130-26-7 Hazards Identification
Signal:
Danger
GHS Hazard Statements:
H301 (41.1%): Toxic if swallowed [Danger Acute toxicity, oral]
H315 (68.49%): Causes skin irritation [Warning Skin corrosion/irritation]
H319 (68.49%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
H335 (100%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]
H361fd (11.64%): Suspected of damaging fertility; Suspected of damaging the unborn child [Warning Reproductive toxicity]
H372 (11.64%): Causes damage to organs through prolonged or repeated exposure [Danger Specific target organ toxicity, repeated exposure]
H400 (54.79%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]
Precautionary Statement Codes:
P203, P260, P261, P264, P264+P265, P270, P271, P273, P280, P301+P316, P302+P352, P304+P340, P305+P351+P338, P318, P319, P321, P330, P332+P317, P337+P317, P362+P364, P391, P403+P233, P405, and P501
Hazard Classes and Categories:
Acute Tox. 3 (41.1%)
Skin Irrit. 2 (68.49%)
Eye Irrit. 2 (68.49%)
STOT SE 3 (100%)
Repr. 2 (11.64%)
STOT RE 1 (11.64%)
Aquatic Acute 1 (54.79%)
Hazards Summary:
Allergic contact dermatitis reported in patients using this antibiotic topically; [Marks, p. 123-4] An epidemic of subacute myelo-optico-neuropathy occurred in Japan from 1956 until 1970. Approximately 10,000 cases were reported with visual impairment, lower extremity paresthesias and weakness, and other symptoms. Symptoms resolved after the oral medication was discontinued. Neurotoxicity developed in patients who received total doses greater that 750 mg/day for four weeks. [HSDB]
130-26-7 Usage
Chemical Properties
Almost white, light yellow, brownish-yellow or yellowish-grey powder.
Originator
Clioquinol,CIBA-GEIGY Corp.
Uses
Different sources of media describe the Uses of 130-26-7 differently. You can refer to the following data:
1. Clioquinol is used as an anti-infective agent; antiamoebic agent; intravaginal trichomonacide; used to impregnate cotton bandages for antibacterial purposes; in animals as an intestinal anti-infective agent.
2. alpha adrenergic blocker, mydriatic, antidepressant
3. Used as a topical antifungal treatment
Definition
ChEBI: A monohydroxyquinoline that is quinolin-8-ol in which the hydrogens at positions 5 and 7 are replaced by chlorine and iodine, respectively. It has antibacterial and atifungal properties, and is used in creams for the treatment of skin infections. It has al
o been investigated as a chelator of copper and zinc ions for the possible treatment of Alzheimer's disease.
Indications
Iodochlorhydroxyquin (Clioquinol), containing 40% iodine, was originally developed
as a substitute for iodoform as an antiseptic dusting powder. Although its
most effective use is in the treatment of amebiasis, it also has mild antibacterial
and antifungal effects and may be used alone or with steroids in the treatment
of eczematous and impetiginized processes and some dermatophyte, yeast, and
Trichomonas infections. However, more specific agents are available. Because of
neurotoxicity, the oral form of this drug has been withdrawn in the United States.
A recent study demonstrating significant percutaneous absorption when applied to
intact human skin raises concern regarding its topical use as well. The medication
may stain the skin, hair, and clothing yellow and may induce contact allergy.
Manufacturing Process
Chlor-5-oxy-8-chinoline (18 kg) was mixed with potassium hydroxide (6.0 kg),
water (400 kg) and heated. To this solution 50 L saturated aqueous solution of
potassium iodide (16.6 kg) was added, mixed and continued to heat. Solution
was filtered at room temperature. Then to this yellow solution the solution of
chloride of lime and 50 kg 5% solution of were added then all this was mixed
and allowed to stand for 24 h.
After eliminating of free iodine by addition of sodium thiosulfate the obtained
precipitate was washed with water. To residue 1% solution of acidum
hydrochloricum (50.0 kg) and rapidly was heated to 50°C. Then it was washed
with water and dried, so 5-chloro-7-iodo-quinolinol-8 was obtained, melting
point 170°-175°C.
Brand name
Domeform-HC (Bayer); Quin-O-Creme
(Marion Merrell Dow); Rheaform Boluses [Veterinary]
(Fort Dodge Animal Health); Vioform (Ciba-Geigy);Amebio-formo;Anterobe;Aristoform "d";Aristoform "r";Barquinol hc;Betnorate-c;Britaderm;Britadex-vioform;Carboform;Cloro-yodo-hidroxi;Clorpine;Combias;Copover;Cortex;Corti-glottyl;Dependal;Dermo-quinol;Dermozolan;Dexalocal;Diaban;Dioderm c-c;Diodotracin;Dizenterol;Enteral;Ente-rivo;Enterokin;Enterosan;Entero-valodon;Entero-vioformo;Enterquinol;Entox;Entrasorb;Entrokinol;Fusalor-yodocloro;Fyloxxal;Gmd;Guanosept;Haelan-c;Hocacorten-vioform;Hydroform;Iodo-cortifair;Iodocortindon;Iodo-max;Isoderm;Khlorlinkotsin;Klinicin;Lecortin;Lederform-d;Lemoderm;Linola;Locorten-vioform;Metrijet;Metrityl;Mexafermento;Mexafom;Nasello;Nefurox;Obstecrim;Pedi-cort;Percural;Phen-ortis;Pricort cream;Propaderm-c;Quadriderm;Quin iii;Quina band;Quiniodochlor;Reticus;Sebryl;Sedacol;Septo-canulase;Silic c;Tequinophil;Toptic;Torofor;Unidiarea;Uteroject;Ventribex;Viform;Vioform bolus;Vioform hydrocortisan;Vioform hydrocortisone;Vioforme.
Therapeutic Function
Antibacterial
World Health Organization (WHO)
Clioquinol, a halogenated hydroxyquinoline derivative, was
introduced into medicine around 1900 as a topical antiseptic and in 1934 oral
preparations for the treatment of amoebic dysentery and simple diarrhoea became
available. By 1964 its use in Japan had been associated with cases of sub-acute
myelo-optic neuropathy (SMON) which reached epidemic proportions resulting in
its withdrawal there in 1970. Although relatively few cases of SMON were
documented elsewhere, clioquinol was subsequently withdrawn from use in many
countries and placed under prescription control in others. It was phased out
worldwide by the major manufacturer between 1983 and 1985 on grounds of
obsolescence. No adequately controlled evidence was ever generated to
demonstrate that clioquinol is effective in bacterial or viral diarrhoea. However,
products containing clioquinol and related halogenated hydroxyquinolines
continue to be used in some tropical and subtropical countries where amoebiasis
remains endemic. Other amoebocides are preferred in the WHO Model List of
Essential Drugs.
(Reference: (WHODI) WHO Drug Information, 77.1, 9, 1977)
General Description
Cream-colored to brownish-yellow powder. Practically odorless. Decomposes at 178-179°C. Used as a topical anti-infective.
Air & Water Reactions
Insoluble in water.
Reactivity Profile
Clioquinol is incompatible with strong oxidizing agents, strong acids, acid chlorides and acid anhydrides . Darkens on exposure to light.
Fire Hazard
Flash point data for Clioquinol are not available; however, Clioquinol is probably combustible.
Flammability and Explosibility
Nonflammable
Clinical Use
5-Chloro-7-iodo-8-quinolinol, 5-chloro8-hydroxy-7-iodoquinoline, or iodochlorhydroxyquin (Vioform) occursas a spongy, light-sensitive, yellowish white powder that isinsoluble in water. Vioform was initially used as a substitutefor iodoform in the belief that it released iodine in the tissues.It has been used as a powder for many skin conditions,such as atopic dermatitis, eczema, psoriasis, and impetigo.A 3% ointment or cream has been used vaginally as a treatmentfor Trichomonas vaginalis vaginitis. The best use forVioform is in the topical treatment of fungal infections suchas athlete’s foot and jock itch. A combination with hydrocortisone(Vioform HC) is also available.
Safety Profile
Poison by ingestion.
Moderately toxic by intraperitoneal route.
Human systemic effects by ingestion:
change in central nervous system electrical
function, optic nerve damage, and changes
in vision. Experimental teratogenic and
reproductive effects. Human mutation data
reported. When heated to decomposition it
emits very toxic fumes of Cl-, I-, and NOx.
Purification Methods
It crystallises from AcOH or xylene and dry it at 70o in vacuo.[Beilstein 21 III/IV 1190.]
Check Digit Verification of cas no
The CAS Registry Mumber 130-26-7 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,3 and 0 respectively; the second part has 2 digits, 2 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 130-26:
(5*1)+(4*3)+(3*0)+(2*2)+(1*6)=27
27 % 10 = 7
So 130-26-7 is a valid CAS Registry Number.
InChI:InChI=1/C10H6ClIO/c11-8-5-9(12)10(13)7-4-2-1-3-6(7)8/h1-5,13H
130-26-7Relevant academic research and scientific papers
One-pot method for preparing chloroquine chloroquine and diiodoquinoline
-
, (2021/08/25)
The method effectively solves the problems of (1) solving the problem of high isomer ratio in reaction products due to the fact that hydroxyl groups are ortho-alignment positioning groups when no guide groups are first C5 halogenated and C7 iodo, and purification difficulty is also increased. (2) The problems of poor atom economy, harsh reaction conditions, tedious aftertreatment steps and the like in first 66% steps C5 C7 C7 are effectively overcome by the method provided by the invention, and the C5-position halogenated product is 60% effectively overcome by overcoming the defects of poor atom economy, harsh reaction conditions, complicated post-treatment steps and the like in the two methods. The method has the advantages of economy of atoms, simplicity in operation, easiness in amplification and the like.
A general method for the metal-free, regioselective, remote C-H halogenation of 8-substituted quinolines
Motati, Damoder Reddy,Uredi, Dilipkumar,Watkins, E. Blake
, p. 1782 - 1788 (2018/02/23)
An operationally simple and metal-free protocol for geometrically inaccessible C5-H halogenation of a range of 8-substituted quinoline derivatives has been established. The reaction proceeds under air, with inexpensive and atom economical trihaloisocyanuric acid as a halogen source (only 0.36 equiv.), at room temperature. Exceptionally high generality with respect to quinoline is observed, and in most instances, the reaction proceeded with complete regioselectivity. Quinoline with a variety of substituents at the 8-position gave, exclusively, the C5-halogenated product in good to excellent yields. Phosphoramidates, tertiary amides, N-alkyl/N,N-dialkyl, and urea derivatives of quinolin-8-amine as well as alkoxy quinolines were halogenated at the C5-position via remote functionalization for the first time. This methodology provides a highly economical route to halogenated quinolines with excellent functional group tolerance, thus providing a good complement to existing remote functionalization methods of quinolin-8-amide derivatives and broadening the field of remote functionalization. The utility of the method is further showcased through the synthesis of several compounds of biological and pharmaceutical interest.
NOVEL RECYCLABLE IODINATING AGENT AND ITS APPLICATIONS
-
Page/Page column 19-20, (2016/11/07)
The present invention provides a novel recyclable catalysts of formula A, [Formula A should be inserted here] wherein X is selected from the group consisting of [Formula should be inserted here] The present invention also provides a novel recyclable iodinating agent of formula I, II or III and a process for the synthesis thereof. [ Formula I, II & III should be inserted here] Further, the present invention provides a process of halogenation of amines and heterocyclic compounds by employing recyclable catalyst of formula (I).
Glycosylated copper(ii) ionophores as prodrugs for β-glucosidase activation in targeted cancer therapy
Oliveri, Valentina,Viale, Maurizio,Caron, Giulia,Aiello, Cinzia,Gangemi, Rosaria,Vecchio, Graziella
, p. 2023 - 2034 (2013/03/14)
8-Hydroxyquinoline derivatives are metal-binding compounds that have recently attracted interest as therapeutic agents for cancer therapy. In this scenario, we designed and synthesized three new glucoconjugates, 5,7-dichloro-8-quinolinyl-β-d-glucopyranoside, 5-chloro-8-quinolinyl- β-d-glucopyranoside and 2-methyl-8-quinolinyl-β-d-glucopyranoside and investigated their biological properties in comparison to the parent 8-hydroxyquinoline derivatives in the presence of Cu2+. In vitro data show that 2 out of 3 glycosylated compounds possess a pharmacologically- relevant antiproliferative activity against tumor cells, similar to that of their parent compounds; this activity is associated with a relevant triggering of apoptosis. The pharmacological profile of the glucoconjugates depends on the cellular enzymatic β-glucosidase activity, as demonstrated by the inhibition of antiproliferative activity in the presence of the 2,5-dideoxy-2,5-imino-d-mannitol. The Royal Society of Chemistry 2013.
Aza-and polyaza-naphthalenly ketones useful as hiv integrase inhibitors
-
Page/Page column 45, (2010/02/10)
Certain aza- and polyaza-naphthalenyl ketones including certain quinolinyl and naphthyridinyl ketones are described as inhibitors of HIV integrase and inhibitors of HIV replication. These compounds are useful in the prevention or treatment of infection by HIV and the treatment or the delay in the onset of AIDS, as compounds or pharmaceutically acceptable salts, or as ingredients in pharmaceutical compositions, optionally in combination with other antivirals, immunomodulators, antibiotics or vaccines. Methods of treating or delaying the onset of AIDS and methods of preventing or treating infection by HIV are also described.
Nonreductive deiodination of ortho-iodo-hydroxylated arenes using tertiary amines
Talekar, Rahul Subhash,Chen, Grace Shiahuy,Lai, Shin-Yu,Chern, Ji-Wang
, p. 8590 - 8593 (2007/10/03)
A convenient and nonreductive deiodination is reported for the ortho-iodo-hydroxylated arenes inch ding derivatives of quinolinol, phenol, and naphthol. Tertiary amines pyridine, triethylamine, and N-methylmorpholine in the presence of water initiated deiodination of ortho-iodo-hydroxylated arenes without affecting para-iodine and other reduction-susceptible groups. This reported method also works efficiently for polyiodinated systems. Simplicity, short reaction times, and absence of reducing catalyst are features of this method.
Metronidazole twin ester prodrugs II: Non identical twin esters of metronidazole and some antiprotozoal halogenated hydroxyquinoline derivatives
Aboul-Fadl, Tarek,Mahfouz, Nadia M.
, p. 309 - 324 (2007/10/03)
New non identical twin ester prodrugs 3a-d were synthesized by linking metronidazole and some antiprotozoal halogented 8-hydroxyquinoline derivatives via dicarboxylic acid spacers with the aim of improving the therapeutic efficacy of both drugs. The synthesis necessitates the preparation of the precursor metronidazole hemisuccinate or hemiphthalate followed by estrification with the respective hydroxyquinoline derivative. To assess their suitability as prodrugs, the lipophilic properties, chemical stability as well as in vitro and in vivo enzymatic hydrolysis were investigated. The lipophilic properties, expressed as Rm values were determined using RP-TLC and showing enhanced lipophilicity as compared with the parent drugs. Hydrolysis kinetics of the prepared twin esters at 37°C using HPLC, indicated a quantitative release of the parent drugs in two step reaction (K1 and K2) via formation of metronidazole hemiesters followed by spontaneous hydrolysis of the later to metronidazole. The twin esters were adequately stable in aqueous buffer solutions than in biological media and the second rate (K2) of hydrolysis is more accelerated than the first (K1). Bioavailability study of 1-(5-chloro-7-iodoquinolin-8-yl)-4-[2-(2-methyl-5- nitro-1-H-imidazolyl)ethyl]butandioate, 3a, as well as equivalent amount of the corresponding physical mixture of metronidazole and 5-chloro 7-iodo-8- hydroxyquinoline in rabbits has shown that, the plasma level of the released metronidazole from the prodrug is higher than that resulting from the physical combination. A considerable amount of 5-chloro-7-iodo- hydroxyquinoline was detected in plasma, however, no measurable concentration of the quinoline derivative was observed in rabbit plasma from the physical mixture.
3-Imino-1,2,4-benzotriazine-1-oxides
-
, (2008/06/13)
New 3-Imino-1,2,4-benzotriazine-1-oxides of formula I SPC1 wherein R represents an alkyl, alkenyl or haloalkyl radical, a phenyl or aralkyl radical optionally substituted by alkyl, alkoxy, haloalkyl, halogen or hydroxy, X and Y each independently represent hydrogen, halogen, an alkyl or alkoxy radical, or one of the two symbols represents a phenoxy or phenylsulphonyl radical optionally substituted by halogen, alkyl, haloalkyl and/or alkoxy which are active against harmful microorganisms are disclosed.
