Sulfamoxole

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Identification

Generic Name

Sulfamoxole

DrugBank Accession Number

DB08798

Background

Sulfamoxole is an antibacterial in the sulfonamide class.

Type

Small Molecule

Groups

Experimental

Structure

Similar Structures

Weight: Average: 267.304
Monoisotopic: 267.067761987
Chemical Formula: C₁₁H₁₃N₃O₃S

Synonyms

2-(p-Aminobenzenesulfonamido)-4,5-dimethyloxazole
2-(p-Aminobenzolsulfonamido)-4,5-dimethyloxazol
4-Amino-N-(4,5-dimethyl-2-oxazolyl)benzenesulfonamide
4,5-Dimethyl-2-sulfanilamidooxazole
N(sup 1)-(4,5-Dimethyl-2-oxazolyl)sulfanilamide
N1-(4,5-Dimethyl-2-oxazolyl)sulfanilamide
Oxasulfa
p-Aminobenzenesulfonyl-2-amino-4,5-dimethyloxazole
Sulfadimethyloxazole
Sulfamoxol
Sulfamoxole
Sulfamoxolum
Sulphamoxole

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Pharmacology

Indication

For the treatment of bacterial infection.

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Contraindications & Blackbox Warnings

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Pharmacodynamics

Sulfamoxole is a sulfonamide antibiotic. The sulfonamides are synthetic bacteriostatic antibiotics with a wide spectrum against most gram-positive and many gram-negative organisms. However, many strains of an individual species may be resistant. Sulfonamides inhibit multiplication of bacteria by acting as competitive inhibitors of p-aminobenzoic acid in the folic acid metabolism cycle. Bacterial sensitivity is the same for the various sulfonamides, and resistance to one sulfonamide indicates resistance to all. Most sulfonamides are readily absorbed orally. However, parenteral administration is difficult, since the soluble sulfonamide salts are highly alkaline and irritating to the tissues. The sulfonamides are widely distributed throughout all tissues. High levels are achieved in pleural, peritoneal, synovial, and ocular fluids. Although these drugs are no longer used to treat meningitis, CSF levels are high in meningeal infections. Their antibacterial action is inhibited by pus.

Mechanism of action

Sulfamoxole is a competitive inhibitor of the bacterial enzyme dihydropteroate synthetase. This enzyme is needed for the proper processing of para-aminobenzoic acid (PABA) which is essential for folic acid synthesis. The inhibited reaction is necessary in these organisms for the synthesis of folic acid.

Target	Actions	Organism
ADihydropteroate synthetase	inhibitor	Plasmodium falciparum

Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism

Not Available

Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects

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Toxicity

Oral Rat LD50: > 12500 mg/kg; Intravenous Mouse LD50: 1 g/kg

Pathways

Not Available

Pharmacogenomic Effects/ADRs

Not Available

Interactions

Drug Interactions

This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.

Drug	Interaction
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Abrocitinib	The metabolism of Abrocitinib can be decreased when combined with Sulfamoxole.
Acarbose	The therapeutic efficacy of Acarbose can be increased when used in combination with Sulfamoxole.
Acenocoumarol	The metabolism of Acenocoumarol can be decreased when combined with Sulfamoxole.
Acetohexamide	The metabolism of Acetohexamide can be decreased when combined with Sulfamoxole.
Acetylsalicylic acid	The metabolism of Acetylsalicylic acid can be decreased when combined with Sulfamoxole.

Food Interactions

Not Available

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International/Other Brands: Sulfmidil / Sulfuno

Chemical Identifiers

UNII: HGG82XE020
CAS number: 729-99-7
InChI Key: CYFLXLSBHQBMFT-UHFFFAOYSA-N
InChI: InChI=1S/C11H13N3O3S/c1-7-8(2)17-11(13-7)14-18(15,16)10-5-3-9(12)4-6-10/h3-6H,12H2,1-2H3,(H,13,14)
IUPAC Name: 4-amino-N-(4,5-dimethyl-1,3-oxazol-2-yl)benzene-1-sulfonamide
SMILES: CC1=C(C)N=C(NS(=O)(=O)C2=CC=C(N)C=C2)O1

References

General References

DUGGER JA: Sulfamoxole (Nuprin), a new sulfonamide, in pediatric practice. J New Drugs. 1961 Sep-Oct;1:223-9. [Article]

External Links

Human Metabolome Database: HMDB0015688
KEGG Drug: D02516
PubChem Compound: 12894
PubChem Substance: 99445268
ChemSpider: 12361
RxNav: 10183
ChEBI: 55548
ChEMBL: CHEMBL2105399
ZINC: ZINC000000057302
PharmGKB: PA165958417
Wikipedia: Sulfamoxole

MSDS

Download (34.3 KB)

Clinical Trials

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Phase	Status	Purpose	Conditions	Count	Start Date	Why Stopped	100+ additional columns
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Pharmacoeconomics

Manufacturers: Not Available
Packagers: Not Available
Dosage Forms: Not Available
Prices: Not Available
Patents: Not Available

Properties

State

Solid

Experimental Properties

Property	Value	Source
melting point (°C)	193 °C	PhysProp
water solubility	1680 mg/L (at 20 °C)	YALKOWSKY,SH & DANNENFELSER,RM (1992)

Predicted Properties

Property	Value	Source
Water Solubility	0.267 mg/mL	ALOGPS
logP	1.04	ALOGPS
logP	0.59	Chemaxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	6.81	Chemaxon
pKa (Strongest Basic)	1.94	Chemaxon
Physiological Charge	-1	Chemaxon
Hydrogen Acceptor Count	4	Chemaxon
Hydrogen Donor Count	2	Chemaxon
Polar Surface Area	98.22 Å²	Chemaxon
Rotatable Bond Count	2	Chemaxon
Refractivity	67.51 m³·mol^-1	Chemaxon
Polarizability	27.44 Å³	Chemaxon
Number of Rings	2	Chemaxon
Bioavailability	1	Chemaxon
Rule of Five	Yes	Chemaxon
Ghose Filter	Yes	Chemaxon
Veber's Rule	No	Chemaxon
MDDR-like Rule	No	Chemaxon

Predicted ADMET Features

Property	Value	Probability
Human Intestinal Absorption	+	0.99
Blood Brain Barrier	+	0.8658
Caco-2 permeable	-	0.5783
P-glycoprotein substrate	Non-substrate	0.8973
P-glycoprotein inhibitor I	Non-inhibitor	0.9293
P-glycoprotein inhibitor II	Non-inhibitor	0.959
Renal organic cation transporter	Non-inhibitor	0.9337
CYP450 2C9 substrate	Non-substrate	0.6623
CYP450 2D6 substrate	Non-substrate	0.8971
CYP450 3A4 substrate	Non-substrate	0.7834
CYP450 1A2 substrate	Non-inhibitor	0.9043
CYP450 2C9 inhibitor	Non-inhibitor	0.8433
CYP450 2D6 inhibitor	Non-inhibitor	0.9269
CYP450 2C19 inhibitor	Non-inhibitor	0.9104
CYP450 3A4 inhibitor	Non-inhibitor	0.9378
CYP450 inhibitory promiscuity	Low CYP Inhibitory Promiscuity	0.7653
Ames test	Non AMES toxic	0.8674
Carcinogenicity	Non-carcinogens	0.8029
Biodegradation	Not ready biodegradable	0.9964
Rat acute toxicity	1.3610 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Weak inhibitor	0.9396
hERG inhibition (predictor II)	Non-inhibitor	0.9361

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	splash10-0903-9520000000-b17afcbf8fbe531fe5f3
LC-MS/MS Spectrum - LC-ESI-QTOF , positive	LC-MS/MS	splash10-0a4i-3900000000-23eed4bc89bcf24079bd
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0a4i-0940000000-62e27c0dfd439f6fc41e
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	splash10-014i-0390000000-691dbc15a2a89c3cf574
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0a4i-1920000000-37afa3ea874d811a3cc6
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	splash10-014j-0950000000-05fcc068bf88ac5b94bb
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	splash10-014l-9030000000-9c5c6583bf12a89d54ea
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	splash10-01bc-9800000000-8537a3e39f1387cce8a9
Predicted 1H NMR Spectrum	1D NMR	Not Applicable
Predicted 13C NMR Spectrum	1D NMR	Not Applicable

Chromatographic Properties

Collision Cross Sections (CCS)

Adduct	CCS Value (Å²)	Source type	Source
[M-H]-	173.1026929	predicted	DarkChem Lite v0.1.0
[M-H]-	173.6814929	predicted	DarkChem Lite v0.1.0
[M-H]-	158.62689	predicted	DeepCCS 1.0 (2019)
[M+H]+	174.7241929	predicted	DarkChem Lite v0.1.0
[M+H]+	174.6082929	predicted	DarkChem Lite v0.1.0
[M+H]+	160.98491	predicted	DeepCCS 1.0 (2019)
[M+Na]+	173.5354929	predicted	DarkChem Lite v0.1.0
[M+Na]+	174.0709929	predicted	DarkChem Lite v0.1.0
[M+Na]+	167.28116	predicted	DeepCCS 1.0 (2019)

Targets

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Details1. Dihydropteroate synthetase

Kind: Protein
Organism: Plasmodium falciparum
Pharmacological action: Yes
Actions: Inhibitor

General Function: Not Available
Specific Function: dihydropteroate synthase activity
Gene Name: Not Available
Uniprot ID: Q27738
Uniprot Name: Dihydropteroate synthetase
Molecular Weight: 43370.845 Da

References

Prabhu V, Lui H, King J: Arabidopsis dihydropteroate synthase: general properties and inhibition by reaction product and sulfonamides. Phytochemistry. 1997 May;45(1):23-7. [Article]

Enzymes

Details1. Cytochrome P450 2C9

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Inhibitor

General Function: A cytochrome P450 monooxygenase involved in the metabolism of various endogenous substrates, including fatty acids and steroids (PubMed:12865317, PubMed:15766564, PubMed:19965576, PubMed:21576599, PubMed:7574697, PubMed:9435160, PubMed:9866708). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:12865317, PubMed:15766564, PubMed:19965576, PubMed:21576599, PubMed:7574697, PubMed:9435160, PubMed:9866708). Catalyzes the epoxidation of double bonds of polyunsaturated fatty acids (PUFA) (PubMed:15766564, PubMed:19965576, PubMed:7574697, PubMed:9866708). Catalyzes the hydroxylation of carbon-hydrogen bonds. Metabolizes cholesterol toward 25-hydroxycholesterol, a physiological regulator of cellular cholesterol homeostasis (PubMed:21576599). Exhibits low catalytic activity for the formation of catechol estrogens from 17beta-estradiol (E2) and estrone (E1), namely 2-hydroxy E1 and E2 (PubMed:12865317). Catalyzes bisallylic hydroxylation and hydroxylation with double-bond migration of polyunsaturated fatty acids (PUFA) (PubMed:9435160, PubMed:9866708). Also metabolizes plant monoterpenes such as limonene. Oxygenates (R)- and (S)-limonene to produce carveol and perillyl alcohol (PubMed:11950794). Contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan (PubMed:25994031)
Specific Function: (R)-limonene 6-monooxygenase activity
Gene Name: CYP2C9
Uniprot ID: P11712
Uniprot Name: Cytochrome P450 2C9
Molecular Weight: 55627.365 Da

References

Zweers-Zeilmaker WM, Horbach GJ, Witkamp RF: Differential inhibitory effects of phenytoin, diclofenac, phenylbutazone and a series of sulfonamides on hepatic cytochrome P4502C activity in vitro, and correlation with some molecular descriptors in the dwarf goat (Caprus hircus aegagrus). Xenobiotica. 1997 Aug;27(8):769-80. [Article]
A Review on Drug Interactions in Oral Hypoglycemic Drugs by Mechanism of Cytochrome P450 Enzyme Inhibition [File]

Drug created at October 14, 2010 19:40 / Updated at February 21, 2021 18:52

Sulfamoxole

Identification

Structure for Sulfamoxole (DB08798)

Pharmacology

Interactions

Products

Categories

Chemical Identifiers

References

Clinical Trials

Clinical Trial & Rare Diseases Add-on Data Package

Pharmacoeconomics

Properties

Spectra

Collision Cross Sections (CCS)

Targets

References

Enzymes

References