tiopronin 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
2676 1953-02-2

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • tiopronin
  • (+/-)-Tiopronin
  • acadione
  • capen
  • captimer
  • hepadigest
  • mercaptopropionylglycine
  • thiolpropionamidoacetic acid
  • thiopronin
  • thiopronine
  • tiopronine
  • alpha-Mercaptopropionylglycine
Sulfhydryl acylated derivative of GLYCINE.
  • Molecular weight: 163.19
  • Formula: C5H9NO3S
  • CLOGP: -0.24
  • LIPINSKI: 0
  • HAC: 4
  • HDO: 2
  • TPSA: 66.40
  • ALOGS: -1.60
  • ROTB: 3

  • Status: OFP

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
0.80 g O

ADMET properties:

PropertyValueReference
BA (Bioavailability) 63 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution) 1.39 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 1.48 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.45 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 55 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
Aug. 11, 1988 FDA MISSION PHARMA

FDA Adverse Event Reporting System (Female)

None

FDA Adverse Event Reporting System (Male)

None

FDA Adverse Event Reporting System (Geriatric)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Nephrotic syndrome 47.15 38.21 10 218 9557 64488947

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

SourceCodeDescription
ATC G04BX16 GENITO URINARY SYSTEM AND SEX HORMONES
UROLOGICALS
UROLOGICALS
Other urologicals
FDA CS M0289359 N-substituted Glycines
FDA MoA N0000175549 Cystine Disulfide Reduction
FDA EPC N0000175898 Reducing and Complexing Thiol

Drug Use | Suggest Off label Use Form| |View source of the data|

DiseaseRelationSNOMED_IDDOID
Cystinuria indication 85020001 DOID:9266
Cystine Renal Calculi indication
Agranulocytosis contraindication 17182001 DOID:12987
Proteinuria contraindication 29738008 DOID:576
Goodpasture's syndrome contraindication 50581000
Nephrotic syndrome contraindication 52254009 DOID:1184
Leukopenia contraindication 84828003 DOID:615
Kidney disease contraindication 90708001 DOID:557
Myasthenia gravis contraindication 91637004 DOID:437
Hypoalbuminemia contraindication 119247004
Disease of liver contraindication 235856003 DOID:409
Pregnancy, function contraindication 289908002
Thrombocytopenic disorder contraindication 302215000 DOID:1588
Aplastic anemia contraindication 306058006 DOID:12449
Breastfeeding (mother) contraindication 413712001




🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 3.57 acidic
pKa2 8.48 acidic
pKa3 13.03 acidic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRouteExclusivity dateDescription
100MG THIOLA MISSION PHARMA N019569 Aug. 11, 1988 RX TABLET ORAL June 28, 2026 INDICATED IN COMBINATION WITH HIGH FLUID INTAKE, ALKALI, AND DIET MODIFICATION, FOR THE PREVENTION OF CYSTINE STONE FORMATION IN PEDIATRIC PATIENTS 20KG TO 9 YEARS OF AGE W/SEVERE HOMOZYGOUS CYSTINURIA, WHO ARE NOT RESPONSIVE TO THESE MEASURES ALONE

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Angiotensin-converting enzyme Enzyme IC50 5.72 CHEMBL

External reference:

IDSource
4019475 VUID
N0000147595 NUI
D01430 KEGG_DRUG
4019475 VANDF
C0025405 UMLSCUI
CHEBI:32229 CHEBI
WJZ PDB_CHEM_ID
CHEMBL1314 ChEMBL_ID
DB06823 DRUGBANK_ID
D008625 MESH_DESCRIPTOR_UI
5483 PUBCHEM_CID
3574 INN_ID
C5W04GO61S UNII
6765 RXNORM
190283 MMSL
5587 MMSL
d01418 MMSL
002371 NDDF
109106000 SNOMEDCT_US
397225004 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Tiopronin HUMAN PRESCRIPTION DRUG LABEL 1 0093-7909 TABLET, SUGAR COATED 100 mg ORAL ANDA 22 sections
Thiola HUMAN PRESCRIPTION DRUG LABEL 1 0178-0900 TABLET, SUGAR COATED 100 mg ORAL NDA 15 sections
Thiola EC HUMAN PRESCRIPTION DRUG LABEL 1 0178-0901 TABLET, DELAYED RELEASE 300 mg ORAL NDA 25 sections
Thiola EC HUMAN PRESCRIPTION DRUG LABEL 1 0178-0902 TABLET, DELAYED RELEASE 100 mg ORAL NDA 25 sections