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HCID 2200Erstellt: 4. November 2026

Antazolin

Orosulfan · 5512-M · Avissul · Azalone · Antastan · Antasten · Antistin · Antazolin

https://huagongshe.com/de/chemical/2200

Molekülstruktur von Antazolin

Identifikatoren & physikalische Daten

CAS No.91-75-8
SummenformelC17H19N3
Durchschnittliche Molmasse265,35 g/mol
Monoisotopische Masse265,15789762 g/mol
SMILESc1ccc(CN(CC2=NCCN2)c2ccccc2)cc1
InChIKeyREYFJDPCWQRWAA-UHFFFAOYSA-N
PubChem CID2200
ChEMBLCHEMBL1305
ChEBICHEBI:84115
EC No.202-094-0
DTXSIDDTXSID3022613
Lokaler NameAntazolin

Chemische & physikalische Eigenschaften

XLogP2,6
Polarare Oberfläche (TPSA)27,6
H-Brücken-Donoren1
H-Brücken-Akzeptoren2
Frei drehbare Bindungen5
Schwere Atome20
Formalladung0
Komplexität314
ArzneimittelPharmaceuticals -> Listed in ZINC15
GeruchOdorless
GeschmackBitter
Color/FormWhite, crystalline powder
LöslichkeitMol wt 301.82. Bitter crystals producing temporary numbness of the tongue. mp 237-241 °C. UV max: 242 nm (E 1% 1cm = 495 to 515)min 222 nm. One gram dissolves in 40 ml water, in 25 ml alc. Practically insol in ether, benzene, chloroform. pH (1% aq soln): 6.3. /Hydrochloride/Crystals. Bitter taste. mp 194-198 °C. Sol in water. Sparingly sol in methanol. Practically insol in benzene, ether. pH (2% aq soln): 4.5. /Phosphate/Sparingly soluble in alcoholpractically insoluble in benzene and etherIn water, 6.63X10+2 mg/L at 30 °C663.4mg/L(30 ºC)
Human DrugsPharmaceuticals
DecompositionWhen heated to decomposition it emits toxic fumes of /nitrogen oxides/.
Schmelzpunkt227-229120-122 °C120-122°
Physical DescriptionSolid
Collision Cross Section163.51 Ų [M+Na]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards]
Siedepunkt398.57°C (rough estimate)
Dichte0.9786 (rough estimate)
Brechungsindex1.6080 (estimate)
pKa (Säurekonstante)pKa 6.65(H2O t = 25 I = 0.05) (Uncertain)
AggregatzustandA solid
FarbeWhite to off-white
CAS Datenbank91-75-8(CAS DataBase Reference)
NIST chemische InformationenAntazoline(91-75-8)

Sicherheit & Vorschriften

GHS-EinstufungWarningH302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 40 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Regulatorische Informationen1H-Imidazole-2-methanamine, 4,5-dihydro-N-phenyl-N-(phenylmethyl)-: Does not have an individual approval but may be used under an appropriate group standard
FDA-AnforderungenThe Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed over-the-counter drug products, incl antazoline, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act.
Hazard Classes and CategoriesAcute Tox. 4 (100%)
EntsorgungsverfahrenSRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
WechselwirkungenThe purpose of this study was to investigate the effects of antazoline and ketotifen (two H1 receptor antagonists) on the anticonvulsant activity of antiepileptic drugs against maximal electroshock (MES)-induced convulsions in mice. The following antiepileptic drugs were used: valproate, carbamazepine, diphenylhydantoin and phenobarbital. In addition, the effects of antiepileptic drugs alone or in combination with antazoline or ketotifen were studied on long-term memory (tested in the passive avoidance task) and motor performance (evaluated in the chimney test), acutely and after 7-day treatment with these H1 receptor antagonists. The influence of antazoline and ketotifen on the free plasma and brain levels of the antiepileptics was also evaluated. Antazoline (at 0.5 mg/kg), given acutely and after 7-day treatment, significantly diminished the electroconvulsive threshold. Similarly, ketotifen, after acute and chronic doses of 8 mg/kg markedly reduced the threshold for electroconvulsions. In both cases, antazoline and ketotifen were without effect upon this parameter at lower doses. Antazoline (0.25 mg/kg) significantly raised the ED50 value of carbamazepine against MES (both, acutely and after 7-day treatment). Furthermore antazoline (0.25 mg/kg) also reduced the anticonvulsant activity of diphenylhydantoin, but only after repeated administration, without modifying the brain and free plasma level of this drug. Moreover, valproate and phenobarbital did not change their protective activity when combined with antazoline. ... Only acute antazoline (0.25 mg/kg) applied with valproate impaired the performance of mice evaluated in the chimney test. Ketotifen (4 mg/kg) co-administered with conventional antiepileptic drugs impaired motor coordination in mice treated with valproate, phenobarbital or diphenylhydantoin. Acute and chronic antazoline (0.25 mg/kg) alone or in combination with antiepileptic drugs did not disturb long-term memory, tested in the passive avoidance task. ... The results of this study indicate that H1 receptor antagonists, crossing the blood brain barrier, should be used with caution in epileptic patients. This is because antazoline reduced the protective potential of diphenylhydantoin and carbamazepine.

Anwendungen & Verwendung

Verwenden

Antihistaminic.

Imidazoline drugs exert neuroprotective effects in cerebral ischaemia models. They also have effects against mouse cerebellar and striatal neuronal death induced by N-methyl-D-aspartate (NMDA) through the blockade of NMDA currents. Here, we investigated the effects of antazoline on NMDA toxicity and current in rat hippocampal neuronal cultures, and on an in vivo model of status epilepticus. In hippocampal cultures, antazoline (30 uM) decreased NMDA-mediated neurotoxicity and also blocked the NMDA current with voltage-dependent and fast-reversible action (inhibition by 85+ or - 3% at -60 mV). Status epilepticus was induced by injecting pilocarpine (200 nmol) directly into the right pyriform cortex of male adult rats. The rats then received immediately three consecutive i.p. injections at 30-min intervals of either PBS (control group) or antazoline at 10 mg/kg (low-dose group) or at 45 mg/kg (high-dose group). During the 6-hr recording, status epilepticus lasted more than 200 min in all groups. In the high-dose group only, seizures completely ceased 1 hr after the third injection of antazoline, then started again 1 hr later. Rats were killed 1 week later, and Cresyl Violet-stained sections of their brain were analysed for damage quantification. On the ipsilateral side to the pilocarpine injection, pyriform cortex and hippocampal CA1 and CA3 areas were significantly protected in both antazoline-treated groups, whilst prepyriform and entorhinal cortices were only in the high-dose group. On the contralateral side to the pilocarpine injection, only the hippocampal CA3 area was significantly protected in the low-dose group, but all investigated structures were in the high-dose group.In conclusion, antazoline is a potent neuroprotective drug in different models of neuronal primary culture, as previously shown in striatal and cerebellar granule neurons, and here in hippocampal neurons. Antazoline is also neuroprotective in vivo in the intra-pyriform pilocarpine-induced status epilepticus model.
Human Toxicity Excerpts/SIGNS AND SYMPTOMS/ In human eyes 0.75% solution between pH 5 and pH 8 was about the maximum suitable for clinical use. Oral administration of 400 mg antazoline hydrochloride per day for five days to patients with normal eyes caused no change in intraocular pressure or tonographic measurements. /Antazoline hydrochloride//SIGNS AND SYMPTOMS/ Allergic thrombocytopenic purpura and agranulocytosis have been reported. Transient dizziness and anorexia have followed the intravenous administration of antazoline, and cardiac arrest has occurred./SIGNS AND SYMPTOMS/ A report of interstitial pneumonitis, with fever, rash, and dyspnea, after antazolinethe condition recurred after challenge./CASE REPORTS/ Antazoline (Antistina) induced thrombocytopenic purpura occurring on three occasions in a 21 year old woman is reported. After withdrawal of the drug therapy the patient recovered promptly. In vitro investigation demonstrated the presence of an antibody in serum, which in association with antazoline caused complement fixation when added to test platelets. Also platelet agglutinins could be detected in the patient's serum when antazoline was added. The reactions were drug specific and they could still be demonstrated 9 months after the last exposure to the drug.For more Human Toxicity Excerpts (Complete) data for ANTAZOLINE (6 total), please visit the HSDB record page.
Non-Human Toxicity Excerpts/LABORATORY ANIMALS: Acute Exposure/ On rabbit eyes 1.5% solution of antazoline hydrochloride was the maximum concentraton that could be applied without causing keratitis epithelialis. /Antazoline hydrochloride//LABORATORY ANIMALS: Acute Exposure/ Mepyramine (Pyrilamine) and antazoline applied as 2.5% solutions to eyes of rabbits have caused rapid clouding the corneal epithelium, local anesthesia and transitory swelling of the cornea, with recovery in a few days. For a series of anthistaminics, concentrations which might be considered maximum suitable for topical ophthalmic use range from 0.5% to 1%./ALTERNATIVE and IN VITRO TESTS/ Imidazolines exert neuroprotection against hypoxia and NMDA toxicity in cerebellar and striatal neuronal cultures, through a voltage-dependent blockade of glutamatergic NMDA receptors. In striatal neuronal cultures from mouse embryos the imidazoline compound, antazoline, inhibits voltage-gated Ca2+ channels by acting at a phencyclidine-like site. This effect was fast, fully reversible, voltage-dependent and predominant on P/Q- and N-type Ca2+ channels. Taken together, these results suggest that imidazolines may elicit neuroprotective effects also by decreasing the release of glutamate through inhibition of presynaptic Ca2+ channels./OTHER TOXICITY INFORMATION/ In unanesthetized cats micturition produced by thyrotropin releasing hormone was investigated after its injection into the cerebral ventricles through chronically implanted cannulae. Thyrotropin releasing hormone in doses from 0.1 to 1.0 mg evoked dose-dependent micturition. In cats treated with intracerebroventricular reserpine and 6-hydroxydopamine, but not with intracerebroventricular 5,6-dihydroxytryptamine and hemicholinium, the micturition caused by intracerebroventricular thyrotropin releasing hormone was abolished. Chlorpromazine and antazoline injected into the cerebral ventricles prevented the micturition induced by intracerebroventricular thyrotropin releasing hormone. On the other hand, mecamylamine, yohimbine, propranolol, atropine and methysergide injected intracerebroventricular had virtually no effect or partially antagonized the micturition evoked by thyrotropin releasing hormone similarly injected. It is apparent therefore that centrally induced thyrotropin releasing hormone micturition could be related to central catecholaminergic mechanisms./OTHER TOXICITY INFORMATION/ The effects were investigated of intracerebroventricular injections in the cat of ganglionic blocking agents, antimuscarinic drugs, alpha and beta adrenergic blocking substances, dopamine antagonists, an antihistamine, reserpine and a 5-hydroxytryptamine antagonist as well as the inhibitors of catecholamines, 5-hydroxytryptamine and acetylcholine synthesis upon convulsions produced by nicotine, which was similarly injected. Mecamylamine and hexamethonium but not atropine, scopolamine, yohimbine, phenoxybenzamine, tolazoline, propranolol, practolol, chlorpromazine, haloperidol, antazoline and methysergide abolished the convulsions evoked by nicotine. Furthermore, reserpine, but not 6-hydroxydopamine, as well as 5,6-dihydroxytryptamine and hemicholinium blocked the convulsions caused by nicotine. It appears, therefore, that the convulsions produced by nicotine are mediated through central nicotinic receptors. However, the depressed catecholaminergic, 5-hydroxytryptaminergic and histaminergic mechanisms induced by reserpine can also suppress the convulsions evoked by nicotine.
Populations at Special RiskParadoxic stimulation may occasionally occur, especially at high doses and in children or the elderly. The sedative effects may diminish after a few days of therapeutic use. /Antihistamines/Antazoline was reported to be a hemolytic agent in subjects deficient in glucose-6-phosphate dehydrogenase but only in conjunction with other factors such as infection.
Antidote and Emergency TreatmentMost patients require only symptomatic and supportive care. Treatment is focused on controlling agitation, maintaining airway, reversing hyperthermia, and supporting hemodynamic function. Gastrointestinal decontamination is not essential, but if not more than 1 hours has elapsed since ingestion of the drug, activated charcoal may be considered. In view of the potential cardiac toxicity in addition to maintenance of the airway, breathing, and circulatory status of the patients, observation for dysrhythmia is warranted. Clinical assessment for signs that may indicated impending seizure activity (hypertonicity, hyperreflexia, or myoclonic jerking) is important. ... /Antihistamines/Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poisons A and B/Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/
Non-Human Toxicity ValuesLD50 Mouse 398 mg/kgLD50 Mouse ip 100 mg/kgLD50 Mouse sc 135 mg/kg
ToxizitätLD50 oral in mouse: 398mg/kg
Gefahrstoffdaten91-75-8(Hazardous Substances Data)