기본 정보
- CAS
456-59-7- 표준 SMILES
CC1CC(OC(=O)C(O)c2ccccc2)CC(C)(C)C1- InChIKey
WZHCOOQXZCIUNC-UHFFFAOYSA-N- 분자식
- C17H24O3
- 평균 분자량
- 276.4 g/mol
- 단동위원소 질량
- 276.17254462
개요
Cyclandelate is the ester obtained by formal condensation of mandelic acid and 3,3,5-tricyclohexanol. It is a direct-acting smooth muscle relaxant used to dilate blood vessels. It has a role as a vasodilator agent. It is a carboxylic ester and a secondary alcohol. It is functionally related to a mandelic acid and a 3,3,5-trimethylcyclohexanol.
이름 및 식별자
- 우선 이름
- Cyclandelate
- IUPAC
- (3,3,5-trimethylcyclohexyl) 2-hydroxy-2-phenylacetate
- 영어명
- CYCLANDELATE
- 분자식
- C17H24O3
- 분자량
- 276.37
이름 및 동의어
cyclandelate456-59-7CyclomandolCyclolytCyclospasmolPerebralSpasmioneCapilanSepyronCiclandelatoCiclospasmolClandilon
이름 더 보기
bs572CydelNatilandeLBS 572AnaspatLejopanDilatan
CyclergineCyclobralSaiclateSancyclanSpasmocyclonArto-espasmol3,3,5-Trimethylcyclohexyl mandelateNovodil
데이터베이스 식별자
- CAS
456-59-7- PubChem CID
- 2893
- DTXSID
DTXSID4022862- ChEMBL
CHEMBL1480987- ChEBI
CHEBI:3988- UNII
- 4139O1OAY2
- EC Number
- 207-271-6
- Nikkaji
- J2.048F
물성
구조 계산 물성
- XLogP
- 4.2
- 극성 표면적
- 46.5 Ų
- 수소 결합 공여자 수
- 1
- 수소 결합 수용자 수
- 3
- 회전 가능 결합 수
- 4
- 무거운 원자 수
- 20
- 형식 전하
- 0
- 복잡도
- 331
실험 및 물리화학적 성질
Color/FormCRYSTALS
Solubility
PRACTICALLY INSOL IN WATER; SOL IN LIPOIDS & THEIR SOLVENTS
FREELY SOL IN PETROLEUM ETHER, ETHANOL; SOL IN DIETHYL ETHER, ACETONE
9.97e-02 g/L
Boiling Point192-194 °C @ 14 MM HG
Melting Point
50-53
50-53 °C
56 °C
Physical DescriptionSolid
Collision Cross Section
186.2 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
184.48 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
물리화학적 성질
- 녹는점
- 55 · 55.0-56.5°
- 끓는 점
- 14 · bp14 192-194°
- 밀도
- 1.0535 · 1.0535 (rough estimate)
- 굴절률
- 1.549 · 1.5490 (estimate)
- 저장 조건
- Sealed in dry,Room Temperature
- 수용성
- 물에 불용성
- 용해도
- 클로로포름(약간 용해됨), 메탄올(약간 용해됨, 초음파처리)
- 물리적 상태
- powder to crystal
- 산도 계수 (pKa)
- 12.13 · 12.13±0.20(Predicted)
- 색상
- 흰색에서 거의 흰색
- Merck
- 14 · 14,2704
- InChI
- InChI=1S/C17H24O3/c1-12-9-14(11-17(2,3)10-12)20-16(19)15(18)13-7-5-4-6-8-13/h4-8,12,14-15,18H,9-11H2,1-3H3
- InChIKey
- WZHCOOQXZCIUNC-UHFFFAOYSA-N
- SMILES
- C1(CC(CC(C)(C)C1)C)OC(=O)C(O)C1C=CC=CC=1
- EPA
- 3 · Benzeneacetic acid, .alpha.-hydroxy-, 3,3,5-trimethylcyclohexyl ester (456-59-7)
안전 및 규제
안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.
GHS 분류
GHS Classification
Warning
H319 (97.5%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
P264+P265, P280, P305+P351+P338, and P337+P317 (click each P-code to see the statement)
Aggregated GHS information provided per 40 reports by companies from 2 notifications to the ECHA C&L Inventory.
유해성 정보
Hazard Classes and CategoriesEye Irrit. 2 (97.5%)
독성 정보
Human Toxicity Excerpts
CYCLANDELATE APPEARS TO PRODUCE LITTLE SERIOUS TOXICITY. HOWEVER, ORAL DOSES OF 200 MG OR MORE ARE ASSOC WITH SIGNIFICANT INCIDENCE OF UNPLEASANT SIDE EFFECTS, INCL GASTROINTESTINAL UPSETS, FLUSHING, TINGLING, HEADACHE, DIZZINESS, & SWEATING.
SIDE EFFECTS INCLUDE...NAUSEA...& HYPOTENSION.
...IT HAS BEEN CLAIMED THAT CYCLANDELATE REDUCED OPHTHALMIC BLOOD PRESSURE BUT INCR FLOW IN RETINAL ARTERIES. IT APPEARS THAT CYCLANDELATE PRESENTS NO SIGNIFICANT THREAT OF RAISING OCULAR PRESSURE IN OPEN-ANGLE GLAUCOMA NOR ANY THREAT OF PRECIPITATING ANGLE-CLOSURE GLAUCOMA...
안전 데이터
- tsca
- TSCA listed
- rtecs
- OO8200000
- 독성
- LD50 oral in rat: 5gm/kg
- HS 번호
- 2918191350
- 유해 물질 데이터
- 456-59-7(Hazardous Substances Data)
화학 및 산업
약리 정보
ATC Code
C - Cardiovascular system
QC - Cardiovascular system
PharmacodynamicsCyclandelate is in a class of drugs called vasodilators. Cyclandelate relaxes veins and arteries, which makes them wider and allows blood to pass through them more easily.
Mechanism of Action
Cyclandelate produces peripheral vasodilation by a direct effect on vascular smooth muscle. Pharmacological action may be due to calcium-channel antagonism.
...MOST OF ITS PHARMACOLOGICAL PROPERTIES ARE VERY SIMILAR TO THOSE OF PAPAVERINE & OF MANY SYNTHETIC ANTISPASMODICS PROMOTED PRIMARILY FOR EFFECTS ON SMOOTH MUSCLE.
PAPAVERINE IS POTENT INHIBITOR OF CYCLIC NUCLEOTIDE PHOSPHODIESTERASE FOUND IN MANY TISSUES & CAN INCR CONCN OF CYCLIC ADENOSINE 3',5'-MONOPHOSPHATE (CYCLIC AMP). SINCE CYCLIC AMP HAS BEEN IMPLICATED AS POSSIBLE MEDIATOR OF BETA-ADRENERGIC RELAXATION OF SMOOTH MUSCLE, SUCH MECHANISM OF ACTION...IS PLAUSIBLE. /PAPAVERINE/
Biological Half-Life(3-)-H-LABELED CYCLANDELATE WAS DETECTED & QUANTITATED. EFFECTIVE HALF-LIFE VALUES IN VARIOUS RAT TISSUES WERE 2.8-4.1 DAYS.
MeSH Pharmacological ClassificationDrugs used to cause dilation of the blood vessels.
Absorption, Distribution and Excretion
Well absorbed following oral administration.
MAX UPTAKE @ 1 HR FOR MOST RAT TISSUES WHILE BRAIN, DIAPHRAGM, STOMACH, & VEIN SHOWED MAX LEVELS @ 24 HR. LEVELS NEGLIGIBLE IN 28 DAYS.
Cellular LocationsMembrane
용도 및 제조
UsesMEDICATION
Methods of Manufacturing
PREPD BY ESTERIFICATION OF MANDELIC ACID WITH 3, 3,5-TRIMETHYLCYCLOHEXANOL USING SULFURIC ACID AS CATALYST: BROCK ET AL, ARZNEIMITTEL-FORSCH 2, 165 (1952); FUNCKE ET AL, IBID 3, 503 (1953)...BRITISH PATENT 707.227 (1954 TO BROCADES-STHEEMAN). PURIFICATION: FLITTER, US PATENT 3,663,597 (1972 TO AMERICAN HOME PRODUCTS).
Formulations/PreparationsDRUG IS AVAILABLE IN 100-MG TABLETS & 200-MG CAPSULES.
General Manufacturing InformationBenzeneacetic acid, .alpha.-hydroxy-, 3,3,5-trimethylcyclohexyl ester: ACTIVE
응용 분야
개요Almond (Amygdalus communis L) is a kind of nut from Xinjiang, China. Traditional Chinese medicine believes that almond can promote blood circulation to dispel blood stasis, lubricate bowels to relieve constipation, and relieve cough and asthma. The indications include amenorrhea, fever, wind arthralgia, malaria, blood stasis and pain, injuries, and blood stasis with constipation.
역사The chemical synthesis of cyclandelate was first synthesized by Funcke et al. from Elan Corporation in Ireland using a-hydroxyphenylacetic acid and cis-3,3,5-cycloalkyl cyclohexanol. The raw material of mandelic acid was obtained by hydrolysis after benzaldehyde reacted to sodium cyanide. However, sodium cyanide is hypertoxic, and because of its unique structure of a-hydroxy acid, it is easy to decompose under the acid condition, which leads to more by-products and low yield. A series of improved methods have been developed, which can reduce the environmental pollution under the premise of ensuring the yield of Zn/HCOONH4/ C2H5OH system . The method was used to synthesize cyclandelate since then. However, this drug has not yet been approved by the Food and Drug Administration in the United States, Canada, and other countries because it easily causes white blood cell deficiency. It has been withdrawn from the market after drug approval in Japan, France, and other countries in the 1970s.
용도vasodilator
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추가 설명
정의ChEBI: The ester obtained by formal condensation of mandelic acid and 3,3,5-tricyclohexanol. It is a direct-acting smooth muscle relaxant used to dilate blood vessels.
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