman E, Banger G
    Ref: J Chem Soc, 127:247, 1925 : PubMed

            


human-BCHE
MutationKiKsiIc50SubstrateConditionPaper
D70G - - 270 nM   Lockridge_1990_Pharmacol.Ther_47_35
WT - - 14 nM   Lockridge_1990_Pharmacol.Ther_47_35

WT Kinetics
Kinetic parametersKiKsiIc50SubstrateConditionsPapers
human-BCHE--14 nM  Lockridge_1990_Pharmacol.Ther_47_35