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사이클리진 및 그 염류

Cyclizine

HCID 6726
노트반응
기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
부분 구조 검색유사 구조 찾기

기본 정보

CAS
82-92-8
표준 SMILES
CN1CCN(C(c2ccccc2)c2ccccc2)CC1
InChIKey
UVKZSORBKUEBAZ-UHFFFAOYSA-N
분자식
C18H22N2
평균 분자량
266.4 g/mol
단동위원소 질량
266.1782987

개요

Cyclizine is an N-alkylpiperazine in which one nitrogen of the piperazine ring is substituted by a methyl group, while the other is substituted by a diphenylmethyl group. It has a role as a central nervous system depressant, a local anaesthetic, a H1-receptor antagonist, a cholinergic antagonist and an antiemetic.

이름 및 식별자

우선 이름
Cyclizine
IUPAC
1-benzhydryl-4-methylpiperazine
현지명
사이클리진 및 그 염류
영어명
Cyclizine
분자식
C18H22N2
분자량
266.38

이름 및 동의어

CYCLIZINE82-92-8NautazineCiclizinaNeo-devomit1-(Diphenylmethyl)-4-methylpiperazineCompound 47-83CyclizinumN-Benzhydryl-N'-methylpiperazineN-Methyl-N'-benzhydrylpiperazine(N-Benzhydryl)(N'-methyl)diethylenediamineWellcome prepn 47-83
이름 더 보기
사이클리진및그염류사이클라진HCLCYCLIZINE HCLValoidEmoquilbw47-83MarzineMarazineMarezineWellcome
1-Benzhydryl-4-methylpiperazinPiperazine, 1-(diphenylmethyl)-4-methyl-BW 47-83QRW9FCR9P2(+-)-1-diphenylmethyl-4-methylpiperazineNSC-26608CHEBI:3994DTXSID4022864

데이터베이스 식별자

CAS
82-92-8
PubChem CID
6726
DTXSID
DTXSID4022864
ChEMBL
CHEMBL648
ChEBI
CHEBI:3994

물성

구조 계산 물성

XLogP
3.6
극성 표면적
6.5 Ų
수소 결합 공여자 수
0
수소 결합 수용자 수
2
회전 가능 결합 수
3
무거운 원자 수
20
형식 전하
0
복잡도
253

실험 및 물리화학적 성질

DrugsPharmaceuticals -> Listed in ZINC15
pHBETWEEN 7.6 & 8.6 (SATURATED SOLUTION)
LogP3
OdorPRACTICALLY ODORLESS
Color/Form · 2건

CRYSTALS FROM PETROLEUM ETHER

WHITE OR CREAMY WHITE CRYSTALLINE POWDER

Solubility · 4건

INSOL IN ETHER 1 G IN ABOUT 115 ML ALC /HYDROCHLORIDE/

SOL IN ALCOHOL & CHLOROFORM; SLIGHTLY SOL IN WATER

FREELY SOL IN ETHER

7.52e-02 g/L

Human Drugs · 3건

Breast Feeding; Lactation; Antiemetics; Antihistamines; Anti-Allergic Agents; Gastrointestinal Agents

Pharmaceuticals

Medicines for other common symptoms in palliative care

Melting Point · 2건

105.5-107.5

105.5 TO 107.5 °C

Physical DescriptionSolid
Stability/Shelf Life · 2건

LIGHT-SENSITIVE

SENSITIVE TO LIGHT /HYDROCHLORIDE/

안전 및 규제

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

GHS 분류

GHS Classification · 4건

Danger

H301 (97.5%): Toxic if swallowed [Danger Acute toxicity, oral]

P261, P264, P264+P265, P270, P271, P280, P301+P316, 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 40 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

유해성 정보

Hazard Classes and CategoriesAcute Tox. 3 (97.5%)

독성 정보

InteractionsCOMBINATIONS OF CAFFEINE 100 MG WITH CYCLIZINE-HCL 50 & 100 MG DID NOT PRODUCE ANY SUBJECTIVE CHANGES OR CHANGES IN PERFORMANCE TESTS, DIFFERING FROM CONTROL.
Human Toxicity Excerpts · 5건

LARGE DOSES MAY CAUSE DROWSINESS & DRYNESS OF MOUTH.

...MOST FREQUENT SIDE EFFECTS INVOLVE DIGESTIVE TRACT & INCL LOSS OF APPETITE, NAUSEA, VOMITING, EPIGASTRIC DISTRESS & CONSTIPATION OR DIARRHEA. ... ALLERGY MAY DEVELOP WHEN...GIVEN ORALLY, BUT MORE COMMONLY IT RESULTS FROM TOPICAL APPLICATION. ALLERGIC DERMATITIS IS NOT UNCOMMON. /H1 RECEPTOR BLOCKERS/

OTHER SIDE EFFECTS INCL DRYNESS OF MOUTH, THROAT, & RESP PASSAGES, SOMETIMES INDUCING COUGH; URINARY FREQUENCY & DYSURIA; PALPITATION; HYPOTENSION; HEADACHE; TIGHTNESS OF CHEST; & TINGLING, HEAVINESS, & WEAKNESS OF HANDS. ... GRAVE COMPLICATIONS SUCH AS LEUKOPENIA & AGRANULOCYTOSIS ARE VERY RARE. /H1 RECEPTOR BLOCKERS/

SIDE EFFECT WITH HIGHEST INCIDENCE, &...COMMON TO ALL DRUGS IN THIS GROUP, IS SEDATION. ... OTHER UNTOWARD REACTIONS REFERABLE TO CENTRAL ACTIONS INCL DIZZINESS, TINNITUS, LASSITUDE, INCOORDINATION, FATIGUE, BLURRED VISION, DIPLOPIA, EUPHORIA, NERVOUSNESS, INSOMNIA & TREMORS. /H1 RECEPTOR BLOCKERS/

For more Human Toxicity Excerpts (Complete) data for CYCLIZINE (10 total), please visit the HSDB record page.

화학 및 산업

약리 정보

ATC Code · 3건

R - Respiratory system

QR - Respiratory system

R06AE03

Pharmacodynamics · 1건

Cyclizine is a piperazine-derivative antihistamine used as an antivertigo/antiemetic agent. Cyclizine is used in the prevention and treatment of nausea, vomiting, and dizziness associated with motion sickness. Additionally, it has been used in the management of vertigo in diseases affecting the vestibular apparatus. Although the mechanism by which cyclizine exerts its antiemetic and antivertigo effects has not been fully elucidated, its central anticholinergic properties are partially responsible. The drug depresses labyrinth excitability and vestibular stimulation, and it may affect the medullary chemoreceptor trigger zone. It also possesses anticholinergic, antihistaminic, central nervous system depressant, and local anesthetic effects.

Mechanism of Action · 2건

Vomiting (emesis) is essentially a protective mechanism for removing irritant or otherwise harmful substances from the upper GI tract. Emesis or vomiting is controlled by the vomiting centre in the medulla region of the brain, an important part of which is the chemotrigger zone (CTZ). The vomiting centre possesses neurons which are rich in muscarinic cholinergic and histamine containing synapses. These types of neurons are especially involved in transmission from the vestibular apparatus to the vomiting centre. Motion sickness principally involves overstimulation of these pathways due to various sensory stimuli. Hence the action of cyclizine which acts to block the histamine receptors in the vomiting centre and thus reduce activity along these pathways. Furthermore since cyclizine possesses anti-cholinergic properties as well, the muscarinic receptors are similarly blocked.

.../IT SEEMS/ THAT STIMULATION OF VESTIBULAR APPARATUS IS NECESSARY & SUFFICIENT...& THAT VESTIBULAR CEREBELLAR MIDBRAIN "INTEGRATIVE VOMITING CENTER" & MEDULLARY CHEMORECEPTIVE TRIGGER ZONE ARE...INVOLVED /IN MOTION SICKNESS/. IT IS...PROBABLE THAT EFFECTIVE ANTIHISTAMINES EXERT.../ACTION/ IN THESE CENTERS. /ANTIHISTAMINE/

Biological Half-Life20 hours
Metabolism/Metabolites · 3건

Cyclizine is metabolised to its N-demethylated derivative, norcyclizine, which has little antihistaminic (H1) activity compared to Cyclizine.

관련 반응

0건
반응 기록 만들기

현재 필터 조건에 해당하는 반응 기록이 없습니다.

화합물 노트

불러오는 중…

이 페이지에서기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
UNII
QRW9FCR9P2
EC Number
201-445-5、919-673-5
Nikkaji
J4.621C
Collision Cross Section · 3건

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

166.7 Ų [M+H]+ [CCS Type: TW; Method: Major Mix IMS/Tof Calibration Kit (Waters)]

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

Other Experimental Properties · 5건

ODORLESS OR NEARLY SO & HAS BITTER TASTE; MELTS INDISTINCTLY & WITH DECOMP @ 285 °C /HYDROCHLORIDE/

PH (POTENTIOMETRICALLY DETERMINED, 1 IN 50 SOLN IN MIXT OF 2 VOL ALC & 3 VOL H2O) BETWEEN 4.5 & 5.5 /HYDROCHLORIDE/

PH BETWEEN 5 & 6 /LACTATE INJECTION/

WHITE, CRYSTALLINE POWDER OR SMALL COLORLESS CRYSTALS /HYDROCHLORIDE/

1 G IN ABOUT 115 ML H2O & 75 ML CHLOROFORM /HCL/

물리화학적 성질

녹는점
105.5 · 105.5-107.5°
끓는 점
399.58 °C · 399.58°C (rough estimate)
밀도
0.9934 · 0.9934 (rough estimate)
굴절률
1.584 · 1.5840 (estimate)
저장 조건
Sealed in dry,Room Temperature
용해도
물과 에탄올(96%)에 약간 용해됩니다.
물리적 상태
Solid
색상
White to off-white

화학적 성질

White or almost white, crystalline powder.

Non-Human Toxicity Excerpts · 3건

TREATMENT /OF PREGNANT SPRAGUE-DAWLEY RATS/ ON VARIOUS DAYS FROM 10-15 WITH CYCLIZINE RESULTED IN 30% RESORPTIONS & APPROX 40% MALFORMED FETUSES. MALFORMATIONS INCL CLEFT PALATE, BRACHYGNATHIA & MICROSTOMIA. THERE WAS ALSO FAILURE TO OSSIFY IN NUMBER OF BONES.

.../EXPTL/ TESTS OF VERY HIGH DOSES IN MICE & RATS...DEMONSTRATED SIGNIFICANT TERATOGENIC ACTION, PARTICULARLY INDUCTION OF CATARACTS, MICROPHTHALMIA & ANOPHTHALMIA.

IN ANIMALS.../CYCLIZINE/ INDUCED HEPATIC MICROSOMAL ENZYMES THAT METAB CERTAIN DRUGS.

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation

안전 데이터

유해 물질 데이터
82-92-8(Hazardous Substances Data)

OXIDATIVE N-DEALKYLATION IS MAIN METABOLIC PATHWAY OF BENZHYDROLPIPERAZINES; CYCLIZINE.../IS/ TRANSFORMED INTO NORCYCLIZINE...

WITH A PURIFIED MIXED FUNCTION OXIDASE FROM LIVER MICROSOMES IN PRESENCE OF REDUCED PYRIDINE NUCLEOTIDE & O2.../CYCLIZINE IS/ OXIDIZED TO N-OXIDE.

MeSH Pharmacological Classification · 2건

Drugs used to prevent NAUSEA or VOMITING.

Drugs that selectively bind to but do not activate histamine H1 receptors, thereby blocking the actions of endogenous histamine. Included here are the classical antihistaminics that antagonize or prevent the action of histamine mainly in immediate hypersensitivity. They act in the bronchi, capillaries, and some other smooth muscles, and are used to prevent or allay motion sickness, seasonal rhinitis, and allergic dermatitis and to induce somnolence. The effects of blocking central nervous system H1 receptors are not as well understood.

Absorption, Distribution and ExcretionBENZHYDROLPIPERAZINES & THEIR N-DEALKYLATION PRODUCTS ARE DISTRIBUTED IN ALL TISSUES OF RAT & ARE TRANSFERRED TO FETUS. /BENZYHYDROLPIPERAZINES/
Cellular LocationsCytoplasm
Metabolite PathwaysCyclizine H1-Antihistamine Action

용도 및 제조

Uses · 2건

MEDICATION (VET)

MEDICATION

Methods of Manufacturing...BY ACTION OF BENZHYDRYL CHLORIDE ON N-METHYL PIPERAZINE: BALTZYL ET AL, J ORG CHEM (14) 775, 1949; US PATENT 2,630,435 (1953 TO BURROUGHS WELLCOME).
Use ClassificationPharmaceuticals
General Manufacturing Information · 4건

CYCLIZINE BASE IS REACTED WITH EQUIMOLAR QUANTITY OF LACTIC ACID. /LACTATE INJECTION/

MAREZINE [HYDROCHLORIDE] (BURROUGHS WELLCOME). ORAL: TABLETS 50 MG. RECTAL: SUPPOSITORIES 50 (PEDIATRIC) & 100 MG. /HYDROCHLORIDE/

MAREZINE [LACTATE] (BURROUGHS WELLCOME). INJECTION: SOLN 50 MG/ML IN 1 ML CONTAINERS. /LACTATE/

VALOID. /HYDROCHLORIDE/

응용 분야 · 2건

용도H1 antihistamine

일반 설명Cyclizine hydrochloride,1-(diphenylmethyl)-4-methylpiperazine monohydrochloride(Marezine), occurs as a light-sensitive, white crystallinepowder with a bitter taste. It is slightly soluble in water(1:115), in alcohol (1:115), and in chloroform (1:75). It isused primarily in the prophylaxis and treatment of motionsickness. The lactate salt (Cyclizine Lactate Injection,United States Pharmacopoeia [USP]) is used for intramuscular(IM) injection because of the limited water solubilityof the hydrochloride. The injection should be stored in acold place, because if it is stored at room temperature forseveral months, a slight yellow tint may develop. This doesnot indicate a loss in biologic potency.

제조 방법

Cyclizine is prepared through the alkylation of N-methylpiperazine with benzhydryl chloride.

상·하류 제품 정보

상류 원료

벤즈히드릴클로라이드N-메틸피페라진

공급사48 곳

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추가 설명

정의ChEBI: An N-alkylpiperazine in which one nitrogen of the piperazine ring is substituted by a methyl group, while the other is substituted by a diphenylmethyl group.