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Chemistry

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Also known as: Calcitonin-salmon, Thyrocalcitonin (salmon), Cibacalcin, Calcitonina, Calcitar, Bionocalcin
Molecular Formula
C145H240N44O48S2
Molecular Weight
3431.9  g/mol
InChI Key
BBBFJLBPOGFECG-VJVYQDLKSA-N

Calcitonin
Synthetic peptide, 32 residues long formulated as a nasal spray.
1 2D Structure

Calcitonin

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(4S)-4-[[(2S)-5-amino-2-[[(2S)-2-[[(2S)-2-[[(2S)-6-amino-2-[[2-[[(2S)-2-[[(2S)-2-[[(4R,7S,10S,13S,16S,19S,22R)-22-amino-16-(2-amino-2-oxoethyl)-7-[(1R)-1-hydroxyethyl]-10,19-bis(hydroxymethyl)-13-(2-methylpropyl)-6,9,12,15,18,21-hexaoxo-1,2-dithia-5,8,11,14,17,20-hexazacyclotricosane-4-carbonyl]amino]-3-methylbutanoyl]amino]-4-methylpentanoyl]amino]acetyl]amino]hexanoyl]amino]-4-methylpentanoyl]amino]-3-hydroxypropanoyl]amino]-5-oxopentanoyl]amino]-5-[[(2S)-1-[[(2S)-1-[[(2S)-6-amino-1-[[(2S)-1-[[(2S)-5-amino-1-[[(2S,3R)-1-[[(2S)-1-[(2S)-2-[[(2S)-1-[[(2S,3R)-1-[[(2S)-4-amino-1-[[(2S,3R)-1-[[2-[[(2S)-1-[[2-[[(2S,3R)-1-[(2S)-2-carbamoylpyrrolidin-1-yl]-3-hydroxy-1-oxobutan-2-yl]amino]-2-oxoethyl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-hydroxy-1-oxobutan-2-yl]amino]-1,4-dioxobutan-2-yl]amino]-3-hydroxy-1-oxobutan-2-yl]amino]-5-carbamimidamido-1-oxopentan-2-yl]carbamoyl]pyrrolidin-1-yl]-3-(4-hydroxyphenyl)-1-oxopropan-2-yl]amino]-3-hydroxy-1-oxobutan-2-yl]amino]-1,5-dioxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-1-oxohexan-2-yl]amino]-3-(1H-imidazol-5-yl)-1-oxopropan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-5-oxopentanoic acid
2.1.2 InChI
InChI=1S/C145H240N44O48S2/c1-65(2)45-86(175-139(232)110(70(11)12)183-136(229)99-63-239-238-62-79(148)117(210)178-96(59-191)134(227)174-92(52-104(151)202)131(224)172-90(49-69(9)10)129(222)180-98(61-193)135(228)187-114(74(16)197)142(235)181-99)118(211)158-55-106(204)162-80(25-18-20-40-146)120(213)169-89(48-68(7)8)128(221)179-97(60-192)133(226)167-83(34-37-102(149)200)122(215)165-85(36-39-109(207)208)123(216)171-88(47-67(5)6)127(220)173-91(51-77-54-156-64-161-77)130(223)164-81(26-19-21-41-147)121(214)170-87(46-66(3)4)126(219)166-84(35-38-103(150)201)125(218)186-113(73(15)196)141(234)177-94(50-76-30-32-78(199)33-31-76)143(236)189-44-24-29-101(189)137(230)168-82(27-22-42-157-145(154)155)124(217)185-112(72(14)195)140(233)176-93(53-105(152)203)132(225)184-111(71(13)194)138(231)160-56-107(205)163-95(58-190)119(212)159-57-108(206)182-115(75(17)198)144(237)188-43-23-28-100(188)116(153)209/h30-33,54,64-75,79-101,110-115,190-199H,18-29,34-53,55-63,146-148H2,1-17H3,(H2,149,200)(H2,150,201)(H2,151,202)(H2,152,203)(H2,153,209)(H,156,161)(H,158,211)(H,159,212)(H,160,231)(H,162,204)(H,163,205)(H,164,223)(H,165,215)(H,166,219)(H,167,226)(H,168,230)(H,169,213)(H,170,214)(H,171,216)(H,172,224)(H,173,220)(H,174,227)(H,175,232)(H,176,233)(H,177,234)(H,178,210)(H,179,221)(H,180,222)(H,181,235)(H,182,206)(H,183,229)(H,184,225)(H,185,217)(H,186,218)(H,187,228)(H,207,208)(H4,154,155,157)/t71-,72-,73-,74-,75-,79+,80+,81+,82+,83+,84+,85+,86+,87+,88+,89+,90+,91+,92+,93+,94+,95+,96+,97+,98+,99+,100+,101+,110+,111+,112+,113+,114+,115+/m1/s1
2.1.3 InChI Key
BBBFJLBPOGFECG-VJVYQDLKSA-N
2.1.4 Canonical SMILES
CC(C)CC1C(=O)NC(C(=O)NC(C(=O)NC(CSSCC(C(=O)NC(C(=O)NC(C(=O)N1)CC(=O)N)CO)N)C(=O)NC(C(C)C)C(=O)NC(CC(C)C)C(=O)NCC(=O)NC(CCCCN)C(=O)NC(CC(C)C)C(=O)NC(CO)C(=O)NC(CCC(=O)N)C(=O)NC(CCC(=O)O)C(=O)NC(CC(C)C)C(=O)NC(CC2=CN=CN2)C(=O)NC(CCCCN)C(=O)NC(CC(C)C)C(=O)NC(CCC(=O)N)C(=O)NC(C(C)O)C(=O)NC(CC3=CC=C(C=C3)O)C(=O)N4CCCC4C(=O)NC(CCCNC(=N)N)C(=O)NC(C(C)O)C(=O)NC(CC(=O)N)C(=O)NC(C(C)O)C(=O)NCC(=O)NC(CO)C(=O)NCC(=O)NC(C(C)O)C(=O)N5CCCC5C(=O)N)C(C)O)CO
2.1.5 Isomeric SMILES
C[C@H]([C@H]1C(=O)N[C@@H](CSSC[C@@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N1)CO)CC(C)C)CC(=O)N)CO)N)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC(C)C)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCC(=O)N)C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC2=CN=CN2)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(=O)N)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC3=CC=C(C=C3)O)C(=O)N4CCC[C@H]4C(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC(=O)N)C(=O)N[C@@H]([C@@H](C)O)C(=O)NCC(=O)N[C@@H](CO)C(=O)NCC(=O)N[C@@H]([C@@H](C)O)C(=O)N5CCC[C@H]5C(=O)N)O
2.2 Synonyms
2.2.1 MeSH Synonyms

1. Calcihexal

2. Calcimar

3. Calcitonin Salmon

4. Forcaltonin

5. Fortical

6. Miacalcic

7. Miacalcin

8. Recombinant Salmon Calcitonin

9. Salcatonin

10. Salmon Calcitonin (1-32)

11. Synthetic Salmon Calcitonin

2.2.2 Depositor-Supplied Synonyms

1. Calcitonin-salmon

2. Thyrocalcitonin (salmon)

3. Cibacalcin

4. Calcitonina

5. Calcitar

6. Bionocalcin

7. Calcimonta

8. Calcitoran

9. Cibacalcine

10. Eptacalcin

11. Miracalcic

12. Osseocalcina

13. Ostostabil

14. Porostenina

15. Prontocalcin

16. Rulicalcin

17. Salmocalcin

18. Salmotonin

19. Tonocalcin

20. Astronin

21. Biocalcin

22. Calciben

23. Calcinil

24. Calcioton

25. Calogen

26. Calsynar

27. Caltine

28. Catonin

29. Citonina

30. Ipocalcin

31. Kalsimin

32. Oseototal

33. Osteobion

34. Osteovis

35. Ostosalm

36. Quosten

37. Riostin

38. Salcatyn

39. Salmofar

40. Stalcin

41. Staporos

42. Steocin

43. Cadens

44. Casalm

45. Ostora

46. Salcat

47. Ucecal

48. Calco

49. Karil

50. Sical

51. Isi-calcin

52. Calcitonin,salmon

53. Calsynar Lyo L

54. Calcitonin(salmon)

55. Calcitonin, Salmar

56. Salmon Calcitonin I

57. Calcitonin Vom Lachs

58. Calcitonine De Saumon

59. Tz-ct

60. Unii-7sfc6u2vi5

61. Salmon Calcitonin-(i-32)

62. 7sfc6u2vi5

63. Salmon Calcitonin-(1-32)

64. Chebi:3306

65. Calcitonin, Salmon, For Bioassay

66. Dtxsid601026667

67. Calcitonin [usan:inn:ban:jan]

68. Einecs 256-342-8

69. Ncgc00167232-01

70. Calcitonin Salmon, >=97% (hplc), Powder

71. Calcitonin Salmon, European Pharmacopoeia (ep) Reference Standard

72. Calcitonin Salmon, United States Pharmacopeia (usp) Reference Standard

73. Cyclo-[cys-ser-asn-leu-ser-thr-cys]-val-leu-gly-lys-leu-ser-gln-glu-leu-his-lys-leu-gln-thr-tyr-pro-arg-thr-asn-thr-gly-ser-gly-thr-pro-nh2

2.3 Create Date
2007-07-16
3 Chemical and Physical Properties
Molecular Weight 3431.9 g/mol
Molecular Formula C145H240N44O48S2
XLogP3-16.6
Hydrogen Bond Donor Count52
Hydrogen Bond Acceptor Count55
Rotatable Bond Count99
Exact Mass3430.7166627 g/mol
Monoisotopic Mass3429.7133079 g/mol
Topological Polar Surface Area1560 Ų
Heavy Atom Count239
Formal Charge0
Complexity7970
Isotope Atom Count0
Defined Atom Stereocenter Count34
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

Used in the treatment of symptomatic Paget's disease for patients unresponsive to alternate treatments or intolerant to such treatments. In addition, it is used in emergency situations when serum calcium levels must be decreased quickly until the underlying condition is identified. It can also be added to existing therapeutic regimens for hypercalcemia such as intravenous fluids and furosemide, oral phosphate or corticosteroids, or other agents. Calcitonin can be used in patients with azotemia and cases where intravenous fluids would be contraindicated due to limited cardiac reserves. Also for the treatment of post-menopausal osteoporosis in women more than 5 years post-menopause.


5 Pharmacology and Biochemistry
5.1 Pharmacology

Calcitonin inhibits bone resorption by osteoclasts (bone remodeling cells) and promotes bone formation by osteoblasts. This leads to a net increase in bone mass and a reduction in plasma calcium levels. It also promotes the renal excretion of ions such as calcium, phosphate, sodium, magnesium, and potassium by decreasing tubular reabsorption. In consequence, there is an increase in the jejunal secretion of water, sodium, potassium, and chloride.


5.2 MeSH Pharmacological Classification

Bone Density Conservation Agents

Agents that inhibit BONE RESORPTION and/or favor BONE MINERALIZATION and BONE REGENERATION. They are used to heal BONE FRACTURES and to treat METABOLIC BONE DISEASES such as OSTEOPOROSIS. (See all compounds classified as Bone Density Conservation 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.)


5.3 Absorption, Distribution and Excretion

Absorption

Salmon calcitonin is rapidly absorbed with bioavailability of 71% following subcutaneous injection and 66% following intramuscular injection in humans. Via the nasal route, the bioavailability varies between 3 to 5% relative to IM.


Route of Elimination

Urine. Studies with injectable calcitonin show increases in the excretion of filtered phosphate, calcium, and sodium by decreasing their tubular reabsorption in the kidney.


Volume of Distribution

0.15 to 0.3 L/kg


5.4 Metabolism/Metabolites

Salmon calcitonin primarily undergoes degradation in the kidneys to form pharmacologically inactive metabolites. It is also metabolized in the blood and the peripheral tissue.


5.5 Biological Half-Life

Half-life elimination (terminal): I.M. 58 minutes; SubQ 59 to 64 minutes; Nasal: ~18 to 23 minutes


5.6 Mechanism of Action

Calcitonin binds to the calcitonin receptor (found primarily in osteoclasts) which then enhances the production of vitamin D producing enzymes (25-hydroxyvitamine D-24-hydroxylase), leading to greater calcium retention and enhanced bone density. Binding of calcitonin to its receptor also activates adenylyl cyclase and the phosphatidyl-inositol-calcium pathway.


API Reference Price

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30-Jan-2021
02-Apr-2024
KGS
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DOSAGE - INJECTABLE;INJECTION - 100 IU/ML **F...DOSAGE - INJECTABLE;INJECTION - 100 IU/ML **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

USFDA APPLICATION NUMBER - 17808

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DOSAGE - INJECTABLE;INJECTION - 200 IU/ML

USFDA APPLICATION NUMBER - 17808

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DOSAGE - SPRAY, METERED;NASAL - 200 IU/SPRAY ...DOSAGE - SPRAY, METERED;NASAL - 200 IU/SPRAY **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

USFDA APPLICATION NUMBER - 20313

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