Scroll

sulfamethoxazole 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definition	Drug id	CAS RN
anti-infectives, sulfonamides	2514	723-46-6

Description:

Molecule	Description
Molfile Inchi Smiles Synonyms: sulfamethoxazole sulfamethalazole sulfamethoxazol sulfisomezole sulphamethoxazole	A bacteriostatic antibacterial agent that interferes with folic acid synthesis in susceptible bacteria. Its broad spectrum of activity has been limited by the development of resistance. (From Martindale, The Extra Pharmacopoeia, 30th ed, p208) Molecular weight: 253.28 Formula: C10H11N3O3S CLOGP: 0.56 LIPINSKI: 0 HAC: 6 HDO: 2 TPSA: 98.22 ALOGS: -2.74 ROTB: 2 Status: OFP Legend: OFP - off patent OFM - off market ONP - on patent

Molecule

Description

Molfile Inchi Smiles

Synonyms:

sulfamethoxazole
sulfamethalazole
sulfamethoxazol
sulfisomezole
sulphamethoxazole

A bacteriostatic antibacterial agent that interferes with folic acid synthesis in susceptible bacteria. Its broad spectrum of activity has been limited by the development of resistance. (From Martindale, The Extra Pharmacopoeia, 30th ed, p208)

Molecular weight: 253.28
Formula: C10H11N3O3S
CLOGP: 0.56
LIPINSKI: 0
HAC: 6
HDO: 2
TPSA: 98.22
ALOGS: -2.74
ROTB: 2

Status: OFP

Legend:
OFP - off patent
OFM - off market
ONP - on patent

Drug dosage:

Dose	Unit	Route
2	g	O

ADMET properties:

Show entries

Search:

Property	Value	Reference
BA (Bioavailability)	99 %	Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
t_half (Half-life)	9.80 hours	Lombardo F, Berellini G, Obach RS
MRTD (Maximum Recommended Therapeutic Daily Dose)	394.82 µM/kg/day	Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BDDCS (Biopharmaceutical Drug Disposition Classification System)	2	Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine)	14 %	Benet LZ, Broccatelli F, Oprea TI
S (Water solubility)	0.50 mg/mL	Bocci G, Oprea TI, Benet LZ
CL (Clearance)	0.36 mL/min/kg	Lombardo F, Berellini G, Obach RS
Vd (Volume of distribution)	0.30 L/kg	Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma)	0.23 %	Lombardo F, Berellini G, Obach RS

Showing 1 to 9 of 9 entries

Previous1Next

Approvals:

Date	Agency	Company	Orphan
July 30, 1973	FDA	MONARCH PHARMS

FDA Adverse Event Reporting System (Female)

Show entries

Search:

MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Sleep disorder due to general medical condition, insomnia type	1387.22	12.91	866	84122	51351	63352683
Folliculitis	1374.95	12.91	963	84025	69354	63334680
Muscle injury	1364.81	12.91	932	84056	64413	63339621
Irritable bowel syndrome	1218.58	12.91	954	84034	81458	63322576
Impaired healing	1028.99	12.91	950	84038	101592	63302442
Gastrointestinal disorder	941.61	12.91	1013	83975	130226	63273808
Blister	903.28	12.91	986	84002	128828	63275206
Stomatitis	861.41	12.91	993	83995	137732	63266302
Lower respiratory tract infection	839.90	12.91	958	84030	131349	63272685
Duodenal ulcer perforation	740.04	12.91	737	84251	86472	63317562

Showing 1 to 10 of 319 entries

Previous1 2 3 4 5…32Next

FDA Adverse Event Reporting System (Male)

Show entries

Search:

MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Pyrexia	153.89	11.55	724	36044	332289	34587874
Drug ineffective	136.18	11.55	169	36599	456582	34463581
Cytomegalovirus infection	107.50	11.55	135	36633	26000	34894163
Off label use	96.35	11.55	185	36583	419339	34500824
Lymphocyte count decreased	91.67	11.55	116	36652	22506	34897657
Immune reconstitution inflammatory syndrome	91.54	11.55	75	36693	8684	34911479
Neutropenia	91.26	11.55	366	36402	156412	34763751
Death	90.96	11.55	176	36592	397873	34522290
Hyperkalaemia	88.39	11.55	213	36555	69176	34850987
Aspartate aminotransferase increased	87.34	11.55	209	36559	67574	34852589

Showing 1 to 10 of 200 entries

Previous1 2 3 4 5…20Next

FDA Adverse Event Reporting System (Geriatric)

Show entries

Search:

MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Muscle injury	1147.05	11.58	722	96233	47839	79599594
Folliculitis	1122.74	11.58	748	96207	54632	79592801
Sleep disorder due to general medical condition, insomnia type	1092.90	11.58	673	96282	42883	79604550
Irritable bowel syndrome	1013.90	11.58	735	96220	61506	79585927
Impaired healing	798.75	11.58	738	96217	86917	79560516
Duodenal ulcer perforation	746.20	11.58	629	96326	65582	79581851
Helicobacter infection	702.05	11.58	621	96334	69083	79578350
Gastrointestinal disorder	687.45	11.58	794	96161	121411	79526022
Blister	678.34	11.58	780	96175	118696	79528737
Stomatitis	585.29	11.58	803	96152	145954	79501479

Showing 1 to 10 of 386 entries

Previous1 2 3 4 5…39Next

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

Show entries

Search:

Source	Code	Description
ATC	J01EC01	ANTIINFECTIVES FOR SYSTEMIC USE ANTIBACTERIALS FOR SYSTEMIC USE SULFONAMIDES AND TRIMETHOPRIM Intermediate-acting sulfonamides
ATC	J01EE01	ANTIINFECTIVES FOR SYSTEMIC USE ANTIBACTERIALS FOR SYSTEMIC USE SULFONAMIDES AND TRIMETHOPRIM Combinations of sulfonamides and trimethoprim, incl. derivatives
ATC	J04AM08	ANTIINFECTIVES FOR SYSTEMIC USE ANTIMYCOBACTERIALS DRUGS FOR TREATMENT OF TUBERCULOSIS Combinations of drugs for treatment of tuberculosis
CHEBI has role	CHEBI:33281	antibiotics
CHEBI has role	CHEBI:33282	bactericides
CHEBI has role	CHEBI:35441	antiinfective agents
CHEBI has role	CHEBI:35703	Xenobiotic
CHEBI has role	CHEBI:50183	P450 inhibitors
CHEBI has role	CHEBI:50502	dihydropteroate synthase inhibitors
CHEBI has role	CHEBI:53000	epitope role

Showing 1 to 10 of 17 entries

Previous1 2Next

Drug Use | Suggest Off label Use Form| |View source of the data|

Show entries

Search:

Disease	Relation	SNOMED_ID	DOID
Acute otitis media	indication	3110003
Haemophilus Influenzae Acute Otitis Media	indication	19021002
Nocardiosis	indication	29227009	DOID:2312
Shigellosis	indication	36188001
Klebsiella cystitis	indication	60867007
Toxoplasmosis	indication	187192000	DOID:9965
Chlamydial conjunctivitis	indication	231861005	DOID:13800
Escherichia coli urinary tract infection	indication	301011002
Proteus urinary tract infection	indication	301012009
Bacterial urinary infection	indication	312124009

Showing 1 to 10 of 57 entries

Previous1 2 3 4 5 6Next

🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation level	Dissociation constant	Type (acidic/basic)
pKa1	5.79	acidic
pKa2	2.08	Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

Show entries

Search:

Target	Class	UniProt	Action	Type	Activity value (-log[M])	Bioact source	MoA source
Dihydropteroate synthase	Enzyme	DHPS_ECOLI	INHIBITOR	IC50	5.33	CHEMBL	CHEMBL
Bifunctional protein FolC	Enzyme	FOLC_ECOLI				WOMBAT-PK
Dihydrofolate reductase	Enzyme	DYR_PNECA		IC50	7	CHEMBL
Pol polyprotein	Enzyme	Q72874_9HIV1		Ki	8	CHEMBL
Endothelin-1 receptor	GPCR	EDNRA_RAT		IC50	5.40	CHEMBL

Showing 1 to 5 of 5 entries

Previous1Next

External reference:

Show entries

Search:

ID	Source
08D	PDB_CHEM_ID
002827	NDDF
10180	RXNORM
10933	IUPHAR_LIGAND_ID
1386	INN_ID
2035	MMSL
363528007	SNOMEDCT_US
4017734	VUID
4017734	VANDF
5329	PUBCHEM_CID

Showing 1 to 10 of 21 entries

Previous1 2 3Next

Pharmaceutical products:

Show entries

Search:

Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
Sulfamethoxazole and Trimethoprim	HUMAN PRESCRIPTION DRUG LABEL	2	0121-0853	SUSPENSION	200 mg	ORAL	NDA	28 sections
Sulfamethoxazole and Trimethoprim	HUMAN PRESCRIPTION DRUG LABEL	2	0121-4793	SUSPENSION	200 mg	ORAL	ANDA	28 sections
Sulfamethoxazole and Trimethoprim	HUMAN PRESCRIPTION DRUG LABEL	2	0440-2406	TABLET	800 mg	ORAL	ANDA	13 sections
Sulfamethoxazole and Trimethoprim	HUMAN PRESCRIPTION DRUG LABEL	2	0527-5180	SUSPENSION	200 mg	ORAL	ANDA	21 sections
Sulfamethoxazole and Trimethoprim	HUMAN PRESCRIPTION DRUG LABEL	2	0527-5180	SUSPENSION	200 mg	ORAL	ANDA	21 sections
Sulfamethoxazole and Trimethoprim	HUMAN PRESCRIPTION DRUG LABEL	2	0527-5181	SUSPENSION	200 mg	ORAL	ANDA	21 sections
Sulfamethoxazole and Trimethoprim	HUMAN PRESCRIPTION DRUG LABEL	2	0527-5181	SUSPENSION	200 mg	ORAL	ANDA	21 sections
Sulfamethoxazole and Trimethoprim	HUMAN PRESCRIPTION DRUG LABEL	2	0615-8121	TABLET	800 mg	ORAL	ANDA	26 sections
Sulfamethoxazole and Trimethoprim	HUMAN PRESCRIPTION DRUG LABEL	2	0703-9503	INJECTION, SOLUTION, CONCENTRATE	80 mg	INTRAVENOUS	ANDA	31 sections
Sulfamethoxazole and Trimethoprim	HUMAN PRESCRIPTION DRUG LABEL	2	0703-9503	INJECTION, SOLUTION, CONCENTRATE	80 mg	INTRAVENOUS	ANDA	31 sections

Showing 1 to 10 of 30 entries

Previous1 2 3Next