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Hodoodo CAT#: H124894

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

Description: 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

CAS# 1333218-50-0 (free acid)

Theoretical Analysis

Hodoodo Cat#: H124894
Name: Upacicalcet
CAS#: 1333218-50-0 (free acid)
Chemical Formula: C11H14ClN3O6S
Exact Mass: 351.03
Molecular Weight: 351.760
Elemental Analysis: C, 37.56; H, 4.01; Cl, 10.08; N, 11.95; O, 27.29; S, 9.11

Price and Availability

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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 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.

Biological target:
In vitro activity:
In vivo activity:

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.

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:
In vitro protocol:
In vivo protocol:

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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.