penicillamine
Trade name: cuprimine
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
Earliest trial started Mar 1, 1999 (NCT00003751)
Timeline
1970s
- Dec 4, 1970
Merck — Earliest FDA Approval
- Dec 4, 1970
Merck — NDA Organization
- Dec 4, 1970
Bausch Health Companies — NDA Secondary Org
- Nov 8, 1978
Mylan — NDA Secondary Org
1990s
- Jan 1, 1999
Earliest Phase 2 Sponsor(trial)
2010s
- Jan 1, 2018
Earliest Phase 3 Sponsor(trial)
- Jan 1, 2019
Earliest Phase 1 Sponsor(trial)
- May 7, 2019
Amerigen Pharmaceuticals — Marketing Organization
- May 7, 2019
Ani Pharmaceuticals — Marketing Organization
- Jun 24, 2019
Watson Pharmaceuticals — Marketing Organization
- Jun 24, 2019
Allergan PLC (2015) — Marketing Organization
- Dec 23, 2019
Par Pharmaceuticals — Marketing Organization
- Dec 23, 2019
Endo Pharmaceuticals — Marketing Organization
- Dec 23, 2019
Bristol-Myers Squibb — Marketing Organization
- Dec 23, 2019
PH HEALTH — Marketing Organization
2020s
- Feb 13, 2020
Teva — Marketing Organization
- Apr 28, 2020
Apotex — Marketing Organization
- Aug 4, 2020
Dr. Reddy's Laboratories — Marketing Organization
- Nov 30, 2020
Lupin — Marketing Organization
- Dec 2, 2020
Granules India — Marketing Organization
- Aug 19, 2021
Invagen Pharms — Marketing Organization
- Aug 19, 2021
Cipla — Marketing Organization
- Aug 23, 2021
Esteve Labs — Marketing Organization
- Aug 23, 2021
Aggrega Pharma — Marketing Organization
- Oct 8, 2021
Navinta — Marketing Organization
Indications
Approved for
Mechanism of action
- CopperCHELATING AGENT
Copper chelating agent
Approval history
- approvedDec 4, 1970
Chemistry & pharmacology
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
Sources
- WikipediaPenicillamine ↗
- NCATSGNN1DV99GX ↗
- ChEMBLCHEMBL1430 ↗
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 ID | Phase | Start date | Sponsor(s) |
|---|---|---|---|
| NCT06103617 | Phase 2 | Nov 15, 2023 | Southern Medical University |
| NCT03957720 | Early Phase 1 (Phase 1) | Mar 15, 2019 | Zhejiang University |
| NCT03660059 | Phase 3 | Sep 30, 2018 | Astellas |
| NCT03539952 | Phase 3 | Jun 4, 2018 | GMP Companies |
| NCT03403205 | Phase 3 | Feb 15, 2018 | Alexion, Wilson Therapeutics AB |
| NCT03106948 | Phase 2 | Feb 1, 2017 | Dialysis Clinic, Inc., Southeast Renal Research Institute |
| NCT01374282 | N/A | Jun 14, 2011 | Merck |
| NCT00552630 | Phase 2/Phase 3 (Phase 3) | Sep 1, 2007 | Bezoloven, Inc., Food and Drug Administration, Harvard University |
| NCT00003751 | Phase 2 | Mar 1, 1999 | Johns Hopkins University, National Cancer Institute (NCI), University of South Florida |
Organizations
Research & Development (15)
| Organization | Org type | Trials | As lead sponsor | Phases | Earliest year |
|---|---|---|---|---|---|
| Alexion | For profit | 1 | 0 | 1 | 2018 |
| Astellas | For profit | 1 | 1 | 1 | 2018 |
| Bezoloven, Inc. | For profit | 1 | 0 | 1 | 2007 |
| Dialysis Clinic, Inc. | Academic/Hospital | 1 | 0 | 1 | 2017 |
| Food and Drug Administration | Government | 1 | 1 | 1 | 2007 |
| GMP Companies | For profit | 1 | 1 | 1 | 2018 |
| Harvard University | Academic/Hospital | 1 | 0 | 1 | 2007 |
| Johns Hopkins University | Academic/Hospital | 1 | 1 | 1 | 1999 |
| Merck | For profit | 1 | 1 | 1 | 2011 |
| National Cancer Institute (NCI) | Government | 1 | 0 | 1 | 1999 |
| Southeast Renal Research Institute | Academic/Hospital | 1 | 1 | 1 | 2017 |
| Southern Medical University | Academic/Hospital | 1 | 1 | 1 | 2023 |
| University of South Florida | Academic/Hospital | 1 | 0 | 1 | 1999 |
| Wilson Therapeutics AB | For profit | 1 | 1 | 1 | 2018 |
| Zhejiang University | Academic/Hospital | 1 | 1 | 1 | 2019 |
Marketing (24)
| Organization | Org type | Relationship | Date |
|---|---|---|---|
| Aggrega Pharma | For profit | MKTG | Aug 23, 2021 |
| Allergan PLC (2015) | For profit | MKTG | Jun 24, 2019 |
| Amerigen Pharmaceuticals | For profit | MKTG | May 7, 2019 |
| Ani Pharmaceuticals | For profit | SYN | May 7, 2019 |
| Ani Pharmaceuticals | For profit | MKTG | May 7, 2019 |
| Apotex | For profit | MKTG | Apr 28, 2020 |
| Bausch Health Companies | For profit | NDA2 | Dec 4, 1970 |
| Bristol-Myers Squibb | For profit | MKTG | Dec 23, 2019 |
| Cipla | For profit | MKTG | Aug 19, 2021 |
| Dr. Reddy's Laboratories | For profit | MKTG | Aug 4, 2020 |
| Endo Pharmaceuticals | For profit | MKTG | Dec 23, 2019 |
| Esteve Labs | For profit | MKTG | Aug 23, 2021 |
| Granules India | For profit | SYN | Dec 2, 2020 |
| Granules India | For profit | MKTG | Dec 2, 2020 |
| Invagen Pharms | For profit | MKTG | Aug 19, 2021 |
| Lupin | For profit | MKTG | Nov 30, 2020 |
| Lupin | For profit | SYN | Nov 30, 2020 |
| Merck | For profit | NDA | Dec 4, 1970 |
| Mylan | For profit | NDA2 | Nov 8, 1978 |
| Navinta | For profit | MKTG | Oct 8, 2021 |
| PH HEALTH | For profit | MKTG | Dec 23, 2019 |
| Par Pharmaceuticals | For profit | MKTG | Dec 23, 2019 |
| Teva | For profit | MKTG | Feb 13, 2020 |
| Watson Pharmaceuticals | For profit | MKTG | Jun 24, 2019 |