Penicillamine

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Cat Number

API52675

CAS Number

52-67-5

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CAS Number

52-67-5

EINECS

200-148-8

Storage

Store at 2-8°C

Synonyms

D-Penicillamine; Penicillamine; Cuprimine; D-(-)-Penicillamine; 3-Mercapto-D-valine; (2S)-2-Amino-3-methyl-3-sulfanylbutanoic acid; Cuprenil; Cupripen; Trolovol

Molecular Formula

C5H11NO2S

Molecular Weight

149.21

Smiles

CC(C)([C@H](C(=O)O)N)S

Appearance

White to off-white solid powder

Melting Point

204-208°C

Boiling Point

251.8±35.0°C at 760 mmHg

Relative Density

1.2±0.1

General Description

Penicillamine is a sulfur-containing amino acid derivative with a thiol group and two methyl groups, belonging to the class of chelating agents. Its chemical structure is 3,3-dimethylcysteine. Penicillamine is a white to off-white crystalline powder, soluble in water. The molecule has a chiral center, and the D-isomer is the pharmacologically active form. It is a degradation product of penicillin but has no antibacterial activity.

Mechanism of Action

Penicillamine acts as a chelating agent by binding to heavy metals, such as copper, lead, and mercury, forming a stable complex that is excreted in the urine. It also reduces the formation of cystine stones by forming a soluble mixed disulfide with cysteine, preventing the crystallization of cystine. The drug also has immunomodulatory effects by reducing the activity of T lymphocytes.

Application

Penicillamine is indicated for the treatment of Wilson's disease (hepatolenticular degeneration), a rare copper overload disorder, by promoting the excretion of copper and reducing its accumulation in the liver and brain. It is also used for the prevention of cystine kidney stones (cystinuria) and for the treatment of rheumatoid arthritis. The drug is effective in improving the symptoms of Wilson's disease and reducing the frequency of stone formation.

D-Penicillamine, a cysteine analog used for rheumatoid arthritis, inhibited H₂S biosynthesis by selectively inhibiting cystathionine-γ-lyase (CSE) in a pyridoxal-5'-phosphate-dependent manner. It reduced L-cysteine-induced vasodilation in mouse aortic rings at concentrations 10-fold lower than those needed for H₂S release. This CSE inhibition may account for its beneficial effects in rheumatoid arthritis, where H₂S is detrimental. D-penicillamine is a selective CSE inhibitor, offering new pharmacological tools for H₂S research.

Fig. 1 Vasoactive effect of d‐penicillamine (d‐pen). (Brancaleone V, et al., 2016)

References

Brancaleone V, et al. D-Penicillamine modulates hydrogen sulfide (H2S) pathway through selective inhibition of cystathionine-γ-lyase. Br J Pharmacol. 2016;173(9):1556-1565.

S‑nitroso‑N‑acetyl‑D‑penicillamine (SNAP), a nitric oxide donor, was encapsulated in PLGA microspheres for controlled release. Capped PLGA released SNAP for >4 weeks; uncapped PLGA for >10 days. Copper ions or ascorbate were needed for sustained NO release, and light could trigger rapid release. The formulation offers potential for site‑specific NO delivery in diabetic wounds, infections, and other conditions.

Fig. 2 SEM images of SNAP crystals before (A) and after (B) cryomilling. (Lautner G, et al., 2016)

References

Lautner G, et al. Biodegradable poly(lactic-co-glycolic acid) microspheres loaded with S-nitroso-N-acetyl-D-penicillamine for controlled nitric oxide delivery. J Control Release. 2016;225:133-139.

Does Penicillamine require protection from oxygen during storage?

Yes, the thiol group is highly susceptible to oxidation, forming disulfide dimers. Store in airtight containers under inert gas (nitrogen) at 2–8°C.

What is the recommended storage temperature for Penicillamine?

Store at 2–8°C (refrigerated). At room temperature, rapid oxidation and degradation occur, leading to loss of chelating activity.

Is Penicillamine stable in tablet formulations with standard excipients?

Yes, when formulated with antioxidants (e.g., ascorbic acid) and moisture‑protective packaging.

How is the impurity penicillamine disulfide (an oxidation product) monitored?

This primary degradation product is specifically quantified using a stability‑indicating HPLC method with electrochemical detection, ensuring it remains below pharmacopoeial limits.