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Etelcalcetide Hydrochloride

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11 API Suppliers, 3 USDMF, 6 NDC API, 9 Listed Suppliers, $ API Reference Price

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24 US Patents

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24 US Patents

Synopsis

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Chemistry

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Also known as: Velcalcetide, Parsabiv, 1262780-97-1, Kai-4169, Amg-416, Telcalcetide

Molecular Formula

C₃₈H₇₃N₂₁O₁₀S₂

Molecular Weight

1048.3 g/mol

InChI Key

ANIAZGVDEUQPRI-ZJQCGQFWSA-N

FDA UNII

60ME133FJB

Etelcalcetide is a calcimimetic and calcium-sensing receptor (CaSR) agonist composed of a synthetic peptide comprised of seven D-amino acids that can be used to treat secondary hyperparathyroidism (sHPT) in hemodialysis patients with chronic kidney disease (CKD). Upon intravenous administration, etelcalcetide mimics calcium and allosterically binds to and activates the CaSR expressed by the parathyroid gland. This suppresses the synthesis and secretion of parathyroid hormone (PTH), thereby reducing PTH levels and lowering serum calcium and phosphorus levels. Elevated PTH is often observed in patients with CKD and is associated with dysregulated calcium-phosphate homeostasis.

Etelcalcetide is a Calcium-sensing Receptor Agonist. The mechanism of action of etelcalcetide is as an Increased Calcium-sensing Receptor Sensitivity.

1 2D Structure

Etelcalcetide

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(2R)-3-[[(2S)-2-acetamido-3-[[(2R)-1-[[(2R)-1-[[(2R)-1-[[(2R)-1-[[(2R)-1-[[(2R)-1-amino-5-(diaminomethylideneamino)-1-oxopentan-2-yl]amino]-1-oxopropan-2-yl]amino]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]amino]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]amino]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]amino]-1-oxopropan-2-yl]amino]-3-oxopropyl]disulfanyl]-2-aminopropanoic acid

2.1.2 InChI

InChI=1S/C38H73N21O10S2/c1-18(28(62)56-22(27(40)61)8-4-12-49-35(41)42)53-30(64)23(9-5-13-50-36(43)44)58-32(66)25(11-7-15-52-38(47)48)59-31(65)24(10-6-14-51-37(45)46)57-29(63)19(2)54-33(67)26(55-20(3)60)17-71-70-16-21(39)34(68)69/h18-19,21-26H,4-17,39H2,1-3H3,(H2,40,61)(H,53,64)(H,54,67)(H,55,60)(H,56,62)(H,57,63)(H,58,66)(H,59,65)(H,68,69)(H4,41,42,49)(H4,43,44,50)(H4,45,46,51)(H4,47,48,52)/t18-,19-,21+,22-,23-,24-,25-,26-/m1/s1

2.1.3 InChI Key

ANIAZGVDEUQPRI-ZJQCGQFWSA-N

2.1.4 Canonical SMILES

CC(C(=O)NC(CCCN=C(N)N)C(=O)N)NC(=O)C(CCCN=C(N)N)NC(=O)C(CCCN=C(N)N)NC(=O)C(CCCN=C(N)N)NC(=O)C(C)NC(=O)C(CSSCC(C(=O)O)N)NC(=O)C

2.1.5 Isomeric SMILES

C[C@H](C(=O)N[C@H](CCCN=C(N)N)C(=O)N)NC(=O)[C@@H](CCCN=C(N)N)NC(=O)[C@@H](CCCN=C(N)N)NC(=O)[C@@H](CCCN=C(N)N)NC(=O)[C@@H](C)NC(=O)[C@@H](CSSC[C@@H](C(=O)O)N)NC(=O)C

2.2 Other Identifiers

2.2.1 UNII

60ME133FJB

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Amg 416

2. Amg-416

3. Etelcalcetide Hydrochloride

4. Kai-4169

5. Parsabiv

6. Velcalcetide

2.3.2 Depositor-Supplied Synonyms

1. Velcalcetide

2. Parsabiv

3. 1262780-97-1

4. Kai-4169

5. Amg-416

6. Telcalcetide

7. 60me133fjb

8. Ono-5163

9. D-argininamide, N-acetyl-d-cysteinyl-d-alanyl-d-arginyl-d-arginyl-d-arginyl-d-alanyl-, Disulfide With L-cysteine

10. Etelcalcetide [usan:inn]

11. Unii-60me133fjb

12. Kai 4169

13. Amg416

14. Etelcalcetide [mi]

15. Etelcalcetide [inn]

16. Etelcalcetide (usan/inn)

17. Etelcalcetide [usan]

18. Etelcalcetide [who-dd]

19. Gtpl8375

20. Chembl3545184

21. Schembl21982605

22. Dtxsid70155132

23. Chebi:134700

24. Etelcalcetide [orange Book]

25. Hy-p1955

26. Akos037648615

27. Etelcalcetide Hydrochloride(amg-416)

28. Db12865

29. Bs-14875

30. Cs-0030931

31. J3.559.823e

32. D10676

33. D71178

34. Q21098973

35. N-acetyl-d-cysteinyl-d-alanyl-d-arginyl-d-arginyl-d-arginyl-d-alanyl-d-argininamide Disulfide With L-cysteine

36. 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

2.4 Create Date

2013-06-10

3 Chemical and Physical Properties

Molecular Formula	C₃₈H₇₃N₂₁O₁₀S₂
Molecular Weight	1048.3 g/mol
XLogP3	-10.7
Hydrogen Bond Donor Count	18
Hydrogen Bond Acceptor Count	17
Rotatable Bond Count	36
Exact Mass	1047.52906996 g/mol
Monoisotopic Mass	1047.52906996 g/mol
Topological Polar Surface Area	618 Å²
Heavy Atom Count	71
Formal Charge	0
Complexity	1910
Isotope Atom Count	0
Defined Atom Stereocenter Count	8
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Information

1 of 1
Drug Name	PARSABIV
Active Ingredient	ETELCALCETIDE
Company	KAI PHARMS INC (Application Number: N208325. Patents: 8377880, 8999932, 9278995, 9701712, 9820938)

4.2 Drug Indication

Etelcalcetide is a calcium-sensing receptor agonist indicated for: Secondary hyperparathyroidism (HPT) in adult patients with chronic kidney disease (CKD) on hemodialysis.

Parsabiv is indicated for the treatment of secondary hyperparathyroidism (SHPT) in adult patients with chronic kidney disease (CKD) on haemodialysis therapy.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Following a single intravenous bolus administration of etelcalcetide, PTH levels decreased within 30 minutes post dose. In the single-dose study, the extent and duration of the reduction in PTH increased with increasing dose. Reduction in PTH levels correlated with plasma etelcalcetide concentrations in hemodialysis patients. The reduction in PTH resulted in reductions in calcium and attenuation of post-dialytic phosphate elevation. The effect of reducing PTH levels was maintained throughout the 6-month dosing period when etelcalcetide was administered by intravenous bolus three times a week.

5.2 FDA Pharmacological Classification

5.2.1 Active Moiety

ETELCALCETIDE

5.2.2 FDA UNII

60ME133FJB

5.2.3 Pharmacological Classes

Increased Calcium-sensing Receptor Sensitivity [MoA]; Calcium-sensing Receptor Agonist [EPC]

5.3 ATC Code

H05BX04

S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355

H - Systemic hormonal preparations, excl. sex hormones and insulins

H05 - Calcium homeostasis

H05B - Anti-parathyroid agents

H05BX - Other anti-parathyroid agents

H05BX04 - Etelcalcetide

5.4 Absorption, Distribution and Excretion

Absorption

The pharmacokinetics of etelcalcetide is linear and does not change over time following single (5 to 60 mg) and multiple intravenous doses (2.5 to 20 mg) in chronic kidney disease patients with secondary hyperparathyroidism requiring hemodialysis. Etelcalcetide exhibited tri-exponential decay following intravenous administration. Based on population pharmacokinetic analysis, following three times a week intravenous dosing at the end of each 3- to 6-hour hemodialysis session in chronic kidney disease patients, etelcalcetide plasma levels reached steady state in 7-8 weeks after dosing with a predicted accumulation ratio of 3- to 4-fold

Route of Elimination

Etelcalcetide is cleared by renal excretion

Volume of Distribution

796 L

Clearance

7.66 L/hr

5.5 Metabolism/Metabolites

Etelcalcetide is not metabolized by CYP450 enzymes. Etelcalcetide is biotransformed in blood by reversible disulfide exchange with endogenous thiols to predominantly form conjugates with serum albumin. Following a single radiolabeled dose of etelcalcetide in chronic kidney disease patients with secondary hyperparathyroidism requiring hemodialysis, the plasma exposure of biotransformation products is approximately 5-fold higher than that of etelcalcetide and their concentration-time course parallels that of etelcalcetide.

5.6 Biological Half-Life

3 to 4 days

5.7 Mechanism of Action

Etelcalcetide is a calcimimetic agent that allosterically modulates the calcium-sensing receptor (CaSR). Etelcalcetide binds to the CaSR and enhances activation of the receptor by extracellular calcium. Activation of the CaSR on parathyroid chief cells decreases PTH secretion.

API SUPPLIERS

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ChemWerth Inc

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Omgene Life Sciences Pvt. Ltd

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MSN Laboratories

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Usv Private Ltd

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Etelcalcetide Hydrochloride

GDUFA

DMF Review : Complete

Rev. Date : 2021-09-07

Pay. Date : 2021-03-24

DMF Number : 35768

Submission : 2021-07-22

Status : Active

Type : II

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Msn Life Sciences Private Ltd

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Established in 1994, Rochem is a distributor of pharmaceutical, food, nutritional and animal health ingredients to some of the largest companies in the world. It sources high-quality ingredients manufactured in China. Headquartered in the Hauppauge, New York, Rochem has 16 offices spread across the globe to cater to the needs of its customers. Rochem’s operations are fully cGMP compliant and has been audited by the USFDA as well as several multinational organizations. It also trains and audits its partners to ensure all of their technologies and systems are FDA-compliant.

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About the Company : Sintaho Pharmaceutical Co., Ltd., located in Chongqing, China, contributes to being the most dependable partner for global pharmaceutical companies. Sintaho specializes in chemosyn...

Sintaho Pharmaceutical Co., Ltd., located in Chongqing, China, contributes to being the most dependable partner for global pharmaceutical companies. Sintaho specializes in chemosynthetic APIs (application contains oncology, nervous system, and metabolic diseases and etc.,) with a product portfolio ranging from small molecule APIs, ADC compounds (linkers and payloads) to polypeptides, also provides CDMO services of cytotoxic and OEB4/5 grade APIs.

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HRV Global is a leading global manufacturer, seller & exporter of a wide range of APIs, advanced intermediates, pellets, food grade chemicals, food additives & food ingredients. It offers services such as sourcing, manufacturing & supply, helping partners enter new markets worldwide. Its strong partnerships with major players in the pharma and food additive industries help HRV Global effectively promote projects and products. HRV Global represents over 30 large Indian drugmakers, primarily targeting Europe, the US & the Middle East markets. Headquartered in India, HRV Global has offices in the US, Switzerland, Dubai, Lithuania & Turkey.

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USV is a leading health care company with focus on Active Pharmaceutical Ingredients (marketed globally with emphasis on regulated markets of USA, European Union and Japan), Branded Generics and Bio-therapeutics. USV also specializes in Research and Development in Biotechnology, Drug Delivery and Chemistry.31 APIs are currently on offer, 13 are in advanced stages of development and 14 are under development. Segments covered include Diabetes, Cardiology, CNS, Oncology, Dermatology and Ophthalmology.

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About the Company : Chunghwa Chemical Synthesis & Biotech Co. Ltd. (CCSB) offers global customers cost-effective APIs with speed, supported by our well-trained staff. As the first company in Southeast...

Chunghwa Chemical Synthesis & Biotech Co. Ltd. (CCSB) offers global customers cost-effective APIs with speed, supported by our well-trained staff. As the first company in Southeast Asia to receive FDA approval for synthetic and biotech APIs, CCSB has a proven track record of commercializing Statin, Immunosuppressant, Muscle Relaxant, and ACE Inhibitor APIs, all with complete DMF or COS. For years, CCSB has partnered with leading brand and generic drug companies to develop and produce APIs and advanced intermediates, focusing on specialty APIs crafted through a sophisticated fusion of fermentation and synthesis technologies in Taiwan.

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About the Company : Omgene Life Sciences Private Limited is an R&D-driven biopharmaceutical company specializing in biopharmaceuticals, peptides, semi-synthetic, and synthetic actives. As a vertically...

Omgene Life Sciences Private Limited is an R&D-driven biopharmaceutical company specializing in biopharmaceuticals, peptides, semi-synthetic, and synthetic actives. As a vertically integrated company, we focus on developing high-quality formulations based on in-house-produced actives. With GMP-certified facilities and partnerships with contract manufacturers, we excel in formulation development for injectables, lyophilized injectables, complex generics, and oral peptide delivery systems, ensuring affordable, top-quality medicines.

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Aurobindo Pharma Limited

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Smaart Pharmaceutticals

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API Reference Price

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11 API Suppliers

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6 NDC API

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6 APIs

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24 US Patents

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