L-Penicillamine

Synonym(s):L-(+)-2-Amino-3-mercapto-3-methylbutanoic acid β,β-Dimethyl-L-cysteine;3,3-Dimethyl-L-cysteine;3-Mercapto-L-valine

CAS NO.：1113-41-3
Empirical Formula: C5H11NO2S
Molecular Weight: 149.21
MDL number: MFCD00064303
EINECS: 214-203-9
SAFETY DATA SHEET (SDS)
Update Date: 2024-04-03 12:01:51

What is L-Penicillamine?

Chemical properties

white to almost white crystalline powder

The Uses of L-Penicillamine

As a Penicillin metabolite, L-Penicillamine can be used in the treatment of Wilson’s disease, Cystinuria, Scleroderma and arsenic poisoning.

The Uses of L-Penicillamine

L-Penicillamine is a metabolite of penicillin. L-Penicillamine is used in the treatment of Wilson’s disease, Cystinuria, Scleroderma and arsenic poisoning.

The Uses of L-Penicillamine

Metal-chelating agent

Definition

ChEBI: The L-enantiomer of penicillamine.

Indications

Penicillamine (Cuprimine) can be used to treat acute, severe rheumatoid arthritis, producing reductions in joint pain, edema, and stiffness.The response to penicillamine is usually delayed (4–12 weeks), and remissions can last several months after withdrawal of treatment. Radiographic evidence of this drug’s efficacy is limited; thus, penicillamine is seldom used to treat rheumatoid arthritis.

Mechanism of action

The mechanism of action of penicillamine is unknown, but some evidence suggests that it may involve the inhibition of angiogenesis, synovial fibroblast proliferation, or transcriptional activation. Because penicillamine can chelate copper and promote its excretion, it is used to treat Wilson’s disease (hepatolenticular degeneration) and has also been used in mercury and lead intoxication.

Pharmacology

Penicillamine is readily absorbed from the GI tract and is rapidly excreted in the urine, largely as the intact molecule. Gradually increasing its dose minimizes side effects, which necessitate discontinuance of penicillamine therapy in perhaps one-third of patients. The most common side effects are maculopapular pruritic dermatitis, GI upset, loss of taste sensation, mild to occasionally severe thrombocytopenia and leukopenia,and mild proteinuria, which at times may progress to the nephritic syndrome. Discontinuance of therapy usually results in a rapid disappearance of side effects.

Safety Profile

A poison by intraperitoneal route. Mutation data reported. Whenheated to decomposition it emits toxic vapors of NOx and SOx.

Purification Methods

Same as preceding entry for its enantiomer. [Beilstein 4 IV 3228.]

Properties of L-Penicillamine

Melting point:	206 °C (dec.)(lit.)
Boiling point:	251.8±35.0 °C(Predicted)
alpha	61.9 º (C=0.5 IN 1 M NAOH)
Density	1.113 (estimate)
refractive index	63 ° (C=1, 1mol/L NaOH)
storage temp.	Keep in dark place,Inert atmosphere,Room temperature
solubility	Aqueous Base (Sparingly), DMSO (Slightly, Heated), Water (Slightly)
pka	2.13±0.12(Predicted)
form	Crystalline Powder
color	White to almost white
optical activity	[α]24/D +61.9°, c = 0.5 in 1 M NaOH
Merck	14,7088
BRN	1722374
Stability:	Hygroscopic
CAS DataBase Reference	1113-41-3(CAS DataBase Reference)

Safety information for L-Penicillamine

Signal word	Danger
Pictogram(s)	Exclamation Mark Irritant GHS07
GHS Hazard Statements	H302:Acute toxicity,oral H315:Skin corrosion/irritation H319:Serious eye damage/eye irritation H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes	P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.