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

Stem definition	Drug id	CAS RN
	2676	1953-02-2

Description:

Molecule	Description
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

Molecule

Description

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:

Dose	Unit	Route
0.80	g	O

ADMET properties:

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

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Approvals:

Date	Agency	Company	Orphan
Aug. 11, 1988	FDA	MISSION PHARMA

FDA Adverse Event Reporting System (Female)

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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	76.69	45.18	13	143	5563	63483303
Tubulointerstitial nephritis	54.55	45.18	12	144	19891	63468975

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FDA Adverse Event Reporting System (Male)

None

FDA Adverse Event Reporting System (Geriatric)

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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	81.03	36.26	16	258	11158	79732956
Tubulointerstitial nephritis	42.57	36.26	12	262	38223	79705891

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FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

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

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

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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

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🐶 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)

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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 CO	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 CO	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

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Orange Book exclusivity data (new drug applications)

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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 CO	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 CO	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)

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Bioactivity Summary:

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Target	Class	Pharos	UniProt	Action	Type	Activity value (-log[M])	Mechanism action	Bioact source	MoA source
Angiotensin-converting enzyme	Enzyme		ACE_RABIT		IC50	5.72		CHEMBL

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External reference:

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ID	Source
WJZ	PDB_CHEM_ID
002371	NDDF
109106000	SNOMEDCT_US
190283	MMSL
3574	INN_ID
397225004	SNOMEDCT_US
4019475	VUID
4019475	VANDF
5483	PUBCHEM_CID
5587	MMSL

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Pharmaceutical products:

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Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
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
Tiopronin	HUMAN PRESCRIPTION DRUG LABEL	1	0093-7909	TABLET, SUGAR COATED	100 mg	ORAL	ANDA	22 sections
Tiopronin	HUMAN PRESCRIPTION DRUG LABEL	1	0093-7909	TABLET, SUGAR COATED	100 mg	ORAL	ANDA	22 sections
tiopronin	HUMAN PRESCRIPTION DRUG LABEL	1	60219-2009	TABLET, DELAYED RELEASE	300 mg	ORAL	ANDA	23 sections

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