| In ZINC since | Heavy atoms | Benign functionality |
|---|---|---|
| October 3rd, 2005 | 9 | No |
Popular Name: Penicillamine Penicillamine
Find On: PubMed — Wikipedia — Google
CAS Numbers: 1113-41-3 , 2219-30-9 , 52-66-4 , 52-67-5 , [52-66-4] , [52-67-5]
(2S)-2-amino-3-methyl-3-sulfanyl-butanoic acid
(2S)-2-amino-3-methyl-3-sulfanylbutanoic acid
(r)-2-amino-3-mercapto-3-methylbutanoicacid
(S)-2-Amino-3-mercapto-3-methyl-butyric acid
(S)-2-Amino-3-mercapto-3-methylbutanoic acid
1113-41-3; 3-mercaptovaline; nsc241261
2-Amino-3-mercapto-3-methylbutanoic acid
2-amino-3-methyl-3-sulfanylbutanoic acid
2219-30-9; D08330; Pemine (TN); Penicillamine hydrochloride
52-66-4; CPD000059161; DL-PENICILLAMINE; SAM002264642
52-67-5; C07418; Penicillamine
52-67-5; Cuprimine (TN); D00496; Depen (TN); Penicillamine (JAN/USP/INN)
alpha-Amino-beta-methyl-beta-mercaptobutyric acid
beta, beta-Dimethyl-DL-cysteine
CPD000059161; DL-PENICILLAMINE; Penicillamine; SAM002264642
D(-)-2-Amino-3-mercapto-3-methylbutanoic acid
D(-)penicillamine hydrochloride
D-(-)-2-Amino-3-mercapto-3-methylbutanoic acid
Depen, Distamine, D-Mercaptovaline, D-Penamine, Kuprenil
DL-2-Amino-3-mercapto-3-methylbutanoic acid
InChI=1/C5H11NO2S/c1-5(2,9)3(6)4(7)8/h3,9H,6H2,1-2H3,(H,7,8
Metalcaptase (*Hydrochloride*)
penicilamina; penicillamine; penicillaminum
| Type pH range | xlogP | Des A‑Pol Apolar desolvation (kcal/mol) | Des Pol Polar desolvation (kcal/mol) | H Don H-bond donors | H Acc H-bond acceptors | Chg Net charge | tPSA (Ų) | MWT Molecular weight (g/mol) | RB Rotatable bonds | DL |
|---|---|---|---|---|---|---|---|---|---|---|
| Ref Reference (pH 7) | -1.90 | 1.59 | -30.24 | 3 | 3 | 0 | 68 | 149.215 | 2 | ↓ |
| Hi High (pH 8-9.5) | -1.90 | 1.29 | -36.93 | 2 | 3 | -1 | 66 | 148.207 | 2 | ↓ |
| Hi High (pH 8-9.5) | -1.90 | 2.14 | -69.08 | 3 | 3 | -1 | 68 | 148.207 | 2 | ↓ |
| Note Type | Comments | Provided By |
|---|---|---|
| mechanism | . | ZereneX Building Blocks |
| Melting_Point | 202-204? dec. | Alfa-Aesar |
| Melting_Point | 202-204° dec. | Alfa-Aesar |
| MP | 204 - 208 | Enamine Building Blocks |
| MP | 204...208 | Enamine Building Blocks |
| MP | 205 | TCI |
| MP | 211 - 213 | Enamine Building Blocks |
| MP | 211...213 | Enamine Building Blocks |
| Mp [°C] | 212 | Acros Organics |
| ALOGPS_SOLUBILITY | 4.65e+00 g/l | DrugBank-approved |
| purity | 9.500000000000000e+001 | Enamine Building Blocks Enamine Building Blocks |
| Purity | 95% | Fluorochem |
| mechanism | a substance that is much more soluble than cystine and is excreted readily. | IBScreen Bioactives |
| UniProt Database Links | ACEA_HYPME; DPEP1_BOVIN; DPEP1_HUMAN; DPEP1_MOUSE; DPEP1_PIG; DPEP1_RABIT; DPEP1_RAT; DPEP1_SHEEP; DPEP2_HUMAN; DPEP2_MOUSE; DPEP2_RAT; DPEP3_HUMAN; DPEP3_MACFA; DPEP3_MOUSE; DPEP3_RAT; LAAA_PSEAZ; LAAA_PSEFS; RSAM_PSESP | ChEBI |
| mechanism | Also unlike cytotoxic immunosuppressants which act on both, penicillamine in vitro depresses T-cell activity but not B-cell activity. | IBScreen Bioactives |
| biological_use | Antiinflammatory | IBScreen Bioactives IBScreen Bioactives |
| biological_use | Antirheumatic | IBScreen Bioactives |
| Melting_Point | ca 212? dec. | Alfa-Aesar |
| Melting_Point | ca 212° dec. | Alfa-Aesar |
| Therapy | chelating agent (Cu), antirheumatic | SMDC Pharmakon |
| mechanism | Chelating agent recommended for the removal of excess copper in patients with Wilson's disease. | IBScreen Bioactives |
| biological_use | Chelating agent used in therapy of metal poisoning, and for Wilson's disease, scleroderma and rheumatoid arthritis | IBScreen Bioactives |
| Patent Database Links | EP0970694; EP0984012; EP1043322; EP1104760; EP1157987; EP1176140; EP1310488; EP1422218; EP1559431; EP1630164; EP1759700; EP1800666; EP1889847; EP1995256; US2001025052; US2002058629; US2003013770; US2003166619; US2004014720; US2004023890; US2004171682; US2 | ChEBI |
| Patent Database Links | EP1705184; EP1738759; EP1815867; EP1990048; US2005075333; US2006205705; US2007207191; US2007225339; US2007243132; WO2005021547; WO2005023761; WO2006098761; WO2007087637; WO2007117394; WO2007135242 | ChEBI |
| mechanism | From in vitro studies which indicate that one atom of copper combines with two molecules of penicillamine. | IBScreen Bioactives |
| PUBCHEM_SUBSTANCE_COMMENT | NCC_SAMPLE_SUPPLIER : LightBiologicals; NCC_SUPPLIER_STRUCTURE_ID : P-8548 | NIH Clinical Collection via PubChem |
| Target | Others | Selleck Chemicals |
| mechanism | Penicillamine also reduces excess cystine excretion in cystinuria. | IBScreen Bioactives |
| mechanism | Penicillamine interferes with the formation of cross-links between tropocollagen molecules and cleaves them when newly formed. | IBScreen Bioactives |
| S phrase | S24/25: Avoid contact with skin and eyes. | Acros Organics |
| PUBCHEM_SUBSTANCE_COMMENT | SAMPLE_SUPPLIER: LightBiologicals; SUPPLIER_STRUCTURE_ID: P-8548 | NIH Clinical Collection via PubChem |
| mechanism | The mechanism of action of penicillamine in rheumatoid arthritis is unknown although it appears to suppress disease activity. | IBScreen Bioactives |
| mechanism | This is done, at least in part, by disulfide interchange between penicillamine and cystine, resulting in formation of penicillamine-cysteine disulfide, | IBScreen Bioactives |
| mechanism | Unlike cytotoxic immunosuppressants, penicillamine markedly lowers IgM rheumatoid factor but produces no significant depression in absolute levels of serum immunoglobulins. | IBScreen Bioactives |
No pre-computed analogs available. Try a structural similarity search.