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Chemistry

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Also known as: 364782-34-3, Cinacalcet hcl, Sensipar, Mimpara, Amg073 hcl, Regpara
Molecular Formula
C22H23ClF3N
Molecular Weight
393.9  g/mol
InChI Key
QANQWUQOEJZMLL-PKLMIRHRSA-N
FDA UNII
1K860WSG25

Cinacalcet Hydrochloride
Cinacalcet Hydrochloride is the orally bioavailable hydrochloride salt of the calcimimetic cinacalcet. Cinacalcet increases the sensitivity of calcium-sensing receptors on chief cells in the parathyroid gland to extracellular calcium, thereby reducing parathyroid hormone (PTH) secretion. A reduction in PTH levels inhibits osteoclast activity, which may result in a decrease in cortical bone turnover and bone fibrosis, and normalization of serum calcium and phosphorus levels. In addition, by reducing PTH levels, cinacalcet may reduce PSA levels; PTH appears to raise PSA levels and may increase prostate cancer cell growth.
1 2D Structure

Cinacalcet Hydrochloride

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
N-[(1R)-1-naphthalen-1-ylethyl]-3-[3-(trifluoromethyl)phenyl]propan-1-amine;hydrochloride
2.1.2 InChI
InChI=1S/C22H22F3N.ClH/c1-16(20-13-5-10-18-9-2-3-12-21(18)20)26-14-6-8-17-7-4-11-19(15-17)22(23,24)25;/h2-5,7,9-13,15-16,26H,6,8,14H2,1H3;1H/t16-;/m1./s1
2.1.3 InChI Key
QANQWUQOEJZMLL-PKLMIRHRSA-N
2.1.4 Canonical SMILES
CC(C1=CC=CC2=CC=CC=C21)NCCCC3=CC(=CC=C3)C(F)(F)F.Cl
2.1.5 Isomeric SMILES
C[C@H](C1=CC=CC2=CC=CC=C21)NCCCC3=CC(=CC=C3)C(F)(F)F.Cl
2.2 Other Identifiers
2.2.1 UNII
1K860WSG25
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Alpha-methyl-n-(3-(3-(trifluoromethyl)phenyl)propyl)-1-naphthalenemethanamine, (alphar)-hydrochloride

2. Amg 073

3. Amg073

4. Cinacalcet

5. Krn 1493

6. Sensipar

2.3.2 Depositor-Supplied Synonyms

1. 364782-34-3

2. Cinacalcet Hcl

3. Sensipar

4. Mimpara

5. Amg073 Hcl

6. Regpara

7. (r)-n-(1-(naphthalen-1-yl)ethyl)-3-(3-(trifluoromethyl)phenyl)propan-1-amine Hydrochloride

8. Cinacalcet, Hcl

9. Cinacalcet Hydrochloride [usan]

10. Cinacalcet (hydrochloride)

11. Amg-073 Hcl

12. Amg073 Hydrochloride

13. Chebi:48391

14. 1k860wsg25

15. Parareg

16. N-[(1r)-1-naphthalen-1-ylethyl]-3-[3-(trifluoromethyl)phenyl]propan-1-amine;hydrochloride

17. Amg-073 Hcl (cinacalcet Hydrochloride)

18. 364782-34-3 (hcl)

19. [(1r)-1-(naphthalen-1-yl)ethyl]({3-[3-(trifluoromethyl)phenyl]propyl})amine Hydrochloride

20. Dsstox_cid_26792

21. Dsstox_rid_81909

22. N-((1r)-1-(naphthalen-1-yl)ethyl)-3-(3-(trifluoromethyl)phenyl)propan-1-amine Hydrochloride

23. N-[(1r)-1-(1-naphthyl)ethyl]-3-[3-(trifluoromethyl)phenyl]propan-1-amine Hydrochloride

24. Dsstox_gsid_46792

25. (r)-n-(1-(naphthalen-1-yl)ethyl)-3-(3-(trifluoro-methyl)phenyl)propan-1-amine Hydrochloride

26. Smr002530058

27. Cas-364782-34-3

28. Krn 1493

29. Ncgc00181002-01

30. Amg 073 Hcl

31. Unii-1k860wsg25

32. Sensipar (tn)

33. Mimpara (tn)

34. Cnc-hcl

35. Cinacelcet Hydrochloride

36. Sensipar(tm)

37. Amg-073 Hydrochloride

38. Amg-073.hcl

39. Mls004774045

40. Mls006010213

41. Chembl1200776

42. Dtxsid3046792

43. Bcpp000409

44. Bcp02533

45. Nps-1493

46. Tox21_112654

47. Cinacalcet Hydrochloride (jan/usan)

48. Cinacalcet Hydrochloride [mi]

49. Hy-70037a

50. Mfcd08067750

51. S1260

52. Cinacalcet Hydrochloride [jan]

53. Akos005146514

54. Akos015969126

55. Tox21_112654_1

56. Ac-1799

57. Am90312

58. Bcp9000286

59. Ccg-268579

60. Cs-0288

61. Gs-4171

62. Cinacalcet Hydrochloride [mart.]

63. Cinacalcet Hydrochloride [usp-rs]

64. Cinacalcet Hydrochloride [who-dd]

65. Ncgc00181002-04

66. 1-naphthalenemethanamine, Alpha-methyl-n-(3-(3-(trifluoromethyl)phenyl)propyl)-, (alphar)-, Hydrochloride

67. Sw219246-1

68. Cinacalcet Hydrochloride [orange Book]

69. D03505

70. 782c343

71. J-520045

72. Q27121179

73. Z1741977003

74. (r)-n-(1-(naphthalen-1-yl)ethyl)-3-(3-(trifluoromethyl)phenyl)propan-1-amine Hcl

75. (r)-n-(3-(3-(trifluoromethyl)phenyl)propyl)-1- -(1-napthyl)ethylamine Hydrochloride

76. (alphar)-alpha-methyl-n-[3-[3-(trifluoromethyl)phenyl)propyl]-1-napthalenemethanamine Hydrochloride

77. 1-naphthalenemethanamine, .alpha.-methyl-n-(3-(3-(trifluoromethyl)phenyl)propyl)-, (.alpha.r)-, Hydrochloride

78. 1-naphthalenemethanamine, Alpha-methyl-n-[3-[3-(trifluoromethyl)phenyl]propyl]-, Hydrochloride (1:1), (alphar)-

79. 1-naphthalenemethanamine,a-methyl-n-[3-[3-(trifluoromethyl)phenyl]propyl]-, Hydrochloride, (ar)-

2.4 Create Date
2005-08-08
3 Chemical and Physical Properties
Molecular Weight 393.9 g/mol
Molecular Formula C22H23ClF3N
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count4
Rotatable Bond Count6
Exact Mass393.1471119 g/mol
Monoisotopic Mass393.1471119 g/mol
Topological Polar Surface Area12 Ų
Heavy Atom Count27
Formal Charge0
Complexity422
Isotope Atom Count0
Defined Atom Stereocenter Count1
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count2
4 Drug and Medication Information
4.1 Drug Information
1 of 4  
Drug NameCinacalcet hydrochloride
PubMed HealthCinacalcet (By mouth)
Drug ClassesCalcium Regulator
Drug LabelSensipar (cinacalcet) is a calcimimetic agent that increases the sensitivity of the calcium-sensing receptor to activation by extracellular calcium. Its empirical formula is C22H22F3NHCl with a molecular weight of 393.9 g/mol (hydrochloride salt...
Active IngredientCinacalcet hydrochloride
Dosage FormTablet
Routeoral
Strength60mg; 30mg; 90mg
Market StatusTentative Approval
CompanyTeva Pharms; Barr

2 of 4  
Drug NameSensipar
Drug LabelSensipar (cinacalcet) is a calcimimetic agent that increases the sensitivity of the calcium-sensing receptor to activation by extracellular calcium. Its empirical formula is C22H22F3NHCl with a molecular weight of 393.9 g/mol (hydrochloride salt...
Active IngredientCinacalcet hydrochloride
Dosage FormTablet
RouteOral
Strengtheq 90mg base; eq 30mg base; eq 60mg base
Market StatusPrescription
CompanyAmgen

3 of 4  
Drug NameCinacalcet hydrochloride
PubMed HealthCinacalcet (By mouth)
Drug ClassesCalcium Regulator
Drug LabelSensipar (cinacalcet) is a calcimimetic agent that increases the sensitivity of the calcium-sensing receptor to activation by extracellular calcium. Its empirical formula is C22H22F3NHCl with a molecular weight of 393.9 g/mol (hydrochloride salt...
Active IngredientCinacalcet hydrochloride
Dosage FormTablet
Routeoral
Strength60mg; 30mg; 90mg
Market StatusTentative Approval
CompanyTeva Pharms; Barr

4 of 4  
Drug NameSensipar
Drug LabelSensipar (cinacalcet) is a calcimimetic agent that increases the sensitivity of the calcium-sensing receptor to activation by extracellular calcium. Its empirical formula is C22H22F3NHCl with a molecular weight of 393.9 g/mol (hydrochloride salt...
Active IngredientCinacalcet hydrochloride
Dosage FormTablet
RouteOral
Strengtheq 90mg base; eq 30mg base; eq 60mg base
Market StatusPrescription
CompanyAmgen

4.2 Drug Indication

* Secondary hyperparathyroidism :

Adults

Treatment of secondary hyperparathyroidism (HPT) in adult patients with end-stage renal disease (ESRD) on maintenance dialysis therapy.

Paediatric population

Treatment of secondary hyperparathyroidism (HPT) in children aged 3 years and older with end-stage renal disease (ESRD) on maintenance dialysis therapy in whom secondary HPT is not adequately controlled with standard of care therapy (see section 4. 4).

Cinacalcet Accordpharma may be used as part of a therapeutic regimen including phosphate binders and/or Vitamin D sterols, as appropriate (see section 5. 1).

* Parathyroid carcinoma and primary hyperparathyroidism in adults:

Reduction of hypercalcaemia in adult patients with:

- parathyroid carcinoma.

- primary HPT for whom parathyroidectomy would be indicated on the basis of serum calcium levels (as defined by relevant treatment guidelines), but in whom parathyroidectomy is not clinically appropriate or is contraindicated.


Treatment of secondary hyperparathyroidism (HPT) in patients with end-stage renal disease (ESRD) on maintenance dialysis therapy.

Cinacalcet Mylan may be used as part of a therapeutic regimen including phosphate binders and/or vitamin D sterols, as appropriate.

Reduction of hypercalcaemia in patients with:

- parathyroid carcinoma

- primary HPT for whom parathyroidectomy

would be indicated on the basis of serum calcium levels (as defined by relevant treatment guidelines), but in whom parathyroidectomy is not clinically appropriate or is contraindicated.


* Secondary hyperparathyroidism :

Adults

Treatment of secondary hyperparathyroidism (HPT) in adult patients with end stage renal disease (ESRD) on maintenance dialysis therapy.

Paediatric population

Treatment of secondary hyperparathyroidism (HPT) in children aged 3 years and older with end stage renal disease (ESRD) on maintenance dialysis therapy in whom secondary HPT is not adequately controlled with standard of care therapy.

Mimpara may be used as part of a therapeutic regimen including phosphate binders and/or Vitamin D sterols, as appropriate.

Parathyroid carcinoma and primary hyperparathyroidism in adults.

Reduction of hypercalcaemia in adult patients with:

- parathyroid carcinoma;

- primary HPT for whom parathyroidectomy would be indicated on the basis of serum calcium levels (as defined by relevant treatment guidelines), but in whom parathyroidectomy is not clinically appropriate or is contraindicated.


Treatment of secondary hyperparathyroidism (HPT) in patients with end-stage renal disease (ESRD) on maintenance dialysis therapy.

Mimpara may be used as part of a therapeutic regimen including phosphate binders and/or Vitamin D sterols, as appropriate (see section 5. 1).

Reduction of hypercalcaemia in patients with:

-parathyroid carcinoma.

- primary HPT for whom parathyroidectomy would be indicated on the basis of serum calcium

levels (as defined by relevant treatment guidelines), but in whom parathyroidectomy is not clinically appropriate or is contraindicated.


Treatment of parathyroid carcinoma, Treatment of primary hyperparathyroidism , Treatment of secondary hyperparathyroidism in patients with end-stage renal disease


5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

Calcimimetic Agents

Small organic molecules that act as allosteric activators of the calcium sensing receptor (CaSR) in the PARATHYROID GLANDS and other tissues. They lower the threshold for CaSR activation by extracellular calcium ions and diminish PARATHYROID HORMONE (PTH) release from parathyroid cells. (See all compounds classified as Calcimimetic Agents.)


Calcium-Regulating Hormones and Agents

Hormones and molecules with calcium-regulating hormone-like actions that modulate OSTEOLYSIS and other extra-skeletal activities to maintain calcium homeostasis. (See all compounds classified as Calcium-Regulating Hormones and Agents.)


5.2 FDA Pharmacological Classification
5.2.1 Pharmacological Classes
Increased Calcium-sensing Receptor Sensitivity [MoA]; Calcium-sensing Receptor Agonist [EPC]
5.3 ATC Code

H05BX01


H05BX01


H05BX01


H05BX01


API Reference Price

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