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HCID 5071Erstellt: 27. Oktober 2026

Rimantadine

RIMANTADINE · LEVOFLOXACIN HCL · 1-Adamantanemethylamine · RiMantidine · RiMantadine (FluMadine) · Levofloxacine Hydrochloride · 1-Adaman · AKOS B022266

https://huagongshe.com/de/chemical/5071

Molekülstruktur von Rimantadine

Identifikatoren & physikalische Daten

CAS No.117857-51-9
SummenformelC12H21N
Durchschnittliche Molmasse179,3 g/mol
Monoisotopische Masse179,16739967 g/mol
SMILESCC(N)C12CC3CC(CC(C3)C1)C2
InChIKeyUBCHPRBFMUDMNC-UHFFFAOYSA-N
PubChem CID5071
ChEMBLCHEMBL1201272
ChEBICHEBI:94440
DTXSIDDTXSID2023561

Chemische & physikalische Eigenschaften

XLogP2,6
Polarare Oberfläche (TPSA)26
H-Brücken-Donoren1
H-Brücken-Akzeptoren1
Frei drehbare Bindungen1
Schwere Atome13
Formalladung0
Komplexität180
LogP (Verteilungskoeffizient)3.6
LöslichkeitHydrochloride salt freely soluble (50 mg/ml at 20 °C)9.15e-03 g/LSoluble in DMSO
Human DrugsBreast FeedingLactationAntiviral AgentsNucleic Acid Synthesis Inhibitors
Schmelzpunkt>300 °C> 300 °C
Physical DescriptionSolid
Collision Cross Section145.1 Ų [M+H]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards]
Other Experimental PropertiesWhite to off-white crystalline powder. MP: 373-375 °CSolubility in water, 50 mg/L at 20 °C. /Hydrochloride/
Siedepunkt248°C
Dichte1.033
Flammpunkt99°C
LagerbedingungenStore at -20°C
AggregatzustandLiquid
pKa (Säurekonstante)11.17±0.29(Predicted)
FarbeColorless to light yellow
InChIInChI=1/C12H21N.ClH/c1-8(13)12-5-9-2-10(6-12)4-11(3-9)7-12/h8-11H,2-7,13H2,1H31H/t8,9-,10+,11-,12-
InChIKeyOZBDFBJXRJWNAV-MZHJCFSPNA-N
SMILES[C@]12(C[C@]3([H])C[C@@]([H])(C[C@@]([H])(C3)C1)C2)C(N)C.Cl |&1:0,2,5,8,r|
CAS Datenbank13392-28-4(CAS DataBase Reference)
NIST chemische Informationen1-Adamantanemethylamine, «alpha»-methyl-(13392-28-4)

Sicherheit & Vorschriften

FDA-AnforderungenThe Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl rimantadine, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act.
LagerbedingungenCommercially available rimantadine hydrochloride tablets and oral solution should be stored in tight, light-resistant containers at 15-30 °C.
EntsorgungsverfahrenSRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air qualitypotential migration in soil or watereffects on animal, aquatic, and plant lifeand conformance with environmental and public health regulations.
WechselwirkungenConcurrent use of a single dose of rimantadine with cimetidine reduces rimantadine clearance by 18% in healthy adultsthe clinical significance si thought to be minimal at this time.Because influenza antiviral agents reduce replication of influenza viruses, do not administer influenza virus vaccine live intranasal until at least 48 hours after rimantadine is discontinued and do not administer rimantadine until at least 2 weeks after administration of influenza virus vaccine live intranasal. CimetidineConcurrent use of acetaminophen or aspirin with rimantadine reduces the peak serum concentration of rimantadine by approximately 11%the clinical significance is thought to be minimal at this time.
HepatotoxicityDespite widespread use, there is little evidence that rimantadine when given orally causes liver injury, either in the form of serum enzyme elevations or clinically apparent liver disease.
Milk ConcentrationsIt is not known whether rimantadine is distributed into breast milk. However, it is distributed into the milk of rats. Rimantadine concentrations in the milk of rats were twice those found in serum 2 to 3 hours after administration.
Drug Induced Liver InjuryDrug-Induced Liver Injury Severity and Toxicity (DILIst)

Anwendungen & Verwendung

Verwenden

Rimantadine act by blocking the M2 ion channel which is required for uptake of protons into the interior of the virus to permit acid-promoted viral uncoating (decapsidation).

rimantadine
DILI Negative
Oral
DOI:10.1016/j.drudis.2019.09.022
Non-Human Toxicity Excerpts/LABORATORY ANIMALS: Developmental or Reproductive Toxicity/ A study in male and female rats given doses of up to 60 mg/kg of body weight per day showed no impairment of fertility./LABORATORY ANIMALS: Developmental or Reproductive Toxicity/ It has been shown to be embryotoxic in rats when given at a dose of 200 mg/kg/day, and has caused fetal resorption. Maternal toxicity included ataxia, tremors, seizures, and significantly reduced weight gain./LABORATORY ANIMALS: Developmental or Reproductive Toxicity/ Rimantadine was not embryotoxic when given to rabbits in doses of up to 50 mg/kg/day. However, there was evidence of a change in the ratio of fetuses with 12 ribs to fetuses with 13 ribsnormally the ratio is 50:50 in a litter, but the ratio was 80:20 after rimantadine treatment./LABORATORY ANIMALS: Developmental or Reproductive Toxicity/ Rimantadine hydrochloride has been reported to be embryotoxic (ie, increased fetal resorption) in rats when administered in a dosage of 200 mg/kg dailythis dose also was associated with several maternal effects including ataxia, tremor, seizures, and substantially reduced weight gain. While developmental abnormality (i.e., change in the ratio of 12 or 13 ribs) was observed in rabbits given rimantadine hydrochloride dosages of 50 mg/kg daily, embryotoxicity was not observed.For more Non-Human Toxicity Excerpts (Complete) data for RIMANTADINE (6 total), please visit the HSDB record page.
Populations at Special RiskWhile the effect of rimantadine therapy on the incidence of seizures in patients with seizure disorders has not been fully evaluated, patients with active seizure disorders appear to be at risk of increased frequency of seizures during amantadine therapy. Therefore, rimantadine-treated patients with a history of epilepsy or other seizures should be observed closely for possible seizure activity.
Environmental Water ConcentrationsWhile data specific to rimantadine were not located(SRC, 2006), the literature suggests that some pharmaceutically active compounds originating from human and veterinary therapy are not eliminated completely in municipal sewage treatment plants and are therefore discharged into receiving waters(1). Wastewater treatment processes often were not designed to remove them from the effluent(2). Selected organic waste compounds may be degrading to new and more persistent compounds that may be released instead of or in addition to the parent compound(2). Studies have indicated that several polar pharmaceutically active compounds can leach through subsoils into aquifers(1).
Antidote and Emergency TreatmentAs with any overdose, supportive therapy should be administered as indicated. Overdoses of a related drug, amantadine, have been reported with adverse reactions consisting of agitation, hallucinations, cardiac arrhythmia and death. The administration of intravenous physostigmine (a cholinergic agent) ... repeated as needed ... has been reported anecdotally to be beneficial in patients with central nervous system effects from overdoses of amantadine.
Effects During Pregnancy and Lactation◉ Summary of Use during Lactation
Zollcode2902190000
GefahrenklasseIRRITANT
Gefahrstoffdaten13392-28-4(Hazardous Substances Data)