基本情報
- CAS
138-56-7- 標準SMILES
COc1cc(C(=O)NCc2ccc(OCCN(C)C)cc2)cc(OC)c1OC- InChIKey
FEZBIKUBAYAZIU-UHFFFAOYSA-N- 分子式
- C21H28N2O5
- 平均分子量
- 388.5 g/mol
- 単同位体質量
- 388.199822
概要
Trimethobenzamide is the amide obtained by formal condensation of 3,4,5-trihydroxybenzoic acid with 4-[2-(N,N-dimethylamino)ethoxy]benzylamine. It is used to prevent nausea and vomitting in humans. It has a role as an antiemetic. It is a member of benzamides and a tertiary amino compound.
名称と識別子
- 優先名称
- Trimethobenzamide
- IUPAC
- N-[[4-[2-(dimethylamino)ethoxy]phenyl]methyl]-3,4,5-trimethoxybenzamide
- 現地名
- トリメトベンズアミド
- 英語名
- Trimethobenzamide
- 分子式
- C21H28N2O5
- 分子量
- 388.46
名称と別名
trimethobenzamide138-56-7TrimetobenzamidaTrimethobenzamidumAmetik damlaBenzamide, N-[[4-[2-(dimethylamino)ethoxy]phenyl]methyl]-3,4,5-trimethoxy-N-[[4-[2-(dimethylamino)ethoxy]phenyl]methyl]-3,4,5-trimethoxybenzamide4-(2-Dimethylaminoethoxy)-N-(3,4,5-trimethoxybenzoyl)benzylamineW2X096QY97DTXSID8023711CHEBI:27796Benzamide, N-(p-(2-(dimethylamino)ethoxy)benzyl)-3,4,5-trimethoxy-
名称をさらに表示
N-[4-[[2-(ジメチルアミノ)エチル]オキシ]ベンジル]-3,4,5-トリメトキシベンズアミドトリメトベンズアミドN-[4-[2-(ジメチルアミノ)エトキシ]ベンジル]-3,4,5-トリメトキシベンズアミドN-({4-[2-(ジメチルアミノ)エトキシ]フェニル}メチル)-3,4,5-トリメトキシベンズアミドC07178Ro 2-9578 free baseTrimethobenzamide USP/EP/BPn-[(2-dimethylaminoethoxy)benzyl]-3,4,5-trimethoxybenzamiden-(p-(2-(dimethylamino)ethoxy)benzyl)-3,4,5-trimethoxy-benzamidN-(4-[2-(Dimethylamino)ethoxy]benzyl)-3,4,5-trimethoxybenzamideN-[p-[2-(Dimethylamino)ethoxy]benzyl]-3,4,5-trimethoxybenzamide
物性
構造計算による物性
- XLogP
- 2.3
- 極性表面積
- 69.3 Ų
- 水素結合供与体数
- 1
- 水素結合受容体数
- 6
- 回転可能結合数
- 10
- 重原子数
- 28
- 形式電荷
- 0
- 複雑度
- 440
実験および物理化学的性質
DrugsPharmaceuticals -> Listed in ZINC15
LogP
2.2
2.04
Solubility
WHITE CRYSTALLINE POWDER; SLIGHT PHENOLIC ODOR; SOL IN WARM ALC; INSOL IN ETHER & BENZENE /HYDROCHLORIDE/
PKA: 8.27; FREELY SOL IN ETHANOL & CHLOROFORM; INSOL IN PETROLEUM ETHER /HYDROCHLORIDE/
3.98e-02 g/L
Human DrugsBreast Feeding; Lactation; Milk, Human; Antiemetics; Gastrointestinal Agents
Melting Point188.7 °C
Physical DescriptionSolid
Dissociation Constants8.78
Collision Cross Section177.39 Ų [M+H-H2O]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Other Experimental PropertiesCRYSTALS; MP: 187.5-190 °C; FREELY SOL IN WATER (MORE THAN 50% @ 25 °C) /HYDROCHLORIDE/
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。
危険有害性情報
Special ReportsPHARMACOLOGY.[BLESSEL ET AL; ANAL PROFILES DRUG SUBST 2: 551 (1973)]
毒性情報
Hepatotoxicity
Serum aminotransferase elevations during trimethobenzamide therapy are uncommon and rates of such elevations have not been reported in large clinical trials. A single case report of hepatitis and jaundice attributed to trimethobenzamide was published in 1967 that predated availability of tests for hepatitis A, B and C and of modern imaging studies. The latency to onset was approximately 2 weeks and the pattern of injury was mixed. There were no immunoallergic or autoimmune features and recovery was prompt once the medication was stopped. Since that report, there has only been a single mention of possible hepatotoxicity due to trimethobenzamide, a somewhat prolonged case of hepatocellular injury with a cholestatic pattern on liver biopsy despite minimal jaundice. Thus, clinically apparent liver injury from trimethobenzamide must be very rare and is generally mild and self-limited in course.
Human Toxicity Excerpts
...WITH LARGER DOSES, DROWSINESS, VERTIGO, DIARRHEA, CUTANEOUS HYPERSENSITIVITY REACTIONS, EXTRAPYRAMIDAL REACTIONS, & EXAGGERATION OF PRE-EXISTING NAUSEA HAVE OCCURRED. PAIN @ SITE OF INJECTION & LOCAL IRRITATION AFTER RECTAL ADMIN HAVE BEEN NOTED. /HYDROCHLORIDE SALT/
CASE REPORT. 2-WK-OLD MALE INFANT WAS WELL UNTIL 7 DAYS PRIOR TO ADMISSION. HE RECEIVED 3 RECTAL 100 MG DOSES IN 24 HR PERIOD PRIOR TO ADMISSION. HE BECAME LISTLESS, HYPOTONIC & CYANOTIC. EXTRAPYRAMIDAL REACTION SECONDARY TO DRUG WAS DIAGNOSIS.
DURING YR 1959-1966, TRIMETHOBENZAMIDE PRESCRIBED TO 11,481 PREGNANT WOMEN FOR NAUSEA & VOMITING IN 1ST 84 DAYS OF PREGNANCY, WAS EVALUATED FOR TERATOGENIC POTENTIAL. THERE WAS SLIGHT SUGGESTION OF EXCESS OF SEVERE CONGENITAL ANOMALIES.
HEPATITIS FOLLOWING THE ADMIN OF TRIMETHOBENZAMIDE HYDROCHLORIDE.
Drug Induced Liver Injury
Drug-Induced Liver Injury Severity and Toxicity (DILIst)
trimethobenzamide
DILI Negative
化学と産業
薬理情報
ATC Code
R - Respiratory system
QR - Respiratory system
Pharmacodynamics
Trimethobenzamide is a novel antiemetic which prevents nausea and vomiting in humans. Its actions are unclear but most likely involves the chemoreceptor trigger zone (CTZ). In dogs pretreated with trimethobenzamide HCl, the emetic response to apomorphine is inhibited, while little or no protection is afforded against emesis induced by intragastric copper sulfate.
Mechanism of Action
The mechanism of action of trimethobenzamide as determined in animals is obscure, but may involve the chemoreceptor trigger zone (CTZ), an area in the medulla oblongata through which emetic impulses are conveyed to the vomiting center; direct impulses to the vomiting center apparently are not similarly inhibited.
DRUG...SHOWN TO INHIBIT STIMULI @ CHEMORECEPTOR TRIGGER ZONE IN ANIMALS... /HYDROCHLORIDE SALT/
Biological Half-LifeThe mean elimination half-life of trimethobenzamide is 7 to 9 hours.
Metabolism/Metabolites
Hepatic.
METABOLIZED IN THE LIVER OF THE DOG TO THE N-DESMETHYL AND N-OXIDE DERIVATIVES. ...IN /HUMAN/ ADULTS, FOLLOWING ORAL OR RECTAL ADMIN OF 500 MG...AN UNIDENTIFIED METABOLITE HAS BEEN DEMONSTRATED.
FDA Pharmacological Classification
W2X096QY97
TRIMETHOBENZAMIDE
Established Pharmacologic Class [EPC] - Antiemetic
Physiologic Effects [PE] - Emesis Suppression
Trimethobenzamide is an Antiemetic. The physiologic effect of trimethobenzamide is by means of Emesis Suppression.
MeSH Pharmacological ClassificationDrugs used to prevent NAUSEA or VOMITING.
Absorption, Distribution and Excretion
関連反応
0 件
現在のフィルター条件では反応記録がありません。
化合物ノート
読み込み中…