PRINOMASTAT

Investigational

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C18H21N3O5S2
Molecular Weight	423.506
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC1(C)SCCN([C@H]1C(=O)NO)S(=O)(=O)C2=CC=C(OC3=CC=NC=C3)C=C2

InChI

InChIKey=YKPYIPVDTNNYCN-INIZCTEOSA-N

InChI=1S/C18H21N3O5S2/c1-18(2)16(17(22)20-23)21(11-12-27-18)28(24,25)15-5-3-13(4-6-15)26-14-7-9-19-10-8-14/h3-10,16,23H,11-12H2,1-2H3,(H,20,22)/t16-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C18H21N3O5S2
Molecular Weight	423.506
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.drugbank.ca/drugs/DB05100 | http://www.medscape.com/viewarticle/412097
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/12930146

Prinomastat is a synthetic hydroxamic acid derivative with potential antineoplastic activity. Prinomastat inhibits matrix metalloproteinases (MMPs) (specifically, MMP-2, 9, 13, and 14), thereby inducing extracellular matrix degradation, and inhibiting angiogenesis, tumor growth and invasion, and metastasis. As a lipophilic agent, prinomastat crosses the blood-brain barrier. Pfizer conducted multicenter, randomized, double-bind, placebo-controlled trials to evaluate the safety and efficacy of prinomastat in combination with standard chemotherapy in patients with advanced hormone refractory prostate cancer and non-small cell lung cancer. However, this study has been terminated for the reason that Prinomastat did not improve the outcome of chemotherapy in non-small cell Lung cancer patients.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Matrix metalloproteinase-2 13 Target ID: CHEMBL333 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12930146 \| https://www.ncbi.nlm.nih.gov/pubmed/15713379	Inhibitor 8504	0.5 nM [IC50]
Matrix metalloproteinase 9 20 Target ID: CHEMBL321 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12930146	Inhibitor 8504	0.2 nM [IC50]
Matrix metalloproteinase 13 8 Target ID: CHEMBL280 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12930146	Inhibitor 8504	1.5 nM [IC50]
Matrix metalloproteinase 3 13 Target ID: CHEMBL283 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12930146	Inhibitor 8504	1.1 nM [IC50]
Matrix metalloproteinase 14 6 Target ID: CHEMBL3869 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15713379	Inhibitor 8504	0.3 nM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Lung cancer 70 Sources: http://adisinsight.springer.com/drugs/800006391 http://www.medscape.com/viewarticle/412097 https://clinicaltrials.gov/ct2/show/NCT00004199	Primary	Phase III 665	Unknown Approved Use Unknown
Prostate cancer 186 Sources: http://adisinsight.springer.com/drugs/800006391 http://www.medscape.com/viewarticle/412097 https://clinicaltrials.gov/ct2/show/NCT00003343	Primary	Phase III 665	Unknown Approved Use Unknown
Non-small cell lung cancer 211 Sources: http://adisinsight.springer.com/drugs/800006391 http://www.medscape.com/viewarticle/412097 https://www.ncbi.nlm.nih.gov/pubmed/15681529	Primary	Phase III 665	Unknown Approved Use Unknown

C_max

Value	Dose	Analyte	Population
291 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/14871966	10 mg 2 times / day steady-state, oral dose: 10 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	PRINOMASTAT plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
1861 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/14871966	50 mg 2 times / day steady-state, oral dose: 50 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	PRINOMASTAT plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
2083 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/14871966	100 mg 2 times / day steady-state, oral dose: 100 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	PRINOMASTAT plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
199 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/14871966	5 mg 2 times / day steady-state, oral dose: 5 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	PRINOMASTAT plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

AUC

Value	Dose	Analyte	Population
413 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/14871966	10 mg 2 times / day steady-state, oral dose: 10 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	PRINOMASTAT plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
3107 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/14871966	50 mg 2 times / day steady-state, oral dose: 50 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	PRINOMASTAT plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
5156 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/14871966	100 mg 2 times / day steady-state, oral dose: 100 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	PRINOMASTAT plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
314 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/14871966	5 mg 2 times / day steady-state, oral dose: 5 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	PRINOMASTAT plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

T_1/2

Value	Dose	Analyte	Population
2.7 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/14871966	10 mg 2 times / day steady-state, oral dose: 10 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	PRINOMASTAT plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
2.08 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/14871966	50 mg 2 times / day steady-state, oral dose: 50 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	PRINOMASTAT plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
2.46 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/14871966	100 mg 2 times / day steady-state, oral dose: 100 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	PRINOMASTAT plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
5.01 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/14871966	5 mg 2 times / day steady-state, oral dose: 5 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	PRINOMASTAT plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

Sourcing

Vendor/Aggregator	ID	URL
1PlusChem LLC	1P002GBE	https://www.1pchem.com/search?query=1P002GBE
BOC Sciences	192329-42-3	http://www.bocsci.com/description.asp?cas=192329-42-3
Chem Scene	CS-0109453	http://www.chemscene.com/goproductList/searchProductList?productObj=CS-0109453
Chem Scene	CS-7961	http://www.chemscene.com/goproductList/searchProductList?productObj=CS-7961
Compound Cloud	466151
eMolecules	261087273	https://orderbb.emolecules.com/search/#?query=261087273
eMolecules	300766223	https://orderbb.emolecules.com/search/#?query=300766223
eMolecules	48656165	https://orderbb.emolecules.com/search/#?query=48656165
Lan Pharmatech	LQT-B38677
MedChem Express	HY-12170	https://www.medchemexpress.com/search.html?q=HY-12170A&ft=&fa=&fp=
MedChem Express	HY-12170A	https://www.medchemexpress.com/search.html?q=HY-12170A&ft=&fa=&fp=
Molnova	M13014	https://www.molnova.com/en/serch-list.html?keywords=M13014
MolPort	MolPort-000-883-336	https://www.molport.com/shop/molecule-link/MolPort-000-883-336
Norris Pharm	NSZB-A213086
Toronto Research Chemicals	P715005	https://www.trc-canada.com/product-detail/?CatNum=P715005

PubMed

Title	Date	PubMed
Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2.	2011-07-14	21599003
Synthesis and in vitro evaluation of targeted tetracycline derivatives: effects on inhibition of matrix metalloproteinases.	2007-03-15	17267227
Protease inhibitors in the clinic.	2005-01	16789888
HIV-1 Tat neurotoxicity is prevented by matrix metalloproteinase inhibitors.	2001-02	11220743

Patents

Sample Use Guides

In Vivo Use Guide

15 mg twice daily orally continuously, in combination with gemcitabine 1,250 mg/m2 days 1 and 8 plus cisplatin 75 mg/m2 day 1, every 21 days for up to six cycles.

Route of Administration: Oral

In Vitro Use Guide

Prinomastat did not significantly inhibit glioma cell growth at concentrations of 100 nM to 100 uM using BrdUrd staining, [3 H]thymidine labeling, or the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide assay; significant inhibition of proliferation occurred only at concentrations of 1 mM

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:07:59 GMT 2025` Edited by `admin` on `Mon Mar 31 18:07:59 GMT 2025`
Record UNII	10T6626FRK
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

AG-3340

Preferred Name

English

PRINOMASTAT

Official Name

English

AG3340

Code

English

3-THIOMORPHOLINECARBOXAMIDE, N-HYDROXY-2,2-DIMETHYL-4-((4-(4-PYRIDINYLOXY)PHENYL)SULFONYL)-, (S)-

Systematic Name

English

PRINOMASTAT [MI]

Common Name

English

PRINOMASTAT [USAN]

Common Name

English

3-THIOMORPHOLINECARBOXAMIDE, N-HYDROXY-2,2-DIMETHYL-4-((4-(4-PYRIDINYLOXY)PHENYL)SULFONYL)-, (3S)-

Systematic Name

English

Prinomastat [WHO-DD]

Common Name

English

prinomastat [INN]

Common Name

English

(S)-2,2-DIMETHYL-4-((P-(4-PYRIDYLOXY)PHENYL)SULFONYL)-3-THIOMORPHOLINECARBOHYDROXAMIC ACID

Common Name

English

KB-R-9896

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C1970