Penicillamine
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MedKoo CAT#: 318462

CAS#: 52-67-5

Description: Penicillamine is an exogenous NOS modulator, found to inhibit urease activity and an antirheumatic and chelating agent used for Wilson's disease. It is D-penicillamine, as L-penicillamine is toxic (it inhibits the action of pyridoxine). It is an α-amino acid metabolite of penicillin, although it has no antibiotic properties.

Chemical Structure

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Penicillamine
CAS# 52-67-5
Instruction

Theoretical Analysis

MedKoo Cat#: 318462
Name: Penicillamine
CAS#: 52-67-5
Chemical Formula: C5H11NO2S
Exact Mass: 149.05
Molecular Weight: 149.210
Elemental Analysis: C, 40.25; H, 7.43; N, 9.39; O, 21.45; S, 21.49

Price and Availability

Size Price Availability Quantity
1g USD 150
2g USD 250
5g USD 450
10g USD 750
20g USD 1250
50g USD 1650
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Synonym: Penicillamine; D-Penicillamine; Penicillamine; 3-Mercapto-D-valine; D-(-)-Penicillamine; Cuprimine; Depen; Penicillaminate, Copper; Penicillamine;

IUPAC/Chemical Name: (2S)-2-amino-3-methyl-3-sulfanylbutanoic acid

InChi Key: VVNCNSJFMMFHPL-VKHMYHEASA-N

InChi Code: InChI=1S/C5H11NO2S/c1-5(2,9)3(6)4(7)8/h3,9H,6H2,1-2H3,(H,7,8)/t3-/m0/s1

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

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 149.21 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Lin SM, Geng S, Li N, Li NB, Luo HQ. D-penicillamine-templated copper
nanoparticles via ascorbic acid reduction as a mercury ion sensor. Talanta. 2016
May 1;151:106-13. doi: 10.1016/j.talanta.2016.01.028. Epub 2016 Jan 15. PubMed
PMID: 26946016.


2: McCarthy CW, Goldman J, Frost MC. Synthesis and Characterization of the Novel
Nitric Oxide (NO) Donating Compound, S-nitroso-N-acetyl-D-penicillamine
Derivatized Cyclam (SNAP-Cyclam). ACS Appl Mater Interfaces. 2016 Mar
9;8(9):5898-905. doi: 10.1021/acsami.5b12548. Epub 2016 Feb 26. PubMed PMID:
26859235.


3: Lautner G, Meyerhoff ME, Schwendeman SP. Biodegradable poly(lactic-co-glycolic
acid) microspheres loaded with S-nitroso-N-acetyl-D-penicillamine for controlled
nitric oxide delivery. J Control Release. 2016 Mar 10;225:133-9. doi:
10.1016/j.jconrel.2015.12.056. Epub 2016 Jan 5. PubMed PMID: 26763376; PubMed
Central PMCID: PMC4769910.


4: Mendoza FA, Bai R, Kebede AG, Jimenez SA. Severe eosinophilic fasciitis:
comparison of treatment with d-penicillamine plus corticosteroids vs.
corticosteroids alone. Scand J Rheumatol. 2016 Mar;45(2):129-34. doi:
10.3109/03009742.2015.1067713. Epub 2015 Nov 3. PubMed PMID: 26525956; PubMed
Central PMCID: PMC4775409.


5: Leahy T, Rickard JP, Aitken RJ, de Graaf S. D-penicillamine prevents ram sperm
agglutination by reducing the disulphide bonds..... Reproduction. 2016 Feb 9.
pii: REP-15-0596. [Epub ahead of print] PubMed PMID: 26860122.


6: Brancaleone V, Esposito I, Gargiulo A, Vellecco V, Asimakopoulou A, Citi V,
Calderone V, Gobbetti T, Perretti M, Papapetropoulos A, Bucci M, Cirino G.
D-penicillamine modulates hydrogen sulfide (H(2) S) pathway through selective
inhibition of cystathionine-γ-lyase (CSE). Br J Pharmacol. 2016 Feb 18. doi:
10.1111/bph.13459. [Epub ahead of print] PubMed PMID: 26890936.


7: Leahy T, Rickard JP, Aitken RJ, de Graaf SP. Penicillamine prevents ram sperm
agglutination in media that support capacitation. Reproduction. 2016
Feb;151(2):167-77. doi: 10.1530/REP-15-0413. PubMed PMID: 26705263.


8: Říha M, Hašková P, Martin J, Filipský T, Váňová K, Vávrová J, Holečková M,
Homola P, Vítek L, Palicka V, Šimůnek T, Mladěnka P. Protective Effects of
D-Penicillamine on Catecholamine-Induced Myocardial Injury. Oxid Med Cell Longev.
2016;2016:5213532. doi: 10.1155/2016/5213532. Epub 2015 Dec 14. PubMed PMID:
26788248; PubMed Central PMCID: PMC4691625.


9: Lee Y, Lee ST, Cho H. D-penicillamine-induced ANA (+) ANCA (+) vasculitis in
pediatric patients with Wilson's disease. Clin Nephrol. 2016 Jan 19. [Epub ahead
of print] PubMed PMID: 26784915.


10: Königsberger LC, Königsberger E, Hefter G, May PM. Formation constants of
copper(I) complexes with cysteine, penicillamine and glutathione: implications
for copper speciation in the human eye. Dalton Trans. 2015 Dec
21;44(47):20413-25. doi: 10.1039/c5dt02129d. Epub 2015 Oct 27. PubMed PMID:
26505238.


11: Zheng Y, Zhai L, Zhao Y, Wu C. Orthogonal Cysteine-Penicillamine Disulfide
Pairing for Directing the Oxidative Folding of Peptides. J Am Chem Soc. 2015 Dec
9;137(48):15094-7. doi: 10.1021/jacs.5b10779. Epub 2015 Nov 30. PubMed PMID:
26588670.


12: Dzieżyc K, Litwin T, Chabik G, Członkowska A. Measurement of urinary copper
excretion after 48-h d-penicillamine cessation as a compliance assessment in
Wilson's disease. Funct Neurol. 2015 Nov 25:1-8. [Epub ahead of print] PubMed
PMID: 26602747.


13: Lee YR, Kang MH, Park HM. Treatment of zinc toxicosis in a dog with chelation
using d-penicillamine. J Vet Emerg Crit Care (San Antonio). 2015 Nov 20. doi:
10.1111/vec.12414. [Epub ahead of print] PubMed PMID: 26587915.


14: Pérez-Ràfols C, Serrano N, Díaz-Cruz JM, Ariño C, Esteban M.
Penicillamine-modified sensor for the voltammetric determination of Cd(II) and
Pb(II) ions in natural samples. Talanta. 2015 Nov 1;144:569-73. doi:
10.1016/j.talanta.2015.06.083. Epub 2015 Jul 4. PubMed PMID: 26452863.


15: Gelaude A, Marin M, Cailliau K, Jeseta M, Lescuyer-Rousseau A, Vandame P,
Nevoral J, Sedmikova M, Martoriati A, Bodart JF. Nitric oxide donor
s-nitroso-n-acetyl penicillamine (SNAP) alters meiotic spindle morphogenesis in
Xenopus oocytes. J Cell Biochem. 2015 Nov;116(11):2445-54. doi:
10.1002/jcb.25211. PubMed PMID: 25923058.


16: Dzieżyc K, Litwin T, Chabik G, Członkowska A. Measurement of urinary copper
excretion after 48-h d-penicillamine cessation as a compliance assessment in
Wilson's disease. Funct Neurol. 2015 Oct-Dec;30(4):264-8. PubMed PMID: 26727705;
PubMed Central PMCID: PMC4758779.


17: Ngamdee K, Puangmali T, Tuntulani T, Ngeontae W. Circular dichroism sensor
based on cadmium sulfide quantum dots for chiral identification and detection of
penicillamine. Anal Chim Acta. 2015 Oct 22;898:93-100. doi:
10.1016/j.aca.2015.09.038. Epub 2015 Oct 1. PubMed PMID: 26526914.


18: Wo Y, Li Z, Brisbois EJ, Colletta A, Wu J, Major TC, Xi C, Bartlett RH,
Matzger AJ, Meyerhoff ME. Origin of Long-Term Storage Stability and Nitric Oxide
Release Behavior of CarboSil Polymer Doped with
S-Nitroso-N-acetyl-D-penicillamine. ACS Appl Mater Interfaces. 2015 Oct
14;7(40):22218-27. doi: 10.1021/acsami.5b07501. Epub 2015 Oct 1. PubMed PMID:
26393943; PubMed Central PMCID: PMC4613868.


19: Martí-Prats L, Zornoza T, López-Moreno JA, Granero L, Polache A. Acetaldehyde
sequestration by D-penicillamine prevents ethanol relapse-like drinking in rats:
evidence from an operant self-administration paradigm. Psychopharmacology (Berl).
2015 Oct;232(19):3597-606. doi: 10.1007/s00213-015-4011-1. Epub 2015 Jul 9.
PubMed PMID: 26153068.


20: Brogan PT, Beitsma M, Henning H, Gadella BM, Stout TA. Liquid storage of
equine semen: Assessing the effect of d-penicillamine on longevity of ejaculated
and epididymal stallion sperm. Anim Reprod Sci. 2015 Aug;159:155-62. doi:
10.1016/j.anireprosci.2015.06.011. Epub 2015 Jun 19. PubMed PMID: 26130601.