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臭化デメカリウム

Demecarium Bromide

HCID 5965
ノート反応
基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
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基本情報

CAS
56-94-0
標準SMILES
CN(CCCCCCCCCCN(C)C(=O)Oc1cccc([N+](C)(C)C)c1)C(=O)Oc1cccc([N+](C)(C)C)c1.[Br-].[Br-]
InChIKey
YHKBUDZECQDYBR-UHFFFAOYSA-L
分子式
C32H52Br2N4O4
平均分子量
716.6 g/mol
単同位体質量
714.23553

概要

Demecarium bromide is the methobromide salt of the N,N'-bis[3-(dimethylamino)phenyl carbamate] derivative of 2,13-diazatetradecane. It is an inhibitor of acetylcholinesterase and pseudocholinesterase, with a long duration of action. It is used in the treatment of chronic open-angle glaucoma: in the eye, it causes constriction of the iris sphincter muscle and the ciliary muscle, facilitating the outflow of the aqueous humor and so reducing intraocular pressure. It has a role as an EC 3.1.1.8 (cholinesterase) inhibitor and an EC 3.1.1.7 (acetylcholinesterase) inhibitor. It is a bromide salt, a carbamate ester and a quaternary ammonium salt. It contains a demarcarium.

名称と識別子

優先名称
Demecarium Bromide
IUPAC
trimethyl-[3-[methyl-[10-[methyl-[3-(trimethylazaniumyl)phenoxy]carbonylamino]decyl]carbamoyl]oxyphenyl]azanium dibromide
現地名
臭化デメカリウム
英語名
Demecarium bromide
分子式
C32H52Br2N4O4
分子量
716.59

名称と別名

DEMECARIUM BROMIDE56-94-0HumorsolFrumtosnilVisumioticTonilenTosmicilTosmileneVisumaticBromuro de demecarioBromure de demecariumDemekastigmine bromide
名称をさらに表示
デメカリウムジブロミドトスミシルフモルソール3,3'-[1,10-デカンジイルビス[(メチルイミノ)カルボニルオキシ]]ビス[N,N,N-トリメチルベンゼンアミニウム]3,3'-[(1,10-デカンジイル)ビス[(メチルイミノ)カルボニルオキシ]]ビス[N,N,N-トリメチルベンゼンアミニウム]デメカリウムブロミドビスマチックビスミオチックデメカスチグミンブロミドトニレン臭化デメカリウムデメカリウム3,3'-[(1,10-デカンジイル)ビス[(メチルイミノ)カルボニルオキシ]]ビス[N,N,N-トリメチルベンゼンアミニウム]·ジブロミドトスミレンフルムトスニル3,3′-[1,10-デカンジイルビス[(メチルイミノ)カルボニルオキシ]]ビス[N,N,N-トリメチルベンゼンアミニウム]3,3′-[(1,10-デカンジイル)ビス[(メチルイミノ)カルボニルオキシ]]ビス[N,N,N-トリメチルベンゼンアミニウム]・ジブロミドN,N,N-トリメチル-3-{[メチル({10-[メチル({[3-(トリメチルアザニウミル)フェノキシ]カルボニル})アミノ]デシル})カルバモイル]オキシ}アニリニウム3,3′-[(1,10-デカンジイル)ビス[(メチルイミノ)カルボニルオキシ]]ビス[N,N,N-トリメチルベンゼンアミニウム]Demecarium2brbc48e)(2:1)tosmilen
Demecarii bromidumDemekarium bromideBC 4861D5V4OKTPN,N'-Bis(3-trimethylammoniumphenoxycarbonyl)-N,N'-dimethyldecamethylenediamine dibromideBC-48(m-Hydroxyphenyl)trimethylammonium bromide decamethylenebis(methylcarbamate)(m-Hydroxyphenyl)trimethylammonium bromide decamethylenebis(methylcarbamate) (2:1)

データベース識別子

CAS
56-94-0
PubChem CID
5965
ChEMBL
CHEMBL1200514
ChEBI
CHEBI:4391
UNII
61D5V4OKTP
EC Number
200-301-9

物性

構造計算による物性

極性表面積
59.1 Ų
水素結合供与体数
0
水素結合受容体数
6
回転可能結合数
17
重原子数
42
形式電荷
0
複雑度
686

実験および物理化学的性質

pHAQ SOLN ARE NEUTRAL
Color/Form · 2 件

WHITE POWDER

SLIGHTLY YELLOW, CRYSTALLINE POWDER

SolubilityFREELY SOL IN WATER, ALCOHOL; SPARINGLY SOL IN ACETONE; INSOL IN ETHER
Human Drugs · 2 件

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

Stability/Shelf Life · 2 件

AQ SOLN ARE STABLE

STABLE TO AUTOCLAVING, & RETAIN THEIR POTENCY FOR PROLONGED PERIODS

Other Experimental Properties · 3 件

DECOMP @ 162-167 °C

CONSISTS OF 2 NEOSTIGMINE MOLECULES CONNECTED @ CARBAMATE NITROGEN ATOMS BY SERIES OF 10 METHYLENE GROUPS /DEMECARIUM/

SLIGHTLY HYGROSCOPIC

物理化学的性質

融点
162 · 162-167 °C (decomp)
貯蔵温度
-20 °C · Store at -20°C
溶解性
160 · DMSO:160.0(Max Conc. mg/mL);223.28(Max Conc. mM)
外見
Solid
色
White
主な用途
医薬品(低分子化合物)
InChIKey
YHKBUDZECQDYBR-UHFFFAOYSA-L
SMILES
C1(=CC=CC([N+](C)(C)C)=C1)OC(=O)N(C)CCCCCCCCCCN(C)C(=O)OC1=CC=CC([N+](C)(C)C)=C1.[Br-].[Br-]
CAS データベース
56 · 56-94-0(CAS DataBase Reference)

化学的性質

化学的特性White Solid

安全と法規制

安全情報は参考情報です。供給元の安全データシート(SDS)、適用法令、専門家による評価に代わるものではありません。

GHS分類

GHS Classification · 4 件

Danger

H300 (100%): Fatal if swallowed [Danger Acute toxicity, oral]

P264, P270, P301+P316, P321, P330, P405, and P501 (click each P-code to see the statement)

The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

危険有害性情報

Hazard Classes and CategoriesAcute Tox. 2 (100%)

毒性情報

Interactions...INHIBITION PRODUCED BY DEMECARIUM IS "REVERSIBLE". LOCAL EFFECTS OF DRUG CAN BE ANTAGONIZED BY ATROPINE AS WELL AS BY PRALIDOXIME (PROTOPAM). EFFECTS OF DEMECARIUM ARE NOT INHIBITED BY PRIOR INSTILLATION OF PHYSOSTIGMINE. /DEMECARIUM/
Human Toxicity Excerpts · 5 件

IN SOME PT, DEMECARIUM MAY PRODUCE CONTACT DERMATITIS. IRIS CYSTS HAVE BEEN REPORTED, PARTICULARLY IN CHILDREN, FOLLOWING PROLONGED USE... /DEMECARIUM/

SIDE EFFECTS OF DEMECARIUM...MAY INCL CILIARY OR ACCOMODATIVE SPASM, BLURRED VISION, OCULAR OR BROW PAIN, HEADACHE, PHOTOPHOBIA, & TWITCHING OF EYELIDS. RARELY, RETINAL DETACHMENT MAY RESULT FROM SEVERE CILIARY SPASM. CONGESTIVE IRITIS, IRIDOCYCLITIS, & CONJUNCTIVAL & INTRAOCULAR HYPEREMIA MAY...OCCUR. /DEMECARIUM/

SYSTEMIC EFFECTS ARE MANIFESTATIONS OF PARASYMPATHETIC STIMULATION & MAY INCL NAUSEA, VOMITING, ABDOMINAL PAIN, DIARRHEA, FREQUENT URINATION, EXCESSIVE SALIVATION & SWEATING, FLUSHING, BRONCHIAL CONSTRICTION, HYPOTENSION, & BRADYCARDIA. ...INGESTION...WILL PRODUCE SIMILAR...EFFECTS &...CONVULSIONS, SHOCK & COLLAPSE.

IT HAS NOW BEEN ESTABLISHED THAT TREATMENT OF GLAUCOMA WITH POTENT, LONG-ACTING ANTI-CHOLINESTERASE AGENTS (INCL DEMECARIUM...) FOR 6 MO OR LONGER CARRIES HIGH RISK OF DEVELOPMENT OF SPECIFIC TYPE OF CATARACT, DESCRIBED AS ANTERIOR SUBCAPSULAR VACUOLES... INCIDENCE OF LENTICULAR OPACITIES...AS HIGH AS 50%... /DEMECARIUM/

For more Human Toxicity Excerpts (Complete) data for DEMECARIUM BROMIDE (6 total), please visit the HSDB record page.

Drug Induced Liver Injury · 4 件

Drug-Induced Liver Injury Severity and Toxicity (DILIst)

demecarium bromide

DILI Positive

DOI:10.1016/j.drudis.2019.09.022

Non-Human Toxicity Excerpts · 2 件

SYSTEMIC ABSORPTION FROM NOSE CAN OCCUR, CAUSING TREMORS & COLLAPSE.

NEUROACTIVE COMPD & VERTEBRAL TERATOGENESIS IN BIRD EMBRYO. QUAIL EMBRYOS EXPOSED TO DEMECARIUM BROMIDE (1.5 MG) SHOWED VERTEBRAL FUSIONS & NECK DEFORMITIES AFTER 3 DAYS. MECHANISM OF TERATOGENESIS IS DISCUSSED.

Antidote and Emergency Treatment · 3 件

...SYSTEMIC TOXICITY, ATROPINE SULFATE OR PRALIDOXIME CHLORIDE, ADMIN SC OR IV, IS EFFECTIVE ANTIDOTE. ADMIN OF SHORT-ACTING BARBITURATE MAY ALSO BE NECESSARY & ARTIFICIAL RESPIRATION MAY BE REQUIRED TO MAINTAIN ADEQUATE VENTILATION.

MARKED INCR IN INTRAOCULAR PRESSURE MAY BE OVERCOME BY LOCAL INSTILLATION OF EPINEPHRINE IF NECESSARY. ... SEVERE HYPEREMIA MAY BE RELIEVED BY LOCAL INSTILLATION OF 1 OR 2% EPINEPHRINE.

APPEARANCE OF.../IRIS CYSTS/ HAS BEEN ATTRIBUTED TO FREQUENCY OF ADMIN & THEY HAVE DISAPPEARED UPON WITHDRAWAL OF DRUG. PT SHOULD BE EXAMINED REGULARLY FOR APPEARANCE OF IRIS CYSTS & THERAPY SHOULD BE DISCONTINUED, AT LEAST TEMPORARILY, IF THEY OCCUR.

安全データ

wgk
WGK 3
hs_code
2924296000
Hazard Classifications
Acute Tox. 2 Oral
ストレージクラス
6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials
有毒物質データの
56-94-0(Hazardous Substances Data)

化学と産業

薬理情報

Mechanism of Action · 2 件

/INCR FACILITY OF AQ OUTFLOW/...ACCOMPANIED BY VASODILATATION OF CONJUNCTIVAL VESSELS & INCR PERMEABILITY OF BLOOD-AQ BARRIER. INDIRECT DECR IN ACTIVITY OF EXTRAOCULAR MUSCLES OF CONVERGENCE ALSO OCCURS. ...CHOLINESTERASE INHIBITION PRODUCED BY DEMECARIUM IS "REVERSIBLE".

DEMECARIUM BROMIDE...IS A QUATERNARY AMMONIUM ANTICHOLINESTERASE DRUG. ... RESULTING ACCUM OF ACETYLCHOLINE PRODUCES MIOSIS & STIMULATES CILIARY MUSCLE...REDUCING INTRAOCULAR PRESSURE BY INCR FACILITY OF AQ OUTFLOW.

MeSH Pharmacological Classification · 1 件

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.

Absorption, Distribution and ExcretionDEMECARIUM IS ABSORBED THROUGH CONJUNCTIVAL SAC AS WELL AS THROUGH INTACT SKIN... /DEMECARIUM/

用途と製造

Uses · 2 件

MEDICATION

MEDICATION (VET)

Methods of Manufacturing · 2 件

N,N'-DIMETHYL-1,10-DECAMETHYLENEDIAMINE IS ADDED TO MOLTEN 3-(DIMETHYLAMINO)PHENYL CARBONATE TO PRODUCE 1,10-DE CAMETHYLENEBIS[3-(DIMETHYL-AMINO)PHENYL N-METHYLCARBAMATE]. AFTER PURIFICATION THIS ESTER...A VISCOUS OIL, IS DISSOLVED IN ETHANOL & DOUBLY QUATERNIZED WITH AID OF AN ACETONE SOLN OF METHYL BROMIDE.

SCHMID, US PATENT 2,789,981 (1957 TO OESTERREICHISCHE STICKSTOFFWERKE).

Formulations/PreparationsDEMECARIUM BROMIDE: HUMORSOL (MERCK SHARP & DOHME). TOPICAL: AQ SOLN (OPHTHALMIC, STERILE) 0.125% & 0.25% WITH SODIUM CHLORIDE & BENZALKONIUM CHLORIDE IN 5 ML CONTAINERS.
応用分野 · 3 件

使用Demecarium is a disymmetrical compound that contains two ammonium and two carbamate groups. It is a reversible cholinesterase inhibitor that is longer lasting than the others. It is used to constrict pupils, elevate intraocular pressure in treating glaucoma, and also for alleviating atropine mydriasis.

使用Demecarium Bromide is an acetylcholinesterase inhibitor and veterinary medicine used to treat elevated intraocular pressure associated with primary glaucoma.

一般的な説明Demecarium bromide,(m-hydroxyphenyl)trimethylammonium bromide, decamethylenebis[methylcarbamate] (Humorsol), is the diester of(m-hydroxyphenyl)trimethylammonium bromide with decamethylene-bis-(methylcarbamic acid) and thus is comparableto a bis-prostigmine molecule.It occurs as a slightly hygroscopic powder that is freelysoluble in water or alcohol. Ophthalmic solutions of the drughave a pH of 5 to 7.5. Aqueous solutions are stable and maybe sterilized by heat. Its efficacy and toxicity are comparableto those of other potent anticholinesterase inhibitor drugs. Itis a long-acting miotic used to treat wide-angle glaucomaand accommodative esotropia. Maximal effect occurs hoursafter administration, and the effect may persist for days.

上流・下流製品情報

上流原料

ブロモメタン3-(ジメチルアミノ)フェノール塩化カルボニルナトリウム

サプライヤー57 社

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補足説明 · 1 件

定義ChEBI: The methobromide salt of the N,N'-bis[3-(dimethylamino)phenyl carbamate] derivative of 2,13-diazatetradecane. It is an inhibitor of acetylcholinesterase and pseudocholinesterase, with a long duration of action. It is u ed in the treatment of chronic open-angle glaucoma: in the eye, it causes constriction of the iris sphincter muscle and the ciliary muscle, facilitating the outflow of the aqueous humor and so reducing intraocular pressure.

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