基本情報
- CAS
84-06-0- 標準SMILES
CC(=O)OCCN1CCN(CCCN2c3ccccc3Sc3ccc(Cl)cc32)CC1- InChIKey
AIUHRQHVWSUTGJ-UHFFFAOYSA-N- 分子式
- C23H28ClN3O2S
- 平均分子量
- 446 g/mol
- 単同位体質量
- 445.159076
概要
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.
名称と識別子
- 優先名称
- Thiopropazate
- IUPAC
- 2-[4-[3-(2-chlorophenothiazin-10-yl)propyl]piperazin-1-yl]ethyl acetate
- 現地名
- チオプロパザート
- 英語名
- thiopropazate
- 分子式
- C23H28ClN3O2S
- 分子量
- 446.01
名称と別名
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
名称をさらに表示
4-[3-(2-クロロ-10H-フェノチアジン-10-イル)プロピル]-1-ピペラジンエタノール=アセタートダルタランチオプロパザートチオプロパゼート酢酸2-[4-[3-(2-クロロ-10H-フェノチアジン-10-イル)プロピル]-1-ピペラジニル]エチルダルタール2-{4-[3-(2-クロロ-10H-フェノチアジン-10-イル)プロピル]ピペラジン-1-イル}エチル アセタート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]ethyl
物性
構造計算による物性
- XLogP
- 4.8
- 極性表面積
- 61.3 Ų
- 水素結合供与体数
- 0
- 水素結合受容体数
- 6
- 回転可能結合数
- 8
- 重原子数
- 30
- 形式電荷
- 0
- 複雑度
- 561
実験および物理化学的性質
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/
物理化学的性質
安全と法規制
安全情報は参考情報です。供給元の安全データシート（SDS）、適用法令、専門家による評価に代わるものではありません。
毒性情報
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.
安全データ
- 有毒物質データの
- 84-06-0(Hazardous Substances Data)
化学と産業
薬理情報
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/
用途と製造
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/
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