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

    2D Structure

    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.