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113-59-7

113-59-7 structure
113-59-7 structure
  • Name: Chlorprothixene
  • Chemical Name: chlorprothixene
  • CAS Number: 113-59-7
  • Molecular Formula: C18H18ClNS
  • Molecular Weight: 315.860
  • Catalog: API Nervous system medication Antipsychotic
  • Create Date: 2018-10-01 14:18:17
  • Modify Date: 2024-01-02 17:50:18
  • Chlorprothixene has strong binding affinities to dopamine and histamine receptors, such as D1, D2, D3, D5, H1, 5-HT2, 5-HT6 and 5-HT7, with Ki of 18 nM, 2.96 nM, 4.56 nM, 9 nM, 3.75 nM, 9.4 nM, 3 nM and 5.6 nM, respectively.Target: Dopamine ReceptorChlorprothixene exerts strong binding affinities to the dopamine and histamine receptors, such as D1, D2, D3, D5 and H1 with Ki values of 18nM, 2.96 nM, 4.56 nM, 9 nM and 3.75 nM, respectively, but has little affinity to H3 (Ki >1000 nM) [1]. Chlorprothixene also shows high affinities for both rat 5-HT6 from stably transfected HEK-293 cells, and rat 5-HT7 receptors from transiently expressed COS-7 cells, with Ki values of 3 nM and 5.6 nM, respectively [2].Administration of Chlorprothixene restores normal ceramide concentrations in murine bronchial epithelial cells, reduces inflammation in the lungs of mice with cystic fibrosis (CF) and prevents infection with Pseudomonas aeruginosa, by inhibiting acidsphingomyelinase (Asm) and not neutral sphingomyelinase (Nsm) [3].

Name chlorprothixene
Synonyms 1-Propanamine, 3-(2-chloro-9H-thioxanthen-9-ylidene)-N,N-dimethyl-, (3Z)-
Ro 4-0403
Tarasan
(Z)-chlorprothixene
Truxaletten
Chlorprothixene
(3Z)-3-(2-chloro-9H-thioxanthen-9-ylidene)-N,N-dimethylpropan-1-amine
chloroprothixene
CPX
N 714C
(Z)-2-Chloro-9-(ω-dimethylaminopropylidene)thioxanthene
(Z)-2-Chloro-9-(3'-dimethylaminopropylidene)thioxanthene
Paxyl
Truxil
(Z)-2-Chloro-N,N-dimethylthioxanthene-D9,g-propylamine
(Z)-a-2-Chloro-10-(3-dimethylaminopropylidene)thiaxanthene
Taractan
EINECS 204-032-8
Truxal
1-Propanamine, 3- (2-chloro-9H-thioxanthen-9-ylidene)-N,N-dimethyl-, (Z)-
1-Propanamine, 3-(2-chloro-9H-thioxanthen-9-ylidene)-N,N-dimethyl-, (Z)-
(3Z)-3-(2-Chloro-9H-thioxanthen-9-ylidene)-N,N-dimethyl-1-propanamine
mk184
n714
Description Chlorprothixene has strong binding affinities to dopamine and histamine receptors, such as D1, D2, D3, D5, H1, 5-HT2, 5-HT6 and 5-HT7, with Ki of 18 nM, 2.96 nM, 4.56 nM, 9 nM, 3.75 nM, 9.4 nM, 3 nM and 5.6 nM, respectively.Target: Dopamine ReceptorChlorprothixene exerts strong binding affinities to the dopamine and histamine receptors, such as D1, D2, D3, D5 and H1 with Ki values of 18nM, 2.96 nM, 4.56 nM, 9 nM and 3.75 nM, respectively, but has little affinity to H3 (Ki >1000 nM) [1]. Chlorprothixene also shows high affinities for both rat 5-HT6 from stably transfected HEK-293 cells, and rat 5-HT7 receptors from transiently expressed COS-7 cells, with Ki values of 3 nM and 5.6 nM, respectively [2].Administration of Chlorprothixene restores normal ceramide concentrations in murine bronchial epithelial cells, reduces inflammation in the lungs of mice with cystic fibrosis (CF) and prevents infection with Pseudomonas aeruginosa, by inhibiting acidsphingomyelinase (Asm) and not neutral sphingomyelinase (Nsm) [3].
Related Catalog
References

[1]. von Coburg, Y., et al., Potential utility of histamine H3 receptor antagonist pharmacophore in antipsychotics. Bioorg Med Chem Lett, 2009. 19(2): p. 538-42.

[2]. Roth, B.L., et al., Binding of typical and atypical antipsychotic agents to 5-hydroxytryptamine-6 and 5-hydroxytryptamine-7 receptors. J Pharmacol Exp Ther, 1994. 268(3): p. 1403-10.

[3]. Becker, K.A., et al., Acid sphingomyelinase inhibitors normalize pulmonary ceramide and inflammation in cystic fibrosis. Am J Respir Cell Mol Biol, 2010. 42(6): p. 716-24.

Density 1.3±0.1 g/cm3
Boiling Point 435.0±45.0 °C at 760 mmHg
Melting Point 97-98°
Molecular Formula C18H18ClNS
Molecular Weight 315.860
Flash Point 216.9±28.7 °C
Exact Mass 315.084839
PSA 28.54000
LogP 6.05
Vapour Pressure 0.0±1.0 mmHg at 25°C
Index of Refraction 1.683
Storage condition -20°C

CHEMICAL IDENTIFICATION

RTECS NUMBER :
XO1050000
CHEMICAL NAME :
Thioxanthene-delta(sup 9),gamma-propylamine, 2-chloro-N,N-dimethyl-, (Z)-
CAS REGISTRY NUMBER :
113-59-7
LAST UPDATED :
199709
DATA ITEMS CITED :
9
MOLECULAR FORMULA :
C18-H18-Cl-N-S
MOLECULAR WEIGHT :
315.88
WISWESSER LINE NOTATION :
T C666 BS IYJ FG IU3N1&1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - man
DOSE/DURATION :
7 mg/kg
TOXIC EFFECTS :
Behavioral - general anesthetic Behavioral - changes in motor activity (specific assay) Behavioral - muscle weakness
REFERENCE :
ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 14,596,1964
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
200 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: 6,252,1982
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
50100 ug/kg
TOXIC EFFECTS :
Tumorigenic - active as anti-cancer agent
REFERENCE :
CNREA8 Cancer Research. (Public Ledger Building, Suit 816, 6th & Chestnut Sts., Philadelphia, PA 19106) V.1- 1941- Volume(issue)/page/year: 47,5944,1987
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
56200 ug/kg
TOXIC EFFECTS :
Tumorigenic - active as anti-cancer agent
REFERENCE :
CNREA8 Cancer Research. (Public Ledger Building, Suit 816, 6th & Chestnut Sts., Philadelphia, PA 19106) V.1- 1941- Volume(issue)/page/year: 47,5944,1987
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
36 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: -,373,1990
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rabbit
DOSE/DURATION :
182 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
29ZVAB "Handbook of Analytical Toxicology," Sunshine, I., ed., Cleveland, OH, Chemical Rubber Co., 1969 Volume(issue)/page/year: -,33,1969 ** REPRODUCTIVE DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
360 mg/kg
SEX/DURATION :
male 15 week(s) pre-mating
TOXIC EFFECTS :
Reproductive - Paternal Effects - impotence
REFERENCE :
AJPSAO American Journal of Psychiatry. (American Psychiatric Assoc., Circulation Dept., 1400 K St., NW, Washington, DC 20005) V.78- 1921- Volume(issue)/page/year: 120,1004,1964 *** REVIEWS *** TOXICOLOGY REVIEW IDPYAK Industrial Pharmacology. (Mount Kisco, NY) V.1-3, 1974-79. Discontinued. Volume(issue)/page/year: 1,203,1974
Hazard Codes Xi
HS Code 2932999099
HS Code 2932999099
Summary 2932999099. other heterocyclic compounds with oxygen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%