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Benzenaminium, 3,3'-(1,10-decanediylbis((methylimino)carbonyloxy))bis(N,N,N-trimethyl-

HCID 5966
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Grundinformationen

CAS
16505-84-3
Standard-SMILES
CN(CCCCCCCCCCN(C)C(=O)Oc1cccc([N+](C)(C)C)c1)C(=O)Oc1cccc([N+](C)(C)C)c1
InChIKey
RWZVPVOZTJJMNU-UHFFFAOYSA-N
Summenformel
C32H52N4O4+2
Durchschnittliche Molmasse
556,8 g/mol
Monoisotopische Masse
556,39885615

Überblick

Demarcarium is the bis(quaternary ammonium) dication obtained by N,N'-dimethylation of the N,N'-bis[3-(dimethylamino)phenyl carbamate] derivative of 2,13-diazatetradecane. It is a carbamate ester and a quaternary ammonium ion.

Namen und Bezeichner

Bevorzugter Name
Benzenaminium, 3,3'-(1,10-decanediylbis((methylimino)carbonyloxy))bis(N,N,N-trimethyl-
IUPAC
trimethyl-[3-[methyl-[10-[methyl-[3-(trimethylazaniumyl)phenoxy]carbonylamino]decyl]carbamoyl]oxyphenyl]azanium
Englischer Name
demarcarium
Summenformel
C32H52N4O4
Molmasse
556.77968

Namen und Synonyme

DemecariumDemecarium ionDemecarium cation16505-84-3ILP8XJ8R5KBenzenaminium, 3,3'-(1,10-decanediylbis((methylimino)carbonyloxy))bis(N,N,N-trimethyl-DTXSID2046965(m-Hydroxyphenyl)trimethylammonium decamethylenebis(methylcarbamate)N,N'-Bis(3-trimethylammoniumphenoxycarbonyl(-N,N'-dimethyldecamethylenediamine3,3'-(1,10-Decanediylbis((methylimino)carbonyloxy))bis(N,N,N-trimethylbenzenaminium)Benzenaminium, 3,3'-[1,10-decanediylbis[(methylimino)carbonyloxy]]bis[N,N,N-trimethyl-N,N,N-trimethyl-3-((methyl(10-(methyl(3-(trimethylazaniumyl)phenoxycarbonyl)amino)decyl)carbamoyl)oxy)anilinium
Weitere Namen anzeigen
demarcariumDemecarium Free Basetrimethyl-[3-[methyl-[10-[methyl-[3-(trimethylazaniumyl)phenoxy]carbonylamino]decyl]carbamoyl]oxyphenyl]azanium
N,N,N-trimethyl-3-{[methyl(10-{methyl[3-(trimethylazaniumyl)phenoxycarbonyl]amino}decyl)carbamoyl]oxy}aniliniumRefChem:57372DTXCID5014745263,3'-(1,10-decanediylbis((methylimino)carbonyloxy))bis(N,N,N-trimethylbenzenaminium)-Benzenaminium, 3,3'-(1,10-Decanediylbis((Methylimino)Carbonyloxy))Bis(N,N,N-Trimethyl)-N,N'-Bis(3-Trimethylammoniumphenoxycarbonyl)-N,N'-DimethyldecamethylenediamineDemecarium [VANDF]Demecarium [WHO-DD]

Eigenschaften

Berechnete Struktureigenschaften

XLogP
6,6
Polarare Oberfläche (TPSA)
59,1 Ų
H-Brücken-Donoren
0
H-Brücken-Akzeptoren
4
Frei drehbare Bindungen
17
Schwere Atome
40
Formalladung
2
Komplexität
686

Experimentelle und physikochemische Eigenschaften

DrugsPharmaceuticals -> Listed in ZINC15
LogP-1.75
Solubility1.69e-05 g/L
Melting Point164-170
Physical DescriptionSolid

Chemie und Industrie

Pharmakologische Informationen

ATC Code · 2 Einträge

S - Sensory organs

QS - Sensory organs

Pharmacodynamics · 1 Eintrag

Demecarium is a long-acting cholinesterase inhibitor and potent miotic. Because of its toxicity, it should be reserved for use in patients with open-angle glaucoma or other chronic glaucomas not satisfactorily controlled with the short-acting miotics and other agents. Application of demecarium to the eye produces intense miosis and ciliary muscle contraction due to inhibition of cholinesterase, allowing acetylcholine to accumulate at sites of cholinergic transmission. These effects are accompanied by increased capillary permeability of the ciliary body and iris, increased permeability of the blood-aqueous barrier, and vasodilation. Myopia may be induced or, if present, may be augmented by the increased refractive power of the lens that results from the accommodative effect of the drug.

Mechanism of Action · 1 Eintrag

Demecarium is an indirect-acting parasympathomimetic agent, also known as a cholinesterase inhibitor and anticholinesterase. Cholinesterase inhibitors prolong the effect of acetylcholine, which is released at the neuroeffector junction of parasympathetic postganglion nerves, by inactivating the cholinesterases that break it down. Demecarium inactivates both pseudocholinesterase and acetylcholinesterase. In the eye, this causes constriction of the iris sphincter muscle (causing miosis) and the ciliary muscle (affecting the accommodation reflex and causing a spasm of the focus to near vision). The outflow of the aqueous humor is facilitated, which leads to a reduction in intraocular pressure. Of the two actions, the effect on the accommodation reflex is the more transient and generally disappears before termination of the miosis.

MeSH Pharmacological Classification · 1 Eintrag

Drugs that inhibit cholinesterases. The neurotransmitter ACETYLCHOLINE is rapidly hydrolyzed, and thereby inactivated, by cholinesterases. When cholinesterases are inhibited, the action of endogenously released acetylcholine at cholinergic synapses is potentiated. Cholinesterase inhibitors are widely used clinically for their potentiation of cholinergic inputs to the gastrointestinal tract and urinary bladder, the eye, and skeletal muscles; they are also used for their effects on the heart and the central nervous system.

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Datenbank-Bezeichner

CAS
16505-84-3、56-94-0
PubChem CID
5966
DTXSID
DTXSID2046965
ChEMBL
CHEMBL1201229
ChEBI
CHEBI:59719
UNII
ILP8XJ8R5K
Nikkaji
J82.023G
Cellular LocationsCytoplasm

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