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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 of PRINOMASTAT

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
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

CNS Penetrant
2554
Curator's Comment: As a lipophilic agent, prinomastat crosses the blood-brain barrier.

Originator

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
 0.5 nM [IC50]
Inhibitor
8297
 0.2 nM [IC50]
Inhibitor
8297
 1.5 nM [IC50]
Inhibitor
8297
 1.1 nM [IC50]
Inhibitor
8297
 0.3 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Phase III
656
Unknown

Approved Use

Unknown
Primary
Phase III
656
Unknown

Approved Use

Unknown
Primary
Phase III
656
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
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

AUC

ValueDoseCo-administeredAnalytePopulation
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
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

Sourcing

Vendor/AggregatorIDURL
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

PubMed

TitleDatePubMed
Protease inhibitors in the clinic.
2005 Jan
Synthesis and in vitro evaluation of targeted tetracycline derivatives: effects on inhibition of matrix metalloproteinases.
2007 Mar 15
Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2.
2011 Jul 14
Patents

Patents

JP2011506455A
51

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 UTC 2023
Edited
by admin
on Fri Dec 15 15:46:14 UTC 2023
Record UNII
10T6626FRK
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PRINOMASTAT
INN   MI   USAN   WHO-DD  
USAN   INN  
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
Created by admin on Fri Dec 15 15:46:14 UTC 2023 , Edited by admin on Fri Dec 15 15:46:14 UTC 2023
Code System Code Type Description
EPA CompTox
DTXSID3043946
Created by admin on Fri Dec 15 15:46:14 UTC 2023 , Edited by admin on Fri Dec 15 15:46:14 UTC 2023
PRIMARY
NCI_THESAURUS
C1811
Created by admin on Fri Dec 15 15:46:14 UTC 2023 , Edited by admin on Fri Dec 15 15:46:14 UTC 2023
PRIMARY
DRUG BANK
DB05100
Created by admin on Fri Dec 15 15:46:14 UTC 2023 , Edited by admin on Fri Dec 15 15:46:14 UTC 2023
PRIMARY
PUBCHEM
466151
Created by admin on Fri Dec 15 15:46:14 UTC 2023 , Edited by admin on Fri Dec 15 15:46:14 UTC 2023
PRIMARY
FDA UNII
10T6626FRK
Created by admin on Fri Dec 15 15:46:14 UTC 2023 , Edited by admin on Fri Dec 15 15:46:14 UTC 2023
PRIMARY
INN
7921
Created by admin on Fri Dec 15 15:46:14 UTC 2023 , Edited by admin on Fri Dec 15 15:46:14 UTC 2023
PRIMARY
SMS_ID
300000034343
Created by admin on Fri Dec 15 15:46:14 UTC 2023 , Edited by admin on Fri Dec 15 15:46:14 UTC 2023
PRIMARY
MESH
C113282
Created by admin on Fri Dec 15 15:46:14 UTC 2023 , Edited by admin on Fri Dec 15 15:46:14 UTC 2023
PRIMARY
CAS
192329-42-3
Created by admin on Fri Dec 15 15:46:14 UTC 2023 , Edited by admin on Fri Dec 15 15:46:14 UTC 2023
PRIMARY
MERCK INDEX
m9139
Created by admin on Fri Dec 15 15:46:14 UTC 2023 , Edited by admin on Fri Dec 15 15:46:14 UTC 2023
PRIMARY Merck Index
CHEBI
138885
Created by admin on Fri Dec 15 15:46:14 UTC 2023 , Edited by admin on Fri Dec 15 15:46:14 UTC 2023
PRIMARY
USAN
KK-121
Created by admin on Fri Dec 15 15:46:14 UTC 2023 , Edited by admin on Fri Dec 15 15:46:14 UTC 2023
PRIMARY
ChEMBL
CHEMBL75094
Created by admin on Fri Dec 15 15:46:14 UTC 2023 , Edited by admin on Fri Dec 15 15:46:14 UTC 2023
PRIMARY
Related Record Type Details
72 KDA TYPE IV COLLAGENASE
TARGET -> INHIBITOR
STROMELYSIN-1
TARGET -> INHIBITOR
MATRIX METALLOPROTEINASE-9
TARGET -> INHIBITOR
Structure of PRINOMASTAT HYDROCHLORIDE
SALT/SOLVATE -> PARENT
COLLAGENASE 3
TARGET -> INHIBITOR
MATRIX METALLOPROTEINASE-14
TARGET -> INHIBITOR
Related Record Type Details
Structure of PRINOMASTAT
ACTIVE MOIETY
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
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