Voclosporin
[CAS 515814-01-4]

Identification

• Classification: Biochemical >> Inhibitor >> Stem cells & wnt signaling paths (Stem cells & wnt)
• Name: Voclosporin
• Synonyms: (3S,6S,9S,12R,15S,18S,21S,24S,30S,33S)-30-ethyl-33-[(1R,2R,4E)-1-hydroxy-2-methylhepta-4,6-dienyl]-1,4,7,10,12,15,19,25,28-nonamethyl-6,9,18,24-tetrakis(2-methylpropyl)-3,21-di(propan-2-yl)-1,4,7,10,13,16,19,22,25,28,31-undecazacyclotritriacontane-2,5,8,11,14,17,20,23,26,29,32-undecone
• Molecular Formula: C₆₃H₁₁₁N₁₁O₁₂
• Molecular Weight: 1214.62
• CAS Registry Number: 515814-01-4
• EC Number: 881-570-5
• SMILES: CC[C@H]1C(=O)N(CC(=O)N([C@H](C(=O)N[C@H](C(=O)N([C@H](C(=O)N[C@H](C(=O)N[C@@H](C(=O)N([C@H](C(=O)N([C@H](C(=O)N([C@H](C(=O)N([C@H](C(=O)N1)[C@@H]([C@H](C)C/C=C/C=C)O)C)C(C)C)C)CC(C)C)C)CC(C)C)C)C)C)CC(C)C)C)C(C)C)CC(C)C)C)C

Properties

• Density: 1.0±0.1 g/cm³ Calc.^*
• Boiling point: 1303.8±65.0 °C 760 mmHg (Calc.)^*
• Flash point: 742.3±34.3 °C (Calc.)^*
• Index of refraction: 1.47 (Calc.)^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS08 Danger
• Risk Statements: H351-H372
• Safety Statements: P203-P260-P264-P270-P280-P318-P319-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Specific target organ toxicity - repeated exposure	STOT RE	1	H372
Carcinogenicity	Carc.	2	H351
Reproductive toxicity	Repr.	2	H361d

chemBlink Chemical Story

Voclosporin is a cyclic-peptide calcineurin inhibitor developed from the cyclosporine scaffold. FDA records list development names including ISA247 and describe a one-carbon modification at amino-acid residue 1 relative to cyclosporine A. The marketed drug substance is enriched to about 90-95% in the trans geometric isomer. The modification changed pharmacodynamic and metabolic behavior while retaining calcineurin inhibition. By suppressing calcineurin-dependent NFAT signaling, voclosporin reduces lymphocyte proliferation and T-cell cytokine production. FDA approved LUPKYNIS in 2021, with background immunosuppressive therapy, for adults with active lupus nephritis.

The exact registry identity matters because related free forms, salts, hydrates, stereoisomers, process intermediates and finished medicines can have separate CAS numbers even when their names share a familiar stem. In pharmaceutical and fine-chemical work this distinction is practical: composition changes formula weight and can alter solubility, crystallization, analytical standards, manufacturing specifications and interpretation of physical-property data.

The molecule also illustrates how chemists use functional groups as deliberate handles. Aromatic rings and heterocycles establish shape and electronic character, while amines, alcohols, carbonyl groups, carboxylic acids, esters or ionic centers control reactivity and intermolecular interactions. In a multistep route, an intermediate may be valuable precisely because one group can be transformed selectively while another survives for a later operation.

Modern development is equally an analytical problem. Chemists must demonstrate identity and purity, control stereochemistry or salt composition where relevant, follow process-related impurities and establish reproducible specifications. Reference materials and isolated intermediates therefore have scientific importance even when they are never administered to a patient or sold as the final commercial product.

A careful Chemical Story must distinguish documented use from structural possibility. A familiar scaffold can suggest a biological hypothesis, but resemblance is not evidence that the exact CAS substance has been tested, approved or commercially adopted for that purpose. The account therefore emphasizes verified identity, development history and supported applications, and deliberately leaves unsupported claims out.

Seen more broadly, the compound shows that useful molecular design rarely depends on one functional group in isolation. Performance emerges from the whole structure, stereochemistry and physical form, the route used to make it, and the environment in which it operates. Connecting those molecular details to a real manufacturing, analytical or therapeutic role turns a technical registry entry into a meaningful chemical story.

The exact registry identity matters because related free forms, salts, hydrates, stereoisomers, process intermediates and finished medicines can have separate CAS numbers even when their names share a familiar stem. In pharmaceutical and fine-chemical work this distinction is practical: composition changes formula weight and can alter solubility, crystallization, analytical standards, manufacturing specifications and interpretation of physical-property data.

The molecule also illustrates how chemists use functional groups as deliberate handles. Aromatic rings and heterocycles establish shape and electronic character, while amines, alcohols, carbonyl groups, carboxylic acids, esters or ionic centers control reactivity and intermolecular interactions. In a multistep route, an intermediate may be valuable precisely because one group can be transformed selectively while another survives for a later operation.

Modern development is equally an analytical problem. Chemists must demonstrate identity and purity, control stereochemistry or salt composition where relevant, follow process-related impurities and establish reproducible specifications. Reference materials and isolated intermediates therefore have scientific importance even when they are never administered to a patient or sold as the final commercial product.

References:
1. U.S. FDA. LUPKYNIS (voclosporin) Prescribing Information.
2. U.S. FDA. Multidisciplinary Review, NDA 213716, 2021.
3. FDA GSRS. Voclosporin, UNII 2PN063X6B1.

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