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Haloperidol Decanoate

Synopsis, Chemistry

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Also known as: 74050-97-8, Halomonth, Haldol decanoate, Neoperidole, Kd 136, Kd 16

Molecular Formula

C₃₁H₄₁ClFNO₃

Molecular Weight

530.1 g/mol

InChI Key

GUTXTARXLVFHDK-UHFFFAOYSA-N

FDA UNII

AC20PJ4101

Haloperidol Decanoate is the decanoate ester of haloperidol, a phenylbutylpiperadine derivative with antipsychotic, neuroleptic and antiemetic effects. Haloperidol competitively blocks postsynaptic dopamine (D2) receptors in the mesolimbic system of the brain leading to anti-delusionary and anti-hallucinogenic effects. The antagonistic activity mediated through D2 dopamine receptors in the chemoreceptive trigger zone (CTZ) account for its antiemetic activity.

1 2D Structure

Haloperidol Decanoate

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

[4-(4-chlorophenyl)-1-[4-(4-fluorophenyl)-4-oxobutyl]piperidin-4-yl] decanoate

2.1.2 InChI

InChI=1S/C31H41ClFNO3/c1-2-3-4-5-6-7-8-11-30(36)37-31(26-14-16-27(32)17-15-26)20-23-34(24-21-31)22-9-10-29(35)25-12-18-28(33)19-13-25/h12-19H,2-11,20-24H2,1H3

2.1.3 InChI Key

GUTXTARXLVFHDK-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CCCCCCCCCC(=O)OC1(CCN(CC1)CCCC(=O)C2=CC=C(C=C2)F)C3=CC=C(C=C3)Cl

2.2 Other Identifiers

2.2.1 UNII

AC20PJ4101

2.3 Synonyms

2.3.1 Depositor-Supplied Synonyms

1. 74050-97-8

2. Halomonth

3. Haldol Decanoate

4. Neoperidole

5. Kd 136

6. Kd 16

7. Kd-136

8. [4-(4-chlorophenyl)-1-[4-(4-fluorophenyl)-4-oxobutyl]piperidin-4-yl] Decanoate

9. Ac20pj4101

10. R-13672

11. R-13,672

12. 4-(4-chlorophenyl)-1-(4-(4-fluorophenyl)-4-oxobutyl)piperidin-4-yl Decanoate

13. Decanoic Acid, Ester With 4-(4-(p-chlorophenyl)-4-hydroxypiperidino)-4'-fluorobutyrophenone

14. Haldol Decanoas

15. Decanoic Acid, 4-(4-chlorophenyl)-1-(4-(4-fluorophenyl)-4-oxobutyl)-4-piperidinyl Ester

16. Depot Haloperidol

17. Haloperidol Depot

18. Halomonth; Haloperidol Decanoate; Kd 136; Kd 16; Neoperidole; R 13762

19. Einecs 277-679-7

20. Haloperidol Decanoate Hcl

21. Unii-ac20pj4101

22. Haldol Dec

23. L-ornithineacetate

24. Halomonth (tn)

25. R 13672

26. Haloperidol-decanoate

27. R 13,672

28. Haloperidol Decanoate [usan:usp:ban:jan]

29. Schembl120575

30. Chembl1200986

31. Chebi:31664

32. Dtxsid50224951

33. Haloperidol Decanoate (jan/usp)

34. Haloperidol Decanoate [mi]

35. Hms3887c07

36. Haloperidol Decanoate [jan]

37. Zinc8214574

38. Haloperidol Decanoate [usan]

39. Bdbm50053408

40. Haloperidol Decanoate [mart.]

41. 4-(4-chlorophenyl)-1-(4-(4-fluorophenyl)-4-oxobutyl)-4-piperidyl Decanoate

42. Akos025392169

43. Haloperidol Decanoate [usp-rs]

44. Haloperidol Decanoate [who-dd]

45. Ks-1419

46. Ncgc00508704-02

47. Haloperidol Decanoate [ep Impurity]

48. Haloperidol Decanoate [orange Book]

49. Haloperidol Decanoate [ep Monograph]

50. Haloperidol Decanoate [usp Impurity]

51. Hy-107969

52. Cs-0031068

53. Ft-0669103

54. Haloperidol Decanoate [usp Monograph]

55. D01898

56. Q27273855

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₃₁H₄₁ClFNO₃
Molecular Weight	530.1 g/mol
XLogP3	7.9
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	16
Exact Mass	529.2759000 g/mol
Monoisotopic Mass	529.2759000 g/mol
Topological Polar Surface Area	46.6 Å²
Heavy Atom Count	37
Formal Charge	0
Complexity	665
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Information

1 of 2
Drug Name	Haloperidol decanoate
PubMed Health	Haloperidol Decanoate (Injection)
Drug Classes	Antipsychotic
Drug Label	Haloperidol decanoate USP is the decanoate ester of the butyrophenone, haloperidol. It has a markedly extended duration of effect. It is available in sesame oil in sterile form for intramuscular (IM) injection. The structural formula of haloperidol d...
Active Ingredient	Haloperidol decanoate
Dosage Form	Injectable
Route	Injection
Strength	eq 50mg base/ml; eq 100mg base/ml
Market Status	Prescription
Company	Teva Pharms Usa; Fresenius Kabi Usa; Eurohlth Intl; Agila Speclts

2 of 2
Drug Name	Haloperidol decanoate
PubMed Health	Haloperidol Decanoate (Injection)
Drug Classes	Antipsychotic
Drug Label	Haloperidol decanoate USP is the decanoate ester of the butyrophenone, haloperidol. It has a markedly extended duration of effect. It is available in sesame oil in sterile form for intramuscular (IM) injection. The structural formula of haloperidol d...
Active Ingredient	Haloperidol decanoate
Dosage Form	Injectable
Route	Injection
Strength	eq 50mg base/ml; eq 100mg base/ml
Market Status	Prescription
Company	Teva Pharms Usa; Fresenius Kabi Usa; Eurohlth Intl; Agila Speclts

5 Pharmacology and Biochemistry

5.1 MeSH Pharmacological Classification

Antipsychotic Agents

Agents that control agitated psychotic behavior, alleviate acute psychotic states, reduce psychotic symptoms, and exert a quieting effect. They are used in SCHIZOPHRENIA; senile dementia; transient psychosis following surgery; or MYOCARDIAL INFARCTION; etc. These drugs are often referred to as neuroleptics alluding to the tendency to produce neurological side effects, but not all antipsychotics are likely to produce such effects. Many of these drugs may also be effective against nausea, emesis, and pruritus. (See all compounds classified as Antipsychotic Agents.)

5.2 FDA Pharmacological Classification

5.2.1 Pharmacological Classes

Typical Antipsychotic [EPC]