Calcitonin salmon
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Calcitonin salmon

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Calcitonin salmon, a calcium regulating hormone, has been shown to be an effective alternative for the treatment of postmenopausal osteoporosis.

Category
Peptide Inhibitors
Catalog number
BAT-006117
CAS number
47931-85-1
Molecular Formula
C145H240N44O48S2
Molecular Weight
3431.85
Calcitonin salmon
Size Price Stock Quantity
5 mg $419 In stock
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-4-yl)-1-oxopropan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-5-oxopentanoic acid
Synonyms
Salmon calcitonin; H-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 (Disulfide bridge: Cys1-Cys7); L-cysteinyl-L-seryl-L-asparagyl-L-leucyl-L-seryl-L-threonyl-L-cysteinyl-L-valyl-L-leucyl-glycyl-L-lysyl-L-leucyl-L-seryl-L-glutaminyl-L-alpha-glutamyl-L-leucyl-L-histidyl-L-lysyl-L-leucyl-L-glutaminyl-L-threonyl-L-tyrosyl-L-prolyl-L-arginyl-L-threonyl-L-asparagyl-L-threonyl-glycyl-L-seryl-glycyl-L-threonyl-L-prolinamide (1->7)-disulfide; Calciben; Calcimar; Calcitonin (salmon reduced), cyclic (1→7)-disulfide; Calsyn; Calsynar; Catonin; Karil; Miacalcic; Miacalcin; Miadenil; Prontocalcin; Rulicalcin; Salcatonin; Salmon calcitonin; Salmon calcitonin I; Salmon calcitonin-(1-32); Salmon Thyrocalcitonin; Salmotonin; SMC 021 A/C; Stalcin; Tonocalcin
Related CAS
24382-00-1 (Deleted CAS)
Appearance
White or Off-white Lyophilized Powder
Purity
98%
Density
1.54±0.1 g/cm3
Sequence
CSNLSTCVLGKLSQELHKLQTYPRTNTGSGTP-NH2 (Disulfide bridge: Cys1-Cys7)
Storage
Store at -20°C
Solubility
Soluble in Water (1 mg/mL), DMSO, Acetic Acid
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
InChI Key
BBBFJLBPOGFECG-VJVYQDLKSA-N
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
1. Impurities identification and quantification for calcitonin salmon by liquid chromatography-high resolution mass spectrometry
Ming Li,Hongmei Li,Xue Wu,Ying Kan,Peize Wu J Pharm Biomed Anal . 2020 Jul 15;186:113271. doi: 10.1016/j.jpba.2020.113271.
Calcitonin salmon is an important peptide pharmaceutical, which is mainly used for the treatment of osteoporosis and hypercalcemia. Structurally related peptide impurities in a peptide pharmaceutical probably have side effect or even toxicity, thus needs to be carefully characterized according to pharmacopoeia. With the improvement of analytical techniques, liquid chromatography-high resolution mass spectrometry (LC-HRMS) has become a pivotal technique for the identification and quantification of structurally related peptide impurities in peptide materials. In this study, an LC-HRMS-based method has been developed for the identification and quantification of structurally related peptide impurities in calcitonin salmon material. With this method, 7 peptide impurities (> 1 mg/g) in United States Pharmacopoeia (USP) reference standard and 9 peptide impurities (> 1 mg/g) in European Pharmacopoeia (EP) reference standard were identified and accurately quantified. Besides the peptide impurities reported by USP and EP, several new impurities such as [7-Dehydroalanine] calcitonin salmon, triple-sulfate-calcitonin salmon, [26-Proline] calcitonin salmon, [14-Glutamic acid] calcitonin salmon, [20-Glutamic acid] calcitonin salmon, [26-Aspartic acid] calcitonin salmon, calcitonin salmon acid were observed in the reference standard materials studied. The total mass fractions of all structurally related peptide impurities in calcitonin salmon study materials were estimated to be 57.4 mg/g for USP and 46.3 mg/g for EP with associated expended uncertainties at a 95 % confidence level of 5.2 mg/g (k = 2) and 3.1 mg/g (k = 2), respectively.
2. Supramolecular nanoassemblies of salmon calcitonin and aspartame for fibrillation inhibition and osteogenesis improvement
Jianshu Li,Hui Sun,Zhao Xu,Jing Xie,Xinyuan Xu,Peng Yu,Xueyuan Zhai,Yanpeng Liu Int J Pharm . 2021 Jan 25;593:120171. doi: 10.1016/j.ijpharm.2020.120171.
Osteoporosis therapy consists of inhibiting the osteoclasts' activity and promoting osteoblasts' osteogenesis. Salmon calcitonin (sCT) could realize both requirements, however, it is limited by the low bioavailability caused by fibrillation. Supramolecular assembly of sCT and biocompatible agents into nanoassemblies provides an opportunity to overcome these shortcomings. Herein, we used a facile method to fabricate salmon calcitonin-aspartame (sCT-APM) nanoassemblies. Supramolecular interactions could not only delay fibrillation time (from 36.9 h to 50.4 h), but also achieve sustained sCT release. Moreover, sCT-APM showed good biocompatibility and higher osteoinductive capacity than free sCT, revealing an osteogenesis improvement effect. Moreover, in vivo studies showed that sCT-APM has enhanced relative bioavailability (2.42-fold of sCT) and increased relative therapeutic efficacy (3.55-fold of sCT) through subcutaneous injection. These findings provide a convenient alternative strategy for osteoporosis therapy via supramolecular assemblies.
3. Salmon calcitonin in the acute management of hypercalcemia
L A Wisneski Calcif Tissue Int . 1990;46 Suppl:S26-30. doi: 10.1007/BF02553290.
Salmon calcitonin has been used for the management of acute hypercalcemia for the past several years. Unlike other hypocalcemic agents, it is effective within 2 hours after first dosing. This pharmacologic agent shows peak effect at 24-48 hours and has a duration of action of 4-7 days in most cases. Its effectiveness may diminish thereafter despite continuous administration (the so-called "escape phenomenon"). Salmon calcitonin has been shown to be effective in the management of acute hypercalcemia due to a variety of causes, and, because of its low toxicity profile, it may be administered to patients with congestive heart failure or azotemia. Salmon calcitonin is also an analgesic agent in patients with pain associated with bone metastases and may be used in conjunction with other hypocalcemic agents such as mithramycin, the bisphosphonates, or gallium nitrate to prolong the clinical response to more than 1 week. Salmon calcitonin is therefore effective and safe in the management of acute hypercalcemia.
4. Salmon calcitonin use and associated cancer risk
Mrudula Borse,Margaret L Gourlay,Robert A Overman Ann Pharmacother . 2013 Dec;47(12):1675-84. doi: 10.1177/1060028013509233.
Objective:To evaluate the strength of evidence supporting a possible association between salmon calcitonin (SCT) use and cancer incidence.Data sources:Searches of MEDLINE/PubMed, MEDLINE/OVID, and EMBASE (January 1973 to September 2013) were performed using the key search terms salmon calcitonin, humans, nasal calcitonin, and (for EMBASE only) randomized controlled trial. We also performed a manual review of data reviewed by the US Food and Drug Administration (FDA) committee in 2013.Study selection and data extraction:All articles identified from the data sources were evaluated and all information deemed relevant was included for this review.Data synthesis:Intranasal and injectable SCT are FDA-approved for the treatment of postmenopausal osteoporosis. After a safety signal suggested a possible link between SCT use and prostate cancer, the European Medicines Agency and FDA regulatory agencies conducted analyses of SCT randomized controlled trial data to assess cancer-related adverse events and to readdress the approval status of SCT. Eighteen studies were found that compared nasal or oral SCT and placebo. In 15 of the 18 studies, the percentage of malignancy was greater in the SCT arm. The studies varied in quality, outcomes, and length. Most of the studies had poor-quality methods to assess new cancer cases.Conclusions:Current evidence may suggest an association between SCT use and cancer incidence based on studies with poor-quality cancer assessment methods. However, considering the lack of demonstrated efficacy of SCT to reduce fractures, clinicians should consider discontinuing its use for osteoporosis treatment regardless of the FDA's final approval decision.
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