SULFAMETHOXYPYRIDAZINE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C11H12N4O3S
Molecular Weight	280.303
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

SMILES

COC1=NN=C(NS(=O)(=O)C2=CC=C(N)C=C2)C=C1

InChI

InChIKey=VLYWMPOKSSWJAL-UHFFFAOYSA-N

InChI=1S/C11H12N4O3S/c1-18-11-7-6-10(13-14-11)15-19(16,17)9-4-2-8(12)3-5-9/h2-7H,12H2,1H3,(H,13,15)

HIDE SMILES / InChI

Molecular Formula	C11H12N4O3S
Molecular Weight	280.303
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description

Sulfamethoxypyridazine is a sulfonamide antibacterial with a broad spector of activity. It acts by inhibiting the enzyme dihydropteroate synthetase (DHPS), required for the synthesis of nucleic acids and microbial cells.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
bacterial dihydropteroate synthetase 2	Inhibitor 8,297		0.017 µM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Urinary tract infections 205	Curative	Approved 8,429	Unknown
Bronchopneumonia 4	Curative	Approved 8,429	Unknown
Rheumatic fever 6	Preventing	Preclinical	Unknown
Dermatitis herpetiformis 9	Primary	Preclinical	Unknown
Herpes gestationis 2	Primary	Preclinical	Unknown
Linear IgA disease 2	Primary	Preclinical	Unknown
Cicatricial pemphigoid 2	Primary	Preclinical	Unknown

C_max

Value	Dose	Co-administered	Analyte	Population
0.75 mg/L	1 g single, oral		SULFAMETHOXYPYRIDAZINE plasma	Homo sapiens
0.85 mg/L	1 g single, oral		SULFAMETHOXYPYRIDAZINE plasma	Homo sapiens

T_1/2

Value	Dose	Co-administered	Analyte	Population
38 h			SULFAMETHOXYPYRIDAZINE unknown	Homo sapiens

F_unbound

Value	Dose	Co-administered	Analyte	Population
6.5%			SULFAMETHOXYPYRIDAZINE plasma	Homo sapiens

Doses

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Dose	Population	Adverse events
3 g 1 times / week multiple, oral Highest studied dose	unhealthy, 5 - 15 n = 6	Disc. AE: Skin rash...
1 g 1 times / day multiple, oral Studied dose	unhealthy, 68 n = 1	Disc. AE: Skin rash, Itching...
0.5 g 1 times / day multiple, oral Studied dose	unhealthy, 89 n = 1	Disc. AE: Exfoliative dermatitis...

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AEs

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AE	Significance	Dose	Population
Skin rash	33% Disc. AE	3 g 1 times / week multiple, oral Highest studied dose	unhealthy, 5 - 15 n = 6
Fever	Disc. AE	1 g 1 times / day multiple, oral Studied dose	unhealthy, 68 n = 1
Hepatitis	acute Disc. AE	1 g 1 times / day multiple, oral Studied dose	unhealthy, 68 n = 1
Itching	severe Disc. AE	1 g 1 times / day multiple, oral Studied dose	unhealthy, 68 n = 1
Skin rash	severe Disc. AE	1 g 1 times / day multiple, oral Studied dose	unhealthy, 68 n = 1

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Sourcing

Sourcing

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Vendor/Aggregator	ID	URL
ChEBI	CHEBI:102516	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:102516
ChemicalBook	CB1107025	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB1107025
MolPort	MolPort-000-697-322	https://www.molport.com/shop/molecule-link/MolPort-000-697-322
ZINC	ZINC000000049141	http://zinc15.docking.org/substances/ZINC000000049141
eMolecules	631768	https://www.emolecules.com/cgi-bin/more?vid=631768

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PubMed

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Title	Date	PubMed
Monodrug efficacies of sulfonamides in prophylaxis for Pneumocystis carinii pneumonia.	1996 Apr	8849260
Sulfamethoxypyridazine-responsive pemphigoid nodularis: a report of two cases.	2005 Aug	16021154
[Qualification and quantification of 10 sulfonamides in animal feedstuff by high performance liquid chromatography-electrospray tandem mass spectrometry].	2005 Jul	16250451
Salmonella in healthy pigs: prevalence, serotype diversity and antimicrobial resistance observed during 1998-1999 and 2004-2005 in Japan.	2008 Aug	17961277
Therapeutic effect of a novel oxazolidinone, DA-7867, in BALB/c mice infected with Nocardia brasiliensis.	2008 Sep 10	18820738

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Patents

Sample Use Guides

In Vivo Use Guide

Single weekly dose

Route of Administration: Oral

In Vitro Use Guide

Unknown

Substance Class	Chemical
Record UNII	T034E4NS2Z
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

SULFAMETHOXYPYRIDAZINE

Official Name

English

SULFAMETHOXYPYRIDAZINE [WHO-IP]

Common Name

English

SULFAMETHOXYPYRIDAZINUM [WHO-IP LATIN]

Common Name

English

CL-13494

Code

English

SULFAMETHOXYPYRIDAZINE [MI]

Common Name

English

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Classification Tree

Code System

Code

Anti-Infective Agent

NCI_THESAURUS

C29739

Combinations of sulfonamides and trimethoprim, incl. derivatives

WHO-VATC

QJ01EW15

Long-acting sulfonamides

WHO-ATC

J01ED05

Sulfonamides (ATC human differently classified, see guidelines)

WHO-VATC

QJ01EQ15

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Code System

Code

Type

Description

NSC

757875

PRIMARY

WIKIPEDIA

SULFAMETHOXYPYRIDAZINE

PRIMARY

CHEBI

102516

PRIMARY

WHO INTERNATIONAL PHARMACOPEIA

SULFAMETHOXYPYRIDAZINE

PRIMARY

Description: A white or yellowish white, crystalline powder; odourless or almost odourless. Solubility: Very slightly soluble in water; sparingly soluble in ethanol (~750 g/l) TS; soluble in acetone R. Category: Antibacterial. Storage: Sulfamethoxypyridazine should be kept in a well-closed container, protected from light. Additional information: Sulfamethoxypyridazine becomes gradually coloured on exposure to light. Definition: Sulfamethoxypyridazine contains not less than 99.0% and not more than 101.0% of C11H12N4O3S, calculated with reference to the dried substance.

ECHA (EC/EINECS)

201-272-5

PRIMARY

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