PRINOMASTAT

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 8297	0.5 nM [IC50]
Matrix metalloproteinase 9 20 Target ID: CHEMBL321 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12930146	Inhibitor 8297	0.2 nM [IC50]
Matrix metalloproteinase 13 8 Target ID: CHEMBL280 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12930146	Inhibitor 8297	1.5 nM [IC50]
Matrix metalloproteinase 3 13 Target ID: CHEMBL283 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12930146	Inhibitor 8297	1.1 nM [IC50]
Matrix metalloproteinase 14 6 Target ID: CHEMBL3869 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15713379	Inhibitor 8297	0.3 nM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Lung cancer 69 Sources: http://adisinsight.springer.com/drugs/800006391 http://www.medscape.com/viewarticle/412097 https://clinicaltrials.gov/ct2/show/NCT00004199	Primary	Phase III 656	Unknown Approved Use Unknown
Prostate cancer 178 Sources: http://adisinsight.springer.com/drugs/800006391 http://www.medscape.com/viewarticle/412097 https://clinicaltrials.gov/ct2/show/NCT00003343	Primary	Phase III 656	Unknown Approved Use Unknown
Non-small cell lung cancer 206 Sources: http://adisinsight.springer.com/drugs/800006391 http://www.medscape.com/viewarticle/412097 https://www.ncbi.nlm.nih.gov/pubmed/15681529	Primary	Phase III 656	Unknown Approved Use Unknown

C_max

Value	Dose	Analyte	Population
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
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
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
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

AUC

Value	Dose	Analyte	Population
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
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
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
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

T_1/2

Value	Dose	Analyte	Population
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
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
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
2.46 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

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
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=
MolPort	MolPort-000-883-336	https://www.molport.com/shop/molecule-link/MolPort-000-883-336
Molnova	M13014	https://www.molnova.com/en/serch-list.html?keywords=M13014
Norris Pharm	NSZB-A213086
Toronto Research Chemicals	P715005	https://www.trc-canada.com/product-detail/?CatNum=P715005
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

PubMed

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

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 `Fri Dec 15 15:46:14 GMT 2023` Edited by `admin` on `Fri Dec 15 15:46:14 GMT 2023`
Record UNII	10T6626FRK
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

PRINOMASTAT

Official Name

English

AG-3340

Code

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