Details of the Drug

General Information of Drug (ID: DM40EF6)

Drug Name

Penicillamine

Synonyms

D-Penicillamine; penicillamine; 52-67-5; Cuprimine; D-(-)-Penicillamine; 3-Mercapto-D-valine; Depen; Cuprenil; D-Penamine; (-)-Penicillamine; (2S)-2-Amino-3-methyl-3-sulfanylbutanoic acid; D-Mercaptovaline; Mercaptovaline; Perdolat; Penicillamin; Pendramine; Kuprenil; Depamine; Mercaptyl; Trolovol; Metalcaptase; Artamine; Cupripen; (S)-3,3-Dimethylcysteine; D-Valine, 3-mercapto-; Penicillaminum; Penicilamina; Sufirtan; beta-Thiovaline; Dimethylcysteine; D-beta,beta-Dimethylcysteine; D-3-Mercaptovaline; beta,beta-Dimethylcysteine; Penicillamina; Penicilllamine; Sufortan; Copper penicillaminate; D Penicillamine; Penicillamina [DCIT]; Reduced penicillamine; D 3 Mercaptovaline; TBB068824; Beta,beta Dimethylcysteine; Beta-Thiovaline; Cuprimine (TN); D-Penicilamine; D-Penicyllamine; Depen (TN); P-1280; Penicilamina [INN-Spanish]; Penicillaminate, Copper; Penicillaminum [INN-Latin]; Reduced D-penicillamine; Beta,beta-Dimethylcysteine; D,3-Mercaptovaline; D-beta-Mercaptovaline; Distamine (*Hydrochloride*); Metalcaptase (*Hydrochloride*); Penicillamine (JAN/USP/INN); Penicillamine [USAN:INN:BAN:JAN]; Alpha-Amino-beta-methyl-beta-mercaptobutyric acid; D-(-)-2-Amino-3-mercapto-3-methylbutanoic acid; (2S)-2-amino-3-methyl-3-sulfanyl-butanoic acid; (D)-PENICILLAMINE; (S)-Penicillamin; (S)-Penicillamine; 2-Amino-3-mercapto-3-methylbutanoic acid; 3,3-Dimethyl-D-cysteine; 3-Mercaptovaline; 3-sulfanyl-D-valine; D-penicillamine

Indication

Disease Entry	ICD 11	Status	REF
Rheumatoid arthritis	FA20	Approved	[1], [2]

Therapeutic Class

Antidotes

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

149.21

Topological Polar Surface Area (xlogp)

-1.8

Rotatable Bond Count (rotbonds)

2

Hydrogen Bond Donor Count (hbonddonor)

3

Hydrogen Bond Acceptor Count (hbondacc)

4

ADMET Property

Absorption: The drug is rapidly but incompletely absorbed [3]
BDDCS Class: Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 3: high solubility and low permeability [4]
Clearance: The drug present in the plasma can be removed from the body at the rate of 10.65 mL/min/kg [5]
Elimination: 45% of drug is excreted from urine in the unchanged form [4]
Half-life: The concentration or amount of drug in body reduced by one-half in 1 hours [5]
Metabolism: The drug is metabolized via the hepatic [3]
Unbound Fraction: The unbound fraction of drug in plasma is 0.12% [5]
Vd: Fluid volume that would be required to contain the amount of drug present in the body at the same concentration as in the plasma 1.26 L/kg [5]

Chemical Identifiers

Formula: C5H11NO2S
IUPAC Name: (2S)-2-amino-3-methyl-3-sulfanylbutanoic acid
Canonical SMILES: CC(C)([C@H](C(=O)O)N)S
InChI: InChI=1S/C5H11NO2S/c1-5(2,9)3(6)4(7)8/h3,9H,6H2,1-2H3,(H,7,8)/t3-/m0/s1
InChIKey: VVNCNSJFMMFHPL-VKHMYHEASA-N

Cross-matching ID

PubChem CID: 5852
ChEBI ID: CHEBI:7959
CAS Number: 771431-20-0
DrugBank ID: DB00859
TTD ID: D08HZC
ACDINA ID: D00514

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Human immunodeficiency virus Tat protein (HIV tat)	TTT3ZC9	TAT_HV1H2	Inhibitor	[6]

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Molecular Interaction Atlas (MIA)

MIA Detail

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Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Disease Different from Penicillamine (Comorbidity)

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Comorbidity	REF
Remdesivir	DMBFZ6L	Moderate	Decreased renal excretion of Penicillamine caused by Remdesivir mediated nephrotoxicity.	1D6YCoronavirus Disease 2019 [1D6YCoronavirus Disease 2019]	[13]
Inotersen	DMJ93CT	Major	Increased risk of nephrotoxicity by the combination of Penicillamine and Inotersen.	Amyloidosis [5D00]	[14]
Iodipamide	DMXIQYS	Major	Increased risk of nephrotoxicity by the combination of Penicillamine and Iodipamide.	Cholelithiasis [DC11]	[15]
Didanosine	DMI2QPE	Moderate	Decreased absorption of Penicillamine due to formation of complexes caused by Didanosine.	Human immunodeficiency virus disease [1C60-1C62]	[16]
Quinapril	DMR8H31	Moderate	Decreased absorption of Penicillamine due to formation of complexes caused by Quinapril.	Hypertension [BA00-BA04]	[14]
Probenecid	DMMFWOJ	Moderate	Decreased renal excretion of Penicillamine caused by Probenecid.	Inborn purine/pyrimidine/nucleotide metabolism error [5C55]	[17]
Iron	DMAP8MV	Moderate	Decreased absorption of Penicillamine due to formation of complexes caused by Iron.	Iron deficiency anaemia [3A00]	[18]
Lanthanum carbonate	DMMJQSH	Moderate	Decreased absorption of Penicillamine due to formation of complexes caused by Lanthanum carbonate.	Mineral absorption/transport disorder [5C64]	[19]
Ocrelizumab	DMEZ2KH	Moderate	Additive immunosuppressive effects by the combination of Penicillamine and Ocrelizumab.	Multiple sclerosis [8A40]	[20]
Omacetaxine mepesuccinate	DMPU2WX	Moderate	Additive myelosuppressive effects by the combination of Penicillamine and Omacetaxine mepesuccinate.	Myeloproliferative neoplasm [2A20]	[21]
Azathioprine	DMMZSXQ	Moderate	Additive myelosuppressive effects by the combination of Penicillamine and Azathioprine.	Transplant rejection [NE84]	[13]
Ganciclovir	DM1MBYQ	Moderate	Additive myelosuppressive effects by the combination of Penicillamine and Ganciclovir.	Virus infection [1A24-1D9Z]	[13]
Valganciclovir	DMS2IUH	Moderate	Additive myelosuppressive effects by the combination of Penicillamine and Valganciclovir.	Virus infection [1A24-1D9Z]	[13]
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⏷ Show the Full List of 13 DDI Information of This Drug

Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG

DIG Name	DIG ID	PubChem CID	Functional Classification
Quinoline yellow WS	E00309	24671	Colorant
Beta-D-lactose	E00099	6134	Diluent; Dry powder inhaler carrier; Lyophilization aid
Magnesium stearate	E00208	11177	lubricant
Titanium dioxide	E00322	26042	Coating agent; Colorant; Opacifying agent
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Pharmaceutical Formulation

Formulation Name	Drug Dosage	Dosage Form	Route
Penicillamine 250 mg capsule	250 mg	Oral Capsule	Oral

Jump to Detail Pharmaceutical Formulation Page of This Drug

References

1	URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 7264).
2	How many modes of action should an antibiotic have Curr Opin Pharmacol. 2008 Oct;8(5):564-73.
3	FDA approval: ado-trastuzumab emtansine for the treatment of patients with HER2-positive metastatic breast cancer. Clin Cancer Res. 2014 Sep 1;20(17):4436-41.
4	BDDCS applied to over 900 drugs
5	Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
6	Docking studies reveal a selective binding of D-penicillamine to the transactivator protein of human immunodeficiency virus type 1. FEBS Lett. 2002 Apr 10;516(1-3):43-6.
7	A randomized trial of the activity and safety of Ro 24-7429 (Tat antagonist) versus nucleoside for human immunodeficiency virus infection. The AIDS Clinical Trials Group 213 Team. J Infect Dis. 1995 Nov;172(5):1246-52.
8	Anti-human immunodeficiency virus type 1 activity of an oligocationic compound mediated via gp120 V3 interactions. J Virol. 1996 May;70(5):2825-31.
9	Clinical gene therapy research utilizing ribozymes: application to the treatment of HIV/AIDS. Methods Mol Biol. 2004;252:581-98.
10	EM2487, a novel anti-HIV-1 antibiotic, produced by Streptomyces sp. Mer-2487: taxonomy, fermentation, biological properties, isolation and structure elucidation. J Antibiot (Tokyo). 1999 Nov;52(11):971-82.
11	Durhamycin A, a potent inhibitor of HIV Tat transactivation. J Nat Prod. 2002 Aug;65(8):1091-5.
12	RNA as a target for small molecules. Curr Opin Chem Biol. 2000 Dec;4(6):678-86.
13	Cerner Multum, Inc. "Australian Product Information.".
14	Cerner Multum, Inc. "UK Summary of Product Characteristics.".
15	Wong GT, Lee EY, Irwin MG. Contrast induced nephropathy in vascular surgery.?Br J Anaesth. 2016;117 Suppl 2:ii63-ii73. [PMID: 27566809]
16	Haagsma CJ "Clinically important drug interactions with disease-modifying antirheumatic drugs." Drugs Aging 13 (1998): 281-9. [PMID: 9805209]
17	Yu T-F, Roboz J, Johnson S, Kaung C "Studies on the metabolism of D-penicillamine and its interaction with probenecid in cystinuria and rheumatoid arthritis." J Rheumatol 11 (1984): 467-70. [PMID: 6481720]
18	Lyle WH "Penicillamine and iron." Lancet 2 (1976): 420. [PMID: 73880]
19	Canadian Pharmacists Association.
20	Product Information. Ocrevus (ocrelizumab). Genentech, South San Francisco, CA.
21	Product Information. Synribo (omacetaxine). Teva Pharmaceuticals USA, North Wales, PA.