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Sulfamoxole

Sulfamoxole structure

CAS No:
729-99-7
Formula:
C11H13N3O3S
Chemical Name:
Sulfamoxole
Synonyms:
Benzenesulfonamide,4-amino-N-(4,5-dimethyl-2-oxazolyl)-;Sulfanilamide,N1-(4,5-dimethyl-2-oxazolyl)-;4-Amino-N-(4,5-dimethyl-2-oxazolyl)benzenesulfonamide;N1-(4,5-Dimethyl-2-oxazolyl)sulfanilamide;Sulfamoxole;2-Sulfanilamido-4,5-dimethyloxazole;Sulfano;Sulfmidil;Sulfuno;Tardamid;Sulfadimethyloxazole;2-(p-Aminobenzolsulfonamido)-4,5-dimethyloxazole;N′-(4,5-Dimethyl-2-oxazolyl)sulfanilamide;Tardamide;Sulfamoxolum;Oxasulfa;Sulfabutin;Sulfavigor;Justamil;Sulfune;Sulfono;NSC 683535
Categories:
Analytical Chemistry > Standard

Description

Pale Yellow Solid

Solid

Sulfamoxole is a sulfonamide antibiotic in which 4-aminobenzenesulfonic acid and 4,5-dimethyl-1,3-oxazol-2-amine have combined to form the sulfonamide bond. It has a role as an antimicrobial agent and a drug allergen. It is a sulfonamide, an oxazole and a sulfonamide antibiotic.|Sulfamoxole is an antibacterial in the sulfonamide class.|A sulfanilamide antibacterial agent.

Sulfamoxole Basic Attributes

Molecular Weight：

267.3

Exact Mass：

267.30

EC Number：

211-982-7

UNII：

HGG82XE020

NSC Number：

683535

DSSTox ID：

DTXSID5023617

ATC Code：

J - Antiinfectives for systemic use

Characteristics

PSA：

107

XLogP3：

3.40940

Appearance：

Solid

Density：

1.3786 g/cm³

Melting Point：

193 °C

Boiling Point：

481ºC at 760 mmHg

Flash Point：

244.7ºC

Refractive Index：

1.626

Water Solubility：

961mg/L(20 ºC)

Toxicity：

Oral-mouse LD50: 15200 mg/kg; intraperitoneal-rat LD50: 2500 mg/kg

Flammability characteristics：

Flammable; burning produces toxic nitrogen oxides and sulfur oxide fumes

Safety Information

Transport codes：

NONH for all modes of transport

wgk germany：

hazard class code：

safety instructions：

36/37

RTECS Number：

WO9150000

Marks：

Storage features：

Warehouse ventilated, low temperature and dry

Precautionary statement(s)：

P280

Hazard Statements：

H317

GHS Classification：

|Warning|H317 (100%): May cause an allergic skin reaction [Warning Sensitization, Skin]|P261, P272, P280, P302+P352, P321, P333+P313, P363, and P501|Aggregated GHS information provided by 38 companies from 1 notifications to the ECHA C&L Inventory.

Toxicity

Toxicity class：

moderately toxic

Toxicity Summary：

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

Drug Information

Drug Indication：

For the treatment of bacterial infection.

Pharmacology：

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.

MeSH：

Substances that prevent infectious agents or organisms from spreading or kill infectious agents in order to prevent the spread of infection. (See all compounds classified as Anti-Infective Agents.)

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.

MeSH Entry Terms：

Sulfamoxole

Sulfamoxole Use and Manufacturing

Uses

Silversulfadiazine and Sulfamoxol are common drugs in treatment of bacterial disease.

Use Classification：

Pharmaceuticals

Computed Properties

Molecular Weight:267.31
XLogP3:1.3
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:3
Exact Mass:267.06776246
Monoisotopic Mass:267.06776246
Topological Polar Surface Area:107
Heavy Atom Count:18
Complexity:374
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Drug Function and Efficacy

This product is a sulfonamide antibiotic that interferes with the first step of folic acid synthesis. When used in combination with trimethoprim, it can double-block the bacterial folic acid metabolism, especially against Escherichia coli, Haemophilus influenzae, and Staphylococcus aureus. The antibacterial effect is significantly enhanced compared with a single drug.

This ingredient has been used in drugs with the following functions (note: it does not mean that the ingredient itself has the following health functions)

Related Drugs

Co-sulfamethoxazole Tablets
Ingredients	Each tablet of this product contains 0.4g of sulfadiazine and 0.08g of trimethoprim
Indication	1. Urine alkalinizing drugs can increase the solubility of this product in alkaline urine and increase excretion. 2. It cannot be used in combination with para-aminobenzoic acid, which can replace this product for bacterial uptake, and the two are antagonistic. 3. When the following drugs are used together with this product, this product can replace the protein binding sites of these drugs, or inhibit their metabolism, resulting in prolonged drug action or toxic reactions. Therefore, when these drugs are used at the same time as this product, or when used after the application of this product, their dosages need to be adjusted. Such drugs include oral anticoagulants, oral hypoglycemic drugs, methotrexate, phenytoin sodium and thiopental sodium. 4. Combination with bone marrow suppressive drugs may enhance the adverse reactions of such drugs to the hematopoietic system. Such as leukopenia and thrombocytopenia, etc. If there is an indication for the use of the two drugs together, possible toxic reactions should be closely observed. 5. Long-term combination with contraceptives (estrogens) can reduce the reliability of contraception and increase the chance of extramenstrual bleeding. 6. When used in combination with thrombolytic drugs, their potential toxic effects may be increased. 7 When used in combination with hepatotoxic drugs, the incidence of hepatotoxicity may increase. Liver function should be monitored for such patients, especially those who have been taking the drug for a long time and have a history of liver disease. 8 When used in combination with photosensitive drugs, photosensitization may be additive. 9 Patients receiving this product have an increased need for vitamin K. 10 It should not be used in combination with methenamine, because methenamine can decompose in acidic urine to produce formaldehyde, which can form insoluble precipitates with this product. The risk of crystalluria increases. 11 This product can replace the plasma protein binding site of phenylbutazone, and when the two are used together, the effect of phenylbutazone can be enhanced. 12 When sulfinpyrazone is used in combination with this product, the latter's secretion from the renal tubules can be reduced. The prolonged increase in its blood concentration is prone to toxic reactions. Therefore, the dose of this product may need to be adjusted during or after the application of sulfinpyrazone. When the course of sulfinpyrazone treatment is long, the blood concentration of this product should be monitored to help adjust the dose and ensure safe medication. 13 The TMP in this product can inhibit the metabolism of warfarin and enhance its anticoagulant effect. 14 The TMP in this product can increase renal toxicity when used in combination with cyclosporine. 15 When rifampicin is used in combination with this product, the clearance of TMP in this product can be significantly increased and the serum half-life can be shortened. 16 It is not suitable to be used in combination with anti-tumor drugs and 2,4-diaminopyrimidine drugs, nor should it be used between courses of treatment with other folic acid antagonists, because it may cause bone marrow aplasia or megaloblastic anemia. 17 It is not suitable to be used in combination with dapsone, because the blood concentration of both dapsone and TMP in this product can be increased when used in combination. The increase in dapsone concentration increases and aggravates adverse reactions, especially the occurrence of methemoglobinemia. 18 Avoid using it in combination with penicillins, because this product may interfere with the bactericidal effect of such drugs.
Specifications	Sulfamethoxazole 0.4g; trimethoprim 80mg
Manufacturer	Shanghai Pukang Pharmaceutical Industry Co., Ltd.

Co-sulfamethoxazole Tablets
Ingredients	Sulfadiazine tablets 0.4g, trimethoprim 0.08g
Indication	1. Urine alkalinizing drugs can increase the solubility of this product in alkaline urine and increase excretion. 2. It cannot be used in combination with para-aminobenzoic acid, which can replace this product for bacterial uptake, and the two are antagonistic. 3. When the following drugs are used together with this product, this product can replace the protein binding sites of these drugs, or inhibit their metabolism, resulting in prolonged drug action or toxic reactions. Therefore, when these drugs are used at the same time as this product, or when used after the application of this product, their dosages need to be adjusted. Such drugs include oral anticoagulants, oral hypoglycemic drugs, methotrexate, phenytoin sodium and thiopental sodium. 4. Combination with bone marrow suppressive drugs may enhance the adverse reactions of such drugs to the hematopoietic system. Such as leukopenia and thrombocytopenia, etc. If there is an indication for the use of the two drugs together, possible toxic reactions should be closely observed. 5. Long-term combination with contraceptives (estrogens) can reduce the reliability of contraception and increase the chance of extramenstrual bleeding. 6. When used in combination with thrombolytic drugs, their potential toxic effects may be increased. 7 When used in combination with hepatotoxic drugs, the incidence of hepatotoxicity may increase. Liver function should be monitored for such patients, especially those who have been taking the drug for a long time and have a history of liver disease. 8 When used in combination with photosensitive drugs, photosensitization may be additive. 9 Patients receiving this product have an increased need for vitamin K. 10 It should not be used in combination with methenamine, because methenamine can decompose in acidic urine to produce formaldehyde, which can form insoluble precipitates with this product. The risk of crystalluria increases. 11 This product can replace the plasma protein binding site of phenylbutazone, and when the two are used together, the effect of phenylbutazone can be enhanced. 12 When sulfinpyrazone is used in combination with this product, it can reduce the latter's secretion from the renal tubules, and its blood concentration increases and lasts for a long time, thereby producing toxic reactions. Therefore, the dose of this product may need to be adjusted during or after the application of sulfinpyrazone. When the course of sulfinpyrazone treatment is long, the blood concentration of this product should be monitored to help adjust the dose and ensure safe medication. 13 The TMP in this product can inhibit the metabolism of warfarin and enhance its anticoagulant effect. 14 The TMP in this product can increase renal toxicity when used in combination with cyclosporine. 15 When rifampicin is used in combination with this product, the clearance of TMP in this product can be significantly increased and the serum half-life can be shortened. 16 It is not suitable to be used in combination with anti-tumor drugs and 2,4-diaminopyrimidine drugs, nor should it be used between courses of treatment with other folic acid antagonists, because it may cause bone marrow aplasia or megaloblastic anemia. 17 It is not suitable to be used in combination with dapsone, because the blood concentration of both dapsone and TMP in this product can be increased when used in combination. The increase in dapsone concentration increases and aggravates adverse reactions, especially the occurrence of methemoglobinemia. 18 Avoid using it in combination with penicillins, because this product may interfere with the bactericidal effect of such drugs.
Specifications	Sulfadimethoxazole 0.4g, trimethoprim 80mg
Manufacturer	Dalian Making Charm Pharmaceutical Co., Ltd.

Co-sulfamethoxazole Tablets
Ingredients	Sulfadiazine tablets 0.4g, trimethoprim 0.08g
Indication	1. The combined use of urine alkalinizing drugs can increase the solubility of this product in alkaline urine and increase excretion. 2. It cannot be used in combination with para-aminobenzoic acid, which can replace this product for bacterial uptake, and the two are antagonistic. 3. When the following drugs are used together with this product, this product can replace the protein binding sites of these drugs, or inhibit their metabolism, resulting in prolonged drug action time or toxic reactions. Therefore, when these drugs are used at the same time as this product, or when used after the application of this product, their dosages need to be adjusted. Such drugs include oral anticoagulants, oral hypoglycemic drugs, methotrexate, phenytoin sodium and thiopental sodium. 4. The combined use with bone marrow suppressive drugs may enhance the adverse reactions of such drugs to the hematopoietic system. For example, leukopenia and thrombocytopenia, etc. If there is an indication for the combined use of the two drugs, the possible toxic reactions should be closely observed. 5. Long-term combined use with contraceptives (estrogens) can reduce the reliability of contraception and increase the chance of extramenstrual bleeding. 6. When used in combination with thrombolytic drugs, their potential toxic effects may be increased. 7. When used in combination with hepatotoxic drugs, the incidence of hepatotoxicity may increase. Liver function should be monitored for such patients, especially those who have been taking the drug for a long time and have a history of liver disease. 8. When used in combination with photosensitive drugs, photosensitization may be additive. 9. Patients receiving this product have an increased need for vitamin K. 10. It should not be used in combination with methenamine, because methenamine can decompose in acidic urine to produce formaldehyde, which can form insoluble precipitates with this product. This increases the risk of crystalluria. 11. This product can replace the plasma protein binding site of phenylbutazone, and when the two are used together, the effect of phenylbutazone can be enhanced. 12. When sulfinpyrazone is used in combination with this product, the latter's secretion from the renal tubules can be reduced. The prolonged increase in its blood concentration is prone to toxic reactions. Therefore, the dose of this product may need to be adjusted during or after the application of sulfinpyrazone. When the course of sulfinpyrazone treatment is long, the blood concentration of this product should be monitored to help adjust the dose and ensure safe medication. 13. TMP in this product can inhibit the metabolism of warfarin and enhance its anticoagulant effect. 14. TMP in this product can increase renal toxicity when used in combination with cyclosporine. 15. When rifampicin is used in combination with this product, the clearance of TMP in this product can be significantly increased and the serum half-life can be shortened. 16. It should not be used in combination with anti-tumor drugs and 2,4-diaminopyrimidine drugs, nor should it be used between courses of treatment with other folic acid antagonists, because it may cause bone marrow aplasia or megaloblastic anemia. 17. It should not be used in combination with dapsone, because the blood concentration of both dapsone and TMP in this product can be increased when used in combination. The increase in dapsone concentration increases and aggravates adverse reactions, especially the occurrence of methemoglobinemia. 18. Avoid using it in combination with penicillins, because this product may interfere with the bactericidal effect of such drugs.
Specifications	Sulfadimethoxazole 0.4g, trimethoprim 80mg

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