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Prinomastat

HCID 466151
NotesReactions
Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
192329-42-3
Standard SMILES
CC1(C)SCCN(S(=O)(=O)c2ccc(Oc3ccncc3)cc2)[C@H]1C(=O)NO
InChIKey
YKPYIPVDTNNYCN-INIZCTEOSA-N
Molecular formula
C18H21N3O5S2
Average molar mass
423.5 g/mol
Monoisotopic mass
423.09226313

Overview

Prinomastat is a hydroxamic acid that is (3S)-N-hydroxy-2,2-dimethylthiomorpholine-3-carboxamide in which the hydrogen attached to the thiomorpholine nitrogen has been replaced by a [4-(pyridin-4-yloxy)phenyl]sulfonyl group. It is a selective inhibitor with of matrix metalloproteinases (MMPs) 2, 3, 9, 13, and 14. It has a role as an antineoplastic agent, a matrix metalloproteinase inhibitor and an EC 3.4.24.35 (gelatinase B) inhibitor. It is a hydroxamic acid, a member of pyridines, a sulfonamide, an aromatic ether and a member of thiomorpholines. It is a conjugate base of a prinomastat(1+).

Names & identifiers

Preferred name
Prinomastat
IUPAC
(3S)-N-hydroxy-2,2-dimethyl-4-(4-pyridin-4-yloxyphenyl)sulfonylthiomorpholine-3-carboxamide
English name
Prinomastat
Molecular formula
C18H21N3O5S2
Molecular weight
423.51

Names & synonyms

Prinomastat192329-42-3AG-3340AG3340prinomastatumAG 3340(3S)-N-hydroxy-2,2-dimethyl-4-(4-pyridin-4-yloxyphenyl)sulfonylthiomorpholine-3-carboxamide10T6626FRKKB-R-9896DTXSID3043946CHEBI:138885(S)-2,2-Dimethyl-4-((p-(4-pyridyloxy)phenyl)sulfonyl)-3-thiomorpholinecarbohydroxamic acid
Show more names
AG3340 hydrochlorideAG 3340 hydrochlorideAG-3340 hydrochloridePhenprobamate Impurity 2Prinomastat hydrochloride
(S)-2,2-dimethyl-4-{[p-(4-pyridyloxy)phenyl]sulfonyl}-3-thiomorpholinecarbohydroxamic acidRefChem:868518DTXCID1023946(3S)-N-Hydroxy-2,2-dimethyl-4-((4-(4-piridinyloxy)phenyl)sulfonyl)-3-thiomorpholinecarboxamidePrinomastat (USAN/INN)UNII-10T6626FRKKB-R 9896CHEMBL75094

Database identifiers

CAS
192329-42-3
PubChem CID
466151
DTXSID
DTXSID3043946

Properties

Computed structural properties

XLogP
1.5
Topological polar surface area
143 Ų
Hydrogen bond donors
2
Hydrogen bond acceptors
8
Rotatable bonds
5
Heavy atoms
28
Formal charge
0
Complexity
638

Experimental & physicochemical properties

DrugsPharmaceuticals -> Listed in ZINC15

Physicochemical properties

Melting point
149.8 ° · 149.8°
Density
1.377 · 1.377±0.06 g/cm3(Predicted)
storage temp.
room temp
solubility
2 O: · H2O: soluble15mg/mL (clear solution)
form
powder
pka
9.25 · 9.25±0.23(Predicted)
color
white to beige
Water Solubility
2 O: · H2O: 15mg/mL (clear solution)
InChI
1S/C18H21N3O5S2.ClH/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);1H/t16-;/m0./s1
InChIKey
UQGWXXLNXBRNBU-NTISSMGPSA-N
SMILES
Cl.CC1(C)SCCN([C@H]1C(=O)NO)S(=O)(=O)c2ccc(Oc3ccncc3)cc2
NCI Dictionary of Cancer Terms

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 4 items

Danger

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]

P203, P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P318, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

Hazard information

Hazard Classes and CategoriesSkin Irrit. 2 (100%)

Safety data

wgk
3
risk_code
60-61
Signal word
Danger
Symbol(GHS)
GHS08
hazard_code
T
safety_code
53-45
Storage Class
6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
Hazard statements
H360
Hazard Classifications
Repr. 1B
Precautionary statements
P201-P308+P313

Chemistry & industry

Pharmacology

Biological Half-Life2-5 hours
MeSH Pharmacological ClassificationCompounds that inhibit the enzyme activity or activation of MATRIX METALLOPROTEINASES.
Applications · 4 items

UsesTreatment of HaCaT-ras A-5RT3 tumor xenografts with Prinomastat (Ag3340) for 6 days strongly reduces tumor invasion and vascularization. Prinomastat is also a broad spectrum MMP inhibitor

UsesPrinomastat hydrochloride has been used as an antagonist for metalloproteinases (MMPs) in Crotalus atrox venom samples and mouse embryo cultures. It may be used as a MMP-2 inhibitor in HepG2 cells.

UsesAntineoplastic; antiangiogenic; treatment for retinal and subfoveal choroidal neovascularization (matrix metalloproteinase inhibitor).

General DescriptionPrinomastat comprises hydroxamic acid group and chelates with zinc ion.

Suppliers23 total

北京华美互利生物化工010-56205725 · [email protected]
Career Henan Chemica Co+86-0371-86658258 +86-13203830695 · [email protected]
上海毕得医药科技股份有限公司400-1647117 13681763483 · [email protected]
United Life Science020-82099279 18988968278 · [email protected]
銳迪國際科技有限公司18024082417 · [email protected]
四川省维克奇生物科技有限公司

Related reactions

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
ChEMBL
CHEMBL75094
ChEBI
CHEBI:138885
UNII
10T6626FRK
EC Number
850-562-3
Nikkaji
J1.207.127B
3340 · AG3340; prinomastat
FDA UNII
10 T6626FRK · 10T6626FRK
NCI Drug Dictionary
prinomastat
UNSPSC Code
12352200 · 12352200
NACRES
77 · NA.77
Symbol(GHS)
8 · GHS08
Signal word
Danger
Hazard statements
360 · H360
Precautionary statements
201 · P201-P308+P313
Hazard Codes
T
Risk Statements
60 · 60-61
Safety Statements
53 · 53-45
WGK Germany
3 · 3
Storage Class
6.1 C · 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
Hazard Classifications
1 B · Repr. 1B
028-81700200 18116577057 · [email protected]
天津普西唐生物医药科技有限公司010-60605840 · [email protected]
Sigma-Aldrich西格玛奥德里奇(上海)贸易有限公司021-61415566 800-8193336 · [email protected]
上海陶术生物科技股份有限公司+1-781-999-5354; +1-00000000000 · [email protected]
北京建强伟业科技有限公司（FUSION弗珍试剂品牌）0531-88924771 15614660963 · [email protected]
风咏生物（AbMole）021-10000000 13000000000 · [email protected]
BOC Sciences16314854226 · [email protected]
上海一飞生物科技有限公司021-65675885 18964387627 · [email protected]
上海瀚香生物科技有限公司17754423994 · [email protected]
TargetMol中国（陶术生物）4008200310 15002144251 · [email protected]
BOC Sciences+1-631-485-4226 · [email protected]
ChemeGen 中国18818260767 · [email protected]
重庆卡兰医药有限公司[email protected]
HANGZHOU CLAP TECHNOLOGY CO.,LTD86-571-88216897,88216896 13588875226 · [email protected]
DAYANG CHEM (HANGZHOU) CO.,LTD+86-88938639 +86-17705817739 · [email protected]
上海泽叶生物科技有限公司021-57896695 13122526631 · [email protected]
南京世洲生物科技有限公司025-85560043 15850508050 · [email protected]
上海安毕达生物科技有限公司021-61629020 18201956406 · [email protected]
Additional notes · 1 item

DefinitionChEBI: Prinomastat is a hydroxamic acid that is (3S)-N-hydroxy-2,2-dimethylthiomorpholine-3-carboxamide in which the hydrogen attached to the thiomorpholine nitrogen has been replaced by a [4-(pyridin-4-yloxy)phenyl]sulfonyl group. It is a selective inhibitor with of matrix metalloproteinases (MMPs) 2, 3, 9, 13, and 14. It has a role as an antineoplastic agent, a matrix metalloproteinase inhibitor and an EC 3.4.24.35 (gelatinase B) inhibitor. It is a hydroxamic acid, a member of thiomorpholines, a sulfonamide, an aromatic ether and a member of pyridines. It is a conjugate base of a prinomastat(1+).