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CAS 119356-77-3
PharmaCompass
  • Chemistry
CAS 119356-77-3
Also known as: 119356-77-3, Dapoxetine hydrochloride, (s)-n,n-dimethyl-3-(naphthalen-1-yloxy)-1-phenylpropan-1-amine, Dapoxetinum, Dapoxetina, Dapoxetinum [inn-latin]
Molecular Formula
C21H23NO
Molecular Weight
305.421  g/mol
InChI Key
USRHYDPUVLEVMC-FQEVSTJZSA-N
FDA UNII
GB2433A4M3

Dapoxetine is a selective serotonin reuptake inhibitor, for the treatment of premature ejaculation. In a phase II proof-of-concept study conducted by PPD, dapoxetine demonstrated a statistically significant increase in ejaculatory latency when compared to placebo. Alza submitted a NDA to the FDA for dapoxetine for the treatment of premature ejaculation in December 2004. In October 2005, the company received a FDA Non-Approvable letter from the FDA, at which time they planned to work with regulators to address outstanding questions.
1 2D Structure

CAS 119356-77-3

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(1S)-N,N-dimethyl-3-naphthalen-1-yloxy-1-phenylpropan-1-amine
2.1.2 InChI
InChI=1S/C21H23NO/c1-22(2)20(18-10-4-3-5-11-18)15-16-23-21-14-8-12-17-9-6-7-13-19(17)21/h3-14,20H,15-16H2,1-2H3/t20-/m0/s1
2.1.3 InChI Key
USRHYDPUVLEVMC-FQEVSTJZSA-N
2.1.4 Canonical SMILES
CN(C)C(CCOC1=CC=CC2=CC=CC=C21)C3=CC=CC=C3
2.1.5 Isomeric SMILES
CN(C)[C@@H](CCOC1=CC=CC2=CC=CC=C21)C3=CC=CC=C3
2.2 Other Identifiers
2.2.1 UNII
GB2433A4M3
2.3 Synonyms
2.3.1 Depositor-Supplied Synonyms

1. 119356-77-3

2. Dapoxetine Hydrochloride

3. (s)-n,n-dimethyl-3-(naphthalen-1-yloxy)-1-phenylpropan-1-amine

4. Dapoxetinum

5. Dapoxetina

6. Dapoxetinum [inn-latin]

7. Dapoxetina [inn-spanish]

8. Ly 210448

9. Unii-gb2433a4m3

10. Ly210448

11. Ly-210448

12. Ak-75706

13. (1s)-n,n-dimethyl-3-naphthalen-1-yloxy-1-phenylpropan-1-amine

14. Benzenemethanamine, N,n-dimethyl-alpha-(2-(1-naphthalenyloxy)ethyl)-, (+)-

15. Dapoxetine [inn]

16. (s)-dapoxetine

17. Priligy (tn)

18. (1s)-n,n-dimethyl-3-(1-naphthyloxy)-1-phenylpropan-1-amine

19. (s)-(+)-dapoxetine

20. Kutub, Priligy, Duratia

21. D0h5lk

22. Dsstox_cid_31416

23. Dsstox_rid_97302

24. Dsstox_gsid_57627

25. Schembl34479

26. Ac1l2g02

27. Ac1q583d

28. Gtpl7901

29. Chembl2110900

30. Dtxsid0057627

31. Ctk8c4400

32. Ks-00000yxq

33. Chebi:135962

34. Molport-006-170-018

35. Usrhydpuvlevmc-fqevstjzsa-n

36. Gb2433a4m3

37. Zinc1482019

38. 129938-20-1 (hydrochloride)

39. Tox21_113784

40. An-609

41. Anw-71765

42. Akos015895183

43. Api0006377

44. Db04884

45. Rtr-003255

46. Ncgc00253658-01

47. Ncgc00253658-02

48. Ac-22603

49. Aj-26308

50. Cc-26257

51. Kb-49572

52. Ls-30482

53. M246

54. Ax8009147

55. Bg01597565

56. Cas-119356-77-3

57. Ft-0603130

58. St24046417

59. Ab01274725-01

60. Ab01274725_02

61. 356d773

62. C-19027

63. I06-1892

64. (1s)-n,n-dimethyl-3-(1-naphthyloxy)-1-phenyl-propan-1-amine

2.4 Create Date
2005-08-08
3 Chemical and Physical Properties
Molecular Weight 305.421 g/mol
Molecular Formula C21H23NO
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count2
Rotatable Bond Count6
Exact Mass305.178 g/mol
Monoisotopic Mass305.178 g/mol
Topological Polar Surface Area12.5 A^2
Heavy Atom Count23
Formal Charge0
Complexity337
Isotope Atom Count0
Defined Atom Stereocenter Count1
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Indication

For the treatment of premature ejaculation.


Treatment of premature ejaculation (PE) in men 18 to 64 years of age


5 Pharmacology and Biochemistry
5.1 Pharmacology

Dapoxetine is a selective serotonin reuptake inhibitor currently undergoing trials through Alza (under license from GenuPro, a collaboration between Eli Lilly and PPD). Dapoxetine is a short-acting SSRI drug currently being considered for approval by the Food and Drug Administration (FDA) for the treatment of premature ejaculation in men, which would make it the first drug approved for such treatment. Despite two clinical trials finished in 2006, experts doubt it will be approved by the FDA soon because SSRIs come with undesirable side-effects after long-term use, such as psychiatric problems, dermatological reactions, increase in body weight, lower sex-drive, nausea, headache, upset stomach and weakness, thus not significantly outweighing the benefit of premature ejaculation medication versus the risks. By contrast with SSRIs approved for depression, which take 2 weeks or longer to reach steady-state concentration, dapoxetine has a unique pharmacokinetic profile, with a short time to maximum serum concentration (about 1 h) and rapid elimination (initial half-life of 1-2 h).


5.2 ATC Code

G - Genito urinary system and sex hormones
G04 - Urologicals
G04B - Urologicals
G04BX - Other urologicals
G04BX14 - Dapoxetine


5.3 Absorption, Distribution and Excretion

Absorption

Rapidly absorbed.


5.4 Biological Half-Life

Initial half-life of 1-2 hours.


5.5 Mechanism of Action

The drug's mechanism of action is thought to be related to inhibition of neuronal reuptake of serotonin and subsequent potentiation of serotonin activity. The central ejaculatory neural circuit comprises spinal and cerebral areas that form a highly interconnected network. The sympathetic, parasympathetic, and somatic spinal centers, under the influence of sensory genital and cerebral stimuli integrated and processed at the spinal cord level, act in synergy to command physiologic events occurring during ejaculation. Experimental evidence indicates that serotonin (5-HT), throughout brain descending pathways, exerts an inhibitory role on ejaculation. To date, three 5-HT receptor subtypes (5-HT(1A), 5-HT(1B), and 5-HT(2C)) have been postulated to mediate 5-HT's modulating activity on ejaculation.


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