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클로르족사존

Chlorzoxazone

HCID 2733
노트반응
기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
부분 구조 검색유사 구조 찾기

기본 정보

CAS
95-25-0
표준 SMILES
O=c1[nH]c2cc(Cl)ccc2o1
InChIKey
TZFWDZFKRBELIQ-UHFFFAOYSA-N
분자식
C7H4ClNO2
평균 분자량
169.56 g/mol
단동위원소 질량
168.9930561

개요

Chlorzoxazone is a member of the class of 1,3-benzoxazoles that is 1,3-benzoxazol-2-ol in which the hydrogen atom at position 5 is substituted by chlorine. A centrally acting muscle relaxant with sedative properties, it is used for the symptomatic treatment of painful muscle spasm. It has a role as a sedative and a muscle relaxant. It is an organochlorine compound, a member of 1,3-benzoxazoles and a heteroaryl hydroxy compound.

이름 및 식별자

우선 이름
Chlorzoxazone
IUPAC
5-chloro-3H-1,3-benzoxazol-2-one
현지명
클로르족사존
영어명
Chlorzoxazone
분자식
C7H4ClNO2
분자량
169.57

이름 및 동의어

chlorzoxazone95-25-0Paraflex5-Chloro-2(3H)-benzoxazolone5-Chloro-2-benzoxazolone2(3H)-Benzoxazolone, 5-chloro-5-Chloro-2-benzoxazolinone5-ChlorobenzoxazolidoneParafon Forte DSC5-chloro-3H-1,3-benzoxazol-2-one5-Chloro-2-benzoxazolol5-Chloro-2-hydroxybenzoxazole
이름 더 보기
클로르족사존Chloroxazone5-CHLOROBENZO[D]OXAZOL-2(3H)-ONEChlorzoxazonCHLOROZOXAZONEMioranorzoxazoneCLORZOXAZONEChlorzoxazone-13C,15N,D2
ChlorzoxaneParafonStrifon Forte Dsc2-Hydroxy-5-chlorobenzoxazoleChlorzoxazonumClorzoxazonaStrifon5-chlorobenzoxazolin-2-one

데이터베이스 식별자

CAS
95-25-0
PubChem CID
2733
DTXSID
DTXSID9022813
ChEMBL
CHEMBL1371

물성

구조 계산 물성

XLogP
1.8
극성 표면적
38.3 Ų
수소 결합 공여자 수
1
수소 결합 수용자 수
2
회전 가능 결합 수
0
무거운 원자 수
11
형식 전하
0
복잡도
185

실험 및 물리화학적 성질

DrugsPharmaceuticals -> Listed in ZINC15
LogP · 2건

1.6

2.11

Solubility · 2건

2.96e+00 g/L

>25.4 [ug/mL] (The mean of the results at pH 7.4)

Human Drugs · 3건

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

Pharmaceuticals

Melting Point · 2건

191-191.5

191.5 °C

Physical DescriptionSolid
Collision Cross Section126.64 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

물리화학적 성질

녹는점
191 · 191-192 °C (lit.)
밀도
1.3771 · 1.3771 (rough estimate)
굴절률
1.5557 · 1.5557 (estimate)
저장 조건
room temp

안전 및 규제

안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.

GHS 분류

GHS Classification · 4건

Warning

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

P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, 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 54 reports by companies from 11 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

유해성 정보

Other Safety InformationIMAP assessments - 2(3H)-Benzoxazolone, 5-chloro-: Human health tier I assessment
Hazard Classes and CategoriesAcute Tox. 4 (100%)

독성 정보

Hepatotoxicity · 1건

There have been no adequate prospective studies demonstrating the rates ofALT or AST elevations on chlorzoxazone therapy. Rare instances of clinicalapparent liver disease due to chlorzoxazone have appeared, including fatalcases. While case reports have been few, in many instances chlorzoxazone wasclearly implicated; furthermore, a related muscle relaxant with similarstructure (zoxazolamine) was withdrawn from use in 1961, largely because ofhepatotoxicity. The usual latency period to onset of liver injury is 1 to 4weeks, and the pattern of disease is typically hepatocellular with markedelevations in ALT levels and jaundice, but minimal increases in alkalinephosphatase. Cholestatic enzyme elevations after exposure to chlorzoxazonehave also been described. Allergic manifestations (rash and fever) arecommon, particularly in cases with a short latency (Case 1); autoantibodiesare rare. Recovery is rapid once chlorzoxazone is stopped, but fatal caseshave been reported, with disease progression despite early discontinuationof the agent (Case 2). There is rapid recurrence of injury with reexposure,often accompanied by fever.

화학 및 산업

약리 정보

ATC Code · 2건

M - Musculo-skeletal system

QM - Musculo-skeletal system

Protein Binding13-18%
Pharmacodynamics · 1건

Chlorzoxazone is a centrally-acting agent for painful musculoskeletal conditions. Data available from animal experiments as well as human study indicate that chlorzoxazone acts primarily at the level of the spinal cord and subcortical areas of the brain where it inhibits multisynaptic reflex a.c. involved in producing and maintaining skeletal muscle spasm of varied etiology. The clinical result is a reduction of the skeletal muscle spasm with relief of pain and increased mobility of the involved muscles.

Mechanism of Action · 1건

Chlorzoxazone inhibits degranulation of mast cells, subsequently preventing the release of histamine and slow-reacting substance of anaphylaxis (SRS-A), mediators of type I allergic reactions. Chlorzoxazone also may reduce the release of inflammatory leukotrienes. Chlorzoxazone may act by inhibiting calcium and potassium influx which would lead to neuronal inhibition and muscle relaxation. Data available from animal experiments as well as human study indicate that chlorzoxazone acts primarily at the level of the spinal cord and subcortical areas of the brain where it inhibits multisynaptic reflex arcs involved in producing and maintaining skeletal muscle spasm

Metabolism/Metabolites · 2건

Chlorzoxazone is rapidly metabolized in the liver and is excreted in the urine, primarily in a conjugated form as the glucuronide.

Chlorzoxazone has known human metabolites that include 6-Hydroxychlorzoxazone.

FDA Pharmacological Classification · 6건

H0DE420U8G

CHLORZOXAZONE

Physiologic Effects [PE] - Centrally-mediated Muscle Relaxation

Established Pharmacologic Class [EPC] - Muscle Relaxant

Chlorzoxazone is a Muscle Relaxant. The physiologic effect of chlorzoxazone is by means of Centrally-mediated Muscle Relaxation.

CHLORZOXAZONE

관련 반응

19건
반응 기록 만들기
HRID 195055 반응식
HRID 195055반응물로Training data from https://doi.org/10.1039/C8SC04228D (6/10)
HRID 270113 반응식
HRID 270113반응물로uspto-grants-2008_11
HRID 355036 반응식
HRID 355036반응물로uspto-grants-1983_03
HRID 358418 반응식
HRID 358418반응물로uspto-grants-1984_08
HRID 362462 반응식
HRID 362462반응물로uspto-grants-1999_02
HRID 650048 반응식
HRID 650048반응물로uspto-grants-2001_08
HRID 858159 반응식
HRID 858159반응물로uspto-grants-2006_12
HRID 986673 반응식
HRID 986673반응물로uspto-grants-1987_12
1 / 3 페이지

화합물 노트

불러오는 중…

이 페이지에서기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
ChEBI
CHEBI:3655
UNII
H0DE420U8G
EC Number
202-403-9
Nikkaji
J3.950K
용해도
50 mg/mL, · DMSO: 용해성50mg/mL, 투명
물리적 상태
가루
산도 계수 (pKa)
8.3 · pKa 8.3 (Uncertain)
색상
흰색에서 황백색까지
수용성
0.1 g/100mL · 0.1g/100mL
Merck
14 · 14,2194
주요 응용
제약
InChI
InChI=1S/C7H4ClNO2/c8-4-1-2-6-5(3-4)9-7(10)11-6/h1-3H,(H,9,10)
InChIKey
TZFWDZFKRBELIQ-UHFFFAOYSA-N
SMILES
O1C2=CC=C(Cl)C=C2NC1=O
LogP
1.816 · 1.816 (est)
NIST
Chlorzoxazone(95-25-0)
EPA
Chlorzoxazone (95-25-0)

화학적 성질

White to Off-White Solid

Drug Induced Liver Injury · 6건

Drug Induced Liver Injury Rank (DILIrank 2.0)

Chlorzoxazone

vMost-DILI-concern

8

Warnings & precautions

DOI:10.1016/j.drudis.2016.02.015

안전 데이터

wgk
3
tsca
TSCA listed
rtecs
DM5250000
독성
LD50 in mice (mg/kg): 3650 orally, 380 i.p. (suspensions); 440 orally, 183 i.p. (solns of Na salt) (Hofrichter)
HS 번호
29349990
risk_code
22-36/37/38-20/21/22
hazard_code
Xn,T,Xi
safety_code
26-36-24/25-37/39
위험 등급
IRRITANT
기존화학 물질
KE-05538
위험 참고 사항
Toxic/Irritant
Hazard Classifications
Acute Tox. 4 OralEye Irrit. 2Skin Irrit. 2STOT SE 3
스토리지 클래스
11 - Combustible Solids
MeSH Pharmacological Classification · 1건

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)

Absorption, Distribution and ExcretionChlorzoxazone is rapidly metabolized and is excreted in the urine, primarily in a conjugated form as the glucuronide.
Cellular LocationsMembrane

용도 및 제조

Use ClassificationPharmaceuticals
General Manufacturing Information2(3H)-Benzoxazolone, 5-chloro-: ACTIVE
응용 분야 · 3건

개요Chlorzoxazone is a muscle relaxant. It acts by blocking nerve impulses or pain sensations that are sent to brain. Typically, it is used together with rest and physical therapy to treat skeletal muscle conditions such as pain or injury. Chlorzoxazone, 5-chloro-2-benzoxazolione, is synthesized by a heterocyclization reaction of 2-amino-4-chlorophenol with phosgene. Skeletal muscle relaxants have conventionally been classified into one group; however, they are actually a heterogeneous group of medications commonly used to treat two different types of underlying conditions – spasticity from upper motor neuron syndromes and muscular pain or spasms from peripheral musculoskeletal conditions. Medications classified as skeletal muscle relaxants are baclofen, carisoprodol, chlorzoxazone, cyclobenzaprine, dantrolene, metaxalone, methocarbamol, orphenadrine, and tizanidine. These drugs may impair mental and/or physical abilities required for driving vehicles. As a class, skeletal muscle relaxants have central nervous system (CNS)-related side effects: drowsiness, dizziness, decreased alertness, blurred vision, and ataxia. Their use has been associated with a twofold increase in the risk for motor vehicle crashes. Muscle relaxants are included in the ‘Beers List’ of potentially inappropriate medications in older adults. Most muscle relaxants are poorly tolerated by elderly patients because they cause anticholinergic adverse effects, sedation, and weakness. Although extremely uncommon, this compound may yield to idiosyncratic and unpredictable type of liver toxicity. The concomitant use of alcohol or other CNS depressants may have an additive effect. Individuals on chlorzoxazone containing drugs should be monitored for abnormal liver enzymes (e.g., aspartate transaminase (AST), alanine transaminase (ALT), alkaline phosphatase, bilirubin, etc.).

용도Chlorzoxazone is a benzoxazolone derivative that causes skeletal muscle relaxation and blocks spasticity in clinical studies. Chlorzoxazone enhances small and intermediate conductance calcium-activated potassium channels (EC50s = 87 and 98 μM for KCa2.2 and KCa3.1, respectively). The cytochrome P450 isoform CYP2E1 converts chlorzoxazone to 6-hydroxy chlorzoxazone . The urinary excretion of this 6-hydroxy metabolite is often used as a probe of CYP2E1 activity in studies of hepatotoxicity.

일반 설명Chlorzoxazone is a centrally active muscle relaxant used to treat painful muscle spasms linked to musculoskeletal disorders, such as fibrositis, bursitis, myositis, spondylitis, etc.Pharmaceutical secondary standard for application in quality control. Provides pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards.

상·하류 제품 정보

상류 원료

4-CHLORO-2-NITROPHENOLp-클로로페놀수산화나트륨족사졸아민염산

하류 제품

1-페닐-1H-테트라졸-5-티올3-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2(3H)-benzoxazolone

공급사100 곳

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추가 설명 · 1건

정의ChEBI: A member of the class of 1,3-benzoxazoles that is 1,3-benzoxazol-2-ol in which the hydrogen atom at position 5 is substituted by chlorine. A centrally acting muscle relaxant with sedative properties, it is used for the symptomatic treatment of painful mus le spasm.