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(-)-Penicillamine

(-)-Penicillamine structure

CAS No:
52-67-5
Formula:
C5H11NO2S
Chemical Name:
(-)-Penicillamine
Synonyms:
D-Valine,3-mercapto-;Valine,3-mercapto-,D-;3-Mercapto-D-valine;Cuprimine;D-3-Mercaptovaline;D-Penicillamine;Penicillamine;Metalcaptase;Cuprenil;Trolovol;D-Mercaptovaline;D-(-)-Penicillamine;Penicillamin;D-Penamine;Reduced D-penicillamine;Reduced penicillamine;DPA;Kuprenil;Cupripen;(S)-3,3-Dimethylcysteine;(-)-Penicillamine;2-Amino-3-mercapto-3-methylbutanoic acid;(2S)-2-Amino-3-methyl-3-sulfanylbutanoic acid;(S)-Penicillamine;Perdolat;Mercaptyl;Pendramine;Depen;Sufirtan;β-Thiovaline;Depamine;NSC 81549;Artamin;Dimethylcysteine;(2S)-2-Azaniumyl-3-methyl-3-sulfanylbutanoate;(2S)-2-Amino-3-methyl-3-sulfanylbutanoic acid;16414-54-3;937590-88-0
Categories:
Active Pharmaceutical Ingredients > Specialty Drugs

Description

Penicillamine is the most characteristic degradation product of the penicillin antibiotics. It is used as an antirheumatic and as a chelating agent in Wilson's disease.Target: OthersPenicillamine(Cuprimine, Depen) is used as an antirheumatic and as a chelating agent in Wilson's disease and is a chelating agent recommended for the removal of excess copper in patients with Wilson's disease. From in vitro studies which indicate that one atom of copper combines with two molecules of penicill

(-)-Penicillamine Basic Attributes

Molecular Weight：

149.21

Exact Mass：

149.21

BRN：

1722375

EC Number：

200-148-8

HScode：

2930909090

Characteristics

PSA：

64.3

XLogP3：

-1.8

Appearance：

White to almost white Powder

Density：

1.2±0.1 g/cm3

Melting Point：

202-206 °C

Boiling Point：

251.8±35.0°C at 760 mmHg

Flash Point：

106.1±25.9 °C

Refractive Index：

-63 ° (C=1, 1mol/L NaOH)

Water Solubility：

H2O: 11.1 g/100 mL (20 ºC)

Storage Conditions：

2-8°C

Toxicity：

LD50 in rats (mg/kg): >10000 orally, >660 i.p. (Jaffe)

Specific rotation：

-65 º (c=5, 1M NaOH, on dry)

Odor：

SLIGHT CHARACTERISTIC ODOR

Taste：

SLIGHTLY BITTER

PKA：

1.8None

Safety Information

Transport codes：

NONH for all modes of transport

wgk germany：

hazard class code：

36/37/38-40-20/21/22

safety instructions：

26-36-24/25-22

RTECS Number：

YV9425000

Marks：

Xi,T,Xn

Stability/Shelf Life：

Stable. Incompatible with strong oxidizing agents.

Precautionary statement(s)：

P261-P305 + P351 + P338

Hazard Statements：

H315-H319-H335

(-)-Penicillamine Use and Manufacturing

It is used as an antirheumatic and as a chelating agent in Wilson′s disease. It is used as a copper chelator to form mixed disulfides with cysteine or other sulfide media components. It is used to inactivate protein-1 DNA binding and to inhibit the growth of asynchronous cultures of rabbit articular chondrocytes.

Material

4-Methylaniline

p-Phenylenediamine

o-Toluidine

o-Phenylenediamine

Drug Function and Efficacy

1. Complexation. ① Heavy metal poisoning: this product can complex heavy metals such as copper, iron, mercury, lead, and arsenic to form stable and soluble complexes that are excreted in urine. Its lead removal effect is not as good as that of calcium sodium edetate, and its mercury removal effect is not as good as that of dimercaprol; but this product can be taken orally, with slightly fewer adverse reactions, and can be used for mild heavy metal poisoning or when other complexing agents are contraindicated. ② Wilson's disease is a common chromosomal recessive genetic disease, mainly with a large amount of copper deposited in the liver and brain tissues, causing lenticular degeneration and cirrhosis. This product can combine with copper deposited in the tissues to form a soluble complex that is excreted in urine. ③ Cystinuria and its stones: this product can react with cystine to form a mixture of cysteine-penicillamine disulfide, thereby reducing the concentration of cystine in urine; the solubility of this mixture is 50 times greater than that of cystine, so it can prevent the formation of cystine stones; long-term use for 6 to 12 months may gradually dissolve the already formed cystine stones. 2. Anti-rheumatoid arthritis: The mechanism of action for the treatment of rheumatoid arthritis is not yet clear. After taking the drug, it was found that the lymphocyte function was improved, and the levels of IgM rheumatoid factor and immune complex in serum and joint capsule fluid were significantly reduced, but there was no significant reduction in the absolute value of serum immunoglobulin. It inhibited the activity of T cells in vitro, but had no effect on B cells. This product can also inhibit the cross-linking of newly synthesized procollagen, so it is also used to treat skin and soft tissue collagen diseases.

This ingredient has been used in drugs with the following functions (note: it does not mean that the ingredient itself has the following health functions)

Related Drugs

Penicillamine Tablets
Ingredients	Penicillamine
Indication	This product can aggravate the adverse reactions of antimalarial drugs, gold preparations, immunosuppressants, and phenylbutazone on the hematopoietic system and kidneys. For patients taking oral iron preparations, this product should be taken 2 hours before taking iron preparations to avoid weakening the efficacy of this product.
Specifications	0.125 g
Manufacturer	Shanghai Sine Pharmaceutical Laboratories Co., Ltd.

Penicillamine Tablets
Ingredients	The main ingredient of this product is penicillamine.
Indication	This product can aggravate the adverse reactions of antimalarial drugs, gold preparations, immunosuppressants, and phenylbutazone on the hematopoietic system and kidneys. For patients taking oral iron preparations, this product should be taken 2 hours before taking iron preparations to avoid weakening the efficacy of this product.
Specifications	0.125g
Manufacturer	Shanghai Sine WANXIANG Pharmaceuticals Co., Ltd.

Penicillamine
Ingredients	Main ingredients: The main ingredient of this product is penicillamine. Molecular formula: C5H11NO2S Molecular weight: 149.21
Manufacturer	Sichuan Pharmaceutical Co., Ltd.

See More Related Drugs

Registered Holders

API PHARMA TECH LLC

United States
Active
MSN LIFE SCIENCES PRIVATE LTD

United States
Active
OPTIMUS DRUGS PRIVATE LTD

United States
Active

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