penicillamine

Trade name: cuprimine

Small moleculeapproved

Approved

Dec 4, 1970

Penicillamine, sold under the trade names of Cuprimine among others, is a medication primarily used for treatment of Wilson's disease, cystinuria and active rheumatoid arthritis. Penicillamine 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 penicillamine. Penicillamine also reduces excess cystine excretion in cystinuria. This is done, at least in part, by disulfide interchange between penicillamine and cystine, resulting in formation of penicillamine-cysteine disulfide, a substance that is much more soluble than cystine and is excreted readily. Penicillamine interferes with the formation of cross-links between tropocollagen molecules and cleaves them when newly formed. The mechanism of action of penicillamine in rheumatoid arthritis is unknown although it appears to suppress disease activity. Unlike cytotoxic immunosuppressants, penicillamine markedly lowers IgM rheumatoid factor but produces no significant depression in absolute levels of serum immunoglobulins. Also unlike cytotoxic immunosuppressants which act on both, penicillamine in vitro depresses T-cell activity but not B-cell activity. — NCATS

Clinical trial activity

9 trials · 15 clinical orgs · 21 marketing orgs

Phase 1
1
Phase 2
6
Phase 3
4
Phase 4
0

Earliest trial started Mar 1, 1999 (NCT00003751)

Timeline

1970s

  1. Dec 4, 1970

    Merck — Earliest FDA Approval

  2. Dec 4, 1970

    Merck — NDA Organization

  3. Dec 4, 1970

    Bausch Health Companies — NDA Secondary Org

  4. Nov 8, 1978

    Mylan — NDA Secondary Org

1990s

  1. Jan 1, 1999

    Earliest Phase 2 Sponsor(trial)

2010s

  1. Jan 1, 2018

    Earliest Phase 3 Sponsor(trial)

  2. Jan 1, 2019

    Earliest Phase 1 Sponsor(trial)

  3. May 7, 2019

    Amerigen Pharmaceuticals — Marketing Organization

  4. May 7, 2019

    Ani Pharmaceuticals — Marketing Organization

  5. Jun 24, 2019

    Watson Pharmaceuticals — Marketing Organization

  6. Jun 24, 2019

    Allergan PLC (2015) — Marketing Organization

  7. Dec 23, 2019

    Par Pharmaceuticals — Marketing Organization

  8. Dec 23, 2019

    Endo Pharmaceuticals — Marketing Organization

  9. Dec 23, 2019

    Bristol-Myers Squibb — Marketing Organization

  10. Dec 23, 2019

    PH HEALTH — Marketing Organization

2020s

  1. Feb 13, 2020

    Teva — Marketing Organization

  2. Apr 28, 2020

    Apotex — Marketing Organization

  3. Aug 4, 2020

    Dr. Reddy's Laboratories — Marketing Organization

  4. Nov 30, 2020

    Lupin — Marketing Organization

  5. Dec 2, 2020

    Granules India — Marketing Organization

  6. Aug 19, 2021

    Invagen Pharms — Marketing Organization

  7. Aug 19, 2021

    Cipla — Marketing Organization

  8. Aug 23, 2021

    Esteve Labs — Marketing Organization

  9. Aug 23, 2021

    Aggrega Pharma — Marketing Organization

  10. Oct 8, 2021

    Navinta — Marketing Organization

Indications

Mechanism of action

  • CopperCHELATING AGENT

    Copper chelating agent

Approval history

  • approvedDec 4, 1970

Chemistry & pharmacology

Loading structure…

SMILES

CC(C)(S)[C@@H](N)C(O)=O
Mol. weight
149.211 g/mol
Lipinski Ro5
Pass
Rule of 3
No
Chirality
Single Stereoisomer
Inorganic
No
Polymer
No
Delivery
Oral
Availability
Prescription Only

Oral

Yes

Parenteral

No

Topical

No

Black box warning

Sources

Also known as

  • 3-mercapto-d-valine
  • 3-mercapto-d-valine
  • cuprenil
  • cuprimine
  • cuprimine
  • cuprimine
  • cuprimine
  • cuprimine
  • cupripen
  • depamine
  • depen
  • depen
  • dimethylcysteine
  • dimethylcysteine
  • distamine
  • d mercaptovaline
  • d mercaptovaline
  • d-mercaptovaline
  • d penicillamine
  • d penicillamine
  • d-penicillamine
  • d-penicillamine
  • d-penicillamine
  • d-penicillamine
  • d-(−)-penicillamine
  • d-(−)-penicillamine
  • d-β,β-dimethylcysteine
  • d-β,β-dimethylcysteine
  • pendramine
  • penicillamine
  • penicillamine
  • penicillamine
  • penicillamine
  • penicillamine
  • penicillamine
  • penicillamine
  • penicillamine
  • penicillamine
  • penicillamine
  • penicillamine
  • (−)-penicillamine
  • (−)-penicillamine
  • (s)-2-amino-3-mercapto-3-methylbutanoic acid
  • (s)-2-amino-3-mercapto-3-methylbutanoic acid
  • (s)-3,3-dimethylcysteine
  • (s)-3,3-dimethylcysteine
  • trolovol
  • trolovol

Clinical trials

NCT IDPhaseStart dateSponsor(s)
NCT06103617Phase 2Nov 15, 2023Southern Medical University
NCT03957720Early Phase 1 (Phase 1)Mar 15, 2019Zhejiang University
NCT03660059Phase 3Sep 30, 2018Astellas
NCT03539952Phase 3Jun 4, 2018GMP Companies
NCT03403205Phase 3Feb 15, 2018Alexion, Wilson Therapeutics AB
NCT03106948Phase 2Feb 1, 2017Dialysis Clinic, Inc., Southeast Renal Research Institute
NCT01374282N/AJun 14, 2011Merck
NCT00552630Phase 2/Phase 3 (Phase 3)Sep 1, 2007Bezoloven, Inc., Food and Drug Administration, Harvard University
NCT00003751Phase 2Mar 1, 1999Johns Hopkins University, National Cancer Institute (NCI), University of South Florida
Showing 9 of 9 trials
Page 1 / 1

Organizations

Research & Development (15)

OrganizationOrg typeTrialsAs lead sponsorPhasesEarliest year
AlexionFor profit1012018
AstellasFor profit1112018
Bezoloven, Inc.For profit1012007
Dialysis Clinic, Inc.Academic/Hospital1012017
Food and Drug AdministrationGovernment1112007
GMP CompaniesFor profit1112018
Harvard UniversityAcademic/Hospital1012007
Johns Hopkins UniversityAcademic/Hospital1111999
MerckFor profit1112011
National Cancer Institute (NCI)Government1011999
Southeast Renal Research InstituteAcademic/Hospital1112017
Southern Medical UniversityAcademic/Hospital1112023
University of South FloridaAcademic/Hospital1011999
Wilson Therapeutics ABFor profit1112018
Zhejiang UniversityAcademic/Hospital1112019
15 organizations
Page 1 / 1

Marketing (24)

OrganizationOrg typeRelationshipDate
Aggrega PharmaFor profitMKTGAug 23, 2021
Allergan PLC (2015)For profitMKTGJun 24, 2019
Amerigen PharmaceuticalsFor profitMKTGMay 7, 2019
Ani PharmaceuticalsFor profitSYNMay 7, 2019
Ani PharmaceuticalsFor profitMKTGMay 7, 2019
ApotexFor profitMKTGApr 28, 2020
Bausch Health CompaniesFor profitNDA2Dec 4, 1970
Bristol-Myers SquibbFor profitMKTGDec 23, 2019
CiplaFor profitMKTGAug 19, 2021
Dr. Reddy's LaboratoriesFor profitMKTGAug 4, 2020
Endo PharmaceuticalsFor profitMKTGDec 23, 2019
Esteve LabsFor profitMKTGAug 23, 2021
Granules IndiaFor profitSYNDec 2, 2020
Granules IndiaFor profitMKTGDec 2, 2020
Invagen PharmsFor profitMKTGAug 19, 2021
LupinFor profitMKTGNov 30, 2020
LupinFor profitSYNNov 30, 2020
MerckFor profitNDADec 4, 1970
MylanFor profitNDA2Nov 8, 1978
NavintaFor profitMKTGOct 8, 2021
PH HEALTHFor profitMKTGDec 23, 2019
Par PharmaceuticalsFor profitMKTGDec 23, 2019
TevaFor profitMKTGFeb 13, 2020
Watson PharmaceuticalsFor profitMKTGJun 24, 2019