Grundinformationen
- CAS
84-06-0- Standard-SMILES
CC(=O)OCCN1CCN(CCCN2c3ccccc3Sc3ccc(Cl)cc32)CC1- InChIKey
AIUHRQHVWSUTGJ-UHFFFAOYSA-N- Summenformel
- C23H28ClN3O2S
- Durchschnittliche Molmasse
- 446 g/mol
- Monoisotopische Masse
- 445,159076
Überblick
Thiopropazate is a phenothiazine derivative in which 10H-phenothiazine has a chloro subsitituent at the 2-position and a 3-[4-(2-acetoxyethyl)piperazin-1-yl]propyl group at N-10. It has a role as a phenothiazine antipsychotic drug and a dopaminergic antagonist. It is an organochlorine compound, a member of phenothiazines, a N-alkylpiperazine and an acetate ester.
Namen und Bezeichner
- Bevorzugter Name
- Thiopropazate
- IUPAC
- 2-[4-[3-(2-chlorophenothiazin-10-yl)propyl]piperazin-1-yl]ethyl acetate
- Lokaler Name
- Thiopropazat
- Englischer Name
- thiopropazate
- Summenformel
- C23H28ClN3O2S
- Molmasse
- 446.01
Namen und Synonyme
THIOPROPAZATEThiopropazat84-06-0DartalanTiopropazatoThiopropazatum4-(3-(2-Chlorophenothiazin-10-yl)propyl)-1-piperazineethanol acetate0JFY081Q2X1-(2-Acetoxyethyl)-4-(3-(2-chloro-10-phenothiazinyl)propyl)piperazine10-(3-(1-(2-Acetoxyethyl)-4-piperazinyl)propyl)-2-chlorophenothiazine2-Chloro-10-(3-(1-(2-acetoxyethyl)-4-piperazinyl)propyl)phenothiazineN-(beta-Acetoxyethyl)-N'-(gamma-(2'-chloro-10'-phenothiazinyl)propyl)piperazine
Weitere Namen anzeigen
Dartalhiopropazate4-[3-(2-Chloro-10H-phenothiazin-10-yl)propyl]-1-piperazineethanol=acetate1-Piperazineethanol, 4-[3-(2-chloro-10H-phenothiazin-10-yl)propyl]-, 1-acetateAcetic acid 2-[4-[3-(2-chloro--10H-phenothiazin-10-yl)propyl]-1-piperazinyl]ethylAcetic acid 2-[4-[3-(2-chloro-10H-phenothiazin-10-yl)propyl]-1-piperazinyl]ethyl ester
DTXSID6023654CHEBI:591191-Piperazineethanol, 4-(3-(2-chlorophenothiazin-10-yl)propyl)-, acetate (ester)2-{4-[3-(2-chloro-10H-phenothiazin-10-yl)propyl]piperazin-1-yl}ethyl acetate1-Piperazineethanol, 4-(3-(2-chloro-10H-phenothiazin-10-yl)propyl)-, acetate (ester)1-Piperazineethanol, 4-[3-(2-chloro-10H-phenothiazin-10-yl)propyl]-, acetate (ester)2-Chloro-10-[3-[1-(2-acetoxyethyl)-4-piperazinyl]propyl]phenothiazine1-(2-Acetoxyethyl)-4-[3-(2-chloro-10-phenothiazinyl)propyl]piperazine
Datenbank-Bezeichner
- CAS
84-06-0- PubChem CID
- 6762
- DTXSID
DTXSID6023654- ChEMBL
CHEMBL1697851- ChEBI
CHEBI:59119- UNII
- 0JFY081Q2X
- EC Number
- 201-513-4
- Nikkaji
- J4.891G
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 4,8
- Polarare Oberfläche (TPSA)
- 61,3 Ų
- H-Brücken-Donoren
- 0
- H-Brücken-Akzeptoren
- 6
- Frei drehbare Bindungen
- 8
- Schwere Atome
- 30
- Formalladung
- 0
- Komplexität
- 561
Experimentelle und physikochemische Eigenschaften
DrugsDEA NFLIS-Drug Category -> Depressants and Tranquilizers
SolubilitySOL IN ETHER
Human DrugsPharmaceuticals
Boiling Point214-218 °C @ 0.1 MM HG
Melting PointMP: 167-169 °C /DIMALEATE/
Refractive IndexINDEX OF REFRACTION: 1.589 (ALPHA), 1.609 (BETA), 1.700 (GAMMA) /DIHYDROCHLORIDE/
Stability/Shelf LifeSENSITIVE TO LIGHT; UNSTABLE IN HEAT /DIHYDROCHLORIDE/
Dissociation ConstantsPKA= 7.3
Other Experimental Properties
DECOMP BETWEEN 223-229 °C /DIHYDROCHLORIDE/
SADTLER REFERENCE NUMBER: 691 /DIHYDROCHLORIDE/
CRYSTALS FROM 95% ETHANOL /DIHYDROCHLORIDE/
CRYSTALS FROM METHANOL + ETHANOL /DIMALEATE/
WHITE, CRYSTALLINE POWDER /DIHYDROCHLORIDE/
Physikochemische Eigenschaften
- Siedepunkt
- 0.1 · bp0.1 214-218°
- Dichte
- 1.1147 · 1.1147 (rough estimate)
- Brechungsindex
- 1.61 · 1.6100 (estimate)
- pka
- 3.2 · pKa 3.20(H2O (extrap) t = 24±1 I ~ 0.002) (Uncertain);7.15(H2O (extrap) t = 24±1 I ~ 0.002) (Uncertain)
- Wasserlöslichkeit
- 8.92 mg/L · 8.92mg/L(24 ºC)
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
Toxikologische Informationen
Interactions
...POTENTIATES THE ACTIONS OF BARBITURATES. /DIHYDROCHLORIDE/
...POTENTIALLY DANGEROUS SEIZURES MAY OCCUR /WITH PIPERAZINE & THIOPROPAZATE HYDROCHLORIDE/.
...LEVODOPA & /THIOPROPAZATE/...MAY BLOCK THE EFFECTS OF EACH OTHER WHEN THESE DRUGS ARE ADMIN TOGETHER. /DIHYDROCHLORIDE/
/THIOPROPAZATE/...MAY BE ABLE TO REVERSE THE ANTIHYPERTENSIVE ACTIVITY OF GUANETHIDINE. /DIHYDROCHLORIDE/
For more Interactions (Complete) data for THIOPROPAZATE (7 total), please visit the HSDB record page.
Human Toxicity Excerpts
PHENOTHIAZINES INHIBIT EJACULATION WITHOUT INTERFERING WITH ERECTION. /PHENOTHIAZINES/
MOST DANGEROUS EFFECTS OF PHENOTHIAZINES ARE THOSE RESULTING FROM HYPERSENSITIVITY REACTIONS, PARTICULARLY BLOOD DYSCRASIAS. THERAPEUTIC DOSES... MAY CAUSE FAINTNESS, PALPITATION, NASAL STUFFINESS, DRY MOUTH, & SOME SLIGHT CONSTIPATION. PT MAY COMPLAIN OF BEING COLD, DROWSY, OR WEAK. /PHENOTHIAZINES/
MOST TROUBLESOME SIDE EFFECT IS ORTHOSTATIC HYPOTENSION, WHICH MAY RESULT IN SYNCOPE. ... THERE IS GENERAL AGREEMENT THAT JAUNDICE FOLLOWING PHENOTHIAZINE ADMIN IS HYPERSENSITIVITY REACTION. ... LEUKOCYTOSIS, LEUKOPENIA, & EOSINOPHILIA OCCUR WITH PHENOTHIAZINE MEDICATION. /PHENOTHIAZINES/
DERMATOLOGICAL REACTIONS TO PHENOTHIAZINES ARE NOT UNCOMMON. ... PHOTOSENSITIVITY OCCURS...RESEMBLING THAT SEEN WITH SEVERE SUNBURN. /PHENOTHIAZINES/
For more Human Toxicity Excerpts (Complete) data for THIOPROPAZATE (7 total), please visit the HSDB record page.
Sicherheitsdaten
- Giftige Stoffe Daten
- 84-06-0(Hazardous Substances Data)
Chemie und Industrie
Pharmakologische Informationen
ATC Code
N - Nervous system
QN - Nervous system
Mechanism of Action
THERE IS AN ADENYLATE CYCLASE IN LIMBIC SYSTEM, AS WELL AS IN CAUDATE NUCLEUS, THAT IS SPECIFICALLY ACTIVATED BY DOPAMINE. ...ACTIVATION OF...ENZYME IS... BLOCKED BY...PHENOTHIAZINES. ...THERAPEUTIC EFFICACY & SIDE EFFECTS MAY RELATE TO INHIBITION OF DOPAMINE ACTIVATION OF ADENYLATE CYCLASE. /PHENOTHIAZINES/
Metabolism/Metabolites
...METAB...BY OXIDATIVE PROCESSES MEDIATED LARGELY BY HEPATIC MICROSOMAL & OTHER DRUG-METABOLIZING ENZYMES. CONJUGATION WITH GLUCURONIC ACID...PROMINENT ROUTE.../PRC: REACTIONS INCL HYDROXYLATION, DEMETHYLATION, SULFOXIDE FORMATION; METABOLIC ALTERATIONS IN SIDE CHAIN MAY ALSO OCCUR. /PHENOTHIAZINES/
Absorption, Distribution and Excretion
APPROX HALF OF METABOLITES OF COMMONLY USED PHENOTHIAZINES ARE FOUND IN URINE & REST IN FECES. 6 MO AFTER DISCONTINUATION OF THESE DRUGS, VARIOUS METABOLITES ARE DETECTABLE IN URINE. /PHENOTHIAZINES/
PHENOTHIAZINE TRANQUILIZERS CROSS PLACENTA RAPIDLY, & THEY HAVE BEEN MEASURED...IN URINE & TISSUES OF NEONATES OF TREATED MOTHERS, BUT VERY LOW BLOOD LEVELS OF MOTHERS & FETUSES HAVE BEEN MEASURED ONLY RECENTLY... /PHENOTHIAZINES/
Verwendung und Herstellung
UsesMEDICATION
Methods of Manufacturing
FROM 2-CHLORO-10-(GAMMA-CHLOROPROPYL)-PHENOTHIAZINE & PIPERAZINE IN BUTANONE FOLLOWED BY TREATMENT WITH BETA-BROMOETHYL ACETATE IN TOLUENE: CUSIC, US PATENT 2,766,235 (1956); ANDERSON ET AL, ARZNEIMITTEL-FORSCH 12, 937 (1962).
10-(3-CHLOROPROPYL) PHENOTHIAZINE IS CONDENSED WITH PIPERAZINE IN BUTANONE SOLN &...CONDENSED WITH 2-BROMOETHYL ACETATE WITH...SUITABLE DEHYDROBROMINATING AGENT SUCH AS SODAMIDE TO FORM THIOPROPAZATE. REACTION OF BASE WITH DOUBLE MOLAR PORTION OF HYDROGEN CHLORIDE YIELDS THE SALT. /DIHYDROCHLORIDE/
Formulations/PreparationsDARTAL, DARTALAN. /DIHYDROCHLORIDE/
Use ClassificationPharmaceuticals
General Manufacturing InformationA FEW AVAIL AGENTS...ARE NOW KNOWN TO HAVE INFERIOR ANTIPSYCHOTIC EFFECTS OR... ARE NO LONGER COMMONLY USED IN PSYCHIATRIC PT. THESE INCL...THIOPROPAZATE (DARTAL).
Vor- und nachgelagerte Produkte
Vorgelagerte Rohstoffe
Anbieter2 Anbieter
Shaanxi Didu New Materials Co. Ltd+86-86-17392712779 +86-13289823923 · [email protected]
湖北玖天生物医药科技有限公司027-88013699 17354350817 · [email protected]
Ergänzende Hinweise
DefinitionChEBI: A phenothiazine derivative in which 10H-phenothiazine has a chloro subsitituent at the 2-position and a 3-[4-(2-acetoxyethyl)piperazin-1-yl]propyl group at N-10.
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