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tiopronin 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | PK/Tox | Related Drugs | BioActivity |
| Stem definition | Drug id | CAS RN |
|---|---|---|
| 2676 | 1953-02-2 |
Description:
| Molecule | Description |
|---|---|
|
Synonyms:
|
Sulfhydryl acylated derivative of GLYCINE.
Legend: OFP - off patent OFM - off market ONP - on patent |
Drug dosage:
| Dose | Unit | Route |
|---|---|---|
| 0.80 | g | O |
ADMET properties:
| Property | Value | Reference |
|---|---|---|
| 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 |
Predicted pharmacokinetic/toxicological properties (PK-AZ):
| Property | Description | Value | Unit | Confidence | Similarity |
|---|---|---|---|---|---|
| kinase-safety-class | ACVR2A,ACVR2B,ACVRL1,ALK,AURKA,AXL,BRAF,BTK,CAMK2B,CAMK2D,CDK4,CDK5,CDK9,DDR1,DYRK1B,EGFR,EIF2AK3,EPHB4,ERBB2,FLT3,GRK2,GSK3B,ITK,JAK1,JAK2,JAK3,KDR,MAP2K6,MAP3K14,MAP3K21,MAP3K7,MAPK10,MAPK7,MAPKAPK2,MTOR,NTRK2,PDK1,PDK2,PDK4,PIK3CB,PIK3CG,PIM2,PLK1,PRKCD,PRKDC,SIK2,SIK3,STK33,SYK,TEK,TGFBR1,TTK,ZAP70 | 53 | |||
| kinase-selectivity-class | ACVR2B,AXL,BRAF,CDK9,EIF2AK3,EPHB4,GRK2,MAP2K6,MAPK7,PIK3CG,PRKDC,STK33,TEK,TGFBR1 | 14 | |||
| pfas-class | PFAS structural alert (1 = True, 0 = False) | 0 |
Approvals:
| Date | Agency | Company | Orphan |
|---|---|---|---|
| Aug. 11, 1988 | FDA | MISSION PHARMA |
FDA Adverse Event Reporting System (Female)
| MedDRA adverse event term | Likelihood ratio | Likelihood ratio threshold | Patients taking drug having adverse event | Patients taking drug not having adverse event | Patients not taking drug having adverse event | Patients not taking drug not having adverse event |
|---|---|---|---|---|---|---|
| Nephrotic syndrome | 70.83 | 46.47 | 13 | 248 | 7326 | 90620860 |
| Tubulointerstitial nephritis | 49.58 | 46.47 | 12 | 249 | 25331 | 90602855 |
FDA Adverse Event Reporting System (Male)
None
FDA Adverse Event Reporting System (Geriatric)
| MedDRA adverse event term | Likelihood ratio | Likelihood ratio threshold | Patients taking drug having adverse event | Patients taking drug not having adverse event | Patients not taking drug having adverse event | Patients not taking drug not having adverse event |
|---|---|---|---|---|---|---|
| Nephrotic syndrome | 75.00 | 41.53 | 16 | 427 | 13815 | 110575041 |
| Drug ineffective | 44.70 | 41.53 | 41 | 402 | 1520499 | 109068357 |
FDA Adverse Event Reporting System (Pediatric)
None
Pharmacologic Action:
| Source | Code | Description |
|---|---|---|
| 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 |
Related Drugs by ATC class:
G04BX Other urologicals 10 drugs
Drug Use | Suggest Off label Use Form| |View source of the data|
| Disease | Relation | SNOMED_ID | DOID |
|---|---|---|---|
| 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 level | Dissociation constant | Type (acidic/basic) |
|---|---|---|
| pKa1 | 3.57 | acidic |
| pKa2 | 8.48 | acidic |
| pKa3 | 13.03 | acidic |
Orange Book patent data (new drug applications)
| Formulation strength | Trade name | Applicant | Application number | Approval date | Type | Dose form | Route | Patent number | Patent expiration date | Patent use |
|---|---|---|---|---|---|---|---|---|---|---|
| 100MG | THIOLA EC | MISSION PHARMACAL | N211843 | June 28, 2019 | RX | TABLET, DELAYED RELEASE | ORAL | 11458104 | Nov. 14, 2038 | A METHOD OF TREATING CYSTINURIA BY ORALLY ADMINISTERING TIOPRONIN WITH FOOD TO PREVENT CYSTINE STONE FORMATION IN ADULTS AND PEDIATRIC PATIENTS WITH SEVERE HOMOZYGOUS CYSTINURIA |
| 300MG | THIOLA EC | MISSION PHARMACAL | N211843 | June 28, 2019 | RX | TABLET, DELAYED RELEASE | ORAL | 11458104 | Nov. 14, 2038 | A METHOD OF TREATING CYSTINURIA BY ORALLY ADMINISTERING TIOPRONIN WITH FOOD TO PREVENT CYSTINE STONE FORMATION IN ADULTS AND PEDIATRIC PATIENTS WITH SEVERE HOMOZYGOUS CYSTINURIA |
Orange Book exclusivity data (new drug applications)
| Formulation strength | Trade name | Applicant | Application number | Approval date | Type | Dose form | Route | Exclusivity date | Description |
|---|---|---|---|---|---|---|---|---|---|
| 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 |
| 100MG | THIOLA EC | MISSION PHARMACAL | N211843 | June 28, 2019 | RX | TABLET, DELAYED RELEASE | ORAL | June 28, 2026 | FDA HAS NOT RECOGNIZED ORPHAN-DRUG EXCLUSIVITY (ODE) FOR THIS DRUG, BUT IT CONTAINS THE SAME ACTIVE MOIETY OR MOIETIES AS ANOTHER DRUG(S) THAT WAS ELIGIBLE FOR ODE, AND ALSO SHARES ODE-PROTECTED USE(S) OR INDICATION(S) WITH THAT DRUG(S). AN APPLICATION SEEKING APPROVAL FOR THE SAME ACTIVE MOIETY OR MOIETIES, INCLUDING AN ANDA THAT CITES THIS NDA AS ITS BASIS OF SUBMISSION, MAY NOT BE APPROVED FOR SUCH ODE-PROTECTED USE(S) AND INDICATION(S) |
| 300MG | THIOLA EC | MISSION PHARMACAL | N211843 | June 28, 2019 | RX | TABLET, DELAYED RELEASE | ORAL | June 28, 2026 | FDA HAS NOT RECOGNIZED ORPHAN-DRUG EXCLUSIVITY (ODE) FOR THIS DRUG, BUT IT CONTAINS THE SAME ACTIVE MOIETY OR MOIETIES AS ANOTHER DRUG(S) THAT WAS ELIGIBLE FOR ODE, AND ALSO SHARES ODE-PROTECTED USE(S) OR INDICATION(S) WITH THAT DRUG(S). AN APPLICATION SEEKING APPROVAL FOR THE SAME ACTIVE MOIETY OR MOIETIES, INCLUDING AN ANDA THAT CITES THIS NDA AS ITS BASIS OF SUBMISSION, MAY NOT BE APPROVED FOR SUCH ODE-PROTECTED USE(S) AND INDICATION(S) |
Bioactivity Summary:
| Target | Class | Pharos | UniProt | Action | Type | Activity value (-log[M]) | Mechanism action | Bioact source | MoA source |
|---|---|---|---|---|---|---|---|---|---|
| Angiotensin-converting enzyme | Enzyme | IC50 | 5.72 | CHEMBL | |||||
| Beta-lactamase NDM-1 | Enzyme | IC50 | 4.08 | CHEMBL |
External reference:
| ID | Source |
|---|---|
| 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:
| Product | Category | Ingredients | NDC | Form | Quantity | Route | Marketing | Label |
|---|---|---|---|---|---|---|---|---|
| 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 | 14 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 | 0178-0901 | 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 |
| Thiola EC | HUMAN PRESCRIPTION DRUG LABEL | 1 | 0178-0902 | TABLET, DELAYED RELEASE | 100 mg | ORAL | NDA | 25 sections |
| TIOPRONIN | HUMAN PRESCRIPTION DRUG LABEL | 1 | 0254-3034 | TABLET, DELAYED RELEASE | 100 mg | ORAL | ANDA | 24 sections |
| TIOPRONIN | HUMAN PRESCRIPTION DRUG LABEL | 1 | 0254-3035 | TABLET, DELAYED RELEASE | 300 mg | ORAL | ANDA | 24 sections |
| Tiopronin | HUMAN PRESCRIPTION DRUG LABEL | 1 | 0480-7824 | TABLET, DELAYED RELEASE | 300 mg | ORAL | ANDA | 24 sections |
| Tiopronin | HUMAN PRESCRIPTION DRUG LABEL | 1 | 0480-9227 | TABLET, DELAYED RELEASE | 100 mg | ORAL | ANDA | 24 sections |
| TIOPRONIN | HUMAN PRESCRIPTION DRUG LABEL | 1 | 13668-691 | TABLET, DELAYED RELEASE | 100 mg | ORAL | ANDA | 24 sections |
| TIOPRONIN | HUMAN PRESCRIPTION DRUG LABEL | 1 | 13668-692 | TABLET, DELAYED RELEASE | 300 mg | ORAL | ANDA | 24 sections |
| Tiopronin | HUMAN PRESCRIPTION DRUG LABEL | 1 | 44523-054 | TABLET, DELAYED RELEASE | 100 mg | ORAL | NDA authorized generic | 16 sections |
| Tiopronin | HUMAN PRESCRIPTION DRUG LABEL | 1 | 44523-055 | TABLET, DELAYED RELEASE | 300 mg | ORAL | NDA authorized generic | 16 sections |
| tiopronin | HUMAN PRESCRIPTION DRUG LABEL | 1 | 60219-2009 | TABLET, DELAYED RELEASE | 300 mg | ORAL | ANDA | 23 sections |
| tiopronin | HUMAN PRESCRIPTION DRUG LABEL | 1 | 60219-2009 | TABLET, DELAYED RELEASE | 300 mg | ORAL | ANDA | 23 sections |
| VENXXIVA | HUMAN PRESCRIPTION DRUG LABEL | 1 | 70709-121 | TABLET, DELAYED RELEASE | 100 mg | ORAL | ANDA | 24 sections |
| VENXXIVA | HUMAN PRESCRIPTION DRUG LABEL | 1 | 70709-123 | TABLET, DELAYED RELEASE | 300 mg | ORAL | ANDA | 24 sections |