クロルメザノン

SOL (% WT/VOL) @ 25 °C: LESS THAN 0.25% IN WATER, LESS THAN 1.0% IN 95% ETHANOL

FREELY SOL IN CHLOROFORM; SLIGHTLY SOL IN DIETHYL ETHER; SPARINGLY SOL IN N-HEXANE

1.61e+00 g/L

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

Pharmaceuticals

116.2-118.6

116.2-118.2 °C

116.2 °C

154.1 Ų [M-H]- [CCS Type: DT; Buffer gas: N2; Ionization: ESI-; Dataset: TOXCAST; Source Identifier: DTXSID3022798]

156.85 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

158.2 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

Warning

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 4 reports by companies from 2 notifications to the ECHA C&L Inventory.

CHLORMEZANONE MAY LOWER TOLERANCE OF PATIENTS TO ALCOHOL...POSSIBLE ADDITIVE EFFECTS /WITH CHLORMEZANONE &/ CNS DEPRESSANTS SUCH AS ALCOHOL, PHENOTHIAZINES, BARBITURATES, NARCOTICS, OTHER PSYCHOTHERAPEUTIC AGENTS, & MONOAMINE OXIDASE INHIBITORS.

Chlormezanone binds to central benzodiazepine receptors which interact allosterically with GABA receptors. This potentiates the effects of the inhibitory neurotransmitter GABA, increasing the inhibition of the ascending reticular activating system and blocking the cortical and limbic arousal that occurs following stimulation of the reticular pathways.

...COMMONLY PRODUCE DROWSINESS, DIZZINESS, HEADACHE, BLURRED VISION, WEAKNESS, LETHARGY, ATAXIA, & NYSTAGMUS. NAUSEA, VOMITING, HEARTBURN, & ABDOMINAL DISTRESS...ESP AFTER LARGE ORAL DOES. ...SKIN RASH & PRURITUS &, RARELY, ANAPHYLACTOID REACTIONS & LEUKOPENIA. /CENTRALLY ACTING MUSCLE RELAXANTS/

INCIDENCE OF UNTOWARD REACTIONS IS ABOUT 3% & MINOR IN NATURE...MALAISE, EXCITEMENT... PETECHIAE, OR ECCHYMOSES SOMETIMES DEVELOP; LIVER DAMAGE...OR ANGIONEUROTIC EDEMA ARE RARE.

LETHARGY & FLUSHING HAVE BEEN OBSERVED & JAUNDICE HAS OCCURRED RARELY.

...ORAL TOXICITY LESS THAN MEPROBAMATE, ZOXAZOLAMINE, OR METHOCARBAMOL. ... IN CLINICAL TRIALS ONLY 2.3% OF 4653 PT HAS SIDE EFFECTS... OVERDOSAGE UP TO 10 G HAS NOT CAUSED DEATH. EVEN LARGE AMT PRODUCE ONLY MILD SIDE EFFECTS.

Drug Induced Liver Injury Rank (DILIrank 2.0)

Chlormezanone

vMost-DILI-concern

8

Withdrawn

DOI:10.1016/j.drudis.2016.02.015

M - Musculo-skeletal system

QM - Musculo-skeletal system

Chlormezanone binds to central benzodiazepine receptors which interact allosterically with GABA receptors. This potentiates the effects of the inhibitory neurotransmitter GABA, increasing the inhibition of the ascending reticular activating system and blocking the cortical and limbic arousal that occurs following stimulation of the reticular pathways.

NEURONAL CONDUCTION, NEUROMUSCULAR TRANSMISSION, & MUSCLE EXCITABILITY ARE NOT DEPRESSED EXCEPT AFTER NEARLY LETHAL DOSES. PROMINENT EFFECT...IS TO DEPRESS SPINAL POLYSYNAPTIC REFLEXES PREFERENTIALLY OVER MONOSYNAPTIC REFLEXES. /CENTRALLY ACTING MUSCLE RELAXANTS/

IN ABSENCE OF DEFINITIVE STUDIES IT APPEARS REASONABLE TO ASCRIBE BENEFICIAL EFFECTS...TO THEIR SEDATIVE PROPERTIES. /CENTRALLY ACTING MUSCLE RELAXANTS/

CHLORMEZANONE...IS EXCRETED UNCHANGED IN HUMAN URINE & DOG BILE. FORMATION OF 4-CHLOROHIPPURIC ACID, MAJOR URINARY METABOLITE IN MAN, INVOLVES NON-ENZYMIC HYDROLYSIS, FOLLOWED BY OXIDATION & CONJUGATION OF 4-CHLOROBENZALDEHYDE PRODUCT OF HYDROLYSIS.

(14)C-CHLORMEZANONE, METABOLITES IN URINE OF RATS & MICE WERE P-CHLOROBENZOIC ACID, P-CHLOROHIPPURIC ACID, N-METHYL-P-CHLOROBENZAMIDE, 2-[N-METHYL-N-(P-CHLOROBENZOYL)]CARBAMOYLETHYLSULFONIC ACID, 3-SULFOPROPIONIC ACID & GLUCURONIDE OF P-CHLOROBENZOIC ACID.

A heterogeneous group of drugs used to produce muscle relaxation, excepting the neuromuscular blocking agents. They have their primary clinical and therapeutic uses in the treatment of muscle spasm and immobility associated with strains, sprains, and injuries of the back and, to a lesser degree, injuries to the neck. They have been used also for the treatment of a variety of clinical conditions that have in common only the presence of skeletal muscle hyperactivity, for example, the muscle spasms that can occur in MULTIPLE SCLEROSIS. (From Smith and Reynard, Textbook of Pharmacology, 1991, p358)

Agents that alleviate ANXIETY, tension, and ANXIETY DISORDERS, promote sedation, and have a calming effect without affecting clarity of consciousness or neurologic conditions. ADRENERGIC BETA-ANTAGONISTS are commonly used in the symptomatic treatment of anxiety but are not included here.

RAPIDLY ABSORBED FROM GI TRACT...EFFECT WITHIN 15 TO 30 MIN...DURATION OF ACTION OF 4 TO 6 HR...FREE DRUG & /4-CHLOROHIPPURIC ACID/ EXCRETED IN URINE /HUMAN, ORAL/...PRESENT IN HIGH CONCN IN KIDNEY, LIVER, MUSCLE, HEART, & BODY FAT, & IN LESSER CONCN IN LUNG & PLASMA /RATS, ORAL/.

AFTER ORAL ADMIN OF (14)C-CHLORMEZANONE, ABOUT 74% OF DOSE WAS EXCRETED INTO URINE OF RATS WITHIN 24 HR & 21% INTO URINE OF MICE WITHIN 2 HR. BILIARY EXCRETION OF RADIOACTIVITY WAS ABOUT 10% OF DOSE IN RATS.

MEDICATION

Used in the management of anxiety and in the treatment of muscle spasm.