What is Penicillamine? and What are Its Various Health Benefits and Hazards

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What is Penicillamine? and What are Its Various Health Benefits and Hazards

What is Penicillamine?

Did you ever hear about Penicillamine? It’s a well-known antibiotic medicine, so you’ve probably heard of it before.

Penicillamine is a prescription medication in an oral tablet and an oral capsule. It is used to treat rheumatoid arthritis-related pain, swelling, and discomfort.

It is also used to remove some undesirable elements in the body. Cuprimine, Depen, and D-Penamine are some of the brand names.

What is the Structure and Properties of Penicillamine?

what is penicillamine

Source: Chemspider.com

Penicillamine is a chemical molecule composed of a thiol, an amine, and a carboxylic acid. It has a similar structure to the α-amino acid cysteine but with geminal dimethyl substituents to the thiol.

Like other amino acids, it is a white solid that occurs in the zwitterionic state at physiological pH. Penicillamine is a disease-modifying antirheumatic medication that is 3-mercapto-D-valine.Its IUPAC name is (2S)-2-amino-3-methyl-3-sulfanylbutanoic acid.

 It is a crystalline powder. It is white or nearly white, easily soluble in water, mildly soluble in alcohol, and insoluble in ether, acetone, benzene, and carbon tetrachloride.

Despite its D configuration, it is levorotatory. C5H11NO2S is the empirical formula, and it has a molecular weight of 149.21.

What is the Difference between L-Penicillamine and D-Penicillamine?

Penicillamine is a chiral chemical having one stereogenic core and two enantiomers. It is why it exists as two enantiomer compounds as L-Penicillamine and D-Penicillamine.

One of the two, the (S)-enantiomer, the eutomer, is termed as D-Penicillamine. This type shows many antibacterial and antiarthritic properties of L-Penicillamine.

 Another distomer (R)-penicillamine, is very poisonous. It is termed L-penicillamine, and it comes with R absolute configuration. L-Penicillamine is the more poisonous of the two enantiomers.

It is so because it inhibits the activity of pyridoxine (also known as vitamin B6). This is why although L-Penicillamine enantiomer is a penicillin metabolite, it lacks antibacterial activity.

what is the difference between l penicillamine and d penicillamine

Source: Techify.com

Who Discovered Penicillamine?

In 1956, John Walshe documented the use of Penicillamine in Wilson’s disease. He detected the chemical in the urine of penicillin-treated individuals (including himself) and experimentally demonstrated that it enhanced urinary copper excretion via chelation.

He first struggled to persuade major global specialists at the time (Denny Brown and Cumings) of its users because they believed Wilson’s illness was largely an issue of amino acid metabolism, not copper homeostasis, and that dimercaprol should be used as a chelator.

Subsequent research supported both the copper-centered idea and the effectiveness of D-penicillamine. Walshe was also a pioneer in developing additional chelators in Wilson’s, such as triethylenetetramine and tetrathiomolybdate.

How is Penicillamine Manufactured?

John Cornforth was the first to synthesize Penicillamine under the direction of Robert Robinson. Since the first successful instance in 1964, Penicillamine has been used to treat rheumatoid arthritis.

Penicillamine is a dimethylated cysteine. It comes with two bulky methyl groups around the thiol group, making it more resistant to in vivo interactions. Penicillamine is synthesized mainly by the chelation process.

The chelation of the free portion of copper in blood plasma produces a mixed-valence copper-penicillamine complex. This chelate complex is thought to be in charge of urine elimination.

What is the Mechanism of Action of Penicillamine?

Heavy metals like copper, lead, and mercury can be chelated by Penicillamine and formed into a soluble complex eliminated in the urine via the kidneys. These heavy metals can cause serious health hazards if this does not happen.

Penicillamine can also react with cysteine and generate disulfide bonds, making urine excretion easier. This helps to prevent cystine calculi from forming. It can reduce T cell activity in people with rheumatoid arthritis, thus minimizing the chance of arthritis.

The 250 mg dosage has a 1 to 3 hours plasma peak time and a peak plasma concentration of 1 to 2 mg/L. It is protein-bound to the extent that more than 80% of it is eliminated in the urine.

Is Pencilline the Same as Penicillamine?

There is a difference in both Penicillin and Penicillamine. Penicillin is a medicinal medication that belongs to a class of antibiotics derived from Penicillium molds or manufactured.

They are beta-lactam antibiotics that are active against gram-positive bacteria and are used to treat various infections and ailments.

Whereas Penicillamine is made from Penicillin by modifying it further. Penicillamine is a breakdown product of Penicillin used as a chelating agent to treat heavy metal toxicity.

What is the Use of Penicillamine in Wilson Disease?

wilson disease
Source: Scientific Animations

This drug is used to treat rheumatoid arthritis, Wilson’s disease. It is a condition in which the body’s copper levels are too high, causing damage to the liver, brain, and other organs.

 Penicillamine binds to copper and aids its removal from the body to treat Wilson’s disease. Reduced copper levels assist in improving liver function and the mental/mood/nervous difficulties associated with the condition (such as disorientation, trouble speaking/walking).

Is Penicillamine Helpful in Renal Failure?

renal failure
Source: Very Well Health

It is an effective remedy for kidney stone issues (cystinuria). Penicillamine is used to treat cystinuria by lowering the quantity of a substance (cystine) in the urine, which can cause kidney stones.

In cystinuria, Penicillamine also lowers excess cystine excretion. At least in part, this is accomplished by disulfide exchange between Penicillamine and cystine.

xcThis results in creating penicillamine-cysteine disulfide, a considerably more soluble molecule than cystine and is easily excreted.

Penicillamine inhibits the production of tropocollagen cross-links and cleaves them when they are freshly created.

Does Penicillamine Cause Bronchitis?

D-penicillamine is an effective therapy for rheumatoid arthritis, although it is not without side effects. The research study describes four occurrences of respiratory sickness that occurred during D-penicillamine therapy and for which the medicine is most likely to blame.

Two individuals presented diffuse alveolitis, which improved when the D-penicillamine was discontinued. Two patients arrived with quickly escalating dyspnea, and a chest X-ray revealed enlarged lungs.

Their lung function tests revealed substantial airflow restriction with air trapping, and bronchodilators and corticosteroids were ineffective. In recent years, several examples of individuals with comparable characteristics have been recorded; pathologic tests revealed bronchiolitis.

Health physicians should be aware of the severity of this kind of bronchiolitis and quickly discontinue D-penicillamine in patients who present with early respiratory symptoms.

Would Penicillamine Help With Covid?

Covid is a respiratory disease caused by coronaviruses. Coronaviruses are responsible for illness in mammals and birds. Coronaviruses cause respiratory tract infections in humans that vary from mild to fatal.

Penicillamine is reported to harm the lungs. It causes enlargement of lungs and diffused alveoli. It is mostly not used as an antibiotic. So; Penicillamine should be avoided during Covid.

Can Penicillamine Cause Side Effects?

Penicillamine may result in It is possible to have stomach discomfort, nausea, vomiting, lack of appetite, diarrhea, and a loss of taste.

Penicillamine may have a few uncommon but significant adverse effects. It may show indications of renal disease such as changes in urine volume, bloody urine, coughing up blood, shortness of breath, and muscular weakness.

 It can also cause drooping eyelids, clouded vision, severe stomach or abdominal discomfort, black urine, and yellowing eyes and skin.

It is uncommon for this medicine to cause a severe allergic response. However, get emergency medical assistance if you detect any of the following signs of a severe allergic reaction: rash, itching/swelling (particularly of the face/tongue/throat), extreme dizziness, and difficulty breathing.

You must inform your doctor or pharmacist right once if any of these side effects persist or worsen.

Can Penicillamine Cause Toxicity in Rheumatoid Arthritis?

Penicillamine is reported to show toxic effects while treating rheumatoid arthritis. In a clinical research study, it was evaluated for its toxic effect.

 A total of 101 rheumatoid arthritis patients was followed prospectively to examine the effectiveness and toxicity of D-penicillamine treatment.

There was a 70% overall improvement rate with two full remissions after a mean total follow-up of 11.5 months (38 patients completed two years of treatment).

 Sixty-one individuals experienced 84 distinct adverse responses, 36 of which necessitated medication withdrawal.

The most prevalent adverse effects of treatment at a mean D-penicillamine dosage of 463 mg/day were skin rashes (27/84), proteinuria (15/84), low platelets (14/84), and taste abnormalities (10/84). Most hazardous events (85%) occurred within the first six months.

Even at 500 mg/day, D-penicillamine-related toxicity appears to be a substantial issue; however, after nine months of continuous therapy, the medication can be taken with a higher safety margin.

Does Penicillamine Have Side Effects in Pregnancy?

Although the outcome of most pregnancies is normal under D-penicillamine, a teratogenic effect of the drug is known from animal studies.

 A few cases of children with congenital disabilities whose mothers received D-penicillamine during pregnancy are reported in the literature.

It is not advised to take Penicillamine when pregnant. It has the potential to damage an unborn child. However, it is administered throughout pregnancy in rare circumstances, such as treating Wilson’s disease.

In treating cystinuria and Wilson’s disease, D-impact penicillamine’s on collagen might induce unwanted side effects; yet, it is required to treat rheumatoid arthritis and scleroderma.

 Furthermore, because D-penicillamine passes the placental barrier, it can be teratogenic. According to the literature and our observations of two pregnancies, 46 of the 87 pregnant women who got D-penicillamine were treated throughout the pregnancy.

In the latter group, two of the babies had serious connective-tissue abnormalities. According to our findings, the dose of D-penicillamine in pregnant women with cystinuria and Wilson’s disease should be kept as low as feasible. D-penicillamine should not be used during pregnancy if you have rheumatoid arthritis.

Is Penicillamine Responsible for Neurological Side Effects?

Penicillamine administration comes with several neurological side effects often. A patient with Wilson’s disease who had neurologic symptoms was treated with D-penicillamine and experienced a rapid neurologic deterioration resulting from the treatment.

Repeat brain magnetic resonance imaging scans observed the formation of new brain lesions after six weeks and 11 months of penicillamine medication. In contrast, liver biopsy specimen data revealed good hepatic decoppering.

A retrospective survey of 25 additional patients was done who was with Wilson’s disease was done. These patients met the criteria of presenting with neurologic disease. Having been treated with Penicillamine was conducted to develop information on the relative rarity or frequency of neurologic worsening with the initiation of penicillamine therapy.

According to the responses, this condition frequently happens, at least according to the patient’s perspective. However, further research is required.

Frequently Asked Questions (FAQs)

Does Penicillamine Cause Penicillin Allergy?

Penicillin has cross-sensitivity; hence Penicillamine should not be administered to persons sensitive to Penicillin. Although clinical effects from d-penicillamine therapy are uncommon, Penicillamine antagonizes pyridoxine.

Hence, it is advised not to use Penicillamine if you are already allergic to Penicillin.

Is Penicillamine A Kind Of Antibiotic?

Penicillamine is a chelator-type medication. D-penicillamine is the medicinal version since L-penicillamine is hazardous (it inhibits the action of pyridoxine). It is penicillin -amino acid metabolite with no antibiotic activity. `

How Long Should Penicillamine Be Taken?

Penicillamine’s impact should be expected to build up gradually. This implies that you may not observe considerable improvement in your health until 6 to 12 weeks after beginning to take the pills.

You must keep your regular doctor’s or clinic appointments so that you must track your progress.

What Exactly is A Penicillamine Challenge Test?

What does a Penicillamine Challenge Test entail? Your doctor has ordered a ‘Penicillamine Challenge Test’ to be performed on you. This test is only done once to determine if you have Wilson’s Disease, a rare genetic condition.

What is The Purpose of Penicillamine?

Penicillamine is used to treat medical conditions such as Wilson’s disease (excess copper in the body) and rheumatoid arthritis. It is also used to avoid kidney stones. Penicillamine may also be prescribed for other problems by your doctor.

Is Pencillamine an Immunosuppressant?

Penicillamine is an immunosuppressive medication, which means it acts by suppressing the immune system’s function (your body’s defense mechanisms). It is used to treat Rheumatoid Arthritis, Wilson’s disease, and other illnesses such as scleroderma.


So, all that was regarding Pencillamine, its uses, and side effects. Although Pencillamine is Penicilline modified product but does not use an antibiotic. Anyways, it has shown great medical use in Rheumatoid Arthritis and to prevent renal failure.

This compound shows a lot of side effects also. A lot of care is needed while handling it. A lot of toxic effects are associated with including neurological toxicity. It is not advisable to use in pregnancy and lactation.

Before beginning therapy with this product, be sure to inform your doctor and pharmacist about all the items you take (including prescription pharmaceuticals, nonprescription drugs, and herbal products).

It is important to ensure that they provide you with the best care possible. Do not start, stop, or modify the dosage of any other medicines you are taking while using this product without first seeing your doctor.

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