Azenosertib
Also known as 1-[(7R)-7-ethyl-7-hydroxy-5,6-dihydrocyclopenta[b]pyridin-2-yl]-6-[4-(4-methylpiperazin-1-yl)anilino]-2-prop-2-enylpyrazolo[3,4-d]pyrimidin-3-one, compound 16, ZN-C3
Key facts
What buyers check first
- CAS number
- 2376146-48-2
- Formula
- C29H34N8O2
- Molar mass
- 526.65 g/mol
- EC number
- 189-014-7
- HS code
- 293359
- Category
- Screening compounds
What is Azenosertib?
Plain description, key identifiers and synonyms
Azenosertib is an inhibitor of the tyrosine kinase Wee1 (Wee1-like protein kinase, Wee1A kinase, WEE1hu) with potential antineoplastic sensitizing activity. Although the exact mechanism of action by which this agent inhibits Wee1 has yet to be disclosed, upon administration of ZN-c3, this agent targets and inhibits Wee1. Inhibition of Wee1 promotes both premature mitosis and a prolonged mitotic arrest leading to cell death in susceptible tumor cells, such as p53-deficient or mutated human cancers that lack the G1 checkpoint, upon treatment with DNA-damaging chemotherapeutic agents. Unlike normal cells, most p53-deficient or mutated human cancers lack the G1 checkpoint as p53 is the key regulator of the G1 checkpoint and these cells rely on the G2 checkpoint for DNA repair to damaged cells.
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Annulment of the G2 checkpoint may therefore make p53-deficient tumor cells more vulnerable to antineoplastic agents and enhance their cytotoxic effect. Overexpression of Wee1 occurs in several cancer types and high expression of Wee1 is associated with poor outcomes. Wee1 phosphorylates Cdc2 in the Cdc2/cyclin B (CDK1/cyclin B) complex which blocks progression from G2 into mitosis, it negatively regulates the G2 checkpoint by disallowing entry into mitosis in response to DNA damage.
Identifiers
Registry numbers, names and line notations, tap to copy
- IUPAC name
- 1-[(7R)-7-ethyl-7-hydroxy-5,6-dihydrocyclopenta[b]pyridin-2-yl]-6-[4-(4-methylpiperazin-1-yl)anilino]-2-prop-2-enylpyrazolo[3,4-d]pyrimidin-3-one
- CAS number
- 2376146-48-2
- EC number
- 189-014-7
- Molecular formula
- C29H34N8O2
- UNII
- 9J13XU96Z1
- InChIKey
- OXTSYWDBUVRXFF-GDLZYMKVSA-N
- InChI
- InChI=1S/C29H34N8O2/c1-4-14-36-27(38)23-19-30-28(31-21-7-9-22(10-8-21)35-17-15-34(3)16-18-35)33-26(23)37(36)24-11-6-20-12-13-29(39,5-2)25(20)32-24/h4,6-11,19,39H,1,5,12-18H2,2-3H3,(H,30,31,33)/t29-/m1/s1
- Canonical SMILES
- C=CCn1c(=O)c2cnc(Nc3ccc(N4CCN(C)CC4)cc3)nc2n1-c1ccc2c(n1)C(O)(CC)CC2
- Isomeric SMILES
- CC[C@]1(CCC2=C1N=C(C=C2)N3C4=NC(=NC=C4C(=O)N3CC=C)NC5=CC=C(C=C5)N6CCN(CC6)C)O
Synonyms
- 1-[(7R)-7-ethyl-7-hydroxy-5,6-dihydrocyclopenta[b]pyridin-2-yl]-6-[4-(4-methylpiperazin-1-yl)anilino]-2-prop-2-enylpyrazolo[3,4-d]pyrimidin-3-one
- compound 16
- ZN-C3
- compound 16 (PMID: 34423975)
- 1-((7R)-7-ethyl-7-hydroxy-5,6-dihydrocyclopenta(b)pyridin-2-yl)-6-(4-(4-methylpiperazin-1-yl)anilino)-2-prop-2-enylpyrazolo(3,4-d)pyrimidin-3-one
- Wee1 Inhibitor ZN-c3
- ZN c3
- Azenosertib (Zn-C3)
- ZNc3
Physical and chemical properties
Measured values and descriptors computed from the structure
Physical and chemical properties
Measured values, check the supplier specification for your grade
No measured properties are recorded for this substance yet. Ask suppliers for a technical data sheet.
Values vary by grade. Ask suppliers for the COA or TDS of the batch you buy.
Computed descriptors
Calculated from the structure, useful for screening and formulation
| Molecular weight | 526.65 g/molcalc.Computed value |
|---|---|
| Exact mass | 526.2805 Dacalc.Computed value |
| LogP (octanol/water) | 3.2calc.Computed value |
| Topological polar surface area | 104.3 Ųcalc.Computed value |
| Hydrogen bond donors | 2calc.Computed value |
| Hydrogen bond acceptors | 8calc.Computed value |
| Rotatable bonds | 7calc.Computed value |
| Heavy atoms | 39calc.Computed value |
| Rings | 6calc.Computed value |
| Aromatic rings | 4calc.Computed value |
| Fraction sp3 carbons | 0.38calc.Computed value |
| Formal charge | 0calc.Computed value |
| Stereocentres | 1calc.Computed value |
| Lipinski rule of five | Passes (1 violation)calc.Computed value |
Calculated for screening. Confirm critical figures with the supplier.
Murcko scaffold
The ring system that remains when every side chain is removed
![Murcko scaffold of this chemical, O=c1[nH]n(-c2ccc3c(n2)CCC3)c2nc(Nc3ccc(N4CCNCC4)cc3)ncc12](/scaffold/OGXLGZCNDFFMOY-UHFFFAOYSA-N/structure.svg)
O=c1[nH]n(-c2ccc3c(n2)CCC3)c2nc(Nc3ccc(N4CCNCC4)cc3)ncc12
6 rings, 32 atoms.
No other chemical in our database has this scaffold.
Safety and hazards
GHS classification summary, not a safety data sheet
No GHS hazard classification is recorded for this substance yet. That does not mean it is harmless.
GHS classification summary, not a safety data sheet (SDS). Classifications can differ by supplier, grade and concentration. Always check the supplier's SDS.
Azenosertib suppliers
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Azenosertib price
Indicative price range per kg from live supplier offers
Suppliers quote this chemical on request. Send one free request and compare quotes side by side.
Uses and applications
What the substance is used for, by industry and function
Industries and functions
Roles
- antineoplastic agent
- pharmaceutical
Regulatory status
Inventories, regulations and trade controls that list this substance
No regulatory list memberships are recorded for this substance yet. Always check the rules of the importing and exporting country before trade.
HS code and trade data
Customs classification and reported world trade statistics
Global trade
World import and export statistics for the HS code Azenosertib is traded under.
Compounds containing a pyrimidine ring (whether or not hydrogenated) or piperazine ring, other
- Ireland43.6%
- Switzerland * partner reported26.3%
- China7.9%
- Slovenia30.3%
- United States30.1%
- Germany15.3%
* Partner reported figures, a lower bound.
The HS code shown for Azenosertib is indicative (it was assigned by structure rules). Confirm the classification with your customs broker before shipping.
Related chemicals
Parent and salt forms, stereoisomers, similar structures and isomers
Similar structures
Nearest neighbours by Morgan fingerprint Tanimoto similarity
![(R)-2-Allyl-1-(7-ethyl-7-hydroxy-6,7-dihydro-5H-cyclopenta[b]pyridin-2-yl)-6-(methylthio)-1H-pyrazolo[3,4-d]pyrimidin-3(2H)-one chemical structure, C19H21N5O2S, CAS 2376147-62-3](/s/AAYCHKCUROMSRP-LJQANCHMSA-N.svg)
![2-Allyl-1-(7-ethyl-7-hydroxy-6,7-dihydro-5H-cyclopenta[b]pyridin-2-yl)-6-(methylthio)-1,2-dihydro-3H-pyrazolo[3,4-d]pyrimidin-3-one chemical structure, C19H21N5O2S, CAS 2376147-58-7](/s/AAYCHKCUROMSRP-UHFFFAOYSA-N.svg)
Same formula isomers
Different compounds that share this molecular formula
Frequently asked questions
Quick answers about Azenosertib, based on the data on this page
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Guides for buyers
Practical guides that help when you source, ship or handle Azenosertib
- Guide, Chemical identityCAS registry numbers explainedWhat a CAS number identifies, how the check digit works, why one chemical can have several numbers and what a CAS number cannot tell you about a product.Read
- Article, SourcingHow to write an RFQ that gets fast and accurate quotesWhat suppliers need to quote quickly and comparably: exact product identity, quantity and packing, delivery terms, documents, samples and payment, with a ready to use template.Read
- Guide, Trade and logisticsHS codes for chemicals and why they matterHow the Harmonized System classifies chemicals, the chapters that matter, the rules for chemically defined compounds and mixtures, and practical steps to find the right code.Read
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