Nalidixic Acid

Details

• Internal ID: 29880a34-f5e8-4ffd-83ce-8ef2c813dac2
• Taxonomy: Organoheterocyclic compounds > Diazanaphthalenes > Naphthyridines > Naphthyridine carboxylic acids and derivatives
• IUPAC Name: 1-ethyl-7-methyl-4-oxo-1,8-naphthyridine-3-carboxylic acid
• InChI: InChI=1S/C12H12N2O3/c1-3-14-6-9(12(16)17)10(15)8-5-4-7(2)13-11(8)14/h4-6H,3H2,1-2H3,(H,16,17)
• InChI Key: MHWLWQUZZRMNGJ-UHFFFAOYSA-N
• Popularity: 13,169 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₂H₁₂N₂O₃
• Molecular Weight: 232.23 g/mol
• Exact Mass: 232.08479225 g/mol
• Topological Polar Surface Area (TPSA): 70.50 Ų
• XlogP: 1.40
• Atomic LogP (AlogP): 1.42
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

• 389-08-2
• NegGram
• Nevigramon
• Nalidixin
• Nalidixan
• Nalidic acid
• Nalidixinic acid
• Wintomylon
• Dixiben
• Nalurin
• Naxuril
• Nogram
• Urisal
• Nalix
• 1-Ethyl-7-methyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid
• Betaxina
• Specifin
• Urodixin
• Negram
• Uralgin
• Uriben
• Uriclar
• Uroneg
• Acide nalidixique
• Acido nalidixico
• Acide nalidixico
• NSC-82174
• WIN 18,320
• Acidum nalidixicum
• 1-ethyl-7-methyl-4-oxo-1,8-naphthyridine-3-carboxylic acid
• 1-Ethyl-1,4-dihydro-7-methyl-4-oxo-1,8-naphthyridine-3-carboxylic acid
• NCI-C56199
• 3-Carboxy-1-ethyl-7-methyl-1,8-naphthyridin-4-one
• 1,4-Dihydro-1-ethyl-7-methyl-4-oxo-1,8-naphthyridine-3-carboxylic acid
• 1,8-Naphthyridine-3-carboxylic acid, 1-ethyl-1,4-dihydro-7-methyl-4-oxo-
• 3-Carboxy-1-ethyl-7-methyl-1,8-naphthidin-4-one
• WIN-18320
• Win 18320
• 1-Ethyl-7-methyl-1,4-dihydro-1,8-naphthyridin-4-one-3-carboxylic acid
• 1-Aethyl-7-methyl-1,8-naphthyridin-4-on-3-karbonsaeure
• 3B91HWA56M
• DTXSID3020912
• NSC82174
• Acide 1-etil-7-metil-1,8-naftiridin-4-one-3-carbossilico
• DTXCID70912
• CHEBI:100147
• 1-Ethyl-7-methyl-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid
• Acid, Nalidixic
• 1-Ethyl-7-methyl-4-oxo-1,4-dihydro-(1,8)naphthyridine-3-carboxylic acid
• Neg Gram
• Sodium Nalidixic Acid, Anhydrous
• RefChem:55688
• Anhydrous, Nalidixate Sodium
• J01MB02
• 206-864-7
• Nalidixate
• Uronidix
• Innoxalon
• Nalitucsan
• Unaserus
• Sicmylon
• Cybis
• Dixinal
• Jicsron
• Uroman
• Kusnarin
• Nalidicron
• Nicelate
• Narigix
• Poleon
• Uropan
• Specifen
• Naldixic acid
• Eucistin
• MFCD00006884
• Nalidixane
• Nalidixic acid (NegGram)
• MLS000028504
• 1,4-Dihydro-1-ethyl-7-methyl-1,8-naphthyridin-4-one-3-carboxylic acid
• 1,8-Naphthyridine-3-carboxylic acid,1-ethyl-1,4-dihydro-7-methyl-4-oxo-
• NCGC00018181-08
• SMR000058264
• Wintron
• Acido nalidissico
• Nalidixic acid 100 microg/mL in Acetonitrile
• Acido nalidissico [DCIT]
• Acide nalidixico [Italian]
• Acide nalidixique [French]
• Eucisten
• Nalidixic
• Acide nalidixique [INN-French]
• Acido nalidixico [INN-Spanish]
• Acidum nalidixicum [INN-Latin]
• CAS-389-08-2
• NegGram (TN)
• CCRIS 2365
• HSDB 3241
• EINECS 206-864-7
• BRN 0750515
• UNII-3B91HWA56M
• Innoxalomn
• nalidixic-acid
• SR-01000003086
• 1-Aethyl-7-methyl-1,8-naphthyridin-4-on-3-karbonsaeure [German]
• Acide 1-etil-7-metil-1,8-naftiridin-4-one-3-carbossilico [Italian]
• NALIDIXICACID
• WIN 183203
• CHEMBL5
• Spectrum_000918
• Nalidixic acid [USAN:USP:INN:BAN:JAN]
• Maybridge1_007101
• Opera_ID_1064
• Prestwick0_000187
• Prestwick1_000187
• Prestwick2_000187
• Prestwick3_000187
• Spectrum2_001360
• Spectrum3_000075
• Spectrum4_000817
• Spectrum5_001540
• Nalidixic acid (Standard)
• Nalidixic acid, >=98%
• UPCMLD-DP129
• NALIDIXIC ACID [MI]
• NCIOpen2_004342
• Lopac0_000837
• Oprea1_010545
• SCHEMBL21736
• BSPBio_000113
• BSPBio_001889
• KBioGR_001333
• KBioSS_001398
• NALIDIXIC ACID [INN]
• NALIDIXIC ACID [JAN]
• 5-25-07-00384 (Beilstein Handbook Reference)
• MLS001148578
• MLS002303041
• MLS004820190
• MLS006011875
• 1-ethyl-7-methyl-4-oxo-1
• BIDD:GT0529
• DivK1c_000058
• NALIDIXIC ACID [HSDB]
• NALIDIXIC ACID [USAN]
• SPECTRUM1500756
• SPBio_001579
• SPBio_002034
• NALIDIXIC ACID [VANDF]
• BPBio1_000125
• orb1710668
• NALIDIXIC ACID [MART.]
• NALIDIXIC ACID [WHO-DD]
• SCHEMBL29367723
• UPCMLD-DP129:001
• BDBM21691
• GTPL12773
• HMS500C20
• HMS561K17
• HY-B0398R
• KBio1_000058
• KBio2_001398
• KBio2_003966
• KBio2_006534
• KBio3_001109
• MSK5735
• NINDS_000058
• HMS1921G10
• HMS2092K04
• HMS2232H24
• HMS3259O13
• HMS3374G11
• HMS3656K05
• HMS5080P10
• Pharmakon1600-01500756
• Nalidixic acid (JP18/USP/INN)
• Nalidixic acid, analytical standard
• ALBB-021275
• HY-B0398
• MSK5735-1000DM
• Tox21_110835
• Tox21_201477
• Tox21_302754
• BBL012279
• CCG-39298
• MSK5735-100M
• NALIDIXIC ACID [EP IMPURITY]
• NALIDIXIC ACID [ORANGE BOOK]
• NSC757432
• SBB002146
• STK735579
• NALIDIXIC ACID [USP IMPURITY]
• 1-Ethyl-1,4-dihydro-7-methyl-4-oxo-1,8-naphthyridine-3-carboxilic acid
• AKOS000120074
• Tox21_110835_1
• AN16320
• DB00779
• NC00494
• NSC-757432
• SDCCGSBI-0050814.P004
• IDI1_000058
• NCGC00018181-01
• NCGC00018181-02
• NCGC00018181-03
• NCGC00018181-04
• NCGC00018181-05
• NCGC00018181-06
• NCGC00018181-07
• NCGC00018181-09
• NCGC00018181-10
• NCGC00018181-12
• NCGC00018181-13
• NCGC00021730-03
• NCGC00021730-04
• NCGC00021730-05
• NCGC00021730-06
• NCGC00021730-07
• NCGC00256581-01
• NCGC00259028-01
• AS-13289
• NCI60_041807
• SMR004703506
• SY049448
• WLN: T66 BN EV JNJ B2 DVQ I1
• Nalidixic acid 100 microg/mL in Methanol
• SBI-0050814.P003
• DB-049349
• Nalidixic acid 1000 microg/mL in Methanol
• 1, 1-ethyl-1,4-dihydro-7-methyl-4-oxo-
• N0490
• NS00009829
• S2328
• SW219624-1
• 1-Ethyl-1,8-naphthyridine-3-carboxilic acid
• 1-Ethyl-1,8-naphthyridine-3-carboxylic acid
• EN300-20573
• VU0239598-6
• C05079
• D00183
• D91720
• Nalidixic acid Solution in Methanol, 100ug/mL
• Nalidixic acid, meets USP testing specifications
• 389N082
• F358268
• Q281082
• SR-01000003086-4
• SR-01000003086-6
• BRD-K47886988-001-21-4
• BRD-K47886988-001-22-2
• BRD-K47886988-323-03-0
• Nalidixic acid Solution in DMSO/Methanol, 1000ug/mL
• SR-01000003086-10
• F0850-6751
• Z104478940
• 1-Ethyl-7-methyl-1,8-naphthyridin-4-one-3-carboxylic acid
• 1-ethyl-7-methyl-4-oxo-[1,8]naphthyridine-3-carboxylic acid
• Nalidixic acid, European Pharmacopoeia (EP) Reference Standard
• Nalidixic acid, United States Pharmacopeia (USP) Reference Standard
• 1-ethyl-7-methyl-4-oxohydropyridino[2,3-b]pyridine-3-carboxylic acid
• 1-ETHYL-7-METHYL-4-OXO-1,4-DIHYDRO[1,8]NAPHTHYRIDINE-3-CARBOXYLIC ACID
• InChI=1/C12H12N2O3/c1-3-14-6-9(12(16)17)10(15)8-5-4-7(2)13-11(8)14/h4-6H,3H2,1-2H3,(H,16,17

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9600	96.00%
Caco-2	+	0.5842	58.42%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	+	0.9286	92.86%
Subcellular localzation	Mitochondria	0.8541	85.41%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9515	95.15%
OATP1B3 inhibitior	+	0.9480	94.80%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.8570	85.70%
P-glycoprotein inhibitior	-	0.9582	95.82%
P-glycoprotein substrate	-	0.6990	69.90%
CYP3A4 substrate	-	0.7932	79.32%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9281	92.81%
CYP3A4 inhibition	-	0.9531	95.31%
CYP2C9 inhibition	-	0.8934	89.34%
CYP2C19 inhibition	-	0.7834	78.34%
CYP2D6 inhibition	-	0.9115	91.15%
CYP1A2 inhibition	-	0.7888	78.88%
CYP2C8 inhibition	-	0.7299	72.99%
CYP inhibitory promiscuity	-	0.8555	85.55%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8857	88.57%
Carcinogenicity (trinary)	Warning	0.5225	52.25%
Eye corrosion	-	0.9917	99.17%
Eye irritation	+	0.6947	69.47%
Skin irritation	-	0.8431	84.31%
Skin corrosion	-	0.9649	96.49%
Ames mutagenesis	+	0.7100	71.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7085	70.85%
Micronuclear	+	0.8300	83.00%
Hepatotoxicity	+	0.7533	75.33%
skin sensitisation	-	0.9109	91.09%
Respiratory toxicity	+	0.9111	91.11%
Reproductive toxicity	+	0.5889	58.89%
Mitochondrial toxicity	+	0.9500	95.00%
Nephrotoxicity	+	0.5814	58.14%
Acute Oral Toxicity (c)	III	0.7888	78.88%
Estrogen receptor binding	+	0.5530	55.30%
Androgen receptor binding	-	0.6676	66.76%
Thyroid receptor binding	-	0.7869	78.69%
Glucocorticoid receptor binding	-	0.4749	47.49%
Aromatase binding	-	0.6779	67.79%
PPAR gamma	-	0.6270	62.70%
Honey bee toxicity	-	0.9671	96.71%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.7800	78.00%
Fish aquatic toxicity	+	0.7348	73.48%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293235	P02545	Prelamin-A/C	125.9 nM; 125.9 nM	Potency; Potency	via CMAUP; via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.01%	96.09%
CHEMBL2581	P07339	Cathepsin D	93.99%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.09%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.16%	99.23%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.16%	86.33%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	88.82%	93.00%
CHEMBL1811	P34995	Prostanoid EP1 receptor	88.31%	95.71%
CHEMBL1293294	P51151	Ras-related protein Rab-9A	88.07%	87.67%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	86.30%	94.42%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	85.85%	93.65%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.97%	94.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	81.97%	85.14%
CHEMBL1929	P47989	Xanthine dehydrogenase	80.23%	96.12%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	80.00%	81.11%

Plants that contains it

• Aconitum carmichaelii

Cross-Links

• PubChem: 4421
• NPASS: NPC285923
• ChEMBL: CHEMBL5