Zotepine

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Zotepine
Zotepine.svg
Systematic (IUPAC) name
2-(3-chlorobenzo[b][1]benzothiepin-5-yl)oxy-N,N-dimethylethanamine
Clinical data
Trade names Zoleptil
AHFS/Drugs.com International Drug Names
Legal status
  • ℞ (Prescription only)
Routes of
administration		 Oral
Pharmacokinetic data
Bioavailability 7-13% (Oral)[1]
Metabolism N-desmethylation to norzotepine (30-40%)[1]
Biological half-life 13.7-15.9 hours, 12 hours (Norzotepine)[1]
Excretion 17% (Urine)[1]
Identifiers
CAS Number 26615-21-4 N
ATC code N05AX11 (WHO)
PubChem CID: 5736
IUPHAR/BPS 103
DrugBank DB09225 N
ChemSpider 5534 YesY
UNII U29O83JAZW YesY
KEGG D01321 YesY
ChEBI CHEBI:32316 YesY
ChEMBL CHEMBL285802 YesY
Chemical data
Formula C18H18ClNOS
Molecular mass 331.86
  • Clc2cc1C(/OCCN(C)C)=C\c3c(Sc1cc2)cccc3
  • InChI=1S/C18H18ClNOS/c1-20(2)9-10-21-16-11-13-5-3-4-6-17(13)22-18-8-7-14(19)12-15(16)18/h3-8,11-12H,9-10H2,1-2H3 YesY
  • Key:HDOZVRUNCMBHFH-UHFFFAOYSA-N YesY
 NYesY (what is this?)  (verify)

Zotepine (brand names: Losizopilon (JP), Lodopin (ID, JP), Setous (JP), Zoleptil (CZ, PT, TR, UK†); where † indicates a formulation that has been discontinued) is an atypical antipsychotic drug indicated for acute and chronic schizophrenia. It has been used in Germany since 1990 (although it has been discontinued in Germany) and Japan since 1982.

Zotepine is not approved for use in the United States, United Kingdom, Australia, Canada or New Zealand.[2]

Medical Uses

Zotepine's primary use is as a treatment for schizophrenia[3] although clinical trials have been conducted (with positive results) into its efficacy as an antimanic agent in patients with acute bipolar mania.[4][5][6]

Side effects

Common[1][3]

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Unknown Frequency[1][3]

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Rare[1][3]

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Pharmacology

The antipsychotic effect of zotepine is thought to be mediated through antagonist activity at dopamine and serotonin receptors. Zotepine has a high affinity for the D1 and D2 receptors. It also affects the 5-HT2A, 5-HT2C, 5-HT6, and 5-HT7 receptors.[8] In addition, its active metabolite, norzotepine, serves as a potent norepinephrine reuptake inhibitor.[9]

Macromolecule (Receptor or transporter protein) Ki [nM][8]
SERT 151
NET 530
DAT 3621
5-HT1A 470.5
5-HT1B 59.5
5-HT1D 119
5-HT1E 700
5-HT2A 2.7
5-HT2C 2.6
5-HT3 472
5-HT5A 29
5-HT6 6
5-HT7 12
α1A 7
α1B 5
α2A 180
α2B 5.35
α2C 106
M1 18
M2 140
M3 73
M4 77
M5 260
D1 71
D2 25
D2S 5.4
D2L 11
D3 6.4
D4 18
D5 248
H1 3.21
H2 500
H4 1977

Dosing

The most common dosage used is 150 mg daily. It is suggested that zotepine therapy starts at 75 mg to 150 mg divided into three daily doses. Some people may need to have their dosage increased to 300 mg.[2]

50 mg Lodopin® pills

See also

References

  1. ↑ 1.0 1.1 1.2 1.3 1.4 1.5 1.6 Truven Health Analytics, Inc. DRUGDEX® System (Internet) [cited 2013 Jun 25]. Greenwood Village, CO: Thomsen Healthcare; 2013.
  2. ↑ 2.0 2.1 2.2 Lua error in package.lua at line 80: module 'strict' not found.
  3. ↑ 3.0 3.1 3.2 3.3 British National Formulary 58. British Medical Association and Royal Pharmaceutical Society of Great Britain; 2009.
  4. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  5. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  6. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  7. ↑ 7.0 7.1 7.2 Lua error in package.lua at line 80: module 'strict' not found.
  8. ↑ 8.0 8.1 Lua error in package.lua at line 80: module 'strict' not found.
  9. ↑ Lua error in package.lua at line 80: module 'strict' not found.
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