Art. -Nr.: HY-B0300

Penicillamine

(Synonyms: D-(-)-Penicillamine)

3 Cited Publications

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Penicillamine (D-(-)-Penicillamine) is a penicillin metabolic degradation product, can be used as a heavy metal chelator. Penicillamine increases free copper and increases oxidative stress. Penicillamine has effect of seizures through nitric oxide/NMDA pathways. Penicillamine is a potential immune modulator. Penicillamine can be used for the research of Wilson disease, rheumatoid arthritis, and cystinuria.

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Reinheit: 98.0%
CAS. Nr.: 52-67-5
Formel: C₅H₁₁NO₂S
Molecular Weight:149.22

Speicherung:

Powder -20°C, 3 years , 4°C, 2 years ; In solvent -80°C, 2 years , -20°C, 1 year

Penicillamine Chemical Structure

CAS. Nr.: 52-67-5

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Biologische Aktivität
- Beschreibung
- Cellular Effect
- In Vitro
- In Vivo
- Clinical Trial
Chemical Information
Publications (3)
Lösungsmittel & Löslichkeit
- In Vitro
- In Vivo
Reinheit & Dokumentation
Verweise
Help & FAQs
Bioz

Biologische Aktivität

Beschreibung

Cellular Effect

Cell Line	Type	Value	Description	References
KB 3-1	IC₅₀	4.04 mM Compound: D-penicillamine	Cytotoxicity against human KB-3-1 cells incubated for 72 hrs by MTT assay Cytotoxicity against human KB-3-1 cells incubated for 72 hrs by MTT assay	[PMID: 21657271]
KB-V1	IC₅₀	6.93 mM Compound: D-penicillamine	Cytotoxicity against drug-resistant human KBV1 cells expressing P-gp incubated for 72 hrs by MTT assay Cytotoxicity against drug-resistant human KBV1 cells expressing P-gp incubated for 72 hrs by MTT assay	[PMID: 21657271]
Sf21	IC₅₀	>1000 μM Compound: D-Penicillamine	Inhibition of human BSEP expressed in plasma membrane vesicles of Sf21 cells assessed as inhibition of ATP-dependent [3H]taurocholate uptake Inhibition of human BSEP expressed in plasma membrane vesicles of Sf21 cells assessed as inhibition of ATP-dependent [3H]taurocholate uptake	[PMID: 21965623]
Sf21	IC₅₀	>1000 μM Compound: D-Penicillamine	Inhibition of Sprague-Dawley rat Bsep expressed in plasma membrane vesicles of Sf21 cells assessed as inhibition of ATP-dependent [3H]taurocholate uptake Inhibition of Sprague-Dawley rat Bsep expressed in plasma membrane vesicles of Sf21 cells assessed as inhibition of ATP-dependent [3H]taurocholate uptake	[PMID: 21965623]

In Vitro

Penicillamine (D-(-)-Penicillamine) (5 mg; 7 d; CD4⁺ and CD⁺ splenocytes) promotes cellular immune responses^[3].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Western Blot Analysis^[3]

Cell Line:

CD4⁺ and CD⁺ splenocytes
Concentration:

5 mg
Incubation Time:

7 days
Result:

Increased IL-4 and IFN-γ mRNA expression in response to high dose treatment and remained high in both CD4⁺ and CD⁺ splenocytes.

In Vivo

Penicillamine (D-(-)-Penicillamine) (200 mg/kg; i.g.; daily, for 3, 10 and 14 d; tx mice and DL mice) increases serum free copper concentration^[1].
Penicillamine (200 mg/kg; i.g.; daily, for 3, 10 and 14 d; tx mice and DL mice) increases ATP7A and CTR1 mRNA expression in the brain of tx mice^[1].
Penicillamine (200 mg/kg; i.g.; daily, for 3, 10 and 14 d; tx mice and DL mice) induces oxidative-stress in the central nervous system^[1].
Penicillamine (0.1-250 mg/kg; i.p.; once, for 90 min; male NMRI mice) has binaural phase effect on seizure^[2].
Penicillamine (5 mg/kg; i.v.; daily, for 8 weeks; male BN rats) prevents the onset of autoimmunity at a low dose^[3].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Animal Model:

Toxic milk mutant mice (tx mice) and DL mice^[1]
Dosage:

200 mg/kg
Administration:

Oral gavage; daily, for 3, 10 and 14 days
Result:

Increased the free copper concentrations in the tx mice serum on the 3rd day.

Animal Model:

Toxic milk mutant mice (tx mice) and DL mice^[1]
Dosage:

200 mg/kg
Administration:

Oral gavage; daily, for 3, 10 and 14 days
Result:

Increased the mRNA expression of ATP7A by 4-fold. Increased CTR1 mRNA expression by 6.9-fold in the cortex and 9.1-fold in the basal ganglia of tx mice.

Animal Model:

Toxic milk mutant mice (tx mice) and DL mice^[1]
Dosage:

200 mg/kg
Administration:

Oral gavage; daily, for 3, 10 and 14 days
Result:

Increased the concentration of MDA and decreased GSH/GSSG ratios through nitric oxide/NMDA pathways.

Animal Model:

Male NMRI mice^[2]
Dosage:

0.1, 0.5, 1, 10, 100, 150 and 250 mg/kg
Administration:

Intraperitoneal injection; once, for 90 minutes
Result:

Had anticonvulsant effects at a low dose (0.5 mg/kg) and had anticonvulsant effects at a high dose (250 mg/kg). Reversed the anti- and proconvulsant effects by acute pretreatment of L-NAME (a nonselective nitric oxide synthase inhibitor) and 7-NI (a selective neuronal nitric oxide synthase inhibitor).

Animal Model:

Male BN rats^[3]
Dosage:

5 mg/kg
Administration:

Intravenous injection; daily, for 8 weeks
Result:

Inhibited IgE upregulation and prevented the onset of autoimmunity.

Clinical Trial

NCT Number	Sponsor	Condition	Start Date	Phase A549
NCT01329991	Plexxikon\|		2011-05	PHASE1

Chemical Information

CAS. Nr. 52-67-5
Appearance Solid
Molecular Weight 149.22
Formel C₅H₁₁NO₂S
Color White to off-white
SMILES

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

D-(-)-Penicillamine
Structure Classification
- Ketones, Aldehydes, Acids
Initial Source
- Microorganisms
Penicillium
Versand

Room temperature in continental US; may vary elsewhere.

Speicherung

Powder	-20°C	3 years
	4°C	2 years
In solvent	-80°C	2 years
	-20°C	1 year

Publications (3)

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Journal Impact Factor

J Colloid Interface Sci

Photoactive metal-covalent organic framework nanozymes with enhanced peroxidase-mimicking activity for eliminating drug-resistant bacterial infections. [Abstract]

2025 Jun 12;699(Pt 1):138178. PMID: 40527142

Penicillamine purchased from MedChemExpress. Usage Cited in: J Colloid Interface Sci. 2025 Jun 12;699(Pt 1):138178. [Abstract]

Effects of Penicillamine (0-400 μM) on MRSA cell viability after CuSA-COF treatment.
Antioxidants (Basel)

Characterization of the Inducible and Slow-Releasing Hydrogen Sulfide and Persulfide Donor P*: Insights into Hydrogen Sulfide Signaling. [Abstract]

2021 Jun 29;10(7):1049. PMID: 34209813

Penicillamine purchased from MedChemExpress. Usage Cited in: Antioxidants (Basel). 2021 Jun 29;10(7):1049. [Abstract]

ATDC5 cells were incubated with 1 mM P* or penicillamine (Peni) for 1 h followed by stimulation with IL-1β/IFN-γ for 24 h. IL-6 levels were determined by ELISA and normalized against stimulated cells (Stim) set to 100 %.

Penicillamine purchased from MedChemExpress. Usage Cited in: Antioxidants (Basel). 2021 Jun 29;10(7):1049. [Abstract]

Primary human chondrocytes from OA patients were preincubated for 1 h with 0.5 mM P* or penicillamine (Peni) and stimulated for 24 h with IL-1β. IL-6 mRNA levels were determined by qPCR with SDHA as a reference gene and normalized to Stim (100 %).
Nitric Oxide

Polysulfides derived from the hydrogen sulfide and persulfide donor P* inhibit IL-1β-mediated inducible nitric oxide synthase signaling in ATDC5 cells: are CCAAT/enhancer-binding proteins β and δ involved in the anti-inflammatory effects of hydrogen sulfide and polysulfides?. [Abstract]

2022 Dec 1:129:41-52. PMID: 36216240

Lösungsmittel & Löslichkeit

In Vitro:

H₂O : 83.33 mg/mL (558.44 mM; ultrasonic and warming and heat to 60°C)

DMSO : 1.43 mg/mL (9.58 mM; Need ultrasonic; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO)

View the Complete Stock Solution Preparation Table

Preparing Stock Solutions

View the Complete Stock Solution Preparation Table

Concentration Solvent Mass

1 mg

5 mg

10 mg

Concentration

Solvent

Mass

1 mM

6.7015 mL

33.5076 mL

67.0151 mL

5 mM

1.3403 mL

6.7015 mL

13.4030 mL

10 mM

0.6702 mL

3.3508 mL

6.7015 mL

Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.

Storage method and period of stock solution: -80°C, 2 years; -20°C, 1 year. When stored at -80°C, please use it within 2 years. When stored at -20°C, please use it within 1 year.

* Note: If you choose water as the stock solution, please dilute it to the working solution, then filter and sterilize it with a 0.22 μm filter before use.

Molaritätsrechner

Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

Mass Mass

Konzentration Konzentration

Volumen Volumen

Molecular Weight Molecular Weight

Verdünnungsrechner

Konzentration _{(Stammlösung)} × Volumen _{(Stammlösung)} = Konzentration _{(Ziellösung)} × Volumen _{(Ziellösung)}

Konzentration _{(Stammlösung)} Konzentration _{(Stammlösung)}

Volumen _{(Stammlösung)} Volumen _{(Stammlösung)}

Konzentration _{(Ziellösung)} Konzentration _{(Ziellösung)}

Volumen _{(Ziellösung)} Volumen _{(Ziellösung)}

In Vivo:

Working Solution

For the following dissolution methods, please prepare the working solution directly:

It is recommended to prepare fresh solutions and use them promptly within a short period of time.

The percentages shown for the solvents indicate their volumetric ratio in the final prepared solution. If precipitation or phase separation occurs during preparation, heat and/or sonication can be used to aid dissolution.

Protocol 1

Add each solvent one by one: PBS

Solubility: 100 mg/mL (670.15 mM); Clear solution; Need ultrasonic

Reinheit & Dokumentation

Select Batch:

Reinheit: 99.98%

Assay: 99.98%

ee.: 99.98%

Data Sheet (278 KB)
SDS (418 KB)
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COA (2659 KB)
Elemental Analysis Report (2659 KB)
HNMR (2659 KB)
CNMR (2659 KB)
RP-HPLC (2659 KB)
NP-HPLC (2659 KB)
MS (2659 KB)
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IR (2659 KB)
GC (2659 KB)
OR (2659 KB)
SDS-PAGE (2659 KB)
SEC-HPLC (2659 KB)
Other Report (2659 KB)
Handling Instructions (2659 KB)

Verweise

[1]. Chen DB, et, al. Penicillamine increases free copper and enhances oxidative stress in the brain of toxic milk mice. PLoS One. 2012;7(5):e37709. [Content Brief]

[2]. Rahimi N, et, al. Effects of D-penicillamine on pentylenetetrazole-induced seizures in mice: involvement of nitric oxide/NMDA pathways. Epilepsy Behav. 2014 Oct;39:42-7. [Content Brief]

[3]. Masson MJ, et, al. Tolerance induced by low dose D-penicillamine in the brown Norway rat model of drug-induced autoimmunity is immune-mediated. Chem Res Toxicol. 2004 Jan;17(1):82-94. [Content Brief]

[4]. Ishak R, et, al. Penicillamine revisited: historic overview and review of the clinical uses and cutaneous adverse effects. Am J Clin Dermatol. 2013 Jun;14(3):223-33. [Content Brief]

Help & FAQs

How should lyophilized recombinant proteins be reconstituted and stored?

1. Before opening the cap, centrifuge the vial at 13000 rpm for 20-30 seconds. This step will ensure that any lyophilized powder that may have adhered to the cap or walls is collected at the bottom of the vial, minimizing the risk of product loss.

Complete Stock Solution Preparation Table

Storage method and period of stock solution: -80°C, 2 years; -20°C, 1 year. When stored at -80°C, please use it within 2 years. When stored at -20°C, please use it within 1 year.

Optional Solvent	Concentration Solvent Mass	1 mg	5 mg	10 mg	25 mg
DMSO / H₂O	1 mM	6.7015 mL	33.5076 mL	67.0151 mL	167.5379 mL
DMSO / H₂O	5 mM	1.3403 mL	6.7015 mL	13.4030 mL	33.5076 mL
H₂O	10 mM	0.6702 mL	3.3508 mL	6.7015 mL	16.7538 mL
	15 mM	0.4468 mL	2.2338 mL	4.4677 mL	11.1692 mL
	20 mM	0.3351 mL	1.6754 mL	3.3508 mL	8.3769 mL
	25 mM	0.2681 mL	1.3403 mL	2.6806 mL	6.7015 mL
	30 mM	0.2234 mL	1.1169 mL	2.2338 mL	5.5846 mL
	40 mM	0.1675 mL	0.8377 mL	1.6754 mL	4.1884 mL
	50 mM	0.1340 mL	0.6702 mL	1.3403 mL	3.3508 mL
	60 mM	0.1117 mL	0.5585 mL	1.1169 mL	2.7923 mL
	80 mM	0.0838 mL	0.4188 mL	0.8377 mL	2.0942 mL
	100 mM	0.0670 mL	0.3351 mL	0.6702 mL	1.6754 mL

* Note: If you choose water as the stock solution, please dilute it to the working solution, then filter and sterilize it with a 0.22 μm filter before use.

Keywords

Penicillamine

3 Cited Publications

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Publications Citing Use of MedChemExpress (MCE) Penicillamine

Biologische Aktivität

Chemical Information

Publications (3)

Lösungsmittel & Löslichkeit

Reinheit & Dokumentation

Verweise

Help & FAQs

Complete Stock Solution Preparation Table

Penicillamine Related Classifications

Art. -Nr.: HY-B0300