Etelcalcetide HCl
featured

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 326730

CAS#: 1334237-71-6 (HCl)

Description: Etelcalcetide, also known as AMG 416 and KAI-4169, is a D-amino peptide calcimimetic undergoing clinical evaluation for the treatment of secondary hyperparathyroidism for patients with chronic kidney disease (CKD) on hemodialysis. Etelcalcetide is administered intravenously at the end of each dialysis session. It functions by binding to and activating the calcium-sensing receptor (CaSR) in the parathyroid gland as an allosteric activator, resulting in PTH reduction and suppression. Elevated PTH is often observe in patients with CKD. On August 25, 2015 Amgen Inc. announced its submission of a New Drug Application to the Food and Drug Administration for etelcalcetide.

Chemical Structure

img
Etelcalcetide HCl
CAS# 1334237-71-6 (HCl)
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 326730
Name: Etelcalcetide HCl
CAS#: 1334237-71-6 (HCl)
Chemical Formula: C38H77Cl4N21O10S2
Exact Mass: 0.00
Molecular Weight: 1,194.090
Elemental Analysis: C, 38.22; H, 6.50; Cl, 11.88; N, 24.63; O, 13.40; S, 5.37

Price and Availability

Size Price Availability Quantity
1mg USD 210 2 Weeks
5mg USD 430 2 Weeks
10mg USD 715 2 Weeks
Bulk inquiry

Related CAS #: 1334237-71-6 (HCl)   1262780-97-1 (free base),  

Synonym: AMG-416, AMG416, AMG 416, KAI-4169, KAI 4169, KAI4169, ONO5163, ONO-5163, ONO 5163, Etelcalcetide, Velcalcetide, Telcalcetide. Ac-D-Cys-D-Ala-D-Arg-D-Arg-D-Arg-D-Ala-D-Arg-NH2.Etelcalcetide HCl.

IUPAC/Chemical Name: S-(((S)-2-acetamido-3-(((R)-1-(((R)-1-(((R)-1-(((R)-1-(((R)-1-(((R)-1-amino-5-guanidino-1-oxopentan-2-yl)amino)-1-oxopropan-2-yl)amino)-5-guanidino-1-oxopentan-2-yl)amino)-5-guanidino-1-oxopentan-2-yl)amino)-5-guanidino-1-oxopentan-2-yl)amino)-1-oxopropan-2-yl)amino)-3-oxopropyl)thio)-L-cysteine tetrahydrochloride

InChi Key: SXOYZYNHXAPULT-OAZPLHIQSA-N

InChi Code: C[C@H](C(N[C@H](CCCNC(N)=N)C(N)=O)=O)NC([C@@H](CCCNC(N)=N)NC([C@@H](CCCNC(N)=N)NC([C@@H](CCCNC(N)=N)NC([C@@H](C)NC([C@@H](CSSC[C@@H](C(O)=O)N)NC(C)=O)=O)=O)=O)=O)=O.Cl.Cl.Cl.Cl

SMILES Code: C[C@H](C(N[C@H](CCCNC(N)=N)C(N)=O)=O)NC([C@@H](CCCNC(N)=N)NC([C@@H](CCCNC(N)=N)NC([C@@H](CCCNC(N)=N)NC([C@@H](C)NC([C@@H](CSSC[C@@H](C(O)=O)N)NC(C)=O)=O)=O)=O)=O)=O.Cl.Cl.Cl.Cl

Appearance: Solid powder

Purity: >95% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Product Data:
Product Data
Instruction:
View handling instruction
Biological target: Etelcalcetide hydrochloride (AMG 416 hydrochloride) is a synthetic peptide as an activator of the calcium sensing receptor (CaSR).
In vitro activity: TBD
In vivo activity: Etelcalcetide administration significantly decreased the setpoint from 9.03 ± 0.56 mg/dL to 6.80 ± 0.28 mg/dL, which was restored to 8.81 ± 0.38 mg/dL after vehicle administration. In the second group of mice, vehicle administration did not alter the setpoint (8.84 ± 0.69 mg/dL to 8.98 ± 0.63 mg/dL), but subsequent etelcalcetide administration significantly decreased it to 7.10 ± 0.72 mg/dL. Reference: J Bone Miner Metab. 2021 May;39(3):430-438. https://pubmed.ncbi.nlm.nih.gov/33196900/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 10.0 8.37
PBS (pH 7.2) 10.0 8.37
Water 50.0 41.87

Preparing Stock Solutions

The following data is based on the product molecular weight 1,194.09 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. Hayashi N, Imanishi Y, Hirakawa T, Kobayashi I, Tateishi T, Miyaoka D, Nagata Y, Mori K, Morioka T, Inoue A, Harada K, Inaba M, Emoto M. Etelcalcetide decreases the PTH-calcium setpoint without changing maximum and minimum PTH secretion in mice with primary hyperparathyroidism. J Bone Miner Metab. 2021 May;39(3):430-438. doi: 10.1007/s00774-020-01169-z. Epub 2020 Nov 16. PMID: 33196900. 2. Subramanian R, Zhu X, Kerr SJ, Esmay JD, Louie SW, Edson KZ, Walter S, Fitzsimmons M, Wagner M, Soto M, Pham R, Wilson SF, Skiles GL. Nonclinical Pharmacokinetics, Disposition, and Drug-Drug Interaction Potential of a Novel d-Amino Acid Peptide Agonist of the Calcium-Sensing Receptor AMG 416 (Etelcalcetide). Drug Metab Dispos. 2016 Aug;44(8):1319-31. doi: 10.1124/dmd.115.068007. Epub 2016 Feb 19. PMID: 26895981.
In vitro protocol: TBD
In vivo protocol: 1. Hayashi N, Imanishi Y, Hirakawa T, Kobayashi I, Tateishi T, Miyaoka D, Nagata Y, Mori K, Morioka T, Inoue A, Harada K, Inaba M, Emoto M. Etelcalcetide decreases the PTH-calcium setpoint without changing maximum and minimum PTH secretion in mice with primary hyperparathyroidism. J Bone Miner Metab. 2021 May;39(3):430-438. doi: 10.1007/s00774-020-01169-z. Epub 2020 Nov 16. PMID: 33196900. 2. Subramanian R, Zhu X, Kerr SJ, Esmay JD, Louie SW, Edson KZ, Walter S, Fitzsimmons M, Wagner M, Soto M, Pham R, Wilson SF, Skiles GL. Nonclinical Pharmacokinetics, Disposition, and Drug-Drug Interaction Potential of a Novel d-Amino Acid Peptide Agonist of the Calcium-Sensing Receptor AMG 416 (Etelcalcetide). Drug Metab Dispos. 2016 Aug;44(8):1319-31. doi: 10.1124/dmd.115.068007. Epub 2016 Feb 19. PMID: 26895981.

Molarity Calculator

Calculate the mass, volume, or concentration required for a solution.
=
x
x
g/mol

*When preparing stock solutions always use the batch-specific molecular weight of the product found on the vial label and SDS / CoA (available online).

Reconstitution Calculator

The reconstitution calculator allows you to quickly calculate the volume of a reagent to reconstitute your vial. Simply enter the mass of reagent and the target concentration and the calculator will determine the rest.

=
÷

Dilution Calculator

Calculate the dilution required to prepare a stock solution.
x
=
x

1: Shigematsu T, Fukagawa M, Yokoyama K, Akiba T, Fujii A, Shinoda A, Akizawa T. The influence of dialysate Ca concentrations on the therapeutic effects of etelcalcetide with concomitant drugs in patients with secondary hyperparathyroidism. Nephrology (Carlton). 2019 Nov 25. doi: 10.1111/nep.13682. [Epub ahead of print] PubMed PMID: 31765028.

2: Dörr K, Kammer M, Reindl-Schwaighofer R, Lorenz M, Loewe C, Marculescu R, Erben R, Oberbauer R. Effect of etelcalcetide on cardiac hypertrophy in hemodialysis patients: a randomized controlled trial (ETECAR-HD). Trials. 2019 Oct 24;20(1):601. doi: 10.1186/s13063-019-3707-7. PubMed PMID: 31651370; PubMed Central PMCID: PMC6813957.

3: Russo D, Tripepi R, Malberti F, Di Iorio B, Scognamiglio B, Di Lullo L, Paduano IG, Tripepi GL, Panuccio VA. Etelcalcetide in Patients on Hemodialysis with Severe Secondary Hyperparathyroidism. Multicenter Study in "Real Life". J Clin Med. 2019 Jul 20;8(7). pii: E1066. doi: 10.3390/jcm8071066. PubMed PMID: 31330805; PubMed Central PMCID: PMC6678718.

4: Cunningham J, Block GA, Chertow GM, Cooper K, Evenepoel P, Iles J, Sun Y, Ureña-Torres P, Bushinsky DA. Etelcalcetide Is Effective at All Levels of Severity of Secondary Hyperparathyroidism in Hemodialysis Patients. Kidney Int Rep. 2019 Apr 16;4(7):987-994. doi: 10.1016/j.ekir.2019.04.010. eCollection 2019 Jul. PubMed PMID: 31317120; PubMed Central PMCID: PMC6611952.

5: Hain D, Tomlin H, Gibson C. Administration of Etelcalcetide for the Treatment of Secondary Hyperparathyroidism in Patients with CKD-MBD on Hemodialysis: A Nephrology Nursing Perspective. Nephrol Nurs J. 2019 May-Jun;46(3):315-290. PubMed PMID: 31199098.

6: Block GA, Chertow GM, Sullivan JT, Deng H, Mather O, Tomlin H, Serenko M. An integrated analysis of safety and tolerability of etelcalcetide in patients receiving hemodialysis with secondary hyperparathyroidism. PLoS One. 2019 Mar 15;14(3):e0213774. doi: 10.1371/journal.pone.0213774. eCollection 2019. PubMed PMID: 30875390; PubMed Central PMCID: PMC6420005.

7: Bushinsky DA, Chertow GM, Cheng S, Deng H, Kopyt N, Martin KJ, Rastogi A, Ureña-Torres P, Vervloet M, Block GA. One-year safety and efficacy of intravenous etelcalcetide in patients on hemodialysis with secondary hyperparathyroidism. Nephrol Dial Transplant. 2019 Mar 11. pii: gfz039. doi: 10.1093/ndt/gfz039. [Epub ahead of print] Erratum in: Nephrol Dial Transplant. 2019 May 15;:. PubMed PMID: 30859218.

8: Xipell M, Montagud-Marrahi E, Rubio MV, Ojeda R, Arias-Guillén M, Fontseré N, Rodas L, Vera M, Broseta JJ, Torregrosa V, Filella X, Maduell F. Improved Control of Secondary Hyperparathyroidism in Hemodialysis Patients Switching from Oral Cinacalcet to Intravenous Etelcalcetide, Especially in Nonadherent Patients. Blood Purif. 2019;48(2):106-114. doi: 10.1159/000496562. Epub 2019 Jan 30. PubMed PMID: 30699421.

9: Shigematsu T, Fukagawa M, Yokoyama K, Akiba T, Fujii A, Odani M, Akizawa T. Effects of the Intravenous Calcimimetic Etelcalcetide on Bone Turnover and Serum Fibroblast Growth Factor 23: Post Hoc Analysis of an Open-label Study. Clin Ther. 2018 Dec;40(12):2099-2111. doi: 10.1016/j.clinthera.2018.10.016. Epub 2018 Nov 23. PubMed PMID: 30473399.

10: Harada K, Fujioka A, Konno M, Inoue A, Yamada H, Hirota Y. Pharmacology of Parsabiv(®) (etelcalcetide, ONO-5163/AMG 416), a novel allosteric modulator of the calcium-sensing receptor, for secondary hyperparathyroidism in hemodialysis patients. Eur J Pharmacol. 2019 Jan 5;842:139-145. doi: 10.1016/j.ejphar.2018.10.021. Epub 2018 Oct 19. PubMed PMID: 30342948.

11: Mima A, Tansho K, Nagahara D, Watase K. Treatment of secondary hyperparathyroidism in patients on hemodialysis using a novel synthetic peptide calcimimetic, etelcalcetide: a short-term clinical study. J Int Med Res. 2018 Nov;46(11):4578-4585. doi: 10.1177/0300060518786913. Epub 2018 Jul 20. PubMed PMID: 30027791; PubMed Central PMCID: PMC6259360.

12: Patel J, Bridgeman MB. Etelcalcetide (Parsabiv) for Secondary Hyperparathyroidism in Adults With Chronic Kidney Disease on Hemodialysis. P T. 2018 Jul;43(7):396-399. PubMed PMID: 30013296; PubMed Central PMCID: PMC6027851.

13: Eidman KE, Wetmore JB. Treatment of secondary hyperparathyroidism: How do cinacalcet and etelcalcetide differ? Semin Dial. 2018 Sep;31(5):440-444. doi: 10.1111/sdi.12734. Epub 2018 Jul 15. Review. PubMed PMID: 30009474.

14: Yoshimura K, Funakoshi Y, Terawaki H. Dramatic Regression of Parathyroid Gland Swelling After Conversion of Calcimimetic Medication From Cinacalcet to Etelcalcetide. Ther Apher Dial. 2018 Oct;22(5):553-554. doi: 10.1111/1744-9987.12701. Epub 2018 Jun 21. PubMed PMID: 29927050.

15: Friedl C, Zitt E. Role of etelcalcetide in the management of secondary hyperparathyroidism in hemodialysis patients: a review on current data and place in therapy. Drug Des Devel Ther. 2018 Jun 1;12:1589-1598. doi: 10.2147/DDDT.S134103. eCollection 2018. Review. PubMed PMID: 29910605; PubMed Central PMCID: PMC5989700.

16: Bellasi A, Cozzolino M, Malberti F, Cancarini G, Esposito C, Genderini A, Guastoni CM, Ondei P, Pontoriero G, Teatini U, Vezzoli G, Messa P, Locatelli F. [New scenarios in secondary hyperparathyroidism: etelcalcetide. Position paper of Nephrologists form Lombardy]. G Ital Nefrol. 2018 May;35(3). pii: 2018-vol3. Italian. PubMed PMID: 29786181.

17: Ye J, Deng G, Gao F. Theoretical overview of clinical and pharmacological aspects of the use of etelcalcetide in diabetic patients undergoing hemodialysis. Drug Des Devel Ther. 2018 Apr 19;12:901-909. doi: 10.2147/DDDT.S160223. eCollection 2018. Review. PubMed PMID: 29719376; PubMed Central PMCID: PMC5914547.

18: Rose M, Shepherd J, Harris P, Pickett K, Lord J. Etelcalcetide for Treating Secondary Hyperparathyroidism: An Evidence Review Group Evaluation of a NICE Single Technology Appraisal. Pharmacoeconomics. 2018 Nov;36(11):1299-1308. doi: 10.1007/s40273-018-0661-2. Review. PubMed PMID: 29691773.

19: Villabón Ochoa P, Sánchez Heras M, Zapata Balcázar A, Sánchez Escudero P, Rodríguez Palomares JR, de Arriba de la Fuente G. A light in the control of secondary hyperparathyroidism. Etelcalcetide IV in hemodialysis. Nefrologia. 2018 Nov - Dec;38(6):677-678. doi: 10.1016/j.nefro.2018.02.003. Epub 2018 Mar 27. English, Spanish. PubMed PMID: 29602519.

20: Wu B, Melhem M, Subramanian R, Chen P, Jaramilla Sloey B, Fouqueray B, Hock MB, Skiles GL, Chow AT, Lee E. Clinical Pharmacokinetics and Pharmacodynamics of Etelcalcetide, a Novel Calcimimetic for Treatment of Secondary Hyperparathyroidism in Patients With Chronic Kidney Disease on Hemodialysis. J Clin Pharmacol. 2018 Jun;58(6):717-726. doi: 10.1002/jcph.1090. Epub 2018 Mar 13. Review. PubMed PMID: 29534286.