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Tiopronin

PubChem CID
5483
Structure
Tiopronin_small.png
Tiopronin_3D_Structure.png
Molecular Formula
Synonyms
  • tiopronin
  • 1953-02-2
  • N-(2-Mercaptopropionyl)glycine
  • Acadione
  • Thiopronine
Molecular Weight
163.20 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2005-03-25
  • Modify:
    2025-01-18
Description
Tiopronin is a N-acyl-amino acid.
Tiopronin is a prescription thiol drug used primarily in the treatment of severe homozygous cystinuria. Patients with cystinuria excrete high levels of cystine in their urine and are at risk for kidney stone formation. Tiopronin is used as a second-line therapy to control the rate of cystine precipitation and excretion, and prevent kidney stone formation. It is used after a failure of the non-pharmacological first line treatment consisting of increased fluid intake, restriction of sodium and protein, and urinary alkalinization. As cystinuria is a relatively rare disease, tiopronin is classified as an orphan drug and is not patented in the United States. It is similar to d-penicillamine in use and efficacy, but offers the advantage of far less adverse effects. Tiopronin is dosed on an individual basis using close monitoring of urinary cystine concentrations and urinary output. Tiopronin may also be used to bind metal nanoparticles in Wilson's disease, which is an overload of copper in the body. It has been investigated for use in the treatment of arthritis and as a neuroprotective agent in aneurysmal subarachnoid hemorrhage.
Tiopronin is a Reducing and Complexing Thiol. The mechanism of action of tiopronin is as a Cystine Disulfide Reduction.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Tiopronin.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

2-(2-sulfanylpropanoylamino)acetic acid
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C5H9NO3S/c1-3(10)5(9)6-2-4(7)8/h3,10H,2H2,1H3,(H,6,9)(H,7,8)
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

YTGJWQPHMWSCST-UHFFFAOYSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.4 SMILES

CC(C(=O)NCC(=O)O)S
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C5H9NO3S
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

2.3.2 European Community (EC) Number

2.3.3 UNII

2.3.4 ChEBI ID

2.3.5 ChEMBL ID

2.3.6 DrugBank ID

2.3.7 DSSTox Substance ID

2.3.8 HMDB ID

2.3.9 KEGG ID

2.3.10 Metabolomics Workbench ID

2.3.11 NCI Thesaurus Code

2.3.12 Nikkaji Number

2.3.13 NSC Number

2.3.14 RXCUI

2.3.15 Wikidata

2.3.16 Wikipedia

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • 2 Mercaptopropionylglycine
  • 2 Thiol propionamido acetic Acid
  • 2 Thiolpropionamidoacetic Acid
  • 2-Mercaptopropionylglycine
  • 2-Thiol-propionamido-acetic Acid
  • 2-Thiolpropionamidoacetic Acid
  • Acadione
  • Acid, 2-Thiol-propionamido-acetic
  • Acid, 2-Thiolpropionamidoacetic
  • alpha Mercaptopropionylglycine
  • alpha-Mercaptopropionylglycine
  • Captimer
  • Meprin
  • Mercaptopropionylglycine
  • Thiola
  • Thiopronine
  • Tiopronin
  • Tiopronine

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
163.20 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3-AA
Property Value
-0.1
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
3
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
4
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
3
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
163.03031432 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
163.03031432 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
67.4 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
10
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
148
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
1
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
1
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2021.10.14)

3.2 Chemical Classes

3.2.1 Drugs

Pharmaceuticals
S10 | SWISSPHARMA | Pharmaceutical List with Consumption Data | DOI:10.5281/zenodo.2623484
3.2.1.1 Human Drugs
Human drug -> Prescription
Human drug -> Prescription; Discontinued; Active ingredient (TIOPRONIN)

4 Spectral Information

4.1 1D NMR Spectra

4.1.1 1H NMR Spectra

Source of Spectrum
Sigma-Aldrich Co. LLC.
Source of Sample
Sigma-Aldrich Co. LLC.
Catalog Number
280968
Copyright
Copyright © 2021-2024 Sigma-Aldrich Co. LLC. - Database Compilation Copyright © 2021 John Wiley & Sons, Inc. All Rights Reserved.
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Thumbnail

4.1.2 13C NMR Spectra

Source of Spectrum
Sigma-Aldrich Co. LLC.
Source of Sample
Sigma-Aldrich Co. LLC.
Catalog Number
280968
Copyright
Copyright © 2021-2024 Sigma-Aldrich Co. LLC. - Database Compilation Copyright © 2021 John Wiley & Sons, Inc. All Rights Reserved.
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Thumbnail

4.2 Mass Spectrometry

4.2.1 MS-MS

1 of 2
NIST Number
1187257
Instrument Type
IT/ion trap
Collision Energy
0
Spectrum Type
MS2
Precursor Type
[M+H]+
Precursor m/z
164.0376
Total Peaks
8
m/z Top Peak
76
m/z 2nd Highest
145.9
m/z 3rd Highest
117.9
Thumbnail
Thumbnail
2 of 2
NIST Number
1187282
Instrument Type
IT/ion trap
Collision Energy
0
Spectrum Type
MS2
Precursor Type
[M-H]-
Precursor m/z
162.023
Total Peaks
25
m/z Top Peak
105
m/z 2nd Highest
127.9
m/z 3rd Highest
118
Thumbnail
Thumbnail

4.3 IR Spectra

4.3.1 FTIR Spectra

Technique
KBr WAFER
Source of Sample
Fluka Chemie AG, Buchs, Switzerland
Catalog Number
63794
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail

4.3.2 ATR-IR Spectra

1 of 2
Instrument Name
Bio-Rad FTS
Technique
ATR-Neat (DuraSamplIR II)
Source of Spectrum
Forensic Spectral Research
Source of Sample
Riedel-De Haen Vetranal, Sigma-Aldrich Inc.
Catalog Number
33986
Lot Number
7232X
Copyright
Copyright © 2009-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail
2 of 2
Source of Sample
Aldrich
Catalog Number
280968
Copyright
Copyright © 2018-2024 Sigma-Aldrich Co. LLC. - Database Compilation Copyright © 2018-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail

4.4 Raman Spectra

Technique
FT-Raman
Source of Spectrum
Forensic Spectral Research
Source of Sample
Fluka Vetranal, Sigma-Aldrich Inc.
Catalog Number
33986
Lot Number
7232X
Copyright
Copyright © 2012-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail

6 Chemical Vendors

7 Drug and Medication Information

7.1 Drug Indication

Tiopronin is indicated for the prevention of kidney stone formation in patients with severe homozygous cystinuria consisting of a urinary cystine concentration greater than 500 mg/day, and who have failed treatment with non-pharmacological measures of increased fluid intake, decreased sodium and protein intake, and urine alkalinization.

7.2 FDA Approved Drugs

7.3 FDA Orange Book

7.4 FDA National Drug Code Directory

7.5 Drug Labels

Drug and label
Active ingredient and drug

7.6 Clinical Trials

7.6.1 ClinicalTrials.gov

7.6.2 EU Clinical Trials Register

8 Pharmacology and Biochemistry

8.1 FDA Pharmacological Classification

1 of 2
FDA UNII
C5W04GO61S
Active Moiety
TIOPRONIN
Pharmacological Classes
Mechanisms of Action [MoA] - Cystine Disulfide Reduction
Pharmacological Classes
Chemical Structure [CS] - N-substituted Glycines
Pharmacological Classes
Established Pharmacologic Class [EPC] - Reducing and Complexing Thiol
FDA Pharmacology Summary
Tiopronin is a Reducing and Complexing Thiol. The mechanism of action of tiopronin is as a Cystine Disulfide Reduction.
2 of 2
Non-Proprietary Name
TIOPRONIN
Pharmacological Classes
N-substituted Glycines [CS]; Reducing and Complexing Thiol [EPC]; Cystine Disulfide Reduction [MoA]

8.2 ATC Code

G - Genito urinary system and sex hormones

G04 - Urologicals

G04B - Urologicals

G04BX - Other urologicals

G04BX16 - Tiopronin

8.3 Absorption, Distribution and Excretion

Absorption
Tiopronin undergoes slow absorption, reaching peak plasma concentration 3-6 hours after ingestion. In a study of healthy subjects, the bioavailability of total and unbound tiopronin was found to be 63% and 40%, respectively.
Route of Elimination
Tiopronin is 100% excreted in urine.
Volume of Distribution
The volume of distribution of tiopronin is high at 455 L, indicating that a large portion of the drug is bound to tissues outside plasma.
Clearance
Total renal clearance for the total and unbound fractions of tiopronin were found to be 3.3 and 13.3 L/h respectively.

8.4 Metabolism / Metabolites

The principle metabolite of tiopronin is 2-mercaptopropionic acid (2-MPA). Between 10-15% of the drug is metabolized to 2-MPA via hydrolysis.

8.5 Biological Half-Life

Tiopronin has a long terminal half life of 53 hours in healthy subjects. However, the unbound drug fraction of tiopronin is eliminated much more rapidly from plasma with a calculated half life of 1.8 hours.

8.6 Mechanism of Action

Kidney stones form when the solubility limit is exceeded and urine becomes supersaturated with endogenous cystine. Tiopronin is an active reducing agent which undergoes a thiol-disulfide exchange with cystine to form a water-soluble mixed disulfide complex. Thus, the amount of sparingly soluble cystine is reduced. By reducing urinary cystine concentrations below the solubility limit, tiopronin helps reduce cystine stone formation.

8.7 Transformations

9 Use and Manufacturing

9.1 Uses

Use (kg; approx.) in Germany (2009): >50

Consumption (g per capita; approx.) in Germany (2009): 0.000611

Calculated removal (%): 92.1

9.1.1 Use Classification

Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients

10 Safety and Hazards

10.1 Hazards Identification

10.1.1 GHS Classification

Pictogram(s)
Irritant
Signal
Warning
GHS Hazard Statements
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
Precautionary Statement Codes

P264, P270, P301+P317, P330, and P501

(The corresponding statement to each P-code can be found at the GHS Classification page.)

ECHA C&L Notifications Summary

Aggregated GHS information provided per 50 reports by companies from 1 notifications to the ECHA C&L Inventory.

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

10.1.2 Hazard Classes and Categories

Acute Tox. 4 (100%)

11 Toxicity

11.1 Toxicological Information

11.1.1 Drug Induced Liver Injury

Compound
tiopronin
DILI Annotation
Ambiguous DILI-concern
Severity Grade
3
Label Section
Warnings and precautions
References

M Chen, V Vijay, Q Shi, Z Liu, H Fang, W Tong. FDA-Approved Drug Labeling for the Study of Drug-Induced Liver Injury, Drug Discovery Today, 16(15-16):697-703, 2011. PMID:21624500 DOI:10.1016/j.drudis.2011.05.007

M Chen, A Suzuki, S Thakkar, K Yu, C Hu, W Tong. DILIrank: the largest reference drug list ranked by the risk for developing drug-induced liver injury in humans. Drug Discov Today 2016, 21(4): 648-653. PMID:26948801 DOI:10.1016/j.drudis.2016.02.015

11.1.2 Acute Effects

11.1.3 Protein Binding

Tiopronin undergoes extensive protein binding in plasma. It is thought that this occurs through the formation of a disulphide bridge to the free thiol group of albumin.

12 Associated Disorders and Diseases

13 Literature

13.1 Consolidated References

13.2 NLM Curated PubMed Citations

13.3 Springer Nature References

13.4 Thieme References

13.5 Chemical Co-Occurrences in Literature

13.6 Chemical-Gene Co-Occurrences in Literature

13.7 Chemical-Disease Co-Occurrences in Literature

14 Patents

14.1 Depositor-Supplied Patent Identifiers

14.2 WIPO PATENTSCOPE

14.3 FDA Orange Book Patents

14.4 Chemical Co-Occurrences in Patents

14.5 Chemical-Disease Co-Occurrences in Patents

14.6 Chemical-Gene Co-Occurrences in Patents

15 Interactions and Pathways

15.1 Chemical-Target Interactions

15.2 Drug-Drug Interactions

15.3 Drug-Food Interactions

  • Take at the same time every day. Take each dose at the same time every day.
  • Take on an empty stomach. Take tiopronin at least 1 hour before or 2 hours after eating food.

16 Biological Test Results

16.1 BioAssay Results

17 Classification

17.1 MeSH Tree

17.2 NCI Thesaurus Tree

17.3 ChEBI Ontology

17.4 KEGG: Drug

17.5 KEGG: USP

17.6 KEGG: ATC

17.7 KEGG: Animal Drugs

17.8 WHO ATC Classification System

17.9 FDA Pharm Classes

17.10 ChemIDplus

17.11 ChEMBL Target Tree

17.12 UN GHS Classification

17.13 NORMAN Suspect List Exchange Classification

17.14 EPA DSSTox Classification

17.15 FDA Drug Type and Pharmacologic Classification

17.16 MolGenie Organic Chemistry Ontology

18 Information Sources

  1. CAS Common Chemistry
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    https://creativecommons.org/licenses/by-nc/4.0/
  2. ChemIDplus
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    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  6. European Chemicals Agency (ECHA)
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    https://echa.europa.eu/web/guest/legal-notice
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  13. ClinicalTrials.gov
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  14. Comparative Toxicogenomics Database (CTD)
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    http://ctdbase.org/about/legal.jsp
  15. Drug Gene Interaction database (DGIdb)
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    http://www.dgidb.org/downloads
  16. Therapeutic Target Database (TTD)
  17. DailyMed
  18. Drug Induced Liver Injury Rank (DILIrank) Dataset
    LICENSE
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  19. Drugs@FDA
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  20. EU Clinical Trials Register
  21. FDA Orange Book
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  24. Japan Chemical Substance Dictionary (Nikkaji)
  25. KEGG
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    Therapeutic category of drugs in Japan
    http://www.genome.jp/kegg-bin/get_htext?br08301.keg
    Anatomical Therapeutic Chemical (ATC) classification
    http://www.genome.jp/kegg-bin/get_htext?br08303.keg
  26. Metabolomics Workbench
  27. NIST Mass Spectrometry Data Center
    LICENSE
    Data covered by the Standard Reference Data Act of 1968 as amended.
    https://www.nist.gov/srd/public-law
    (2-Mercaptopropionylamino)acetic acid
    http://www.nist.gov/srd/nist1a.cfm
  28. NLM RxNorm Terminology
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    https://www.nlm.nih.gov/research/umls/rxnorm/docs/termsofservice.html
  29. NORMAN Suspect List Exchange
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    https://creativecommons.org/licenses/by/4.0/
    TIOPRONIN
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  30. SpectraBase
    N-(2-Mercaptopropionyl)glycine
    https://spectrabase.com/spectrum/Gpwn0D9x3a
    N-(2-MERCAPTOPROPIONYL)GLYCINE
    https://spectrabase.com/spectrum/5N8VaDShFLm
    N-(2-Mercaptopropionyl)glycine
    https://spectrabase.com/spectrum/u95NQGRxwc
    N-(2-Mercaptopropionyl)glycine
    https://spectrabase.com/spectrum/J9ywN7E7q4S
  31. Springer Nature
  32. Thieme Chemistry
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  33. WHO Anatomical Therapeutic Chemical (ATC) Classification
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  37. PubChem
  38. GHS Classification (UNECE)
  39. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  40. PATENTSCOPE (WIPO)
  41. NCBI
CONTENTS