Drug Information
| Drug General Information | Top | |||
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| Drug ID |
D0DJ1B
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| Former ID |
DIB008644
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| Drug Name |
Naproxen
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| Synonyms |
NAPROXEN; 22204-53-1; (S)-Naproxen; Naproxene; Naprosyn; (+)-Naproxen; Equiproxen; Laraflex; Naproxenum; Naproxeno; d-Naproxen; (S)-(+)-2-(6-Methoxy-2-naphthyl)propionic acid; (S)-(+)-Naproxen; Calosen; Nycopren; Naprosyne; Bonyl; Reuxen; Naixan; Axer; (+)-(S)-Naproxen; Ec-Naprosyn; (S)-2-(6-methoxynaphthalen-2-yl)propanoic acid; Flexipen; Clinosyn; Artrixen; Anexopen; Acusprain; Novonaprox; Arthrisil; Leniartil; Danaprox; Bipronyl; Artroxen; Napren; Naposin; Napflam; Genoxen; Daprox; Atiflan; Artagen; Apronax; Naprius; Nalyxan; Lefaine; Congex
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| Drug Type |
Small molecular drug
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| Indication | Osteoarthritis [ICD-11: FA00-FA05] | Approved | [1] | |
| Pain [ICD-11: MG30-MG3Z] | Phase 2 | [2], [3] | ||
| Endometriosis [ICD-11: GA10; ICD-10: N80, N80.9] | Investigative | [4] | ||
| Company |
Iroko pharmaceuticals; PLx Pharma; CeNeS Pharmaceuticals plc
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| Structure |
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Download2D MOL |
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| Formula |
C14H14O3
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| Canonical SMILES |
CC(C1=CC2=C(C=C1)C=C(C=C2)OC)C(=O)O
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| InChI |
1S/C14H14O3/c1-9(14(15)16)10-3-4-12-8-13(17-2)6-5-11(12)7-10/h3-9H,1-2H3,(H,15,16)/t9-/m0/s1
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| InChIKey |
CMWTZPSULFXXJA-VIFPVBQESA-N
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| CAS Number |
CAS 22204-53-1
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| PubChem Compound ID | ||||
| PubChem Substance ID |
4682, 597410, 3248704, 7847186, 7980083, 8149438, 10252902, 10321400, 11112669, 11335417, 11360656, 11363871, 11366433, 11368995, 11371667, 11373736, 11377157, 11461628, 11466819, 11467939, 11484702, 11486597, 11488859, 11490330, 11491884, 11494791, 15172373, 15172374, 22391409, 24857178, 24870224, 24883816, 24897861, 25649496, 26527900, 26611833, 26679674, 26755231, 46232210, 46487915, 46505508, 47291026, 47588882, 47810639, 48334369, 48334370, 48426145, 49833549, 50025704, 50103854
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| ChEBI ID |
CHEBI:7476
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| ADReCS Drug ID | BADD_D01533 ; BADD_D01534 | |||
| Interaction between the Drug and Microbe | Top | |||
|---|---|---|---|---|
| The Metabolism of Drug Affected by Studied Microbe(s) | ||||
| The Order in the Taxonomic Hierarchy of the following Microbe(s): Bacteroidales | ||||
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Studied Microbe: Bacteroides fragilis ATCC43859
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|
[5] | |||
| Hierarchy | ||||
| Experimental Method | High-throughput screening | |||
| Description | Naproxen(+) can be metabolized by Bacteroides fragilis ATCC43859 (log2FC = -0.765; p = 0.011). | |||
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Studied Microbe: Bacteroides fragilis HMW 610
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|
[5] | |||
| Hierarchy | ||||
| Experimental Method | High-throughput screening | |||
| Description | Naproxen(+) can be metabolized by Bacteroides fragilis HMW 610 (log2FC = -0.654; p = 0.024). | |||
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Studied Microbe: Bacteroides fragilis HMW 615
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|
[5] | |||
| Hierarchy | ||||
| Experimental Method | High-throughput screening | |||
| Description | Naproxen(+) can be metabolized by Bacteroides fragilis HMW 615 (log2FC = -0.569; p = 0.039). | |||
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Studied Microbe: Bacteroides fragilis str. 3397 T10
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|
[5] | |||
| Hierarchy | ||||
| Experimental Method | High-throughput screening | |||
| Description | Naproxen(+) can be metabolized by Bacteroides fragilis str. 3397 T10 (log2FC = -0.447; p = 0.032). | |||
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Studied Microbe: Bacteroides fragilis str. 3986 T(B)9
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[5] | |||
| Hierarchy | ||||
| Experimental Method | High-throughput screening | |||
| Description | Naproxen(+) can be metabolized by Bacteroides fragilis str. 3986 T(B)9 (log2FC = -0.387; p = 0.005). | |||
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Studied Microbe: Bacteroides thetaiotaomicron 3731
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|
[5] | |||
| Hierarchy | ||||
| Experimental Method | High-throughput screening | |||
| Description | Naproxen(+) can be metabolized by Bacteroides thetaiotaomicron 3731 (log2FC = -0.364; p = 0.012). | |||
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Studied Microbe: Bacteroides thetaiotaomicron 7330
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|
[5] | |||
| Hierarchy | ||||
| Experimental Method | High-throughput screening | |||
| Description | Naproxen(+) can be metabolized by Bacteroides thetaiotaomicron 7330 (log2FC = -0.362; p = 0.006). | |||
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Studied Microbe: Bacteroides uniformis ATCC 8492
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[5] | |||
| Hierarchy | ||||
| Experimental Method | High-throughput screening | |||
| Description | Naproxen(+) can be metabolized by Bacteroides uniformis ATCC 8492 (log2FC = -0.454; p = 0.005). | |||
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Studied Microbe: Bacteroides vulgatus ATCC 8482
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|
[5] | |||
| Hierarchy | ||||
| Experimental Method | High-throughput screening | |||
| Description | Naproxen(+) can be metabolized by Bacteroides vulgatus ATCC 8482 (log2FC = -0.455; p = 0.02). | |||
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Studied Microbe: Bacteroides xylanisolvens DSM18836
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[5] | |||
| Hierarchy | ||||
| Experimental Method | High-throughput screening | |||
| Description | Naproxen(+) can be metabolized by Bacteroides xylanisolvens DSM18836 (log2FC = -0.376; p = 0.039). | |||
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Studied Microbe: Odoribacter splanchnicus
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[5] | |||
| Hierarchy | ||||
| Experimental Method | High-throughput screening | |||
| Description | Naproxen(+) can be metabolized by Odoribacter splanchnicus (log2FC = -0.453; p = 0.004). | |||
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Studied Microbe: Parabacteroides distasonis ATCC 8503
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|
[5] | |||
| Hierarchy | ||||
| Experimental Method | High-throughput screening | |||
| Description | Naproxen(+) can be metabolized by Parabacteroides distasonis ATCC 8503 (log2FC = -0.337; p = 0.007). | |||
| References | Top | |||
|---|---|---|---|---|
| REF 1 | Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015 | |||
| REF 2 | URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 5230). | |||
| REF 3 | ClinicalTrials.gov (NCT01139190) Clinical Trial Evaluating Gastrointestinal Damage Following Administration PL3100 or Naproxen in At-Risk Adults. U.S. National Institutes of Health. | |||
| REF 4 | New drugs in development for the treatment of endometriosis. Expert Opin Investig Drugs. 2008 Aug;17(8):1187-202. | |||
| REF 5 | Mapping human microbiome drug metabolism by gut bacteria and their genes. Nature. 2019 Jun;570(7762):462-467. | |||
| REF 6 | 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. | |||
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