Upacicalcet | CAS#1333218-50-0 | calcium-sensing agonist

MedKoo Cat#: 124894 | Name: Upacicalcet

Description:

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

Upacicalcet, also known as SK-1403 and AJT240, is a positive allosteric modulator of the calcium-sensing receptor. Upacicalcet prevents vascular calcification and bone disorder in a rat adenine-induced secondary hyperparathyroidism model. Upacicalcet acts at the calcium sensing receptor of parathyroid cells and thereby inhibiting parathyroid hormone secretion. Parathyroid hormone regulates the calcium concentration in the blood plasma to maintain calcium homeostasis in the body tissues ("calcium balance").

Chemical Structure

Upacicalcet

CAS#1333218-50-0 (free acid)

Theoretical Analysis

MedKoo Cat#: 124894

Name: Upacicalcet

CAS#: 1333218-50-0 (free acid)

Chemical Formula: C11H14ClN3O6S

Exact Mass: 351.0292

Molecular Weight: 351.76

Elemental Analysis: C, 37.56; H, 4.01; Cl, 10.08; N, 11.95; O, 27.29; S, 9.11

Price and Availability

Size	Price	Availability
10mg	USD 150.00	Ready to ship
25mg	USD 250.00	Ready to ship
50mg	USD 450.00	Ready to ship
100mg	USD 750.00	Ready to ship
200mg	USD 1,250.00	Ready to ship
500mg	USD 2,650.00	Ready to ship
1g	USD 4,250.00	Ready to ship
2g	USD 6,450.00	2 Weeks

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Related CAS #

2052969-18-1 (sodium) 1333218-50-0 (free acid)

Synonym

Upacicalcet; SK-1403; SK 1403; SK1403; AJT240; AJT-240; AJT 240;

IUPAC/Chemical Name

(S,Z)-2-amino-3-((((3-chloro-2-methyl-5-sulfophenyl)amino)(hydroxy)methylene)amino)propanoic acid

InChi Key

LHEYGVSDVBEYQF-QMMMGPOBSA-N

InChi Code

InChI=1S/C11H14ClN3O6S/c1-5-7(12)2-6(22(19,20)21)3-9(5)15-11(18)14-4-8(13)10(16)17/h2-3,8H,4,13H2,1H3,(H,16,17)(H2,14,15,18)(H,19,20,21)/t8-/m0/s1

SMILES Code

CC1=C(Cl)C=C(S(O)(=O)=O)C=C1N/C(O)=N/C[C@@](N)([H])C(O)=O

Appearance

To be determined

Purity

>98% (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

To be determined

Shelf Life

>2 years if stored properly

Drug Formulation

To be determined

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

The human calcium-sensing receptor (CaSR) is a G protein-coupled receptor that maintains extracellular Ca2+ homeostasis by regulating the secretion of parathyroid hormone. Upacicalcet is a novel positive allosteric modulator of CaSR that is used for the treatment of secondary hyperparathyroidism. Upacicalcet interacts with several residues that constitute the amino acid binding site of the calcium-sensing receptor (CaSR) and shows a potent positive allosteric activity. This mechanism differs from those of conventional drugs. Therefore, upacicalcet can be regarded as a novel secondary hyperparathyroidism drug that acts on the amino acid binding site of CaSR.

Product Data

Product Data

Certificate of Analysis

View CoA: current batch, Lot#S24S03C12

QC Data

View QC data: current batch, Lot#S24S03C12

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Biological target:

Upacicalcet suppresses excessive parathyroid hormone (PTH) secretion, thereby lowering blood PTH levels, by acting directly on parathyroid cell membrane calcium-sensing receptors.

In vitro activity:

To be determined

In vivo activity:

Upacicalcet is effective and safe for secondary hyperparathyroidism patients receiving hemodialysis. Upacicalcet decreased serum fibroblast growth factor-23, bone-specific alkaline phosphatase, total type 1 procollagen-N-propeptide, and tartrate-resistant acid phosphatase-5b concentrations. Serum corrected calcium concentrations <7.5 mg/dl were observed in 2% of participants in the upacicalcet group and no participants in the placebo group. Reference: Clin J Am Soc Nephrol. 2023 Oct 1;18(10):1300-1309. https://pubmed.ncbi.nlm.nih.gov/37696667/

Preparing Stock Solutions

The following data is based on the product molecular weight 351.76 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.

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. Inaguma D, Koiwa F, Tokumoto M, Fukagawa M, Yoneda S, Yasuzawa H, Asano K, Hagita K, Inagaki Y, Honda D, Akizawa T. Phase 2 study of upacicalcet in Japanese haemodialysis patients with secondary hyperparathyroidism: an intraindividual dose-adjustment study. Clin Kidney J. 2023 Sep 4;16(12):2614-2625. doi: 10.1093/ckj/sfad213. PMID: 38045997; PMCID: PMC10689153. 2. Shigematsu T, Koiwa F, Isaka Y, Fukagawa M, Hagita K, Watanabe YS, Honda D, Akizawa T. Efficacy and Safety of Upacicalcet in Hemodialysis Patients with Secondary Hyperparathyroidism: A Randomized Placebo-Controlled Trial. Clin J Am Soc Nephrol. 2023 Oct 1;18(10):1300-1309. doi: 10.2215/CJN.0000000000000253. Epub 2023 Sep 11. PMID: 37696667; PMCID: PMC10578632.

In vitro protocol:

To be determined

In vivo protocol:

1: Inaguma D, Koiwa F, Tokumoto M, Fukagawa M, Yoneda S, Yasuzawa H, Asano K, Hagita K, Inagaki Y, Honda D, Akizawa T. Phase 2 study of upacicalcet in Japanese haemodialysis patients with secondary hyperparathyroidism: an intraindividual dose-adjustment study. Clin Kidney J. 2023 Sep 4;16(12):2614-2625. doi: 10.1093/ckj/sfad213. PMID: 38045997; PMCID: PMC10689153. 2: Shigematsu T, Koiwa F, Isaka Y, Fukagawa M, Hagita K, Watanabe YS, Honda D, Akizawa T. Efficacy and Safety of Upacicalcet in Hemodialysis Patients with Secondary Hyperparathyroidism: A Randomized Placebo-Controlled Trial. Clin J Am Soc Nephrol. 2023 Oct 1;18(10):1300-1309. doi: 10.2215/CJN.0000000000000253. Epub 2023 Sep 11. PMID: 37696667; PMCID: PMC10578632. 3: Goto M, Nishimura G, Sato H, Yamaguchi Y, Morimoto N, Hashimoto H, Takahashi N. Pharmacological profile of upacicalcet, a novel positive allosteric modulator of calcium-sensing receptor, in vitro and in vivo. Eur J Pharmacol. 2023 Oct 5;956:175936. doi: 10.1016/j.ejphar.2023.175936. Epub 2023 Aug 2. PMID: 37541363. 4: Sato H, Goto M, Nishimura G, Morimoto N, Tokushima H, Horii Y, Takahashi N. Upacicalcet, a positive allosteric modulator of the calcium-sensing receptor, prevents vascular calcification and bone disorder in a rat adenine-induced secondary hyperparathyroidism model. Bone. 2023 Feb;167:116613. doi: 10.1016/j.bone.2022.116613. Epub 2022 Nov 14. PMID: 36395959. 5: Sato H, Murakami S, Horii Y, Nishimura G, Iwai R, Goto M, Takahashi N. Upacicalcet Is a Novel Secondary Hyperparathyroidism Drug that Targets the Amino Acid Binding Site of Calcium-Sensing Receptor . Mol Pharmacol. 2022 Oct;102(4):183-195. doi: 10.1124/molpharm.122.000522. Epub 2022 Aug 5. PMID: 36122913. 6: Kazama JJ, Koiwa F, Yokoyama K, Fukagawa M, Asano K, Honda D, Akizawa T. First-in-Patient Phase I/II Study of Upacicalcet in Japanese Patients with Secondary Hyperparathyroidism Undergoing Hemodialysis: Pharmacokinetic and Pharmacodynamic Properties. Clin Pharmacokinet. 2022 Sep;61(9):1271-1284. doi: 10.1007/s40262-022-01139-w. Epub 2022 Jun 28. PMID: 35763247; PMCID: PMC9439990. 7: Koiwa F, Yazawa R, Fukagawa M, Honda D, Akizawa T. First-in-Human Phase I Study of the Novel Injectable Calcimimetic Agent Upacicalcet in Healthy Adult Japanese Participants. Drugs R D. 2022 Jun;22(2):131-140. doi: 10.1007/s40268-022-00385-4. Epub 2022 Mar 25. PMID: 35338469; PMCID: PMC9167405. 8: Hoy SM. Upacicalcet: First Approval. Drugs. 2021 Sep;81(13):1593-1596. doi: 10.1007/s40265-021-01578-y. PMID: 34390486.