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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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    05-Jan-2021
    28-Oct-2024
    KGS
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    Average Price (USD/KGS)

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    Quantity (KGS) & Unit rate (USD/KGS) over time

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    (USD/KGS)    		 Number of Transactions

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