Details of the Drug

General Information of Drug (ID: DMA8GI6)

Drug Name

Primary alcohol metabolite of celecoxib

Synonyms

Hydroxy Celecoxib; hydroxycelecoxib; 170571-00-3; CHEMBL745; UNII-1DIW8DT7Q3; 1DIW8DT7Q3; PRIMARY ALCOHOL METABOLITE OF CELECOXIB; Hydroxymethylcelecoxib; 4-[5-[4-(Hydroxymethyl)phenyl]-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzenesulfonamide; 4-[5-[4-(hydroxymethyl)phenyl]-3-(trifluoromethyl)pyrazol-1-yl]benzenesulfonamide; 4-(5-(4-Hydroxymethylphenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)benzenesulfonamide; 4'-Hydroxycelecoxib; Celecoxib metabolite M3

Indication

Disease Entry	ICD 11	Status	REF
Discovery agent	N.A.	Investigative	[1]

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

397.4

Topological Polar Surface Area (xlogp)

2.2

Rotatable Bond Count (rotbonds)

4

Hydrogen Bond Donor Count (hbonddonor)

2

Hydrogen Bond Acceptor Count (hbondacc)

8

Chemical Identifiers

Formula: C17H14F3N3O3S
IUPAC Name: 4-[5-[4-(hydroxymethyl)phenyl]-3-(trifluoromethyl)pyrazol-1-yl]benzenesulfonamide
Canonical SMILES: C1=CC(=CC=C1CO)C2=CC(=NN2C3=CC=C(C=C3)S(=O)(=O)N)C(F)(F)F
InChI: InChI=1S/C17H14F3N3O3S/c18-17(19,20)16-9-15(12-3-1-11(10-24)2-4-12)23(22-16)13-5-7-14(8-6-13)27(21,25)26/h1-9,24H,10H2,(H2,21,25,26)
InChIKey: ICRSYPPLGADZKA-UHFFFAOYSA-N

Cross-matching ID

PubChem CID: 9908776
CAS Number: 170571-00-3
TTD ID: D0T4VL

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Prostaglandin G/H synthase 1 (COX-1)	TT8NGED	PGH1_HUMAN	Inhibitor	[1]
Prostaglandin G/H synthase 2 (COX-2)	TTVKILB	PGH2_HUMAN	Inhibitor	[1]

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Molecular Interaction Atlas (MIA)

MIA Detail

Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease

Discovery agent

ICD Disease Classification

N.A.

Molecule Name	Molecule Type	Gene Name	p-value	Fold-Change	Z-score
Prostaglandin G/H synthase 2 (COX-2)	DTT	PTGS2	7.93E-04	-0.29	-0.34
Prostaglandin G/H synthase 1 (COX-1)	DTT	PTGS1	3.97E-03	0.16	0.43

Molecular Expression Atlas (MEA)

MEA Detail

Jump to Detail Molecular Expression Atlas of This Drug

References

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2	The C50T polymorphism of the cyclooxygenase-1 gene and the risk of thrombotic events during low-dose therapy with acetyl salicylic acid. Thromb Haemost. 2008 Jul;100(1):70-5.
3	Comparative inhibitory activity of rofecoxib, meloxicam, diclofenac, ibuprofen, and naproxen on COX-2 versus COX-1 in healthy volunteers. J Clin Pharmacol. 2000 Oct;40(10):1109-20.
4	How many drug targets are there Nat Rev Drug Discov. 2006 Dec;5(12):993-6.
5	Cox-2 inhibitory effects of naturally occurring and modified fatty acids. J Nat Prod. 2001 Jun;64(6):745-9.
6	Comparison of cyclooxygenase inhibitory activity and ocular anti-inflammatory effects of ketorolac tromethamine and bromfenac sodium. Curr Med Res Opin. 2006 Jun;22(6):1133-40.
7	Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services.
8	Ouellet M, Percival MD: Effect of inhibitor time-dependency on selectivity towards cyclooxygenase isoforms. Biochem J. 1995 Feb 15;306 ( Pt 1):247-51.
9	Differential binding mode of diverse cyclooxygenase inhibitors. J Mol Graph Model. 2002 Mar;20(5):359-71.
10	Differential metabolism of dihomo-gamma-linolenic acid and arachidonic acid by cyclo-oxygenase-1 and cyclo-oxygenase-2: implications for cellular synthesis of prostaglandin E1 and prostaglandin E2. Biochem J. 2002 Jul 15;365(Pt 2):489-96.
11	Maternal toxicity of nonsteroidal anti-inflammatory drugs as an important factor affecting prenatal development. Reprod Toxicol. 2009 Sep;28(2):239-44.
12	Membranous nephropathy associated with the relatively selective cyclooxygenase-2 inhibitor, etodolac, in a patient with early rheumatoid arthritis. Intern Med. 2007;46(13):1055-8.
13	Pfizer. Product Development Pipeline. March 31 2009.
14	Renal effects of nabumetone, a COX-2 antagonist: impairment of function in isolated perfused rat kidneys contrasts with preserved renal function in vivo. Exp Nephrol. 2001;9(6):387-96.
15	Privileged structures: a useful concept for the rational design of new lead drug candidates. Mini Rev Med Chem. 2007 Nov;7(11):1108-19.
16	Flurbiprofen, a cyclooxygenase inhibitor, protects mice from hepatic ischemia/reperfusion injury by inhibiting GSK-3 signaling and mitochondrial permeability transition.Mol Med.2012 Sep 25;18:1128-35.