Grundinformationen
- CAS
456-59-7- Standard-SMILES
CC1CC(OC(=O)C(O)c2ccccc2)CC(C)(C)C1- InChIKey
WZHCOOQXZCIUNC-UHFFFAOYSA-N- Summenformel
- C17H24O3
- Durchschnittliche Molmasse
- 276,4 g/mol
- Monoisotopische Masse
- 276,17254462
Überblick
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.
Namen und Bezeichner
- Bevorzugter Name
- Cyclandelate
- IUPAC
- (3,3,5-trimethylcyclohexyl) 2-hydroxy-2-phenylacetate
- Lokaler Name
- Cyclandelat
- Englischer Name
- CYCLANDELATE
- Summenformel
- C17H24O3
- Molmasse
- 276.37
Namen und Synonyme
cyclandelate456-59-7CyclomandolCyclolytCyclospasmolPerebralSpasmioneCapilanSepyronCiclandelatoCiclospasmolClandilon
Weitere Namen anzeigen
bs572CydelNatilandeLBS 572AnaspatLejopanDilatan
CyclergineCyclobralSaiclateSancyclanSpasmocyclonArto-espasmol3,3,5-Trimethylcyclohexyl mandelateNovodil
Datenbank-Bezeichner
- CAS
456-59-7- PubChem CID
- 2893
- DTXSID
DTXSID4022862- ChEMBL
CHEMBL1480987- ChEBI
CHEBI:3988- UNII
- 4139O1OAY2
- EC Number
- 207-271-6
- Nikkaji
- J2.048F
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 4,2
- Polarare Oberfläche (TPSA)
- 46,5 Ų
- H-Brücken-Donoren
- 1
- H-Brücken-Akzeptoren
- 3
- Frei drehbare Bindungen
- 4
- Schwere Atome
- 20
- Formalladung
- 0
- Komplexität
- 331
Experimentelle und physikochemische Eigenschaften
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]
Physikochemische Eigenschaften
- Schmelzpunkt
- 55 · 55.0-56.5°
- Siedepunkt
- 14 · bp14 192-194°
- Dichte
- 1.0535 · 1.0535 (rough estimate)
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
GHS-Klassifizierung
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.
Gefahrenhinweise
Hazard Classes and CategoriesEye Irrit. 2 (97.5%)
Toxikologische Informationen
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...
Sicherheitsdaten
- tsca
- TSCA listed
- hs_code
- 2918191350
- RTECS-Nr.
- OO8200000
- Toxizität
- LD50 oral in rat: 5gm/kg
- Giftige Stoffe Daten
- 456-59-7(Hazardous Substances Data)
Chemie und Industrie
Pharmakologische Informationen
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
Verwendung und Herstellung
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