MedKoo Cat#: 318462 | Name: Penicillamine
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

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

Penicillamine
Penicillamine
CAS#52-67-5

Theoretical Analysis

MedKoo Cat#: 318462

Name: Penicillamine

CAS#: 52-67-5

Chemical Formula: C5H11NO2S

Exact Mass: 149.0511

Molecular Weight: 149.21

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 150.00
2g USD 250.00
5g USD 450.00
10g USD 750.00
20g USD 1,250.00
50g USD 1,650.00
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Related CAS #
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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

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
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.