Compound Detail

CHEMBL865

VALDECOXIB

💊 Approved Drug

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💊 Approved Drug

Cc1onc(-c2ccccc2)c1-c1ccc(S(N)(=O)=O)cc1

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL865
Name	VALDECOXIB
Phase	Approved
Structure Type	MOL
InChI Key	LNPDTQAFDNKSHK-UHFFFAOYSA-N
Therapeutic	✓ Yes

Known Names

Bextra NSC-759846 SC-65872 Valdecoxib Valdyn Valdyn (previously kudeq)

39

Targets

205

Activities

2

Assay Types

0

PK Parameters

20

Publications

6

Known Names

8

Indications

1

Mechanisms

Molecular Properties

314.4

MW (Da)

2.96

ALogP

4

HBA

1

HBD

86.2

PSA (Å²)

0.80

QED

0

Ro5 Violations

3

Rot. Bonds

Drug Information

Molecule Type	Small molecule
First Approval	2001
Availability	Withdrawn
Chirality	Achiral

Routes of Administration

Oral

Flags

Black Box Warning Withdrawn Natural Product

USAN Stem	-coxib
USAN Year	1998

Extended Properties

Molecular Formula	C16H14N2O3S
MW	314.37
Aromatic Rings	3
Heavy Atoms	22
NP-Likeness	-1.33

Mechanism of Action

Mechanism	Action Type	Target	Direct	Efficacy
Cyclooxygenase-2 inhibitor	INHIBITOR	Prostaglandin G/H synthase 2	✓	✓

Indications

Arthritis, Rheumatoid Dysmenorrhea Osteoarthritis Rheumatic Diseases Pain Pharyngitis Osteoarthritis, Knee Pancreatitis

ATC Classification

M01AH03

valdecoxib

Level 1: MUSCULO-SKELETAL SYSTEM

Level 2: ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS

Drug Warnings

Withdrawn

neurotoxicity

Risk for heart attack and stroke

Country: United States; New Zealand; Bhutan; Canada Year: 2005

Withdrawn

dermatological toxicity

associated with increased risk of serious cardiovascular events and an increased risk of serious skin reactions (e.g., toxic epidermal necrolysis, Stevens-Johnson syndrome, erythema multiforme) compar...

Country: United States; New Zealand; Bhutan; Canada Year: 2005

Withdrawn

cardiotoxicity

Cardiovascular risk, (heart attack or stroke)

Country: United States; New Zealand; Bhutan; Canada Year: 2005

Withdrawn

cardiotoxicity

Cardiovascular risk, (heart attack or stroke)

Country: United States; New Zealand; Bhutan; Canada Year: 2005

Withdrawn

cardiotoxicity

Increased risk of heart attack

Country: United States; New Zealand; Bhutan; Canada Year: 2005

Withdrawn

cardiotoxicity

Risk for heart attack and stroke

Country: United States; New Zealand; Bhutan; Canada Year: 2005

Withdrawn

dermatological toxicity

associated with increased risk of serious cardiovascular events and an increased risk of serious skin reactions (e.g., toxic epidermal necrolysis, Stevens-Johnson syndrome, erythema multiforme) compar...

Country: United States; New Zealand; Bhutan; Canada Year: 2005

Withdrawn

cardiotoxicity

associated with increased risk of serious cardiovascular events and an increased risk of serious skin reactions (e.g., toxic epidermal necrolysis, Stevens-Johnson syndrome, erythema multiforme) compar...

Country: United States; New Zealand; Bhutan; Canada Year: 2005

Withdrawn

dermatological toxicity

Serious skin reactions and cardiovascular problems

Country: United States; New Zealand; Bhutan; Canada Year: 2005

Withdrawn

dermatological toxicity

associated with increased risk of serious cardiovascular events and an increased risk of serious skin reactions (e.g., toxic epidermal necrolysis, Stevens-Johnson syndrome, erythema multiforme) compar...

Country: United States; New Zealand; Bhutan; Canada Year: 2005

Activity Summary

Ki 167 meas. best 8.28

IC50 38 meas. best 8.3

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Prostaglandin G/H synthase 2 CHEMBL230	IC50	8.3	7.5271	5.0	14
Unchecked CHEMBL612545	Ki	8.28	6.2288	5.3	41
Carbonate dehydratase CHEMBL3745586	Ki	8.28	8.28	5.3	1
Carbonic anhydrase 12 CHEMBL3242	Ki	7.89	7.89	13.0	5
Carbonic anhydrase 9 CHEMBL3594	Ki	7.57	7.195	27.0	8
Carbonic anhydrase 9 CHEMBL3594	IC50	7.57	7.57	27.0	1
Alpha carbonic anhydrase CHEMBL1075028	Ki	7.54	7.54	28.7	2
Carbonic anhydrase 2 CHEMBL205	IC50	7.37	6.6933	43.0	3
Carbonic anhydrase 2 CHEMBL205	Ki	7.37	7.295	43.0	40
Carbonic anhydrase 15 CHEMBL5973	Ki	7.18	7.18	66.0	1
Carbonic anhydrase 5B, mitochondrial CHEMBL3969	Ki	7.06	7.06	88.0	1
Carbonic anhydrase CHEMBL6185	Ki	7.01	7.01	97.0	1
Carbonic anhydrase 14 CHEMBL3510	Ki	6.97	6.97	107.0	1
Carbonic anhydrase CHEMBL3932	Ki	6.89	6.755	130.0	2
AGAP002992-PA CHEMBL3399914	Ki	6.79	6.79	164.0	1
Carbonic anhydrase 4 CHEMBL281	IC50	6.47	6.47	340.0	2
Carbonic anhydrase 4 CHEMBL281	Ki	6.47	6.47	340.0	2
Carbonic anhydrase 4 CHEMBL3729	Ki	6.47	6.07	340.0	3
Delta carbonic anhydrase CHEMBL3097982	Ki	6.42	6.42	378.0	1
Carbonic anhydrase 13 CHEMBL2186	Ki	6.37	6.37	425.0	1
Carbonic anhydrase 13 CHEMBL3912	Ki	6.37	6.37	425.0	1
Astrosclerin-3 CHEMBL1944499	Ki	6.29	6.29	517.0	1
Carbonic anhydrase, alpha family CHEMBL3621035	Ki	6.28	6.28	529.0	1
Carbonic anhydrase 6 CHEMBL3025	Ki	6.24	6.24	572.0	2
Carbonic anhydrase CHEMBL5931	Ki	6.18	6.18	654.0	1
Carbonic anhydrase 2 CHEMBL6068	Ki	6.17	6.17	682.0	2
Carbonic anhydrase CHEMBL5337	Ki	6.16	6.16	699.0	2
Carbonic anhydrase 2 CHEMBL1697676	Ki	6.15	6.15	704.0	1
Homo sapiens CHEMBL372	IC50	6.05	5.32	890.0	4
Carbonic anhydrase 5A, mitochondrial CHEMBL4789	Ki	6.04	6.04	912.0	1
Blood CHEMBL613416	IC50	5.96	5.96	1100.0	1
Cytochrome c oxidase subunit 2 CHEMBL6174	IC50	5.96	5.96	1100.0	1
Sodium-dependent noradrenaline transporter CHEMBL222	Ki	5.54	5.54	2903.0	1
Sodium-dependent noradrenaline transporter CHEMBL222	IC50	5.53	5.53	2927.0	1
Carbonic anhydrase 7 CHEMBL2326	Ki	5.41	5.41	3900.0	4
Carbonic anhydrase CHEMBL1649055	Ki	5.24	5.24	5710.0	1
PROBABLE TRANSMEMBRANE CARBONIC ANHYDRASE (CARBONATE DEHYDRATASE) (CARBONIC DEHYDRATASE) CHEMBL5767	Ki	5.11	5.11	7810.0	1
Beta-carbonic anhydrase 1 CHEMBL5631	Ki	4.89	4.89	12970.0	2
Prostaglandin G/H synthase 1 CHEMBL221	IC50	4.57	4.515	27000.0	2
Carbonic anhydrase 1 CHEMBL261	Ki	4.27	4.27	54000.0	32
Carbonic anhydrase 1 CHEMBL261	IC50	4.27	4.27	54000.0	2
Carbonic anhydrase CHEMBL3926	Ki	4.21	4.21	61000.0	1
Carbonic anhydrase 3 CHEMBL2885	Ki	4.11	4.11	78000.0	1
Unchecked CHEMBL612545	IC50	4.06	4.06	88000.0	1
Cytochrome c oxidase subunit 1 CHEMBL6011	IC50	4.02	4.02	96200.0	1

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Prostaglandin G/H synthase 2	IC50	=	5.0	nM	8.3	In Vitro activity of compound against human recombinant Prostaglandin G/H syntha...	10715145
Prostaglandin G/H synthase 2	IC50	=	5.0	nM	8.3	Compound was tested for its inhibitory activity against recombinant human Prosta...	10794682
Prostaglandin G/H synthase 2	IC50	=	5.0	nM	8.3	In Vitro activity of compound against human recombinant Prostaglandin G/H syntha...	10715145
Prostaglandin G/H synthase 2	IC50	=	5.0	nM	8.3	Inhibitory activity against human recombinant cyclooxygenase 2	16153836
Prostaglandin G/H synthase 2	IC50	=	5.0	nM	8.3	Inhibition of recombinant human COX-2 by radioligand displacement assay	30108944
Prostaglandin G/H synthase 2	IC50	=	5.0	nM	8.3	Inhibition of recombinant human COX-2 expressed in Baculovirus infected sf9 cell...	30396033
Prostaglandin G/H synthase 2	IC50	=	5.012	nM	8.3	Inhibition of human Prostaglandin G/H synthase 2	11563921
Unchecked	Ki	=	5.3	nM	8.28	Inhibition of Sulfurihydrogenibium yellowstonense YO3AOP1 recombinant carbonic a...	22883029
Carbonate dehydratase	Ki	=	5.3	nM	8.28	Inhibition of recombinant Sulfurihydrogenibium yellowstonense YO3AOP1 carbonic a...	26691758
Carbonic anhydrase 12	Ki	=	13.0	nM	7.89	Inhibitory activity against cloned human CA12	16290146
Carbonic anhydrase 12	Ki	=	13.0	nM	7.89	Inhibition of human transmembrane carbonic anhydrase 12 by stopped-flow CO2 hydr...	24513184
Carbonic anhydrase 12	Ki	=	13.0	nM	7.89	Inhibition of human carbonic anhydrase 12-catalyzed CO2 hydration activity by st...	21852133
Carbonic anhydrase 12	Ki	=	13.0	nM	7.89	Inhibition of human membrane bound carbonic anhydrase 12 preincubated for 15 min...	23965175
Carbonic anhydrase 12	Ki	=	13.0	nM	7.89	Inhibition of human recombinant CA12 catalytic domain pre-incubated for 15 mins ...	23067387
Unchecked	Ki	=	19.0	nM	7.72	Inhibition of Brucella suis carbonic anhydrase I by spectrophotometry at pH 8.3	21251841
Carbonic anhydrase 9	Ki	=	27.0	nM	7.57	Inhibition of human membrane bound carbonic anhydrase 9 preincubated for 15 mins...	23965175
Carbonic anhydrase 9	Ki	=	27.0	nM	7.57	Inhibitory activity against human carbonic anhydrase IX (hCA IX) by using CO2 hy...	15203157
Carbonic anhydrase 9	Ki	=	27.0	nM	7.57	Inhibition of human transmembrane carbonic anhydrase 9 by stopped-flow CO2 hydra...	24513184
Carbonic anhydrase 9	Ki	=	27.0	nM	7.57	Inhibition of human recombinant carbonic anhydrase 9 catalytic domain by stopped...	19193158
Carbonic anhydrase 9	Ki	=	27.0	nM	7.57	Inhibition of human carbonic anhydrase 9-catalyzed CO2 hydration activity by sto...	21852133

Literature References

PubMed	DOI	Target Context	# Activities
-	10.6019/CHEMBL3885881	Rattus norvegicus	252
22194678	10.1371/journal.pcbi.1002310	Hepatotoxicity	14
14736236	10.1021/jm030912m	Oryctolagus cuniculus	7
37468498	10.1038/s41467-023-40064-9	Alpha-1A adrenergic receptor	6
10715145	10.1021/jm990577v	Rattus norvegicus	6
18353655	10.1016/j.bmc.2008.02.088	Rattus norvegicus	5
26832216	10.1016/j.bmcl.2016.01.023	Unchecked	4
37468498	10.1038/s41467-023-40064-9	Progesterone receptor	4
37468498	10.1038/s41467-023-40064-9	Muscarinic acetylcholine receptor M2	4
37468498	10.1038/s41467-023-40064-9	Prostaglandin G/H synthase 1	4
21852133	10.1016/j.bmcl.2011.07.090	Unchecked	4
37468498	10.1038/s41467-023-40064-9	Androgen receptor	4
10715145	10.1021/jm990577v	Homo sapiens	4
37468498	10.1038/s41467-023-40064-9	5-hydroxytryptamine receptor 2B	4
-	10.6019/CHEMBL4495565	SARS-CoV-2	4
37468498	10.1038/s41467-023-40064-9	5-hydroxytryptamine receptor 1A	4
37468498	10.1038/s41467-023-40064-9	Cannabinoid receptor 1	4
37468498	10.1038/s41467-023-40064-9	Alpha-2A adrenergic receptor	4
37468498	10.1038/s41467-023-40064-9	Histamine H1 receptor	3
37468498	10.1038/s41467-023-40064-9	Muscarinic acetylcholine receptor M1	3

Data from ChEMBL 36 via Core Engine